WINSTAR COMMUNICATIONS INC
DEF 14A, 1999-05-07
TELEPHONE COMMUNICATIONS (NO RADIOTELEPHONE)
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<PAGE>
                           SCHEDULE 14A INFORMATION

               PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE
                        SECURITIES EXCHANGE ACT OF 1934
                              (AMENDMENT NO. __)


Filed by the Registrant                     /X/

Filed by a Party other than the Registrant  / /

Check the appropriate box:
/ / Preliminary Proxy Statement
/ / Confidential, for Use of the Commission Only (as permitted by Rule
    14a-6(e)(2))
/X/ Definitive Proxy Statement
/ / Definitive Additional Materials
/ / Soliciting Material Pursuant to Rule 14a-11(c) or Rule 14a-12

                         WINSTAR COMMUNICATIONS, INC.
   ------------------------------------------------------------------------
               (Name of Registrant as Specified In Its Charter)

                         [NAME OF FILER IF APPLICABLE]
   ------------------------------------------------------------------------
   (Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

/X/ No fee required

/ / Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11

    (1) Title of each class of securities to which transaction applies:

    (2) Aggregate number of securities to which transaction applies:

    (3) Per unit price or other underlying value of transaction computed
        pursuant to Exchange Act Rule 0-11 (set forth the amount on which the
        filing fee is calculated and state how it was determined):

    (4) Proposed maximum aggregate value of transaction:

    (5) Total fee paid:

/ / Fee paid previously with preliminary materials.

/ / Check box if any part of the fee is offset as provided by Exchange Act Rule
    0-11(a)(2) and identify the filing for which the offsetting fee was paid
    previously. Identify the previous filing by registration statement number,
    or the Form or Schedule and the date of its filing.

    (1) Amount Previously Paid:

    (2) Form, Schedule or Registration Statement No.:

    (3) Filing Party:

    (4) Date Filed:

<PAGE>
                          WINSTAR COMMUNICATIONS, INC.
                                230 PARK AVENUE
                            NEW YORK, NEW YORK 10169
                            ------------------------
                    NOTICE OF ANNUAL MEETING OF STOCKHOLDERS
                            ------------------------
                                 TO BE HELD ON
                                  JULY 1, 1999
                            ------------------------
 
     NOTICE IS HEREBY GIVEN that the Annual Meeting of Stockholders ("Meeting")
of WinStar Communications, Inc. ("WinStar") will be held at the W New York
hotel, 541 Lexington Avenue, New York, NY 10022, on Thursday, July 1, 1999, at
10:00 a.m., for the following purposes, all as more fully described in the
attached Proxy Statement:
 
          (i) To elect two Class II Directors, to serve for the ensuing
     three-year period and until their respective successors are elected and
     qualified;
 
          (ii) To approve an amendment to WinStar's 1995 Performance Equity Plan
     to increase the number of shares of Common Stock available for issuance
     upon exercise of options and other awards granted or which may be granted
     thereunder; and
 
          (iii) To transact such other business as may properly come before the
     Meeting and any and all adjournments thereof.
 
     The Board of Directors has fixed the close of business on May 3, 1999 as
the record date for the determination of stockholders entitled to notice of, and
to vote at, the Meeting or any adjournment thereof.
 
     For the first time, WinStar stockholders will have the opportunity to vote
their WinStar shares via telephone or the Internet. Stockholders holding WinStar
shares in their own names (registered stockholders) should refer to the
instructions set forth on the enclosed proxy card. Stockholders holding WinStar
shares in the names of their banks or brokers (beneficial owners) will receive
separate voting instructions from their bank or broker. We encourage you to
utilize these efficient and cost-effective voting methods.
 
                                             By Order of the Board of Directors,
                                             Timothy R. Graham
                                             Secretary
 
New York, New York
May 7, 1999
 
WHETHER OR NOT YOU PLAN TO ATTEND THE MEETING, PLEASE COMPLETE, SIGN, DATE AND
RETURN THE ACCOMPANYING PROXY IN THE ENCLOSED ENVELOPE, OR VOTE VIA THE INTERNET
OR BY TELEPHONE IN ACCORDANCE WITH THE INSTRUCTIONS SET FORTH ON THE PROXY CARD.

<PAGE>
                          WINSTAR COMMUNICATIONS, INC.
 
                           -------------------------
                                PROXY STATEMENT
                           -------------------------
 
                              GENERAL INFORMATION
 
     This Proxy Statement is furnished to stockholders of WinStar
Communications, Inc. ("WinStar") in connection with the solicitation of proxies,
in the accompanying form, by the Board of Directors of WinStar (the "Board") for
use in voting at the Annual Meeting of Stockholders ("Meeting") to be held at
the W New York hotel, 541 Lexington Avenue, New York, NY 10022, on Thursday,
July 1, 1999, at 10:00 a.m., and at any and all adjournments thereof.
 
     WinStar's executive offices are located at 230 Park Avenue, New York, New
York 10169. On or about May 7, 1999, this Proxy Statement and the accompanying
form of proxy, together with a copy of WinStar's Annual Report to Stockholders
for the year ended December 31, 1998, including financial statements, are being
mailed to each stockholder of record at the close of business on May 3, 1999.
 
RECORD DATE AND OUTSTANDING SHARES
 
      The Board has fixed the close of business on May 3, 1999 as the record
date for the determination of stockholders entitled to notice of, and to vote
at, the Meeting. Only stockholders of record at the close of business on that
date will be entitled to vote at the Meeting or any and all adjournments
thereof. As of May 3, 1999, WinStar has issued and outstanding 47,640,046 shares
of Common Stock and 4,212,693 shares of Series A Preferred Stock ("Series A
Stock"), comprising all of WinStar's issued and outstanding voting stock
(together, "Voting Stock"). Each holder of Voting Stock of WinStar will be
entitled to one vote for each share of Voting Stock.
 
SOLICITATION AND REVOCATION
 
     Proxies in the form enclosed are solicited by and on behalf of the Board.
The persons named in the proxy have been designated as proxies by the Board. Any
proxy given pursuant to such solicitation and received in time for the Meeting
will be voted as specified in such proxy. If no instructions are given, proxies
will be voted "FOR" the election of the nominees listed below under Proposal I,
"FOR" the approval of the amendment to the 1995 Performance Equity Plan ("1995
Equity Plan") described below under Proposal II, and in the discretion of the
proxies named on the proxy card with respect to any other matters properly
brought before the Meeting and any adjournments thereof. In the event that any
other matters are properly presented at the Meeting for action, the persons
named in the proxy will vote the proxies in accordance with their best judgment.
Any proxy given pursuant to this solicitation may be revoked by the stockholder
at any time before it is exercised by written notification delivered to the
Secretary of WinStar, by voting in person at the Meeting, or by delivering
another proxy bearing a later date. Attendance by a stockholder at the Meeting
does not alone serve to revoke his or her proxy.
 
QUORUM
 
     The presence, in person or by proxy, of a majority of the votes entitled to
be cast at the Meeting will constitute a quorum at the Meeting. A proxy
submitted by a stockholder may indicate that all or a portion of the shares
represented by such proxy are not being voted ("stockholder withholding") with
respect to a particular matter. Similarly, a broker may not be permitted to vote
stock ("broker nonvote") held in street name on a particular matter in the
absence of instructions from the beneficial owner of such stock. The shares
subject to a proxy which are not being voted on a particular matter (because of
either stockholder withholding or broker nonvote) will not be considered shares
present and entitled to vote on such matter. These shares, however, may be
considered present and entitled to vote on other matters and will count for
purposes of determining the presence of a quorum, unless the proxy indicates
that such shares are not being voted on any matter at the Meeting, in which case
such shares will not be counted for purposes of determining the presence of a
quorum.
<PAGE>
VOTING
 
     Stockholders may vote their WinStar shares in one of three ways: by mail;
by telephone or via the Internet. To vote by mail, date, sign and return the
accompanying form of proxy in the envelope enclosed for that purpose (to which
no postage need to be affixed if mailed in the United States). You can specify
your choices by marking the appropriate boxes on the proxy card. If your proxy
card is signed and returned without specifying choices, the shares will be voted
as recommended by the Board of Directors. To vote by telephone or the Internet,
follow the instructions on the proxy card. Abstentions are voted neither "for"
nor "against," but are counted in the determination of a quorum. The prompt
return of the completed proxy card or telephone or Internet vote will assist
WinStar in preparing for the Meeting. Proxies, as well as telephone and Internet
votes, are revocable by the stockholder at any time prior to the Meeting and
will not affect a stockholder's right to vote in person at the Meeting.
 
     Under Proposal I, the Class II Directors will be elected by a plurality of
the votes cast at the Meeting with respect to the election of directors.
"Plurality" means that the two nominees who receive the highest number of votes
will be elected as the Class II Directors of WinStar for the ensuing three-year
period. Consequently, any shares not voted "FOR" the nominee (because of either
stockholder withholding or broker nonvote), will not be counted in such
nominee's favor.
 
     Proposal II, the amendment to the 1995 Equity Plan, must be approved by the
affirmative vote of a majority of the votes cast at the Meeting. Abstentions
from voting with respect to Proposal II are counted as "votes cast" with respect
to such proposal and, therefore, have the same effect as a vote against the
proposal. Shares deemed present at the Meeting but not entitled to vote on
Proposal II (because of either stockholder withholding or broker nonvote) are
not deemed "votes cast" with respect to Proposal II and therefore will have no
effect on such vote.
 
SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT
 
     The table and accompanying footnotes on the following pages set forth
certain information as of April 26, 1999 with respect to the Common Stock
ownership of (i) those persons or groups who beneficially own more than 5% of
WinStar's Common Stock, (ii) each director and director-nominee of WinStar,
(iii) WinStar's Chief Executive Officer and each of WinStar's other executive
officers, including the former Vice Chairman (the "named executive officers"),
and (iv) all directors and executive officers of WinStar as a group (in each
case, based upon information furnished by such persons). Shares of Common Stock
issuable upon exercise of options which are currently exercisable or exercisable
within 60 days of the date of the record date for the Meeting have been included
in the following table.
 
<TABLE>
<CAPTION>
                                                                                                      PERCENT
                                                                              NUMBER OF SHARES      BENEFICIALLY
NAME AND ADDRESS OF BENEFICIAL OWNER                                          BENEFICIALLY OWNED      OWNED**
- ---------------------------------------------------------------------------   ------------------    ------------------
<S>                                                                           <C>                   <C>
William J. Rouhana, Jr.(1) ................................................        2,255,173(2)              4.7
Nathan Kantor(1) ..........................................................        1,001,506(3)              2.1
Timothy R. Graham(1) ......................................................          460,904(4)              1.0
Charles T. Dickson(1) .....................................................             --(5)                 --
Steven B. Magyar ..........................................................           75,403(6)                *
  Two Pine Point
  Lloyd Harbor, New York 11742
William J. vanden Heuvel ..................................................           74,000(7)                *
  812 Park Avenue
  New York, New York 10021
Bert Wasserman ............................................................          110,000(8)                *
  126 East 56th Street
  New York, New York 10022
James I. Cash .............................................................           70,000(9)                *
  Harvard University
  Graduate School of Business Administration
  Baker Library 187, Soldiers Field Road
  Boston, Massachusetts 02163
</TABLE>
 
                                       2
<PAGE>
<TABLE>
<CAPTION>
                                                                                                      PERCENT
                                                                              NUMBER OF SHARES      BENEFICIALLY
NAME AND ADDRESS OF BENEFICIAL OWNER                                          BENEFICIALLY OWNED      OWNED**
- ---------------------------------------------------------------------------       ----------              ------
<S>                                                                           <C>                   <C>
FMR Corp. .................................................................        4,444,302(10)             9.4
  82 Devonshire Street
  Boston, Massachusetts MA 02019
GBU Inc. ..................................................................        3,764,023(11)             8.0
  GEM Capital Management, Inc.
  Gerald B. Unterman
  70 East 55th Street
  New York, New York 10022
All Directors and Executive Officers as a Group (9 persons) ...............        4,006,986(12)             8.0
</TABLE>
 
- ------------------
  * Less than 1%.
 
 ** These percentages do not give effect to the outstanding Series A Stock.
 
 (1) The address of this person is c/o WinStar Communications, Inc., 230 Park
     Avenue, New York, New York 10169.
 
 (2) Includes 1,380,000 shares of Common Stock issuable upon exercise of certain
     options. Does not include (i) 50,000 shares of Common Stock issuable upon
     exercise of options which become exercisable in two equal annual
     installments commencing in March 2000 and (ii) 300,000 shares of Common
     Stock issuable upon exercise of options which become exercisable in January
     2000. Mr. Rouhana has agreed that, during the term of Nathan Kantor's
     employment agreement with WinStar, he would vote all shares of Common Stock
     he controls in favor of Mr. Kantor as a director of WinStar.
 
 (3) Includes 984,865 shares of Common Stock issuable upon exercise of certain
     options. Does not include (i) 333,833 shares of Common Stock issuable upon
     exercise of options which become exercisable in two equal annual
     installments commencing in September 1999 or (ii) 20,000 shares of Common
     Stock issuable upon exercise of options which become exercisable in two
     equal annual installments commencing in March 2000.
 
 (4) Includes 85,000 shares of Common Stock issuable upon exercise of certain
     options. Does not include (i) 10,000 shares of Common Stock issuable upon
     exercise of options which become exercisable in two equal annual
     installments commencing in March 2000, (ii) 1,000 shares of Common Stock
     issuable upon exercise of options which become exercisable in five equal
     annual installments commencing in October 1999 or (iii) 50,000 shares of
     Common Stock issuable upon exercise of options which become exercisable in
     five equal annual installments commencing in April 2000.
 
 (5) Does not include (i) 200,000 shares of Common Stock issuable upon exercise
     of options exercisable in four equal annual installments commencing in
     December 1999, (ii) 1,000 shares of Common Stock issuable upon exercise of
     options which become exercisable in five equal annual installments
     commencing in October 1999 or (iii) 30,000 shares of Common Stock issuable
     upon exercise of options which become exercisable in five equal annual
     installments commencing in April 2000.
 
 (6) Includes (i) 1,000 shares of Common Stock owned by Mr. Magyar's spouse, as
     to which Mr. Magyar disclaims beneficial ownership, (ii) 1,670 shares of
     Common Stock owned by benefit plans of which Mr. Magyar is the sole trustee
     and primary beneficiary, and (iii) 60,000 shares of Common Stock issuable
     upon exercise of certain options.
 
 (7) Includes 70,000 shares of Common Stock issuable upon exercise of certain
     options. Also includes 500 shares owned by Mr. vanden Heuvel's spouse, as
     to which he disclaims beneficial ownership.
 
 (8) Includes 100,000 shares of Common Stock issuable upon exercise of certain
     options.
 
 (9) Represents 70,000 shares of Common Stock issuable upon exercise of certain
     options.
 
(10) FMR Corp. is the parent holding company of, among others, Fidelity
     Management & Research Company ("Fidelity Management"), a registered
     investment adviser which acts as investment adviser to various registered
     investment companies within the Fidelity family of investment funds. FMR
     Corp. and Fidelity Management are deemed to beneficially own shares of
     WinStar held by those funds over which they exercise control. Information
     with respect to this stockholder was derived from its Schedule 13G filed
     with the SEC in February 1999.
 
                                              (Footnotes continued on next page)
 
                                       3
<PAGE>
(Footnotes continued from previous page)
(11) Each of GBU Inc. ("GBU") and GEM Capital Management, Inc. ("GEM Capital")
     is a registered investment adviser which acts as investment adviser to
     various funds and managed accounts. Gerald B. Unterman is the President, a
     director and principal stockholder of GBU and GEM Capital. Mr. Unterman,
     GBU and GEM Capital are deemed to beneficially own shares of WinStar held
     by those funds and managed accounts over which they exercise control.
     Information with respect to these stockholders was derived from their
     Schedule 13G filed with the SEC in February 1999.
 
(12) Includes shares referred to as being included in notes (2) through (9).
     Excludes shares referred to in such notes as being excluded.
 
     Section 16(a) of the Securities Exchange Act of 1934, as amended (the
"Exchange Act"), requires WinStar's directors and executive officers and persons
who beneficially own more than ten percent of WinStar's Common Stock to file
with the Securities and Exchange Commission ("SEC") initial reports of ownership
and reports of changes in ownership of Common Stock. Executive officers,
directors and greater-than-ten percent stockholders are required by SEC
regulations to furnish WinStar with copies of all such reports they file. To
WinStar's knowledge, based solely on review of the copies of such reports
furnished to WinStar and written representations that no other reports were
required during the year ended December 31, 1998, all filings under Section
16(a) were made as required.
 
                                       4
<PAGE>
                   PROPOSAL I: ELECTION OF CLASS II DIRECTORS
 
     The Board is divided into three classes, each of which generally serves for
a term of three years, with only one class of directors being elected in each
year. The term of office of the first class of directors (Class I), presently
consisting of Timothy R. Graham and James I. Cash, will expire in 2001; the term
of office of the second class of directors (Class II), presently consisting of
Bert Wasserman and Nathan Kantor, will expire at the Meeting; and the term of
office of the third class of directors (Class III), presently consisting of
William J. Rouhana, Jr., William J. vanden Heuvel and Steven B. Magyar, will
expire in 2000. In each case, each director will hold office until the next
annual meeting of stockholders at which his class of directors is to be elected,
or until his successor is duly qualified and appointed. WinStar's by-laws
provide that, through August 1999, a majority of the members of the Board will
be independent directors.
 
INFORMATION CONCERNING NOMINEES
 
     Two persons will be elected at the Meeting to serve as Class II Directors
for a term of three years. The Board has nominated Bert Wasserman and Nathan
Kantor, the incumbent Class II Directors, as the candidates for election. Unless
otherwise specified in the form of proxy, the proxies solicited by the
management will be voted "FOR" the election of these candidates. In case either
of these nominees becomes unavailable for election to the Board, an event which
is not anticipated, the persons named as proxies, or their substitutes, shall
have full discretion and authority to vote or refrain from voting for any other
nominee in accordance with their judgment. The following information was
furnished by the nominees:
 
                               CLASS II DIRECTORS
 
     Nathan Kantor, 56, has been a director of WinStar since October 1994 and
President and Chief Operating Officer of WinStar since September 1995. From 1991
to September 1995, Mr. Kantor was President of ITC Group, Inc. ("ITC"), a
company which specialized in the development of emerging competitive
telecommunications companies. Through ITC, Mr. Kantor coordinated all of
WinStar's telecommunications operations from June 1994 to September 1995. From
January 1985 to December 1990, he was President of MCI Telecommunications
Corporation (Northeast Division). Mr. Kantor was a founder of MCI International,
Inc., and served as its President and Chief Operating Officer from its founding
in July 1982 to December 1984. From 1972 to 1982, Mr. Kantor held a number of
senior management positions with MCI Communications, including Vice President of
National Operations. Mr. Kantor also is currently the Chairman of the Board and
Chief Executive Officer of Image Telecommunications Corp., a company involved in
the development of information and video servers. Mr. Kantor is a graduate of
Florida State University and the United States Military Academy at West Point.
 
     Bert Wasserman, 66, has been a director of WinStar since June 1995.
Mr. Wasserman served as Executive Vice President and Chief Financial Officer of
Time Warner, Inc. from 1990 until his retirement in 1995 and served on the Board
of Directors of Time Warner, Inc. and its predecessor company, Warner
Communications, Inc. ("Warner Communications") from 1981 to 1995. He joined
Warner Communications, Inc. in 1966 and had been an officer of that company
since 1970. Mr. Wasserman is director of several investment companies in the
Dreyfus Family of Funds. He is a director of Malibu Entertainment, Inc., Lillian
Vernon Corporation and PSC Inc. He is a graduate of Baruch College and Brooklyn
Law School.
 
                 THE BOARD OF DIRECTORS RECOMMENDS VOTING "FOR"
                          EACH OF THE ABOVE NOMINEES.
 
INFORMATION CONCERNING OTHER DIRECTORS AND EXECUTIVE OFFICERS
 
                               CLASS I DIRECTORS
 
     James I. Cash, 51, has been a director of WinStar since January 1997.
Professor Cash has been a member of the faculty of Harvard Business School since
1976, having taught in its Masters of Business Administration, Management
Development and Advanced Management programs. Professor Cash currently serves as
a trustee for Massachusetts General Hospital and the Massachusetts Computer
Software Council, overseer for the Boston Museum of Science, and is a member of
the Board of Directors of Cambridge Technology Partners, The Chubb Corporation,
General Electric Company, Knight-Ridder, Inc., State Street Bank and Trust
Company and Tandy Corporation. Professor Cash has authored numerous articles and
several books on topics related to information technology and corporate
management and structure and writes a regular column for Information Week
 
                                       5
<PAGE>
magazine. Professor Cash is a graduate of Texas Christian University, Purdue
University's Graduate School of Mathematical Sciences and Purdue University's
Krannert Graduate School of Management.
 
     Timothy R. Graham, 49, has served as Executive Vice President and General
Counsel of WinStar since October 1994 and has been a director of WinStar since
January 1999. From October 1990 through September 1994, Mr. Graham was engaged
in the private practice of law and served in various capacities with National
Capital Management Corporation, a company engaged through its subsidiaries in
various businesses, including the ownership of real estate rental properties,
industrial manufacturing and insurance matters, including as Corporate Secretary
and as President of its primary real estate and insurance subsidiaries. Prior to
1990, Mr. Graham was a partner in the law firm of Nixon, Hargrave, Devans &
Doyle, specializing in corporate finance, regulatory and business law.
Mr. Graham was a Securities Law Editor of Barrister magazine, an American Bar
Association publication, from 1985 to 1986 and has authored a number of
publications, including "Public Offerings in the United States by Foreign
Companies" and "Financing of Foreign Companies through United States Securities
Markets." Mr. Graham also is a member of the Board of Advisors of the
Instructional Television Station of the Archdiocese of New York. Mr. Graham is a
graduate of Fordham Law School and the Georgetown University School of Foreign
Service.
 
                              CLASS III DIRECTORS
 
     William J. Rouhana, Jr., 46, has been a director of WinStar since its
inception, its Chairman of the Board since February 1991, and its Chief
Executive Officer since May 1994. Mr. Rouhana was President and Chief Executive
Officer of WinStar Companies, Inc., a merchant banking firm which focused on
media and telecommunications investments ("WinStar Companies"), and its
affiliates from 1983 until November 1995. Through WinStar Companies, he served,
from August 1987 to February 1989, as Vice Chairman of the Board and Chief
Operating Officer of Management Company Entertainment Group, Inc., a diversified
distributor of entertainment products and, thereafter, as its Vice Chairman of
the Board until May 1990. Mr. Rouhana was in private legal practice from 1977 to
1984, specializing in the financing of entities involved in the development of
entertainment products and information services. Mr. Rouhana was Vice Chairman
of the Board of Governors of the United Nations Association through 1997 and is
a member of the Board of Directors of Business Executives for National Security.
He also co-founded and is co-Chairman of the Humpty Dumpty Institute and a
member of the Board of the Adopt-A-Minefield program. Mr. Rouhana is a Phi Beta
Kappa graduate of Colby College, a Thomas J. Watson Fellow (1972-1973) and a
graduate of Georgetown University School of Law.
 
     Steven B. Magyar, 50, has been a director of WinStar since June 1993. Since
May 1994, Mr. Magyar has owned and operated a private business which specializes
in financial services for high net worth individuals and business owners. From
1989 to May 1994, Mr. Magyar was a regional vice president of CIGNA Insurance
Co. and during the preceding fifteen years held various sales and sales
management positions with CIGNA. Mr. Magyar has served on CIGNA's strategic
business development committee and has been a guest lecturer at New York
University. Mr. Magyar also is a Certified Life Underwriter and Chartered
Financial Consultant with the American College of Insurance. Mr. Magyar is a
member of the General Agents and Managers Association, the National Association
of Underwriters and the American Society of CLU and ChFC. Mr. Magyar is a
graduate of Colby College.
 
     William J. vanden Heuvel, 69, has been a director of the Company since June
1995. Since 1984, he has served as Senior Advisor to Allen & Co., an investment
banking firm, as well as counsel to the law firm Stroock & Stroock & Lavan. He
served as a director of Time Warner from 1981 to 1993 and currently is a
director of Zemex Corp., a New York Stock Exchange listed company engaged in the
mining and exploitation of industrial minerals. Ambassador vanden Heuvel also
has been a member of the IRC Group, a Washington D.C.-based consulting group
made up of former United States ambassadors, since 1981. He was Chairman of the
Board of Governors of the United Nations Association since 1993. From 1979 to
1981, Ambassador vanden Heuvel served as United States Deputy Permanent
Representative to the United Nations. From 1977 to 1979, he served as United
States Ambassador to the European Office of the United Nations and various other
international organizations. He was Special Assistant to United States Attorney
General Robert F. Kennedy from 1961 to 1964. Ambassador vanden Heuvel is a
graduate of Deep Springs College, Cornell University and Cornell Law School. He
is President of the Franklin and Eleanor Roosevelt Institute and Chairman of the
Council of American Ambassadors.
 
                                       6
<PAGE>
                            OTHER EXECUTIVE OFFICER
 
     Charles T. Dickson, 44, has served as Executive Vice President and Chief
Financial Officer of WinStar since December 1997. For the preceding four years,
Mr. Dickson served as Chief Financial Officer of General Instrument Corporation.
From 1984 to 1993, Mr. Dickson held numerous positions at MCI Communications
Corp., including Vice President, Finance and Administration, for the National
Accounts Division. From 1979 to 1984, Mr. Dickson was a consultant with ICF,
Inc. providing financial analysis to clients in the energy and
telecommunications industries. Mr. Dickson is a Phi Beta Kappa graduate of Clark
University and received a masters degree in public policy from the University of
California at Berkley.
 
BOARD MEETINGS, COMMITTEES AND COMPENSATION
 
     The Board met nine times during the year ended December 31, 1998. Each
director attended seventy five percent or more of the meetings held during such
year, except for Professor Cash who attended six meetings.
 
     The Board currently maintains a standing Audit Committee, Compensation
Committee and Nominating Committee. Additionally, from time to time, the Board
establishes special committees for specific purposes. The membership of the
standing committees is as follows, with the committee chairman listed first:
 
<TABLE>
<CAPTION>
          AUDIT COMMITTEE                    COMPENSATION COMMITTEE                 NOMINATING COMMITTEE
- ------------------------------------  ------------------------------------  ------------------------------------
<S>                                   <C>                                   <C>
           Bert Wasserman                       Steven B. Magyar                  William J. vanden Heuvel
          Steven B. Magyar                  William J. vanden Heuvel                  Steven B. Magyar
           James I. Cash                         James I. Cash                    William J. Rouhana, Jr.
      William J. Rouhana, Jr.               William J. Rouhana, Jr.
</TABLE>
 
     The Board's Audit Committee met twice during the year ended December 31,
1998. The responsibilities of the Audit Committee include, in addition to such
other duties as the Board may specify, (i) recommending to the Board the
appointment of independent accountants; (ii) reviewing the timing, scope and
results of the independent accountants' audit examination and the related fees;
(iii) reviewing periodic comments and recommendations by WinStar's independent
accountants and WinStar's response thereto; (iv) reviewing the scope and
adequacy of internal accounting controls and internal auditing activities; and
(v) making recommendations to the Board with respect to significant changes in
accounting policies and procedures. WinStar's by-laws provide that, through
August 1999, a majority of the members of this Committee must be independent
directors.
 
     The Board's Compensation Committee met four times during the year ended
December 31, 1998. The responsibilities of the Compensation Committee include,
in addition to such other duties as the Board may specify, (i) reviewing and
recommending to the Board the policies relating to salaries, compensation and
benefits of the executive officers and key employees of WinStar, and setting the
salary, benefits and other compensation of the Chief Executive Officer,
(ii) reviewing any related party transactions on an ongoing basis for potential
conflicts of interest and (iii) administering WinStar's stock option, stock
purchase and other employee compensation plans. WinStar's by-laws provide that,
through August 1999, a majority of the members of this Committee must be
independent directors and that, absent approval of a majority of the independent
members of the Compensation Committee, WinStar will not enter into any material
transaction with a director, or an affiliate of a director, of WinStar.
 
     The Board's Nominating Committee met once during the year ended
December 31, 1998. The responsibilities of the Nominating Committee include, in
addition to such other duties as the Board may specify, considering and
recommending to the Board nominees for directors.
 
     WinStar pays each outside director $500 for his attendance at each meeting
of a committee of which he is a member and $1,000 for his attendance at each
meeting of the Board. In addition, on January 13th of each year during the term
of WinStar's 1992 Performance Equity Plan (the "1992 Equity Plan"), assuming
there are enough shares then available for grant under the 1992 Equity Plan,
each person who is then a director of WinStar is awarded stock options to
purchase 10,000 shares of WinStar's Common Stock at the fair market value
thereof (as determined in accordance with the 1992 Equity Plan), all of which
options are immediately exercisable as of the date of grant and have a term of
ten years.
 
                                       7


<PAGE>
EXECUTIVE COMPENSATION
 
     The following table shows the compensation for the years ended December 31,
1998, 1997 and 1996 earned by (i) William J. Rouhana, Jr., the Chairman and
Chief Executive Officer of WinStar, (ii) Nathan Kantor, Timothy R. Graham and
Charles T. Dickson, the other executive officers of WinStar, and (iii) Steven G.
Chrust, WinStar's former Vice Chairman.
 
                           SUMMARY COMPENSATION TABLE
 
<TABLE>
<CAPTION>
                                                                           ANNUAL
                                                                        COMPENSATION
                                                                     ------------------    LONG TERM COMPENSATION
                                                        FISCAL       SALARY      BONUS     ----------------------
NAME AND PRINCIPAL POSITION                            YEAR ENDED      ($)      ($)(1)     OPTIONS (# SHARES)
- ----------------------------------------------------   ----------    -------    -------    ----------------------
<S>                                                    <C>           <C>        <C>        <C>
William J. Rouhana, Jr. ............................    12/31/98     554,387    750,000            910,000(2)(4)
  Chairman of the Board and                             12/31/97     483,658    500,000             10,000(4)
  Chief Executive Officer                               12/31/96     410,076    400,000            135,000(1)(4)
Nathan Kantor ......................................    12/31/98     519,237    625,000            510,000(2)(4)
  President and Chief Operating Officer                 12/31/97     448,085    450,000             10,000(4)
                                                        12/31/96     370,769    300,000             60,000(1)(4)
Timothy R. Graham ..................................    12/31/98     284,416    220,000             51,000(1)
  Executive Vice President                              12/31/97     225,000    225,000                  0
  and General Counsel                                   12/31/96     217,788    125,000             25,000(1)
Charles T. Dickson .................................    12/31/98     321,921    150,000             31,000(1)
  Executive Vice President                              12/31/97      11,923     30,000            250,000(3)
  and Chief Financial Officer                           12/31/96          --         --                 --
Steven G. Chrust(5) ................................    12/31/98     363,474    200,000             10,000(4)
  Former Vice Chairman                                  12/31/97     336,924    225,000             10,000(4)
                                                        12/31/96     317,809    225,000             45,000(1)(4)
</TABLE>
 
- ------------------
(1) Represents or includes bonuses paid or stock options granted as compensation
    for the year indicated, the payment or grant of which was made in the
    subsequent calendar year.
 
(2) Includes options to purchase shares of Common Stock granted pursuant to the
    terms of the executive's employment agreement entered into in such year. See
    "Employment Agreements."
 
(3) Represents options granted to Mr. Dickson on the commencement of his
    employment in December, 1997. These options vest in equal installments over
    a five year period commencing on the first anniversary of the grant date.
 
(4) Includes or represents options to purchase 10,000 shares of Common Stock
    granted annually to directors of WinStar under the 1992 Equity Plan. See
    "Stock Option Plans."
 
(5) Mr. Chrust resigned as Vice Chairman and a director of WinStar, effective
    December 31, 1998.
 
     WinStar cannot determine, without unreasonable effort or expense, the
specific amount of certain personal benefits afforded to its employees, or the
extent to which benefits are personal rather than business. WinStar has
concluded that the aggregate amounts of such personal benefits which cannot be
specifically or precisely ascertained do not in any event exceed, as to each
individual named in the preceding table, the lesser of $50,000 or 10% of the
compensation reported in the preceding table for such individual, and that such
information set forth in the preceding table is not rendered materially
misleading by virtue of the omission of the value of such personal benefits.
 
                                       8
<PAGE>
            COMPENSATION COMMITTEE REPORT ON EXECUTIVE COMPENSATION
 
GENERAL
 
     This Report is made by the Compensation Committee of the Board of Directors
of WinStar (as used in this Report, the "Committee"), which is the committee
charged with establishing and administering the policies and plans which govern
compensation for executive officers, including the named executive officers
listed in the compensation tables in this Proxy Statement. The Committee
consists of three non-employee directors and the Chief Executive Officer. The
Committee's decisions and recommendations regarding the Chief Executive Officer
are made solely by the non-employee members of the Committee.
 
EXECUTIVE COMPENSATION POLICIES AND OBJECTIVES
 
     The Committee evaluates the compensation levels of senior management and
evaluates the various factors affecting compensation of WinStar's highest paid
officers. The Committee believes that compensation to WinStar's executive
officers should be designed to encourage and reward management's efforts to
establish and strengthen WinStar's business and to create added value for
stockholders. Such a compensation program helps to achieve WinStar's business
and financial objectives and also provides incentives needed to attract and
retain the highly qualified executives and other personnel needed for WinStar to
achieve its goal of rapidly developing and expanding its telecommunications and
other businesses and to successfully operate in a competitive marketplace. The
Committee also attributes a substantial portion of each executive officer's
compensation to WinStar's performance and the particular contribution made to
WinStar by such officer and his business unit.
 
     The Committee's executive compensation objectives are:
 
     1) to ensure competitive levels of compensation that enable WinStar to
        attract, retain and motivate executives of outstanding ability and
        character to lead WinStar successfully in its highly competitive
        industry characterized by rapid technological change, innovation and
        significant capital investment requirements;
 
     2) to tie a meaningful portion of compensation to the achievement of
        improved long term stockholder value and other business objectives; and
 
     3) to provide equity-based long term incentives that directly link the
        compensation of executives to appreciation in WinStar's Common Stock and
        align the financial interests of the executives with those of WinStar's
        stockholders.
 
     The Committee reviewed many operational and strategic factors in evaluating
WinStar's performance in 1998. Key factors considered were:
 
     1) achievement of performance targets fixed by the Board, including
        specific financial and operational targets such as revenue growth,
        EBITDA and capital expenditure goals in WinStar's core businesses.
 
     2) the quality of revenues generated, including the development of
        recurrent high-margin revenue streams in the telecommunications and data
        businesses through customer growth and network development, with an
        increased focus on on-net sales;
 
     3) the continued development of WinStar's integrated telecommunications
        services business, including such critical elements as:
 
          o the rapid expansion of WinStar's local broadband networks and the
            interconnection of those networks to create a national end-to-end
            broadband telecommunications network, including: the consummation of
            a strategic network development and equipment supply agreement with
            Lucent Technologies, the acquisition of indefeasible rights of use
            (IRUs) for intracity and intercity fiber from Williams
            Communications and Metromedia Fiber Networks, the acquisition of
            substantial additional roof rights, and the successful integration
            into WinStar's network of additional switches and other assets,
            including the integration of WinStar's voice and data
            telecommunications networks, all of which substantially increased
            the value of the network, as evidenced by the sale in 1998 of 2% of
            our Wireless Fiber capacity to Williams for $400 million;
 
                                       9
<PAGE>
          o the rollout of switched telephony services in an additional 13
            markets in 1998, increasing the total number of markets served to
            30, and the development of sales and support teams in each of those
            markets;
 
          o the inception and rapid growth of WinStar's data and Internet
            business, WinStar Broadband Services, which commenced in January
            1998 when WinStar acquired the PacNet frame relay business from
            Midcom Communications and Tier I Internet service provider GoodNet
            from Telesoft Corp.;
 
          o the inception and growth of WinStar's international business,
            including the hiring of key executives, the acquisition of key
            spectrum rights overseas, and the consummation of a joint venture
            with KDD and Sumitomo for the development of a competitive
            telecommunications business in key Japanese markets; and
 
          o the further development of WinStar's network and management systems,
            including the roll out of WinStar's customer-centric C-Host system.
 
     4) the growth of WinStar's workforce from approximately 1,500 to 2,800
        employees in 1998; and
 
     5) the successful planning for WinStar's future growth through the
        consummation of several key financing arrangements, including a
        $2 billion financing arrangement with Lucent.
 
     The Committee believes that WinStar appropriately rewarded its executive
officers for their efforts throughout 1998 with respect to the Company's long
and short term objectives.
 
EXECUTIVE COMPENSATION POLICY AND STRUCTURE
 
     The compensation of WinStar's executives during the prior year consisted of
three principal parts--a base salary, an incentive bonus and equity
compensation, typically in the form of a stock option grant which vests over a
period of several years. As more fully described below, the bonus and equity
components are discretionary, meaning that the total compensation of these
executives depends upon several factors, including individual contribution,
attainment of individual and business unit performance objectives, and
company-wide performance; however, there is no specific weight given to each
criterion and WinStar is not obligated to provide equity incentives, bonuses or
increased cash compensation at any time. In addition, executives are entitled to
various benefits, including medical and other insurance coverage and a
401(k) plan generally available to all employees of WinStar.
 
  Base Salary
 
     Base salaries are intended to compensate executives for their ongoing
leadership skills and management responsibility and depend upon factors such as
the executive's experience, capabilities and unique talents and strengths. The
Chief Executive Officer and the Chief Operating Officer have employment
agreements with WinStar under which their base salaries are set, subject to
periodic review and adjustment to reflect among other things, changes in the
duties and responsibilities of such officer, his contribution to WinStar's
achievements during the prior year and the salaries paid to executives
performing similar functions at companies of similar size and complexity to
WinStar. The salaries of each of WinStar's executive officers was increased in
1998 based upon the terms of their respective employment agreements and/or the
Committee's review of the factors relating to executive compensation levels
described elsewhere in this Report. Base salaries of WinStar's other officers
are reviewed annually by WinStar's senior executive officers based on the same
policies and objectives applied by the Committee to senior management. The
Committee reviews, but does not approve, the decisions regarding the salaries of
such other officers.
 
  Bonus
 
     The incentive bonuses are dependent upon individual, business unit or
division, and overall company performance. For purposes of determining annual
bonuses, the Committee evaluates the achievement of goals set at the start of
the year and compares WinStar's performance in that year to the prior year. The
1998 bonus amounts awarded to WinStar's executives were based upon these
criteria. These accomplishments included the
 
                                       10
<PAGE>
continued development and expansion in 1998 of WinStar's voice and data
telecommunications businesses and its information services (new media) business,
including the identification and negotiation of key strategic commercial,
acquisition and financing transactions which helped to significantly accelerate
WinStar's development and the growth of its network and business.
 
  Stock Options
 
     The third principal component of compensation arises from WinStar's grant
of stock options. The Committee believes that stock options serve as important
long-term incentives for employees by encouraging their continued employment and
commitment to WinStar's performance. Accordingly, options become exercisable
over a period of years, based on continued employment with WinStar, and
generally remain exercisable for five years after vesting. The Committee
believes that stock options are an excellent means to align the interests of
WinStar's employees with those of its stockholders.
 
     The number of options granted to executive officers is determined by the
Committee and generally is based upon the same factors considered with respect
to that officer's bonus, as described above. In addition, the Committee strives
to grant options at a level sufficient to provide a strong incentive for
executives to work for the long-term success of the business. Option grants to
other officers and employees are determined by senior management pursuant to an
option grant program approved by the Committee. Under that program, employees
are eligible for annual option grants, based once again upon their individual
performance and the performance of their business unit and WinStar during the
prior year, within a fixed range which varies depending upon the aggregate
number of options approved by the Committee and the employee's level within the
company.
 
     The Committee has reviewed the compensation of WinStar's executive officers
and has concluded that their compensation was reasonable in view of WinStar's
performance and the contribution of those officers to that performance.
 
COMPENSATION OF THE CHIEF EXECUTIVE OFFICER
 
     As stated above, Mr. Rouhana's base salary for 1998 was determined in
accordance with his employment agreement in effect for that year. His salary
increased from the 1997 level based on the Committee's review of his
performance, and that of WinStar, in 1998 and the level of compensation paid to
Chief Executives of similarly situated companies. As a portion of his 1998
compensation, the Committee awarded Mr. Rouhana an incentive bonus of $750,000.
This award was based on the Committee's evaluation of his performance and
WinStar's achievements in 1998, which included, among other things, that
WinStar:
 
     o expanded the reach of its switched telecommunications services to 30
       major metropolitan markets throughout the country;
 
     o developed a broad range of data and Internet services;
 
     o greatly accelerated the rollout of its local broadband networks through,
       among other things, WinStar's strategic relationship with Lucent and the
       acquisition of additional spectrum rights;
 
     o acquired key intracity and intercity dark fiber needed to connect
       WinStar's local broadband networks and to create a single national
       end-to-end broadband network;
 
     o commenced the rollout of WinStar's business internationally by making key
       acquisitions and entering into a joint venture in Japan;
 
     o delivered superior long term shareholder value over the past five years,
       based on metrics such as Annual Compound Return and Market Value Added;
       and
 
     o secured significant additional funding for WinStar's development in 1998
       and thereafter, including a substantial multi-year commitment for
       financing of WinStar's network infrastructure development, and positioned
       WinStar to raise substantial equity capital at a favorable price early in
       1999.
 
     In January 1998, WinStar and Mr. Rouhana entered into a new three year
employment agreement, the terms of which were approved by the Committee. See
"Employment Agreements" for a more detailed discussion of the terms of this
agreement. The employment agreement provides for a minimum annual base salary,
with annual
 
                                       11
<PAGE>
increases as agreed upon by WinStar and Mr. Rouhana, a discretionary annual cash
bonus, and a grant of stock options which vest over time and are exercisable at
prices at or substantially above the market price of WinStar's stock on the date
of the agreement. In making the decision regarding the grant of stock options,
the Committee also evaluated Mr. Rouhana's performance relative to the
guidelines described above, WinStar's achievements during the term of his prior
contract, equity awards to the CEOs of comparable companies, his critical
leadership role in WinStar's future success and the degree to which other
companies have linked CEO compensation to stockholder returns. In addition, the
Committee used subjective criteria that it deemed relevant in its reasonable
business discretion, such as its opinions about the business environment and the
particular challenges for WinStar as well as the potential market for
Mr. Rouhana's services. The Committee believes that the new contract and
compensation package is in line with industry and market standards and
appropriate in light of his past performance and WinStar's aggressive plans for
growth.
 
                   The Members of the Compensation Committee

                           Steven B. Magyar, Chairman
                            William J. vanden Heuvel
                                 James I. Cash
                            William J. Rouhana, Jr.
 
                                       12

<PAGE>
                             OPTION GRANTS IN 1998
 
     The following table sets forth certain information concerning individual
grants of stock options during 1998 to each of the named executive officers:
 
<TABLE>
<CAPTION>
                                                         INDIVIDUAL GRANTS                              POTENTIAL REALIZABLE
                                  ----------------------------------------------------------------             VALUE
                                  NUMBER OF                                                           AT ASSUMED ANNUAL RATES
                                  SECURITIES    PERCENT OF                                                 OF STOCK PRICE
                                  UNDERLYING      TOTAL                                                     APPRECIATION
                                   OPTIONS      OPTIONS GRANTED    EXERCISE OR                            FOR OPTION TERM
                                   GRANTED      TO EMPLOYEES IN    BASE PRICE                         ------------------------
NAME                                 (#)        FISCAL YEAR (%)       ($)          EXPIRATION DATE      5%($)         10%($)
- -------------------------------   ----------    ---------------    ------------    ---------------    ----------    ----------
<S>                               <C>           <C>                <C>             <C>                <C>           <C>
William J. Rouhana, Jr. .......      10,000           0.14             29.00           1/13/08           182,000       462,000
  Chairman of the Board and         500,000           7.19             26.00               (1)         4,097,000     9,235,000
  Chief Executive Officer(1)        200,000           2.88             39.00               (1)          (832,000)    1,412,000
                                    200,000           2.88             52.00               (1)        (3,083,000)     (267,000)
                                   --------          -----                                            ----------    ----------
                                    910,000          13.09                                               364,000    10,842,000
                                   --------          -----                                            ----------    ----------
                                   --------          -----                                            ----------    ----------
 
Nathan Kantor .................      10,000           0.14             29.00           1/13/08           182,000       462,000
  President and Chief Operating     277,779           3.99             26.00           (2)               634,000     1,092,000
  Officer(2)                        111,111           1.60             39.00           (2)            (1,132,000)     (980,000)
                                    111,110           1.60             52.00           (2)            (2,416,000)   (1,122,000)
                                   --------          -----                                            ----------    ----------
                                    510,000           7.34                                            (2,732,000)     (548,000)
                                   --------          -----                                            ----------    ----------
                                   --------          -----                                            ----------    ----------
 
Timothy R. Graham .............       1,000           0.01             20.00           (3)                 6,216        14,656
  Executive Vice President and
  General Counsel
 
Charles T. Dickson ............       1,000           0.01             20.00           (3)                 6,216        14,656
  Executive Vice President and
  Chief Financial Officer
 
Steven G. Chrust ..............      10,000           0.14             29.00           1/13/08           182,000       462,000
  Former Vice Chairman(4)
</TABLE>
 
- ------------------
 
(1) Reflects stock options granted to Mr. Rouhana in connection with the renewal
    of his employment agreement with WinStar on January 6, 1998. These options
    expire five years from the date of vesting. See "Employment Agreements."
 
(2) Reflects options granted to Mr. Kantor in connection with the renewal of his
    employment agreement with WinStar on September 6, 1998. These options expire
    five years from the date of vesting. See "Employment Agreements."
 
(3) These options vest in five equal annual installments commencing October 22,
    1999 and have a term extending five years from the date of vesting.
 
(4) Mr. Chrust resigned as Vice Chairman and a director of WinStar, effective
    December 31, 1998.
 
                                       13

<PAGE>
                    AGGREGATED OPTION EXERCISES IN 1998 AND
                         FISCAL YEAR-END OPTION VALUES
 
     The following table sets forth certain information concerning exercises of
stock options during 1998 by each of the named executive officers and the fiscal
year-end value of unexercised options held by such persons.
<TABLE>
<CAPTION>
                                                                                                            VALUE OF
                                                                                                           UNEXERCISED
                                                                                                           IN-THE-MONEY
                                                                                                           OPTIONS AT
                                                                                  NUMBER OF SECURITIES       FISCAL
                                                                                       UNDERLYING          YEAR-END(1)
                                                                                 UNEXERCISED OPTIONS AT      ($'S IN
                                                                                   FISCAL YEAR-END(#)      THOUSANDS)
                                         SHARES ACQUIRED    VALUE REALIZED     --------------------------  -----------
NAME                                     ON EXERCISE (#)  ($'S IN THOUSANDS)   EXERCISABLE  UNEXERCISABLE  EXERCISABLE
- ---------------------------------------- ---------------  -------------------  -----------  -------------  -----------
<S>                                      <C>              <C>                  <C>          <C>            <C>
William J. Rouhana, Jr. ................          --                 --         1,045,000      675,000         25,236
  Chairman of the Board and Chief
  Executive Officer
Nathan Kantor ..........................          --                 --         1,264,865      363,833         34,047
  President and Chief Operating Officer
Timothy R. Graham ......................     150,000              1,997            70,000       16,000          1,966
  Executive Vice President and General
  Counsel
Charles T. Dickson .....................          --                 --            50,000      201,000          1,100
  Executive Vice President and Chief
  Financial Officer
Steven G. Chrust(2) ....................          --                 --           627,000      127,000         18,013
  Former Vice Chairman
 
<CAPTION>
NAME                                      UNEXERCISABLE
- ----------------------------------------  -------------
<S>                                      <C>
William J. Rouhana, Jr. ................       4,625
  Chairman of the Board and Chief
  Executive Officer
Nathan Kantor ..........................       2,261
  President and Chief Operating Officer
Timothy R. Graham ......................         424
  Executive Vice President and General
  Counsel
Charles T. Dickson .....................       4,419
  Executive Vice President and Chief
  Financial Officer
Steven G. Chrust(2) ....................       3,909
  Former Vice Chairman
</TABLE>
 
- ------------------
(1) Represents the difference between the aggregate market value at December 31,
    1998 of the Common Stock underlying the options, based on a last sale price
    of $39.00 on that date, and the options' aggregate exercise price.
 
(2) Mr. Chrust resigned as Vice Chairman and a director of WinStar, effective
    December 31, 1998.
 
                                       14

<PAGE>
                               PERFORMANCE GRAPH
 
     The following graph and table compare the five-year stockholder returns of
an investment in: (i) the Common Stock of WinStar, (ii) the Nasdaq
Telecommunications Index and (iii) the Nasdaq Stock Market--US Index. The
comparison assumes that $100 was invested on December 31, 1993 in WinStar's
Common Stock and in each of the comparison groups and assumes reinvestment of
dividends (though WinStar paid no dividends on its Common Stock during such
period).

                                 [LINE GRAPH]

 
                         INDEXED RETURNS [12/31/93=100]
 
<TABLE>
<CAPTION>
                                          RETURN        RETURN       RETURN       RETURN       RETURN        RETURN
                                         DEC. 1993     DEC. 1994    DEC. 1995    DEC. 1996    DEC. 1997    DEC. 1998
                                         ----------    ---------    ---------    ---------    ---------    ----------
 
<S>                                      <C>           <C>          <C>          <C>          <C>          <C>
WinStar
  Communications, Inc.................    $100.000     $ 288.000    $ 548.000    $ 672.000    $ 798.000    $1,248.000
 
Nasdaq Telecommunications
  Index...............................    $100.000     $  97.752    $ 138.265    $ 170.025    $ 208.532    $  293.832
 
Nasdaq Stock Market
  --US Index..........................    $100.000     $  83.458    $ 109.257    $ 111.717    $ 165.936    $  272.893
</TABLE>
 
                                       15

<PAGE>
EMPLOYMENT AGREEMENTS
 
     In March 1995, William J. Rouhana, Jr. and WinStar entered into a
three-year employment agreement. On January 6, 1998, Mr. Rouhana and WinStar
entered into a new three year employment agreement, effective March 1, 1998,
pursuant to which Mr. Rouhana continues to serve as WinStar's Chairman of the
Board and Chief Executive Officer. The employment agreement provides for a
minimum annual base salary of $537,500, with annual increases as agreed upon by
WinStar and Mr. Rouhana. The employment agreement also provides that
Mr. Rouhana is eligible for an annual cash bonus, payable at the discretion of
the Compensation Committee, not to exceed 150% of his base salary then in
effect. At the time of execution of this employment agreement, Mr. Rouhana was
granted: (i) immediately exercisable options to purchase 300,000 shares of
Common Stock for $26 per share, the closing sale price of the Common Stock on
the day immediately preceding the agreement date; (ii) options to purchase
300,000 shares of Common Stock which vest on January 6, 1999, of which 100,000
are exercisable at a price of $26 per share and 200,000 are exercisable at a
price of $39 per share; and (iii) options to purchase 300,000 shares of Common
Stock which vest on January 6, 2000, of which 100,000 are exercisable at a price
of $26 per share and 200,000 are exercisable at a price of $52 per share.
 
     Nathan Kantor became President and Chief Operating Officer of WinStar in
September 1995, when he entered into a three-year employment agreement with
WinStar. In September 1998, Mr. Kantor entered into a new three-year employment
agreement with WinStar. The employment agreement provides for a minimum annual
base salary of $518,350, with annual increases as agreed upon by WinStar and
Mr. Kantor. The employment agreement also provides that Mr. Kantor is eligible
for an annual cash bonus, payable at the discretion of the Chief Executive
Officer and the Compensation Committee, not to exceed 125% of his base salary
then in effect. At the time of execution of this employment agreement,
Mr. Kantor was granted: (i) immediately exercisable options to purchase 166,167
shares of Common Stock for $26 per share, which is greater than the $21.50
closing sale price of the Common Stock on the business day immediately preceding
the agreement date; (ii) options to purchase 166,917 shares of Common Stock
which vest on September 6, 1999, of which 55,806 are exercisable at a price of
$26 per share and 111,111 are exercisable at a price of $39 per share; and
(iii) options to purchase 166,916 shares of Common Stock which vest on
September 6, 2000, of which 55,806 are exercisable at a price of $26 per share
and 111,110 are exercisable at a price of $52 per share.
 
     Steven G. Chrust resigned as Vice Chairman and a director of WinStar,
effective December 31, 1998. In connection with his resignation from these
positions, Mr. Chrust entered into an amendment to his then existing employment
agreement pursuant to which he continues his employment with WinStar as a
regular, non-officer employee. Mr. Chrust will make himself available to the
Chairman and senior management of WinStar to consult and assist WinStar as
needed in strategic planning, corporate development and other matters.
Mr. Chrust continues to be paid his base salary of $350,000 per year, and is
eligible to participate in WinStar's employee benefit programs. He is not
eligible to participate in any bonus, stock option or similar incentive programs
for 1999 or thereafter, nor is he eligible for benefits under his Executive
Severance Agreement with WinStar described below. Mr. Chrust's amended
employment agreement expires in January 2000.
 
     In April 1997, WinStar entered into Executive Severance Agreements (each a
"Severance Agreement") with each of the named executive officers and certain
other senior officers of WinStar and its subsidiaries. The Severance Agreement
generally provides that, if during the two years following a Change of Control
or potential Change of Control of WinStar (each as defined in the Severance
Agreement), either (A) the covered executive's employment is terminated by
WinStar (other than due to the executive's death or Disability or for Cause, as
defined in the Severance Agreement) or (B) the covered executive terminates his
or her employment with WinStar for Good Reason (as defined in the Severance
Agreement), then such executive will be entitled to receive certain severance
benefits, including a cash severance payment equal to one and one-half times the
aggregate of (i) such executive's annual base salary then in effect plus
(ii) such executive's average full-year bonus over the prior two years.
Additional benefits to which a covered executive would be entitled include
continued medical and other insurance benefits for one and one-half years
following termination and career outplacement services. As defined in the
Severance Agreement, "Change of Control of WinStar" generally means that a third
party has acquired 35% or more of WinStar's voting stock (whether through a
stock purchase, exchange, tender offer or merger) or substantially all of
WinStar's assets. A "potential Change of Control" of WinStar would occur if: (w)
an agreement is entered into, the consummation of which would result in a Change
of Control; (x) a third party makes a public announcement of an intention to
take action that, if consummated,
 
                                       16
<PAGE>
would result in a Change of Control of WinStar; (y) WinStar's Stockholder Rights
Plan is triggered; or (z) the Board makes a good faith determination that a
potential Change of Control has occurred. The Severance Agreement has an initial
term of three years and renews automatically for successive one-year terms
unless WinStar notifies the covered executive within six months prior to the end
of the then current term that the Severance Agreement will terminate at the end
of such term.
 
CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS
 
     On October 9, 1998, a subsidiary of WinStar made the following loans to two
of the named executive officers: (i) a loan in the amount of $2.0 million to
Steven G. Chrust, who at that time was WinStar's Vice Chairman; and (ii) a loan
in the amount of $5.3 million to William J. Rouhana, Jr., WinStar's Chairman and
Chief Executive Officer. Each of these loans was payable on demand and bore
interest at 1% over the prime rate. The proceeds of these loans were used to
repay margin debt which was secured by shares of WinStar's Common Stock owned by
these individuals. Mr. Chrust repaid the entire principal and interest on his
loan on November 19, 1998 and Mr. Rouhana repaid the entire principal and
interest on his loan on December 24, 1998.
 
     WinStar leases office space located in Westport, Connecticut from KKJ
Properties, LLC, an entity controlled by Nathan Kantor. This is a month-to-month
lease under which WinStar pays monthly rent of $6,600, which the company
believes to be a fair market rate.
 
EQUITY COMPENSATION PLANS
 
     WinStar maintains the 1992 Equity Plan, under which a total of 1,500,000
shares of Common Stock were made available for grants to WinStar's key
employees, officers, directors and consultants. Awards consist of stock options
(both non-qualified options and options intended to qualify as "Incentive" stock
options under Section 422 of the Internal Revenue Code of 1986, as amended (the
"Code")), restricted stock awards, deferred stock awards, stock appreciation
rights and other stock-based awards, as described in the 1992 Equity Plan. On
January 13th of each calendar year during the term of the 1992 Equity Plan,
assuming there are enough shares then available for grant under the 1992 Equity
Plan, each person who is then a director of WinStar is awarded stock options to
purchase 10,000 shares of WinStar's Common Stock at the fair market value
thereof (as determined in the accordance with the 1992 Equity Plan), all of
which options are immediately exercisable as of the date of grant and have a
term of ten years. These are the only awards which may be granted to a director
of WinStar under the 1992 Equity Plan. As of April 26, 1999, options to purchase
599,819 shares of Common Stock were outstanding under the 1992 Equity Plan and
there were 269,775 shares available for future grant under the 1992 Equity Plan.
 
     WinStar also maintains the 1995 Equity Plan, under which a total of
10,000,000 shares of Common Stock were made available for grants to WinStar's
key employees, officers, directors and consultants. On March 5, 1999, the Board
approved an amendment to the 1995 Equity Plan increasing the number of shares of
Common Stock available thereunder by 5,000,000 shares, subject to approval by
WinStar's stockholders. See "Proposal II." Awards may consist of stock options
(both non-qualified options and options intended to qualify as "Incentive" stock
options under Section 422 of the Code), restricted stock awards, deferred stock
awards, stock appreciation rights and other stock-based awards, as described in
the 1995 Equity Plan. As of April 26, 1999, options to purchase 9,143,245 shares
of Common Stock were outstanding under the 1995 Equity Plan and there were
45,189 shares available for future grant under the 1995 Equity Plan.
 
     WinStar also maintains a Qualified Employee Stock Purchase Plan ("Stock
Purchase Plan") which covers 750,000 shares of Common Stock. Under the Stock
Purchase Plan, as currently administered by the Compensation Committee,
employees other than senior management may use a portion of their salary to
acquire shares of Common Stock on a monthly basis at a 15% discount to the
market price of the Common Stock at the date of purchase.
 
     WinStar maintains a 401(k) Employee Savings Plan under which employees of
WinStar and its subsidiaries may make voluntary contributions through payroll
deductions. WinStar makes matching contributions, credited as of the date of a
payroll deduction, equal to 25% of the first 6% of compensation contributed by
an employee. WinStar's matching contribution is made by the issuance of Common
Stock to such plan for the accounts of participating employees.
 
                                       17
<PAGE>
     Each of the 1992 Equity Plan and 1995 Equity Plan is administered by the
Compensation Committee, which determines the persons to whom awards will be
granted, the number of awards to be granted and the specific terms of each
grant, including the vesting thereof, subject to the provisions of those plans.
The Stock Purchase Plan is also administered by the Compensation Committee which
defines, prescribes, amends and rescinds rules, regulations, procedures, terms
and conditions relating to that plan, including the fixing of purchase price
discounts and option periods in effect from time to time, and interprets,
administers and construes the plan and makes all other determinations necessary
or advisable for the administration of the plan.
 
COMPENSATION COMMITTEE INTERLOCKS AND INSIDER PARTICIPATION
 
     The Board's Compensation Committee is composed of Mr. Rouhana, WinStar's
Chairman and Chief Executive Officer, Mr. Magyar, Mr. vanden Heuvel and
Professor Cash. No executive officer of WinStar sits on the compensation
committee of another entity, one or more of whose executive officers serves as a
director of WinStar or on WinStar's Compensation Committee, nor does any
executive officer of WinStar serve as a director of another entity, one or more
of whose executive officers serves on WinStar's Compensation Committee.
 
                                       18
<PAGE>
  PROPOSAL II: APPROVAL OF AN AMENDMENT TO THE 1995 PERFORMANCE EQUITY PLAN TO
INCREASE THE NUMBER OF SHARES ISSUABLE UPON EXERCISE OF OPTIONS AND OTHER AWARDS
                   GRANTED OR WHICH MAY BE GRANTED THEREUNDER
 
     WinStar maintains the 1995 Equity Plan under which an aggregate of
10,000,000 shares of Common Stock are reserved for issuance upon exercise of
options and other stock-based awards that may be granted thereunder. On
March 5, 1999, the Board approved an amendment to the 1995 Equity Plan, pursuant
to which the number of shares available for issuance pursuant to grants made
under the 1995 Equity Plan was increased by 5,000,000 shares, subject to
approval by WinStar's stockholders at the Meeting.
 
     WinStar is a very rapidly growing company that operates in an intensely
competitive industry. A particularly competitive area of WinStar's business is
attracting and retaining talented employees (including executives, engineers,
sales and support personnel and others), many of whom are regularly solicited by
other companies offering attractive cash and equity compensation packages. To
date, WinStar has been very successful in competing for this talent pool and has
amassed an outstanding group of employees. In 1998 WinStar expanded its
workforce from approximately 1,500 to 2,800 employees. It has been WinStar's
policy to compensate all employees with stock options, in order to incentivize
them and align their interests with those of the stockholders. Employee option
grants are never made with an exercise price below the market value of WinStar's
Common Stock on the grant date and these options typically vest over a period of
years. During 1998, WinStar granted a total of 6,992,511 options to employees,
with the average option grant being for 2,165 shares.
 
     We anticipate significant additional growth in the next several years, with
our total workforce reaching over 4,300 by the end of 1999. It has been this
growth, and WinStar's ability to attract and retain talented, dedicated
employees, that has fueled the rapid expansion of the company's business and the
creation of substantial shareholder value in recent years. As reported in The
Wall Street Journal, for the five year period ended December 31, 1998, an
investment in WinStar Common Stock yielded an average annual return of
approximately 66%, one of the highest returns of any Nasdaq traded company over
that period of time.
 
     It is imperative that WinStar continue to attract and retain the quality
and quantity of employees that it has in the past in order to continue its
growth and execute its business plan. If unable to do this, WinStar will be at a
significant competitive disadvantage in the marketplace and shareholder value
could be adversely impacted. The ability to continue to compensate employees
with equity-based grants such as stock options is key to competing for talent.
For this reason, we are requesting that the stockholders approve an increase in
the number of shares available under WinStar's 1995 Equity Plan by 5,000,000
shares.
 
     If the 1995 Equity Plan is amended as proposed, then, if all the shares
reserved thereunder were issued upon the exercise of options and other awards,
such shares would be equal to approximately 16.75% of the total fully-diluted
shares of WinStar Common Stock (assuming exercise of all other outstanding
options and convertible securities and the issuance of all shares available
under the Stock Purchase Plan) and 22.95% of the total outstanding shares of
WinStar Common Stock (assuming no exercise of other outstanding options and
convertible securities).
 
          THE BOARD OF DIRECTORS RECOMMENDS VOTING "FOR" PROPOSAL II.
 
                                       19
<PAGE>
                        SUMMARY OF THE 1995 EQUITY PLAN
 
ADMINISTRATION
 
     The 1995 Equity Plan (the "Plan") is administered by the Board or, at its
discretion, by the Compensation Committee (the "Committee"). The Committee has
full authority, subject to the provisions of the Plan, to award (i) Stock
Options, (ii) Stock Appreciation Rights, (iii) Restricted Stock, (iv) Deferred
Stock, (v) Stock Reload Options and/or (vi) other stock-based awards
(collectively "Awards"). Subject to the provisions of the Plan, the Committee
determines, among other things, the persons to whom from time to time Awards may
be granted ("Holders" or "Participants"), the specific type of Awards to be
granted (e.g., Stock Option, Restricted Stock), the number of shares subject to
each Award, share prices, any restrictions or limitations on such Awards (e.g.,
the "Deferral Period" in the grant of Deferred Stock and the "Restriction
Period" when Restricted Stock is subject to forfeiture), and any vesting,
deferral, surrender, cancellation, acceleration, termination, exercise,
forfeiture or other provisions related to such Awards. The interpretation and
construction by the Committee of any provisions of, and the determination by the
Committee of any questions arising under, either of the Plan, or any rule or
regulation established by the Committee pursuant to the Plan, shall be final,
conclusive and binding on all persons interested in either Plan. Awards under
the Plan are evidenced by agreements between WinStar and the Participants.
 
SHARES SUBJECT TO THE PLAN
 
     The Plan, as amended, authorizes the granting of Awards whose exercise
would allow up to an aggregate of 15 million shares of Common Stock to be
acquired by the Holders of such Awards. In order to prevent the dilution or
enlargement of the rights of Holders under the Plan, the shares of Common Stock
authorized by the Plan are subject to adjustment by the Board in the event of a
stock dividend, stock split, reverse stock split, merger, reorganization,
consolidation, recapitalization or other change in corporate structure, in each
case affecting all outstanding shares of WinStar's Common Stock as a whole. The
shares of Common Stock acquirable pursuant to the Awards will be made available,
in whole or in part, from authorized and unissued shares of Common Stock. If any
Award granted under the Plan is forfeited or terminated, the shares of Common
Stock that were available pursuant to such Award shall again be available for
distribution in connection with Awards subsequently granted under the Plan.
 
ELIGIBILITY
 
     Subject to the provisions of the Plan, Awards may be granted to key
employees, officers and directors who are deemed to have rendered or to be able
to render significant services to WinStar and are deemed to have contributed or
to have the potential to contribute to the success of WinStar. Awards may be
granted only to persons who, at the time of such awards are, or have agreed to
become, employees of WinStar or its wholly- or majority-owned subsidiaries
("Subsidiaries").
 
TYPES OF AWARDS
 
     Options.  The Plan provides both for "Incentive" stock options ("Incentive
Options") as defined in Section 422 of the Code, and for options not qualifying
as Incentive Options ("Non-qualified Options"), both of which may be granted
with any other stock based award under the Plan. The Committee will determine
the exercise price per share of Common Stock purchasable under an Incentive or
Non-qualified Option (collectively "Options"). The exercise price of an Option
may not be less than 100% of the fair market value on the last trading day
before the date of grant (or, in the case of an Incentive Option granted to a
person possessing more than 10% of the total combined voting power of all
classes of stock of WinStar, not less than 110% of such fair market value). An
Incentive Option may only be granted within a 10-year period from the date the
Plan was adopted and approved and may only be exercised within 10 years of the
date of the grant (or within 5 years in the case of an Incentive Option granted
to a person who, at the time of the grant, owns stock possessing more than 10%
of the total combined voting power of all classes of stock of WinStar). Subject
to any vesting limitations or conditions the Committee may impose, Options may
be exercised, in whole or in part, at any time during the term of the Option by
giving written notice of exercise to WinStar specifying the number of shares of
Common Stock to be purchased. Such notice must be accompanied by payment in full
of the purchase price, in cash or in the
 
                                       20
<PAGE>
discretion of the Committee, in securities of WinStar, a combination of cash and
such securities or by such other means as the Committee may determine,
consistent with the Plan and applicable law, including, for example, by WinStar
making a loan to such participant to pay such purchase price and any associated
taxes. Options granted under the Plan are generally exercisable only by the
Holder during his or her lifetime. The Options granted under the Plan may not be
transferred other than by will or by the laws of descent and distribution,
except that the Committee may in its sole discretion allow a Non-qualified
Option granted under the Plan to be transferable, subject to compliance with
applicable securities laws.
 
     No Incentive Option, or any portion thereof, granted under the Plan may be
exercised by the Holder unless he or she is employed by WinStar or a Subsidiary
at the time of the exercise and has been so employed continuously from the time
the Incentive Option was granted. However, in the event the Holder's employment
with WinStar is terminated due to disability, the Holder may still exercise his
or her Incentive Option for a period of one year (or such other lesser period as
the Committee may specify at the time of grant) from the date of such
termination or until the expiration of the stated term of the Incentive Option,
whichever period if shorter. Similarly, should a Holder die while in the
employment of WinStar or a Subsidiary, his or her legal representative or
legatee under his or her will may exercise the decedent Holder's Incentive
Option for a period of one year from death (or such other greater or lesser
period as the Committee specifies at the time of grant) or until the expiration
of the stated term of the Incentive Option, whichever is shorter. Further, if
the Holder's employment is terminated without cause or due to normal retirement
(upon attaining the age of 65), then the portion of any Incentive Option which
has vested by the date of such retirement may be exercised for the lesser of
three months after retirement or the balance of the Incentive Option's term. The
Committee is afforded more flexibility with respect to the terms of
Non-qualified Options, since such options are not subject to Code requirements.
 
     Other.  The Committee may grant Stock Appreciation Rights ("SARs" or
singularly "SAR") in conjunction with all or part of any Option granted under
the Plan, or may grant SARs on a free-standing basis. In conjunction with
Nonqualified Options, SARs may be granted either at or after the time of the
grant of such Nonqualified Options. In conjunction with Incentive Options, SARs
may be granted only at the time of the grant of such Incentive Options. An SAR
entitles the Holder thereof to receive an amount (payable in cash and/or Common
Stock as determined by the Committee) equal to the excess fair market value of
one share of Common Stock over the SAR price or the exercise price of the
related Option, multiplied by the number of shares subject to the SAR.
Additionally, the Committee may award shares of Restricted Stock, Deferred Stock
and other stock-based awards either alone or in addition to, or in tandem with,
other Awards granted under the Plan.
 
     Stock Reload Options.  The Committee may grant Stock Reload Options in
conjunction with any Option granted under the Plan. In conjunction with
Incentive Options, Stock Reload Options may be granted only at the time of the
grant of such Incentive Option. In conjunction with Non-qualified Options, Stock
Reload Options may be granted either at or after the time of the grant of such
Non-qualified Options. A Stock Reload Option permits a Holder who exercises an
Option by delivering already owned stock (i.e., the stock-for-stock method), to
receive back from WinStar a new Option (at the current market price) for the
same number of shares delivered to exercise the Option.
 
     Acceleration of Award Vesting.  Generally, under the Plan, if (i) any
person or entity other than WinStar and/or any director, officer or principal
stockholder of WinStar as of the date the Plan was adopted acquires securities
of WinStar (in one or more transactions) representing certain specified
percentages or more of the total voting power of all WinStar's securities then
outstanding and (ii) the Board does not authorize or otherwise approve such
acquisition, then, the vesting periods of any and all Options and other awards
granted and outstanding under the Plan will be accelerated and all such Options
and awards will immediately and entirely vest, and the respective holders
thereof will have the immediate right to purchase and/or receive any and all
shares of Common Stock subject to such Options and awards on the terms set forth
in the Plan and the respective agreements respecting such Options and awards.
 
                                       21
<PAGE>
WITHHOLDING TAXES
 
     Upon the exercise of any Award granted under the Plan, the Holder may be
required to remit to WinStar an amount sufficient to satisfy all federal, state
and local withholding tax requirements prior to delivery of any certificate or
certificates for shares of Common Stock. Subject to certain stringent
limitations under the Plan and at the discretion of the Committee, the Holder
may satisfy these requirements by electing to have WinStar withhold a portion of
the shares to be received upon the exercise of the Award having a value equal to
the amount of the withholding tax due under applicable federal, state and local
laws.
 
TERM AND AMENDMENTS
 
     Unless terminated by the Committee, the Plan shall continue to remain
effective until such time as no further Awards may be granted and all Awards
granted under the Plan are no longer outstanding. The Committee may at any time,
and from time to time, amend the Plan, except that no amendment may be made
which would impair the rights of any Holder of an existing Option or other Award
without such Holder's consent.
 
FEDERAL INCOME TAX CONSEQUENCES
 
     The following discussion of the federal income tax consequences of
participation in the Plan is only a summary of the general rules applicable to
the grant and exercise of Options and does not give specific details or cover,
among other things, state, local and foreign tax treatment of participation in
the Plan. The information contained in this section is based on present law and
regulations, which are subject to being changed prospectively or retroactively.
 
     Incentive Options.  The Participant will recognize no taxable income upon
the grant or exercise of an Incentive Option. WinStar will not qualify for any
deduction in connection with the grant or exercise of Incentive Options. Upon a
disposition of the shares after the later of two years from the date of grant or
one year after the transfer of the shares to the Participant, the Participant
will recognize the difference, if any, between the amount realized and the
exercise price as long-term capital gain or long-term capital loss (as the case
may be) if the shares are capital assets. The excess, if any, of the fair market
value of the shares on the date of exercise of an Incentive Option over the
exercise price will be treated as an item of adjustment for a Participant's
taxable year in which the exercise occurs and may result in an alternative
minimum tax liability for the Participant.
 
     If Common Stock acquired upon the exercise of an Incentive Option is
disposed of prior to the expiration of the holding periods described above, (i)
the Participant will recognize ordinary compensation income in the taxable year
of disposition in an amount equal to the excess, if any, of the lesser of the
fair market value of the shares on the date of exercise or the amount realized
on the disposition of the shares, over the exercise price paid for such shares;
and (ii) WinStar will qualify for a deduction equal to any such amount
recognized, subject to the limitation that the compensation be reasonable. In
the case of a disposition of shares earlier than two years from the date of the
grant or in the same taxable year as the exercise, where the amount realized on
the disposition is less than the fair market value of the shares on the date of
exercise, there will be no adjustment since the amount treated as an item of
adjustment, for alternative minimum tax purposes, is limited to the excess of
the amount realized on such disposition over the exercise price, which is the
same amount included in regular taxable income.
 
     Nonqualified Options.  With respect to Non-qualified Options (i) upon grant
of the option, the Participant will recognize no income; (ii) upon exercise of
the option (if the shares of Common Stock are not subject to a substantial risk
of forfeiture), the Participant will recognize ordinary compensation income in
an amount equal to the excess, if any, of the fair market value of the shares on
the date of exercise over the exercise price, and WinStar will qualify for a
deduction in the same amount, subject to the requirement that the compensation
be reasonable; and (iii) WinStar will be required to comply with applicable
Federal income tax withholding requirements with respect to the amount of
ordinary compensation income recognized by the Participant. On a disposition of
the shares, the Participant will recognize gain or loss equal to the difference
between the amount realized and the sum of the exercise price and the ordinary
compensation income recognized. Such gain or loss will be treated as capital
gain or loss if the shares are capital assets and as short-term or long-term
capital gain or loss, depending upon the length of time that the participant
held the shares.
 
                                       22
<PAGE>
     If the shares acquired upon exercise of a Non-qualified Option are subject
to a substantial risk of forfeiture, the Participant will recognize ordinary
income at the time when the substantial risk of forfeiture is removed, unless
such Participant timely files under Code Section 83(b) to elect to be taxed on
the receipt of shares, and WinStar will qualify for a corresponding deduction at
such time. The amount of ordinary income will be equal to the excess of the fair
market value of the shares at the time the income is recognized over the amount
(if any) paid for the shares.
 
     Stock Appreciation Rights.  Upon the grant of a SAR, the Participant
recognizes no taxable income and WinStar receives no deduction. The Participant
recognizes ordinary income and WinStar receives a deduction at the time of
exercise equal to the cash and fair market value of Common Stock payable upon
such exercise.
 
                              INDEPENDENT AUDITORS
 
     Grant Thornton LLP served as WinStar's independent certified public
accountants for the year ended December 31, 1998. The Board has selected Grant
Thornton LLP as WinStar's independent certified public accountants for the
fiscal year ending December 31, 1999. A representative of Grant Thornton LLP
will have the opportunity to address the stockholders if he so desires and is
expected to be present at the Meeting. The representative will be available to
answer appropriate questions from stockholders.
 
                           1999 STOCKHOLDER PROPOSALS
 
     In order for stockholder proposals for the 2000 Annual Meeting of
Stockholders to be eligible for inclusion in WinStar's Proxy Statement, they
must be received by WinStar at its principal office in New York, New York by
January 7, 2000. A stockholder must have been a registered or beneficial owner
of at least 1% of WinStar's outstanding stock or stock with a market value of at
least $2,000 for at least one year prior to submitting the proposal, and the
stockholder must continue to own such stock through the date on which the 2000
Annual Meeting of Stockholders is held.
 
                                 OTHER MATTERS
 
     The Board knows of no matter that will be presented for consideration at
the Meeting other than the matters referred to in this Proxy Statement. Should
any other matter properly come before the Meeting, it is the intention of the
persons named in the accompanying proxy to vote such proxy in accordance with
their best judgment.
 
                            SOLICITATION OF PROXIES
 
     The cost of proxy solicitations will be borne by WinStar. In addition to
solicitations of proxies by use of the mails, some officers or employees of
WinStar, without additional remuneration, may solicit proxies personally or by
telephone. WinStar may also request brokers, dealers, banks and their nominees
to solicit proxies from their clients, where appropriate, and may reimburse them
for reasonable expenses related thereto. Additional solicitation of proxies may
be made by an independent proxy solicitation firm or other entity possessing the
facilities to engage in such solicitation. WinStar has engaged Georgeson &
Company Inc. to assist in the solicitation of proxies and will be required to
pay such firm reasonable fees and reimburse expenses incurred by such firm in
the rendering of such solicitation services.
 
                                                Timothy R. Graham
                                                Secretary
 
New York, New York
May 7, 1999
 
                                       23

<PAGE>
                                                                WINSTAR [LOGO]

Instructions for Voting Your Proxy

WinStar Communications, Inc. is now offering stockholders of record three
alternative ways of voting your proxies:

o  By Telephone (using a touch-tone phone)  o Via the Internet (using a browser)
                            o By Mail (traditional method)

Your telephone or Internet vote authorizes the named proxies to vote your
shares in the same manner as if you had returned your proxy card. We encourage
you to use these cost-effective and convenient ways of voting, 24 hours a day,
7 days a week.

 TO VOTE BY PHONE  Available only until 5:00 p.m. Eastern time on June 30, 1999.
    o This method of voting is available for residents of the U.S. and Canada.
    o On a touch-tone phone, call TOLL-FREE 1-888-698-4991, 24 hours a day, 
      7 days a week.
    o You will be asked to enter ONLY the CONTROL NUMBER shown below.
    o Have your proxy card ready, then follow the simple recorded instructions.
    o Your vote will be confirmed and cast as you direct.

 TO VOTE BY INTERNET  Available only until 5:00 p.m. Eastern time 
                      on June 30, 1999.
    o Visit our Internet voting Website at http://www.cybervote.georgeson.com.
    o Enter both the COMPANY NUMBER AND CONTROL NUMBER shown below.
    o Follow the simple instructions on the screen. 
    o You will incur only your usual Internet charges.

 TO VOTE BY MAIL
    o Mark, sign and date the attached proxy card and return it in the
    postage-paid envelope enclosed. 
    o If you are voting by telephone or the Internet, please do not mail your 
      proxy card.

                         COMPANY NUMBER           CONTROL NUMBER



              TO VOTE BY MAIL, PLEASE DETACH THE PROXY CARD HERE

|X| Votes must be indicated, 
    as in example to the left,
    in Black or Blue ink.

  THE BOARD OF DIRECTORS RECOMMENDS THAT YOU VOTE "FOR" PROPOSAL NOS. 1 AND 2


1. Election of the following Directors: 
NATHAN KANTOR and BERT WASSERMAN

                  FOR ALL            WITHHOLD AUTHORITY to         FOR ALL 
              Nominees listed    vote for all nominees listed      EXCEPT*
                    |_|                       |_|                   |_|

(*INSTRUCTION: To withhold authority to vote for any individual nominee, mark
the "FOR ALL EXCEPT" box and write that nominee's name in the space provided.)

*Exceptions__________________________________________________


2. Approval of the amendment to WinStar's 1995 Performance Equity Plan.


                    FOR       AGAINST        ABSTAIN
                    |_|         |_|            |_|        

3. In their discretion, the proxies are authorized to vote upon such other
business as may come before the meeting or any adjournment thereof.

|_| Check here if you plan on attending the meeting.

Date                             , 1999
    ----------------------------


- ---------------------------------------
       Name of Stockholder(s)

- ---------------------------------------
              Signature

- ---------------------------------------
       Signature if held jointly


<PAGE>

WINSTAR [LOGO]

                         WINSTAR COMMUNICATIONS, INC.
                  230 Park Avenue, New York, New York 10169

         THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORS
      for the Annual Meeting of Stockholders to be Held on July 1, 1999

                                     PROXY

The undersigned Stockholder(s) of WINSTAR COMMUNICATIONS, INC., a Delaware
corporation ("WinStar "), hereby appoints Timothy R. Graham and William J.
Rouhana, Jr., or either of them, with full power of substitution and power to
act without the other, as the agents, attorneys and proxies of the
undersigned, to vote the shares standing in the name of the undersigned at the
Annual Meeting of Stockholders of WinStar to be held on July 1, 1999 and at
all adjournments thereof. This proxy will be voted in accordance with the
instructions given below.


IF NO INSTRUCTIONS ARE GIVEN, THIS PROXY WILL BE VOTED FOR PROPOSALS 1 AND 2.

PLEASE VOTE, DATE AND SIGN ON OTHER SIDE AND RETURN PROMPTLY IN THE ENCLOSED
ENVELOPE

IMPORTANT: When shares are held by joint tenants, both should sign. When
signing as attorney, executor, administrator, trustee or guardian, please give
FULL title as such. If a corporation, please provide the FULL corporate name
and the signature of the authorized officer signing on its behalf. If a
partnership, please sign in partnership name by authorized person.

HAS YOUR ADDRESS CHANGED?

- ---------------------------------------------------------------

- ---------------------------------------------------------------

DO YOU HAVE COMMENTS?

- ---------------------------------------------------------------

- ---------------------------------------------------------------

                                                              See Reverse Side






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