<PAGE>
UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549
Form 13F
Form 13F COVER PAGE
Report for the Calendar Year or Quarter Ended: December 31, 1999
Check here if Amendment [ ]; Amendment Number:
This Amendment (Check only one.): [ ] is a restatement.
[ ] adds new holdings
entries.
Institutional Investment Manager Filing this Report:
Name: Prospector Partners, LLC
Address: The Webster Memorial Building
36 Trumball Street
Hartford, CT 06103-2404
Form 13F File Number: 28-
The institutional investment manager filing this report and the
person by whom it is signed hereby represent that the person
signing the report is authorized to submit it, that all
information contained herein is true, correct and complete, and
that it is understood that all required items, statements,
schedules, lists, and tables, are considered integral parts of
this form.
Person Signing this Report on Behalf of Reporting Manager:
Name: John D. Gillespie
Title: Managing Member
Phone: (860) 560-6200
Signature, Place, and Date of Signing:
/s/ John D. Gillespie Hartford, CT 2/14/2000
_____________________ _______________ ______________
[Signature] [City, State] [Date]
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Report Type (Check only one.):
[X] 13F HOLDINGS REPORT. (Check here if all holdings of
this reporting manager are reported in this report.)
[ ] 13F NOTICE. (Check here if no holdings reported are in
this report, and all holdings are reported by other
reporting manager(s).)
[ ] 13F COMBINATION REPORT. (Check here if a portion of the
holdings for this reporting manager are reported in this
report and a portion are reported by other reporting
manager(s).)
List of Other Managers Reporting for this Manager:
[If there are no entries in this list, omit this section.]
Form 13F File Number Name
28-
[Repeat as necessary.]
2
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Form 13F SUMMARY PAGE
Report Summary:
Number of Other Included Managers: 0
Form 13F Information Table Entry Total: 72
Form 13F Information Table Value Total: $147,763
[thousands]
List of Other Included Managers:
Provide a numbered list of the name(s) and Form 13F file
number(s) of all institutional investment managers with respect
to which this report is filed, other than the manager filing this
report.
[If there are no entries in this list, state "NONE" and omit the
column headings and list entries.]
No. Form 13F File Number Name
28-
[Repeat as necessary.]
3
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<TABLE>
NAME OF REPORTING MANAGER PROSPECTOR PARTNERS, LLC
<CAPTION>
ITEM 1 ITEM 2 ITEM 3 ITEM 4 ITEM 5 ITEM 6 ITEM 7 ITEM 8
------ ------ ------ ------ ------ ------ ------ ------
FAIR
TITLE CUSIP MARKET SHRS OR INVESTMENT OTHER VOTING AUTHORITY
NAME OF ISSUER OF CLASS NUMBER VALUE PRN AMT SH/PRN PUT/CALL DISCRETION MANAGERS SOLE SHARED NONE
- -------------- -------- ------ ------ ------- ------ -------- ----------- -------- ---- ------ ----
<S> <C> <C> <C> <C> <C> <C> <C> <C> <C> <C> <C>
ACE LTD COM OPTIONS - CALLS G0070K0EC 166 10000 SH CALL SOLE 10000 0 0
ALLMERICA
FINL CORP COM COMMON STOCK 019754100 3624 65150 SH SOLE 56900 0 0
ALLMERICA FINL
CORP COM OPTIONS - CALLS 0197540EK 1112 20000 SH CALL SOLE 20000 0 0
AMBAC FINANCIAL
GROUP INC COMMON STOCK 023139108 1834 35150 SH SOLE 35150 0 0
AMERICAN FINICAL
HOLDINGS COMMON STOCK 026075101 139 11093 SH SOLE 11093 0 0
AON CORP COMMON STOCK 037389103 7568 189200 SH SOLE 173000 0 0
BANK NEW YORK
INC COM COMMON STOCK 064057102 2000 50000 SH SOLE 50000 0 0
BANK ONE CORP COM OPTIONS - CALLS 06423A2AF 960 30000 SH CALL SOLE 30000 0 0
BEAR STEARNS COS
INC USD1 COM COMMON STOCK 073902108 3142 73500 SH SOLE 73500 0 0
BERKSHIRE
HATHAWAY CL A
INC DE COMMON STOCK 084670108 1570 28 SH SOLE 27 0 0
BERKSHIRE
HATHAWAY INC
CLASS B COMMON STOCK 084670207 5484 2997 SH SOLE 2652 0 0
BISYS GROUP
INC COM COMMON STOCK 055472104 1298 19900 SH SOLE 19900 0 0
BLANCH E W
HLDGS INC COM COMMON STOCK 093210102 5145 84000 SH SOLE 77000 0 0
BOSTON PROPERTIES
INC COMMON STOCK 101121101 498 16000 SH SOLE 16000 0 0
BROWN & BROWN
INC COM STK COMMON STOCK 115236101 2934 76600 SH SOLE 76600 0 0
CAPITAL ONE
FINL CORP COM COMMON STOCK 14040H105 1204 25000 SH SOLE 25000 0 0
CHASE MANHATTAN
CORP COM NEW COMMON STOCK 16161A108 3107 40000 SH SOLE 40000 0 0
CLARK/BARDES
HOLDING INC COM COMMON STOCK 180668105 4308 299700 SH SOLE 272800 0 0
4
<PAGE>
DATA BROADCASTING
CORP COMMON STOCK 237596101 123 15000 SH SOLE 15000 0 0
DUKE RLTY INVTS
INC COM NEW COMMON STOCK 264411505 440 22600 SH SOLE 22600 0 0
EQUIFAX INC COM COMMON STOCK 294429105 1974 83800 SH SOLE 77300 0 0
EQUITY OFFICE
PROPERTIES
TRUST REITS/RICS 294741103 492 20000 SH SOLE 20000 0 0
EQUITY RESIDENTIAL
PPTYS TR REITS/RICS 29476L107 512 12000 SH SOLE 12000 0 0
EVEREST REINS
HLDGS INC COMMON STOCK 299808105 2203 98750 SH SOLE 98750 0 0
FANNIE MAE
COM STK COMMON STOCK 313586109 1011 16200 SH SOLE 16200 0 0
FIRST DATA
CORP COM COMMON STOCK 319963104 6797 137850 SH SOLE 126850 0 0
FIRST HEALTH
GROUP CORP COM COMMON STOCK 320960107 403 15000 SH SOLE 15000 0 0
FIRST INVS FINL
SVCS GROUP IN COMMON STOCK 32058A101 1050 200000 SH SOLE 200000 0 0
FIRST UNION
CORP COM COMMON STOCK 337358105 2842 86300 SH SOLE 86300 0 0
FREDDIE MAC
USD0.21 COM COMMON STOCK 313400301 715 15200 SH SOLE 15200 0 0
FRIEDMAN BILLINGS
RAMSEY-A COMMON STOCK 358433100 157 20000 SH SOLE 20000 0 0
FRIEDMAN BILLINGS
RAMSEY-A OPTIONS - CALLS 3584338CU 630 80000 SH CALL SOLE 80000 0 0
FRIEDMAN BILLINGS
RAMSEY-A OPTIONS - CALLS 358433CFU 118 15000 SH CALL SOLE 15000 0 0
GALLAGHER ARTHUR
J & CO COM COMMON STOCK 363576109 550 8500 SH SOLE 8500 0 0
HARTFORD
FIANANCIAL
SERVICES G COMMON STOCK 416515104 1942 41000 SH SOLE 31600 0 0
HCC INS HLDGS
INC COM COMMON STOCK 404132102 2028 153800 SH SOLE 153800 0 0
HELLER FINANCIAL
INC CL A COMMON STOCK 423328103 502 25000
HILB, ROGAL &
HAMILTON CO COMMON STOCK 431294107 355 12600 SH SOLE 12600 0 0
HOSPITALITY
PPTYS TR
COM SH B COMMON STOCK 44106M102 514 27000 SH SOLE 27000 0 0
INTUIT INC COM COMMON STOCK 461202103 5958 99405 SH SOLE 99405 0 0
INVESTMENT
TECHNOLOGY
GROUP COMMON STOCK 46145F105 287 10000 SH SOLE 10000 0 0
5
<PAGE>
JEFFERSON PILOT
CORP COM COMMON STOCK 475070108 2832 41500 SH SOLE 41500 0 0
JEFFERSON PILOT
CORP COM OPTIONS - CALLS 4750700DM 853 12500 SH CALL SOLE 12500 0 0
LASALLE RE
HOLDINGS
LTD COM COMMON STOCK G5383Q101 2434 147500 SH SOLE 114500 0 0
LINCOLN NATL
CORP IND COM COMMON STOCK 534187109 1040 26000 SH SOLE 26000 0 0
LINCOLN NATL
CORP IND COM OPTIONS - CALLS 5341870DH 800 20000 SH CALL SOLE 20000 0 0
LONDON PACIFIC
GROUP LTD ADR ADRS STOCKS 542073101 2236 62100 SH SOLE 42500 0 0
MACK-CALI REALTY
CORP REIT REITS/RICS 554489104 521 20000 SH SOLE 20000 0 0
MARSH & MCLENNAN
COS INC COM COMMON STOCK 571748102 7095 74150 SH SOLE 74150 0 0
MBIA INC COM COMMON STOCK 55262C100 2693 51000 SH SOLE 42000 0 0
MMI CO INC COM COMMON STOCK 553087107 116 13500 SH SOLE 13500 0 0
MUTUAL RISK
MANAGEMENT LTD COMMON STOCK 628351108 4190 249265 SH SOLE 215400 0 0
NORTH FORK
BANCORPORATION COMMON STOCK 659424105 1737 100000 SH SOLE 100000 0 0
PARTNERRE LIMITED
BERMUDA COMMON STOCK G6852T105 3765 116100 SH SOLE 116100 0 0
PROGRESSIVE
CORP OHIO COMMON STOCK 743315103 548 7500 SH SOLE 7500 0 0
PROTECTIVE LIFE
CORP COM COMMON STOCK 743674103 2303 72400 SH SOLE 59800 0 0
PROVIDENT
FINANCIAL
HLDGS INC COMMON STOCK 743868101 514 31200 SH SOLE 31200 0 0
PXRE GROUP LTD
COM STK COMMON STOCK G73018106 1219 93800 SH SOLE 68800 0 0
REDWOOD EMPIRE
BANCORP COMMON STOCK 757897103 191 10000 SH SOLE 10000 0 0
REINSURANCE
GROUP AMER INC COMMON STOCK 759351109 3323 119750 SH SOLE 111400 0 0
RELIASTAR FINL
CORP COM COMMON STOCK 75952U103 979 25000 SH SOLE 25000 0 0
RELIASTAR FINL
CORP COM OPTIONS - CALLS 75952U0DH 783 20000 SH CALL SOLE 20000 0 0
RENAISSANCE RE
HLDGS LTD COM COMMON STOCK G7496G103 2043 50000 SH SOLE 50000 0 0
TERRA NOVA
(BERMUDA)
HOLDS LTD COMMON STOCK G87615103 5225 174195 SH SOLE 173795 O 0
TIMBERLAND
BANCORP INC COMMON STOCK 887098101 281 2500O SH SOLE 2500O O O
6
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TOKIO MARINE &
FIRE INS LTD AD ADRS STOCKS 889090403 65O 1100O SH SOLE 1100O O O
TORCHMARK CORP
COM COMMON STOCK 891027104 179O 6160O SH SOLE 4825O O O
TRAVELERS PROP
CASUALTY CL A C COMMON STOCK 893939108 2096 6120O SH SOLE 5060O O O
U.S. BANCORP COM OPTIONS - CALLS 902973EFE 2381 10000O SH CALL SOLE 10000O O O
WADDELL & REED
FINANCIAL INC COMMON STOCK 93005910O 690O 25440O SH SOLE 23820O O O
WIT CAPITAL
GROUP INC COMMON STOCK 97737K309 85O 5000O SH SOLE 5000O O O
XL CAPITAL LTD
CL-A COM STK COMMON STOCK G98255105 7679 148036 SH SOLE 138036 O O
Records 72 Total Mkt Value 147763
</TABLE>
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