FRONTIER INSURANCE GROUP INC
S-8, 1999-04-01
SURETY INSURANCE
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     As filed with the Securities and Exchange Commission on April 1, 1999.

                                                        Registration No. 33-


                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549

                                   ----------

                                    FORM S-8

                             REGISTRATION STATEMENT
                                      UNDER
                           THE SECURITIES ACT OF 1933

                         FRONTIER INSURANCE GROUP, INC.
             (Exact name of registrant as specified in its charter)

<TABLE>
<S>                                                          <C>
            DELAWARE                                             14-1681606
  (State or other jurisdiction                                (I.R.S. Employer
of incorporation or organization)                            Identification No.)
   195 LAKE LOUISE MARIE ROAD                                    12775-8000
      ROCK HILL, NEW YORK                                        (Zip Code)
     (Address of principal
       executive offices)
</TABLE>

           FRONTIER INSURANCE GROUP, INC. EMPLOYEE STOCK PURCHASE PLAN
                            (Full title of the plan)


                                 HARRY W. RHULEN
                         FRONTIER INSURANCE GROUP, INC.
                           195 LAKE LOUISE MARIE ROAD
                         ROCK HILL, NEW YORK 12775-8000
                     (Name and address of agent for service)

                                 (914) 796-2100
          (Telephone number, including area code, of agent for service)

                         CALCULATION OF REGISTRATION FEE
<TABLE>
<CAPTION>
===============================================================================
                                       PROPOSED      PROPOSED
                                        MAXIMUM      MAXIMUM
 TITLE OF SECURITIES   AMOUNT TO BE    OFFERING     AGGREGATE     AMOUNT OF
  TO BE REGISTERED      REGISTERED     PRICE PER     OFFERING    REGISTRATION
                                       SHARE(1)      PRICE(1)        FEE
- -------------------------------------------------------------------------------
<S>                   <C>              <C>         <C>              <C>
    Common Stock      1,000,000 shs.   $11.6875    $11,687,500      $3,249
===============================================================================
</TABLE>

(1) Estimated solely for the purpose of calculating the registration fee based,
pursuant to Rule 457(h), on the 1,000,000 shares reserved for issuance under the
Employee Stock Purchase Plan and, pursuant to Rule 457(c), the average of the
high and low sale prices of the Common Stock on the New York Stock Exchange on
March 29, 1999.


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                                     PART I

              INFORMATION REQUIRED IN THE SECTION 10(A) PROSPECTUS

ITEM 1.  PLAN INFORMATION.

         *


ITEM 2.  REGISTRANT INFORMATION AND EMPLOYEE PLAN ANNUAL INFORMATION.

         *

         *Information required by Part I to be contained in the Section 10(a)
prospectus is omitted from the Registration Statement in accordance with the
Note to Part I of Form S-8.


                                     PART II

               INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3.  INCORPORATION OF DOCUMENTS BY REFERENCE.

         The following documents which have heretofore been filed by Frontier
Insurance Group, Inc. (the "Registrant") with the Securities and Exchange
Commission (the "Commission") are hereby incorporated by reference in this
Registration Statement:

     a. Registrant's Annual Report on Form 10-K for the fiscal year ended
        December 31, 1998.

     b. All reports and proxy statements filed by the Registrant with the
        Commission pursuant to Sections 13(a), 13(c), 14 and 15(d) of the
        Securities Exchange Act of 1934, as amended, after the date of this
        Registration Statement and prior to the filing of a post-effective
        amendment which indicates that all of the shares to which this
        Registration Statement relates have been sold or which deregisters all
        of the shares then remaining unsold shall likewise be deemed
        incorporated herein and made a constituent part hereof by reference from
        the respective date of the filing of such document.


ITEM 4.  DESCRIPTION OF SECURITIES.

         Not applicable.


ITEM 5.  INTERESTS OF NAMED EXPERTS AND COUNSEL.

         Members of Epstein Becker & Green, P.C., which firm has passed on the
validity of the shares of Common Stock being offered pursuant to this
Registration Statement, own an aggregate of 143,000 shares of Registrant's
Common Stock.


                                       1


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ITEM 6.  INDEMNIFICATION OF DIRECTORS AND OFFICERS.

         Section 145 of the Delaware General Corporation Law grants corporations
the power to indemnify their directors, officers, employees and agents in
accordance with the provisions thereof. Article EIGHTH of the Registrant's
Certificate of Incorporation provides for indemnification of the Registrant's
directors, officers, agents and employees to the fullest extent permissible
under Section 145 of the Delaware General Corporation Law. The Registrant
presently maintains directors' and officers' liability insurance coverage with
an aggregate policy limit of $10,000,000 for each policy year.


ITEM 7.  EXEMPTION FROM REGISTRATION CLAIMED.

         Not applicable.


ITEM 8.  EXHIBITS.

         The following are filed as exhibits to this Registration Statement:

<TABLE>
<CAPTION>
    Exhibit
      No.                            Description
      ---                            -----------
      <S>             <C>
      4.1        -    Copy of the Registrant's Employee Stock Purchase Plan.
       5         -    Opinion of Epstein Becker & Green, P.C.
     23(a)       -    Consent of Ernst & Young LLP.
     23(b)       -    Consent of Epstein Becker & Green, P.C.
                      (included in Exhibit 5).
       24              Power of Attorney (included in signature page of this
                       Registration Statement).
</TABLE>


                                       2


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ITEM 9.  UNDERTAKINGS

          The undersigned Registrant hereby undertakes:

               (1) To file, during any period in which offers or sales are being
made, a post-effective amendment to this Registration Statement to include any
material information with respect to the plan of distribution not previously
disclosed in this Registration Statement or any material change to such
information in this Registration Statement.

               (2) That, for the purpose of determining any liability under the
Securities Act of 1933, each such post-effective amendment shall be deemed to be
a new Registration Statement relating to the securities offered therein, and the
offering of such securities at that time shall be deemed to be the initial bona
fide offering thereof.

               (3) To remove from registration by means of a post-effective
amendment any of the securities being registered which remain unsold at the
termination of the offering.

          The undersigned Registrant hereby undertakes that, for purposes of
determining any liability under the Securities Act of 1933, each filing of the
Registrant's annual report pursuant to Section 13(a) or Section 15(d) of the
Securities Exchange Act of 1934 (and, where applicable, each filing of an
employee benefit plan's annual report pursuant to Section 15(d) of the
Securities Exchange Act of 1934) that is incorporated by reference in this
Registration Statement shall be deemed to be a new Registration Statement
relating to the securities offered therein, and the offering of such securities
at that time shall be deemed to be the initial bona fide offering thereof.

          Insofar as indemnification for liabilities arising under the
Securities Act of 1933, as amended (the "Act"), may be permitted to directors,
officers or controlling persons of the Registrant pursuant to the provisions of
Registrant's Amended and Restated Certificate of Incorporation or Amended and
Restated By-Laws, as amended, or the provisions of the Delaware General
Corporation Law or otherwise, the Registrant has been advised that in the
opinion of the Commission such indemnification is against public policy as
expressed in the Act and is, therefore, unenforceable. In the event that a claim
for indemnification against such liabilities (other than the payment by the
Registrant of expenses incurred or paid by a director, officer or controlling
person of the Registrant in the successful defense of any action, suit or
proceeding) is asserted by such director, officer or controlling person in
connection with the securities being registered, the Registrant will, unless in
the opinion of its counsel the matter has been settled by controlling precedent,
submit to a court of appropriate jurisdiction the question whether such
indemnification by it is against public policy as expressed in the Act and will
be governed by the final adjudication of such issue.


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                                   SIGNATURES

         The Registrant. Pursuant to the requirements of the Securities Act of
1933, the Registrant certifies that it has reasonable grounds to believe that it
meets all of the requirements for filing on Form S-8 and has duly caused this
Registration Statement to be signed on its behalf by the undersigned, thereunto
duly authorized, in the Hamlet of Rock Hill, State of New York, on this 18th day
of March, 1999.

                                  FRONTIER INSURANCE GROUP, INC.

                                  By:  /s/ Harry W. Rhulen
                                      -----------------------------------
                                      Harry W. Rhulen
                                      Chairman, Chief Executive Officer
                                      and President


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                                POWER OF ATTORNEY

         KNOW ALL MEN BY THESE PRESENTS, that each person whose signature
appears below constitutes and appoints HARRY W. RHULEN and MARK H. MISHLER, and
each of them, with full power to act without the other, his true and lawful
attorney-in-fact and agent, with full power of substitution and resubstitution,
for him and in his name, place and stead, in any and all capacities, to sign any
and all amendments (including post-effective amendments) to this Registration
Statement and to file the same, with all exhibits thereto, and other documents
in connection therewith, with the Securities and Exchange Commission and any
other regulatory authority, granting unto said attorneys-in-fact and agents, and
each of them, full power and authority to do and perform each and every act and
thing requisite and necessary to be done in and about the premises, as fully to
all intents and purposes as they or he might or could do in person, hereby
ratifying and confirming all that said attorneys-in-fact and agents, or any of
them, may lawfully do or cause to be done by virtue hereof.

         Pursuant to the requirements of the Securities Act of 1933, this
Registration Statement has been signed by the following persons in the
capacities set forth and on the date indicated.

<TABLE>
<CAPTION>
Signature                      Title                       Date
- ---------                      -----                       ----

<S>                            <C>                         <C> 
/s/ Harry W. Rhulen            Chairman of the Board,      March 18, 1999
- ---------------------------    President, Chief
Harry W. Rhulen                Executive Officer and
                               Director


/s/ Mark H. Mishler            Vice President -            March 18, 1999
- ---------------------------    Treasurer and Chief
Mark H. Mishler                Financial Officer
                               (Principal Financial
                               and Accounting Officer)


/s/ Suzanne L. Rhulen          Executive Vice              March 18, 1999
- ---------------------------    President and Director
Suzanne L. Rhulen


/s/ Peter L. Rhulen            Director                    March 18, 1999
- ---------------------------
Peter L. Rhulen


/s/ Lawrence E. O'Brien        Director                    March 18, 1999
- ---------------------------
Lawrence E. O'Brien


/s/ Douglas C. Moat            Director                    March 18, 1999
- ---------------------------
Douglas C. Moat


/s/ Alan Gerry                 Director                    March 18, 1999
- ---------------------------
Alan Gerry


/s/ Paul B. Guenther           Director                     March 18, 1999
- ---------------------------
Paul B. Guenther
</TABLE>


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                                INDEX TO EXHIBITS

<TABLE>
<CAPTION>
   Exhibit
     No.                            Description
     ---                            -----------
     <S>      <C>
     4.1      Copy of the Registrant's Employee Stock Purchase
              Plan.
      5       Opinion of Epstein Becker & Green, P.C.
    23(a)     Consent of Ernst & Young LLP.
    23(b)     Consent of Epstein Becker & Green, P.C. (included in Exhibit 5).
     24       Power of Attorney (included in signature page of this Registration
              Statement).

</TABLE>


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                                                                     EXHIBIT 4.1

                         FRONTIER INSURANCE GROUP, INC.

                          EMPLOYEE STOCK PURCHASE PLAN

     1.   Purpose and Scope of Plan. The purpose of this employee stock purchase
plan (the "Plan") is to provide the employees of Frontier Insurance Group, Inc
("Frontier") with an opportunity to acquire a proprietary interest in Frontier
through the purchase of its common stock and, thus, to develop a stronger
incentive to work for the continued success of Frontier. The Plan is intended to
be an "employee stock purchase plan" within the meaning of Section 423(b) of the
Internal Revenue Code of 1986, as amended, and shall be interpreted and
administered in a manner consistent with such intent.

     2.   Definitions.

          2.1  The terms defined in this section are used (and capitalized)
               elsewhere in this Plan:

               (a)  "Affiliate" means any corporation that is a "parent
                    corporation" or "subsidiary corporation" of Frontier, as
                    defined in Sections 424(e) and 424(f) of the Code or any
                    successor provision, and whose participation in the Plan has
                    been approved by the Board of Directors.

               (b)  "Board of Directors" means the Board of Directors of
                    Frontier.

               (c)  "Code" means the Internal Revenue Code of 1986, as amended
                    from time to time.

               (d)  "Committee" means two or more Frontier executive officers as
                    designated by the Board of Directors to administer the Plan
                    under Section 13.

               (e)  "Common Stock" means the common stock, par value $.01 per
                    share (as such par value may be adjusted from time to time),
                    of Frontier.

               (f)  "Company" means Frontier Insurance Group, Inc., a Delaware
                    corporation.

               (g)  "Compensation" means the gross cash compensation (including
                    wage, salary, commission, bonus, and overtime earnings) paid
                    by Frontier or any Affiliate to a Participant in accordance
                    with the terms of employment.


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               (h)  "Eligible Employee" means any employee of Frontier or an
                    Affiliate whose customary employment is at least 20 hours
                    per week; provided, however, that "Eligible Employee" shall
                    not include any person who would be deemed, for purposes of
                    Section 423(b)(3) of the Code, to own stock possessing 5% or
                    more of the total combined voting power or value of all
                    classes of stock of Frontier.

               (i)  "Exchange Act" means the Securities Exchange Act of 1934, as
                    amended.

               (j)  "Fair Market Value" of a share of Common Stock as of any
                    date means, the closing price for such Common Stock on the
                    New York Stock Exchange on the preceding trading day. If
                    such determination of Fair Market Value is not consistent
                    with the then current regulations of the Secretary of the
                    Treasury applicable to plans intended to qualify as an
                    "employee stock purchase plan" within the meaning of Section
                    423(b) of the Code, however, Fair Market Value shall be
                    determined in accordance with such regulations. The
                    determination of Fair Market Value shall be subject to
                    adjustment as provided in Section 14.

               (k)  "Participant" means an Eligible Employee who has elected to
                    participate in the Plan in the manner set forth in Section
                    4.

               (l)  "Plan" means this Frontier Employee Stock Purchase Plan, as
                    amended from time to time.

               (m)  "Purchase Period" means each quarter of Frontier's fiscal
                    year. The first Purchase Period will be the quarter that
                    starts January 1, 1999 and ends March 31, 1999.

               (n)  "Recordkeeping Account" means the account maintained in the
                    books and records of Frontier recording the amount withheld
                    from each Participant through payroll deductions made under
                    the Plan.

     3.   Scope of the Plan. Shares of Common Stock may be sold to Eligible
Employees pursuant to this Plan commencing January 1, 1999, as hereinafter
provided, but not more than 1,000,000 shares of Common Stock (subject to
adjustment as provided in Section 14) shall be sold to Eligible Employees
pursuant to this Plan. All sales of Common Stock pursuant to this Plan shall be
subject to the same terms, conditions, rights and privileges. The shares of
Common Stock sold to Eligible Employees pursuant to this Plan may be shares
acquired by purchase on the open market or in privately negotiated transactions,
by direct issuance from Frontier (whether newly issued or treasury shares) or by
any combination thereof. Frontier, during the term of the Plan, shall at all
times reserve and keep available, such number of shares as shall be sufficient
to satisfy the requirements of the Plan.


                                       2


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     4.   Eligibility and Participation. To be eligible to participate in the
Plan for a given Purchase Period, an employee must be an Eligible Employee on
the cutoff date for such Purchase Period. The cutoff date is the 15th day of the
month immediately preceding the Purchase Period. An Eligible Employee may elect
to participate in the Plan by filing an enrollment form and payroll deduction
authorization form with the Frontier Human Resources department before the
prescribed cutoff date for each Purchase Period. Regular payroll deductions from
Compensation will begin with the first payday in such Purchase Period and
continue until the Eligible Employee withdraws from the Plan, modifies his or
her authorization, or ceases to be an Eligible Employee, as hereinafter
provided.

     5.   Amount of Common Stock Each Eligible Employee May Purchase.

          5.1  Subject to the provisions of this Plan, each Eligible Employee
               shall be offered the right to purchase on the last day of the
               Purchase Period the number of shares of Common Stock (including
               fractional shares) that can be purchased at the price specified
               in Section 5.2 with the entire credit balance in the
               Participant's Recordkeeping Account; provided, however, that the
               Fair Market Value (determined on the first day of any Purchase
               Period) of shares of Common Stock that may be purchased by a
               Participant during any calendar year shall not exceed $25,000
               (therefore, with a 15% discount, the maximum cash contribution
               can not exceed $21,250). If the purchases by all Participants
               would otherwise cause the aggregate number of shares of Common
               Stock to be sold under the Plan to exceed the number specified in
               Section 3, each Participant shall be allocated a ratable portion
               of the maximum number of shares of Common Stock which may be
               sold.

          5.2  The purchase price of each share of Common Stock sold pursuant to
               this Plan shall be the lesser of (a) or (b) below:

               (a)  85% of the Fair Market Value of such share on the first day
                    of the Purchase Period.

               (b)  85% of the Fair Market Value of such share on the last day
                    of the Purchase Period.

     6.   Method of Participation.

          6.1  Frontier shall give notice to each Eligible Employee of the
               opportunity to purchase shares of Common Stock pursuant to this
               Plan and the terms and conditions for such offering. Such notice
               is subject to revision by Frontier at any time prior to the date
               of purchase of such shares. Frontier contemplates that for tax
               purposes the first day of a Purchase Period will be the date of
               the offering of such shares.

          6.2  Each Eligible Employee who desires to participate in the Plan for
               a Purchase Period shall signify his or her election to do so by
               signing an enrollment form. An Eligible Employee may elect to
               have any whole


                                       3


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               percent of Compensation withheld per pay period. An election to
               participate in the Plan and to authorize payroll deductions as
               described herein must be made prior to the prescribed cutoff date
               for each Purchase Period to which it relates and shall remain in
               effect unless and until such Participant withdraws from the Plan,
               modifies his or her authorization, or ceases to be an Eligible
               Employee, as hereinafter provided.

          6.3  Any Eligible Employee who does not make a timely election as
               provided in Section 6.2, shall be deemed to have elected not to
               participate in the Plan. Such election shall be irrevocable for
               such Purchase Period.

          6.4  Nothing herein contained shall affect an employee's right to
               participate in and receive benefits under and in accordance with
               the then current provisions of any pension, insurance, retirement
               savings/401(k) plan or other employee welfare plan or program of
               Frontier.

     7.   Recordkeeping Account.

          7.1  Frontier shall maintain a Recordkeeping Account for each
               Participant. Payroll deductions pursuant to Section 6 shall be
               credited to such Recordkeeping Accounts on each payday.

          7.2  No interest shall be credited to a Participant's Recordkeeping
               Account.

          7.3  The Recordkeeping Account is established solely for accounting
               purposes, and all amounts credited to the Recordkeeping Account
               shall remain part of the general assets of Frontier.

          7.4  A Participant may not make any separate cash payment into the
               Recordkeeping Account.

     8.   Right to Adjust Participation or to Withdraw.

          8.1  A Participant may, at any time during a Purchase Period, direct
               Frontier to make no further deductions from his or her future
               Compensation, subject to the limitation in Section 6.2. Upon any
               such action, future payroll deductions with respect to such
               Participant shall cease in accordance with the Participant's
               direction.

          8.2  Any Participant who stops payroll deductions may not thereafter
               resume payroll deductions during such Purchase Period.

          8.3  At any time before the end of a Purchase Period, any Participant
               may withdraw from the Plan. In such event, all future payroll
               deductions shall cease. The Participant may direct that the
               entire credit balance in the Participant's Recordkeeping Account
               be used to purchase stock at the end of the Purchase Period or be
               paid to the Participant, without interest, in


                                       4


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               cash. A Participant who withdraws from the Plan will not be
               eligible to reenter the Plan until the next succeeding Purchase
               Period.

          8.4  Notification of a Participant's election to increase, decrease,
               or terminate deductions, or to withdraw from the Plan, shall be
               made by filing an appropriate form with Frontier. Notification to
               increase or decrease deductions received before the prescribed
               cutoff date for each Purchase Period will become effective that
               Purchase Period.

     9.   Termination of Employment. A Participant's membership in the Plan will
be terminated when the Participant either voluntarily elects to withdraw his or
her entire account, or resigns or is discharged from Frontier or one of its
subsidiaries for twelve (12) consecutive months, unless this period is due to
illness, injury or for other reasons approved by the person or persons appointed
by Frontier to administer the Plan as provided in Paragraph 13 below. Upon
termination of membership, the terminated Participant shall not be entitled to
rejoin the Plan until the first day of the next Purchase Period. Upon
termination of membership, the Participant shall be entitled to receive the
amount of his or her individual account.

     10.  Purchase of Shares.

          10.1 As of the last day of each Purchase Period, the entire credit
               balance in each Participant's Recordkeeping Account shall be used
               to purchase shares (including fractional shares) of Common Stock
               (subject to the limitations of Section 5) unless the Participant
               has filed an appropriate form with Frontier in advance of that
               date (which elects to receive the entire credit balance in cash).

          10.2 Shares of Common Stock acquired by each Participant shall be held
               in an account maintained by American Stock Transfer & Trust Co.
               ("AST") a transfer agent selected by Frontier as its service
               provider. AST shall maintain individual accounts for each
               Participant to which shall be allocated such Participant's shares
               of Common Stock (including fractional shares).

          10.3 Prior to the last day of each Purchase Period, Frontier shall
               determine whether some or all of the shares of Common Stock to be
               purchased as of the last day of such Purchase Period will be
               purchased by AST for the accounts of Participants on the open
               market or in privately negotiated transactions. If some or all of
               such shares are to be so purchased by AST, Frontier shall advise
               AST of the number of shares to be so purchased and shall provide
               to AST such funds, in addition to the funds available from
               Participants' Recordkeeping Accounts, as may be necessary to
               permit AST to so purchase such number of shares (including all
               brokerage fees and expense).


                                       5


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          10.4 Dividends with respect to a Participant's shares of Common Stock
               held in the account maintained by AST shall automatically be
               reinvested in additional shares of Common Stock. AST shall
               commingle all dividends paid on all Participants' shares held in
               the account and shall purchase on the open market, or in
               privately negotiated transactions, as soon as reasonably
               practicable after the receipt of the dividends, as many shares of
               Common Stock as can be acquired with such commingled dividends
               and the purchase price of each such Reinvestment Share shall be
               the average price paid by AST in purchasing all Reinvestment
               Shares for all Participants with the proceeds of such dividend
               payment. There shall be allocated to each Participant's
               individual account such Participant's pro rata portion of the
               Reinvestment Shares purchased with the commingled funds. Frontier
               shall pay all brokerage fees and expenses of AST in connection
               with the reinvestment of dividends.

          10.5 Each Participant shall be entitled to vote all shares held for
               the benefit of such Participant in the account maintained by AST.

          10.6 Certificates for the number of whole shares of Common Stock,
               determined as aforesaid, purchased by each Participant shall be
               issued and delivered to him or her, registered in the form
               directed by the Participant, only upon the request of the
               Participant or his or her representative. Any such request shall
               be made by filing an appropriate form with Frontier. No
               certificates for fractional shares will be issued. Upon closing
               of the account, the Participant will receive a cash distribution
               representing the value of any fractional shares.

     11.  Rights as a Stockholder. A Participant shall not be entitled to any of
the rights or privileges of a stockholder of Frontier with respect to shares of
Common Stock under the Plan, including the right to receive any dividends which
may be declared by Frontier, until (i) he or she actually has paid the purchase
price for such shares and (ii) either the shares have been credited to the
account maintained by AST for the Participant's benefit or certificates have
been issued to the Participant, both as provided in Section 10.

     12.  Rights Not Transferable. A Participant's rights under this Plan are
exercisable only by the Participant during his or her lifetime, and may not be
sold, pledged, assigned or transferred in any manner other than by will or the
laws of descent and distribution. Any attempt to sell, pledge, assign or
transfer the same shall be null and void and without effect. The amounts
credited to a Recordkeeping Account may not be assigned, transferred, pledged or
hypothecated in any way, and any attempted assignment, transfer, pledge,
hypothecation or other disposition of such amounts will be null and void and
without effect.

     13.  Administration of the Plan. This Plan shall be administered by the
Committee, which is authorized to make such uniform rules as may be necessary to
carry out its provisions. The Committee shall determine any questions arising in
the administration, interpretation and application of this Plan, and all such
determinations shall be conclusive and binding on all parties. All costs and
expenses incurred in administering the Plan shall be paid by Frontier. Any

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<PAGE>


taxes applicable to the Participant's account shall be charged or credited to
the Participant's account by Frontier.

     14.  Adjustment upon Changes in Capitalization. In the event of any change
in the Common Stock by reason of stock dividends, split-ups, corporate
separations, recapitalizations, mergers, consolidations, combinations, exchanges
of shares and the like, the aggregate number and class of shares available under
this Plan and the number, class and purchase price of shares available but not
yet purchased under this Plan, shall be adjusted appropriately by the Committee.

     15.  Registration of Certificates. Stock certificates to be issued and
delivered upon the request of the Participant or his or her representative, as
provided in Section 10.6, shall be, registered in the name of the Participant,
or jointly, as joint tenants with the right of survivorship, in the name of the
Participant and another person, as the Participant or his or her representative
may direct on an appropriate form filed with Frontier.

     16.  Amendment of Plan. Frontier expects to continue the Plan until such
time as the shares reserved for issuance under the Plan have been sold. Frontier
reserves, however, the right at any time to amend this Plan in any respect which
shall not adversely affect the rights of Participants pursuant to shares
previously acquired under the Plan, except that, without stockholder approval on
the same basis as required by Section 19.1, no amendment shall be made (i) to
increase the number of shares to be reserved under this Plan, (ii) decrease the
minimum purchase price, (iii) to withdraw the administration of this Plan from
the Committee, or (iv) to change the definition of employees eligible to
participate in the Plan.

     17.  Effective Date of Plan. This Plan shall consist of an offering
commencing January 1, 1999, and continuing on a quarterly basis thereafter. All
rights of Participants in any offering hereunder shall terminate at the earlier
of (i) the day that Participants become entitled to purchase a number of shares
of Common Stock equal to or greater than the number of shares remaining
available for purchase or (ii) at any time, at the discretion of the Board of
Directors, after 30 days' notice has been given to all Participants. Upon
termination of this Plan, shares of Common Stock shall be purchased for
Participants in accordance with Section 10.1, and cash, if any, remaining in the
Participants' Recordkeeping Accounts shall be refunded to them, as if the Plan
were terminated at the end of a Purchase Period.

     18.  Governmental Regulations and Listing. All rights granted or to be
granted to Eligible Employees under this Plan are expressly subject to all
applicable laws and regulations and to the approval of all governmental
authorities required in connection with the authorization, issuance, sale or
transfer of the shares of Common Stock reserved for this Plan, including,
without limitation, there being a current registration statement of Frontier
under the Securities Act of 1933, as amended, covering the shares of Common
Stock purchasable on the last day of the Purchase Period applicable to such
shares, and if such a registration statement shall not then be effective, the
term of such Purchase Period shall be extended until the first business day
after the effective date of such a registration statement, or post-effective
amendment thereto. All such rights hereunder are also similarly subject to
effectiveness of an appropriate listing application to the New York Stock
Exchange, covering the shares of Common Stock under the Plan upon official
notice of issuance.


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     19.  Miscellaneous.

          19.1 This Plan shall be submitted for approval by the stockholders of
               Frontier prior to December 1, 1999. If not so approved prior to
               such date, this Plan shall terminate on November 30, 1999.

          19.2 This Plan shall not be deemed to constitute a contract of
               employment between Frontier and any Participant, nor shall it
               interfere with the right of Frontier to terminate any Participant
               and treat him or her without regard to the effect which such
               treatment might have upon him or her under this Plan.

          19.3 Wherever appropriate as used herein, the masculine gender may be
               read as the feminine gender, the feminine gender may be read as
               the masculine gender, the singular may be read as the plural and
               the plural may be read as the singular.

          19.4 The Plan, and all agreements hereunder, shall be construed in
               accordance with and governed by the laws of the State of
               Delaware.

          19.5 Delivery of shares of Common Stock or of cash pursuant to the
               Plan shall be subject to any required withholding taxes. A person
               entitled to receive shares of Common Stock may, as a condition
               precedent to receiving such shares, be required to pay Frontier a
               cash amount equal to the amount of any required withholdings.


                                       8

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                                                                       EXHIBIT 5

                    [EPSTEIN BECKER & GREEN, P.C. LETTERHEAD]

                                 March 30, 1999


Board of Directors of
  Frontier Insurance Group, Inc.
195 Lake Louise Marie Road
Rock Hill, New York 12775-8000

                        Re: Employee Stock Purchase Plan


Gentlemen:

         We have acted as counsel to Frontier Insurance Group, Inc. (the
"Company") in connection with its filing of a Registration Statement on Form S-8
(the "Registration Statement") covering 1,000,000 shares (the "Shares") of the
Company's authorized and unissued shares of Common Stock, $.01 par value, and/or
outstanding shares of such Common Stock, to be sold to employees pursuant to the
Company's Employee Stock Purchase Plan.

         As such counsel, we have examined originals, or copies certified to our
satisfaction, of the corporate records of the Company, agreements and other
instruments, certificates of public officials, certificates of officers of the
Company and such other documents as we deemed necessary as a basis for the
opinion hereinafter set forth.

         In such examination we have assumed the genuineness of all signatures
and the authenticity of all documents submitted to us as originals and the
conformity to original documents of documents submitted to us as certified or
photostatic copies.

         On the basis of the foregoing, we are of the opinion that the
authorized and unissued Shares have been duly authorized and, when issued,
delivered and paid for in accordance with the Employee Stock Purchase Plan, will
be validly issued, fully paid and non-assessable.

         We hereby consent to the filing of this opinion as an exhibit to the
aforesaid Registration Statement.

                                  Very truly yours,

                                  EPSTEIN BECKER & GREEN, P.C.

                                  By: /s/ Sidney Todres
                                     -------------------------
                                      Sidney Todres

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<PAGE>


                                                                   EXHIBIT 23(a)

                         CONSENT OF INDEPENDENT AUDITORS

         We consent to the incorporation by reference in the Registration
Statement (Form S-8) pertaining to the Frontier Insurance Group, Inc. Employee
Stock Purchase Plan of our report dated March 31, 1998, with respect to the
consolidated financial statements and schedules of Frontier Insurance Group,
Inc. included in its Annual Report (Form 10-K) for the year ended December 31,
1998 filed with the Securities and Exchange Commission.

                                          ERNST & YOUNG LLP


New York, New York
March 31, 1999





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