<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: March 31, 2000
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: 28-4685
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 5/15/2000
_____________________ _______________ ______________
[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: 75
Form 13F Information Table Value Total: $159,597
[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>
13F Report
3/31/00
PROSPECTOR PARTNERS, LLC (Hartford)
<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 COMMON STOCK G0070K103 3866 169000 SH SOLE 169000 0 0
ACE LTD COM OPTIONS - CALLS G0070K0EC 229 10000 SH CALL SOLE 10000 0 0
ACE LTD COM OPTIONS - CALLS G0070K0HC 686 30000 SH CALL SOLE 30000 0 0
ADVANTA CORP
USD.01 CL-B
NONVT COMMON STOCK 007942204 181 12500 SH SOLE 12500 0 0
AFFILIATED
COMPUTER
SERVICES I COMMON STOCK 008190100 513 13500 SH SOLE 13500 0 0
ALLMERICA FINL
CORP COM OPTIONS - CALLS 0197540EK 765 15000 SH CALL SOLE 15000 0 0
AMBAC FINANCIAL
GROUP INC COMMON STOCK 023139108 4289 85150 SH SOLE 85150 0 0
AMER EXPRESS
CO COM COMMON STOCK 025816109 1236 8300 SH SOLE 8300 0 0
AMERICAN FINICAL
HOLDINGS COMMON STOCK 026075101 134 11093 SH SOLE 11093 0 0
AMERICAN GEN
CORP COM COMMON STOCK 026351106 3059 54500 SH SOLE 54500 0 0
AON CORP COMMON STOCK 037389103 4931 152900 SH SOLE 152900 0 0
BANK ONE CORP
COM OPTIONS - CALLS 06423A2AE 1725 50000 SH CALL SOLE 50000 0 0
BANK ONE CORP
COM OPTIONS - CALLS 06423A2AF 1035 30000 SH CALL SOLE 30000 0 0
BEAR STEARNS
COS INC
USD1 COM COMMON STOCK 073902108 3353 73500 SH SOLE 73500 0 0
BERKLEY W R
CORP COM COMMON STOCK 084423102 1916 83100 SH SOLE 83100 0 0
BERKSHIRE
HATHAWAY CL A
INC DE COMMON STOCK 084670108 2231 39 SH SOLE 39 0 0
4
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BERKSHIRE
HATHAWAY
INC CLASS B COMMON STOCK 084670207 7329 4027 SH SOLE 4027 0 0
BISYS GROUP
INC COM COMMON STOCK 055472104 4947 74400 SH SOLE 74400 0 0
BOSTON PROPERTIES
INC COMMON STOCK 101121101 509 16000 SH SOLE 16000 0 0
BROWN & BROWN
INC COM STK COMMON STOCK 115236101 3906 100975 SH SOLE 100975 0 0
BYL BANCORP
COM STK COMMON STOCK 056064108 203 19600 SH SOLE 19600 0 0
CARNIVAL CORP
COM STK COMMON STOCK 143658102 471 19000 SH SOLE 19000 0 0
CLARK/BARDES
HOLDING INC COM COMMON STOCK 180668105 3772 264700 SH SOLE 264700 0 0
CNA FINL CORP COM COMMON STOCK 126117100 1066 33000 SH SOLE 33000 0 0
CONCORD EFS
INC COM COMMON STOCK 206197105 2260 98500 SH SOLE 98500 0 0
DATA BROADCASTING
CORP COMMON STOCK 237596101 153 20000 SH SOLE 20000 0 0
DUKE RLTY INVTS
INC COM NEW COMMON STOCK 264411505 432 22600 SH SOLE 22600 0 0
EQUIFAX INC COM COMMON STOCK 294429105 980 38800 SH SOLE 38800 0 0
EQUITY OFFICE
PROPERTIES
TRUST REITS/RICS 294741103 503 20000 SH SOLE 20000 0 0
EQUITY RESIDENTIAL
PPTYS TR REITS/RICS 29476L107 482 12000 SH SOLE 12000 0 0
EVEREST RE GROUP
LTD COM STK COMMON STOCK G3223R108 3222 98750 SH SOLE 98750 0 0
FIDELITY NATL
FINL INC COM COMMON STOCK 316326107 940 68000 SH SOLE 68000 0 0
FIRST DATA
CORP COM COMMON STOCK 319963104 6117 137850 SH SOLE 137850 0 0
FIRST HEALTH
GROUP CORP COM COMMON STOCK 320960107 402 12700 SH SOLE 12700 0 0
FIRST INVS
FINL SVCS
GROUP IN COMMON STOCK 32058A101 1050 200000 SH SOLE 200000 0 0
FLEET BOSTON
FINANCIAL CORP COMMON STOCK 339030108 2675 73300 SH SOLE 73300 0 0
GALLAGHER ARTHUR
J & CO COM COMMON STOCK 363576109 311 9570 SH SOLE 9570 0 0
HCC INS HLDGS
INC COM COMMON STOCK 404132102 2015 152040 SH SOLE 152040 0 0
HELLER FINL
INC COM COMMON STOCK 423328103 1265 55000 SH SOLE 55000 0 0
HILB, ROGAL &
HAMILTON CO COMMON STOCK 431294107 240 8775 SH SOLE 8775 0 0
5
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HOSPITALITY PPTYS
TR COM SH B COMMON STOCK 44106M102 547 27000 SH SOLE 27000 0 0
IMS HEALTH INC COMMON STOCK 449934108 677 40000 SH SOLE 40000 0 0
INTUIT INC COM COMMON STOCK 461202103 5313 97705 SH SOLE 97705 0 0
INVESTMENT
TECHNOLOGY GROUP COMMON STOCK 46145F105 260 7380 SH SOLE 7380 0 0
J HANCOCK FINL
COM STK COMMON STOCK 41014S106 4353 241000 SH SOLE 241000 0 0
JEFFERSON PILOT
CORP COM OPTIONS - CALLS 4750700DM 832 12500 SH CALL SOLE 12500 0 0
KAYE GROUP
INC COM COMMON STOCK 486589104 130 18500 SH SOLE 18500 0 0
LASALLE RE
HOLDINGS
LTD COM COMMON STOCK G5383Q101 1700 122500 SH SOLE 122500 0 0
LINCOLN NATL
CORP IND COM COMMON STOCK 534187109 838 25000 SH SOLE 25000 0 0
LINCOLN NATL
CORP IND COM OPTIONS - CALLS 5341870DH 670 20000 SH CALL SOLE 20000 0 0
LOEWS CORP COM COMMON STOCK 540424108 1050 21000 SH SOLE 21000 0 0
LONDON PACIFIC
GROUP LTD ADR ADRS STOCKS 542073101 2735 117640 SH SOLE 117640 0 0
MACK-CALI REALTY
CORP REIT REITS/RICS 554489104 510 20000 SH SOLE 20000 0 0
MARKEL CORP COM COMMON STOCK 570535104 898 6175 SH SOLE 6175 0 0
MARSH & MCLENNAN
COS INC COM COMMON STOCK 571748102 6878 62350 SH SOLE 62350 0 0
MBIA INC COM COMMON STOCK 55262C100 1752 33660 SH SOLE 33660 0 0
MBNA CORP COM COMMON STOCK 55262L100 1224 48000 SH SOLE 48000 0 0
MMI CO INC COM COMMON STOCK 553087107 133 13500 SH SOLE 13500 0 0
MUTUAL RISK
MANAGEMENT LTD COMMON STOCK 628351108 9374 468716 SH SOLE 468716 0 0
NORTH FORK
BANCORPORATION COMMON STOCK 659424105 1788 100000 SH SOLE 100000 0 0
PARTNERRE LIMITED
BERMUDA COMMON STOCK G6852T105 1807 49100 SH SOLE 49100 0 0
PNC FINANCIAL
SERVICES GRP COMMON STOCK 693475105 2433 54000 SH SOLE 54000 0 0
PROGRESSIVE CORP
OHIO COMMON STOCK 743315103 4434 58300 SH SOLE 58300 0 0
PROVIDENT
FINANCIAL HLDGS
INC COMMON STOCK 743868101 438 31120 SH SOLE 31120 0 0
PXRE GROUP
LTD COM STK COMMON STOCK G73018106 1595 93800 SH SOLE 93800 0 0
REDWOOD EMPIRE
BANCORP COMMON STOCK 757897103 143 10000 SH SOLE 10000 0 0
REINSURANCE GROUP
AMER INC COMMON STOCK 759351109 3996 167800 SH SOLE 167800 0 0
6
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RENAISSANCE RE
HLDGS LTD COM COMMON STOCK G7496G103 3285 80370 SH SOLE 80370 0 0
SCOTTISH ANNUITY
AND LIFE HOLD COMMON STOCK G7885T104 343 44600 SH SOLE 44600 0 0
STATE STREET
CORP COM COMMON STOCK 857477103 2325 24000 SH SOLE 24000 0 0
TORCHMARK
CORP COM COMMON STOCK 891027104 335 14465 SH SOLE 14465 0 0
U.S. BANCORP COM OPTIONS - CALLS 902973EFE 2188 100000 SH CALL SOLE 100000 0 0
WADDELL & REED
FINANCIAL INC COMMON STOCK 930059100 9626 227500 SH SOLE 227500 0 0
XL CAPITAL LTD
CL-A COM STK COMMON STOCK G98255105 9305 168036 SH SOLE 168036 0 0
ZENITH NATL
INS CORP COMMON STOCK 989390109 283 12760 SH SOLE 12760 0 0
</TABLE>
7
02081001.AI9
