UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 13F Form 13F COVER PAGE Report for the Calendar Year or Quarter Ended: June 30, 2008 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: Alleghany Corporation Address: 7 Times Square Tower, 17th Floor New York, NY 10036 Form 13F File Number: 28-1590 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: Peter R. Sismondo Title: Vice President Phone: 212-752-1356 Signature, Place, and Date of Signing: /s/ Peter R. Sismondo New York, NY August 7, 2008 ------------------------------------- ---------------- --------------------- [Signature] [City, State] [Date] 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).) Form 13F SUMMARY PAGE Report Summary: Number of Other Included Managers: 2 Form 13F Information Table Entry Total: 90 Form 13F Information Table Value Total: $1,377,600 (thousands) List of Other Included Managers: No. Form 13F File Number Name --- -------------------- ---- 2 RSUI Indemnity Company 3 Alleghany Insurance Holdings LLC SECURITIES AND EXCHANGE COMMISSIONS FORM 13F INFORMATION PREPARED FOR ALLEGHANY CORPORATION AS OF 06/30/08 COLUMN 1 COLUMN 2 COLUMN 3 COLUMN 4 COLUMN 5 COLUMN 6 COLUMN 7 COLUMN 8 ---------------------------- -------------- --------- --------- ------------------- --------------- -------- -------------- INVESTMENT VOTING MARKET DISCRETION AUTHORITY VALUE SHRS OR SH/ PUT/ SOLE SHRD OTHER SOLE SHRD NONE NAME OF ISSUER TITLE OF CLASS CUSIP (X 1000) PRIN AMT PRN CALL (A) (B) (C) MANAGER (A) (B) (C) ---------------------------- -------------- --------- --------- ---------- --- ---- ---- ---- ----- -------- ---- ---- ---- NABORS INDUSTRIES LTD SHS G6359F103 41,599 845,000 SH X 2 X NABORS INDUSTRIES LTD SHS G6359F103 7,877 160,000 SH X 3 X WEATHERFORD INTERNATIONAL LT COM G95089101 7,530 151,840 SH X 2 X WEATHERFORD INTERNATIONAL LT COM G95089101 8,926 180,000 SH X 3 X AT&T INC COM 00206R102 1,347 40,000 SH X 3 X AGILENT TECHNOLOGIES INC COM 00846U101 1,088 30,600 SH X 3 X ALEXANDER & BALDWIN INC COM 014482103 911 20,000 SH X 3 X AMERICAN EXPRESS CO COM 025816109 1,386 36,800 SH X 3 X AMERICAN INTL GROUP INC COM 026874107 624 23,600 SH X 3 X APPLERA CORP COM AP BIO GRP 038080103 670 20,000 SH X 3 X APPLIED MATLS INC COM 038222105 955 50,000 SH X 3 X AUTODESK INC COM 052769106 1,014 30,000 SH X 3 X AUTOMATIC DATA PROCESSING IN COM 053015103 838 20,000 SH X 3 X BERKSHIRE HATHAWAY INC DEL CL B 084670207 1,605 400 SH X 3 X BOEING CO COM 097023105 986 15,000 SH X 3 X BURLINGTON NORTHN SANTA FE C COM 12189T104 399,560 4,000,000 SH X 1 X CAMECO CORP COM 13321L108 2,144 50,000 SH X 2 X CAMECO CORP COM 13321L108 1,072 25,000 SH X 3 X CATERPILLAR INC DEL COM 149123101 1,846 25,000 SH X 3 X CHESAPEAKE ENERGY CORP COM 165167101 3,298 50,000 SH X 2 X CHESAPEAKE ENERGY CORP COM 165167101 11,543 175,000 SH X 3 X CHEVRON CORP NEW COM 166764100 31,226 315,000 SH X 2 X CHEVRON CORP NEW COM 166764100 16,961 171,100 SH X 3 X CHICAGO BRIDGE & IRON CO N V NY REGISTRY SH 167250109 15,629 392,500 SH X 2 X CHICAGO BRIDGE & IRON CO N V NY REGISTRY SH 167250109 6,272 157,500 SH X 3 X CHUBB CORP COM 171232101 1,470 30,000 SH X 3 X COCA COLA CO COM 191216100 1,310 25,200 SH X 3 X COMCAST CORP NEW CL A 20030N101 260 13,700 SH X 3 X CONOCOPHILLIPS COM 20825C104 30,205 320,000 SH X 2 X CONOCOPHILLIPS COM 20825C104 61,920 656,000 SH X 3 X COSTCO WHSL CORP NEW COM 22160K105 2,104 30,000 SH X 3 X DARWIN PROFESSIONAL UNDERWRI COM 237502109 288,630 9,371,096 SH X 3 X DEERE & CO COM 244199105 2,164 30,000 SH X 3 X DEVON ENERGY CORP NEW COM 25179M103 53,171 442,500 SH X 2 X DEVON ENERGY CORP NEW COM 25179M103 16,822 140,000 SH X 3 X DISNEY WALT CO COM DISNEY 254687106 1,404 45,000 SH X 3 X DOMTAR CORP COM 257559104 2,376 436,000 SH X 2 X DOMTAR CORP COM 257559104 894 164,000 SH X 3 X DU PONT EI DE NEMOURS & CO COM 263534109 1,287 30,000 SH X 3 X EOG RES INC COM 26875P101 6,298 48,000 SH X 2 X EOG RES INC COM 26875P101 2,230 17,000 SH X 3 X EXXON MOBIL CORP COM 30231G102 2,644 30,000 SH X 3 X FPL GROUP INC COM 302571104 9,575 146,000 SH X 2 X FPL GROUP INC COM 302571104 3,541 54,000 SH X 3 X FEDEX CORP COM 31428X106 1,182 15,000 SH X 3 X FIDELITY NATL FINANCIAL CL A 31620R105 3,072 243,800 SH X 2 X FIDELITY NATL FINANCIAL CL A 31620R105 630 50,000 SH X 3 X FLOTEK INDS INC DEL COM 343389102 4,743 230,000 SH X 2 X FLOTEK INDS INC DEL COM 343389102 3,093 150,000 SH X 3 X GENERAL ELECTRIC CO COM 369604103 11,076 415,000 SH X 2 X GENERAL ELECTRIC CO COM 369604103 6,472 242,500 SH X 3 X GLOBAL INDS LTD COM 379336100 15,689 875,000 SH X 2 X GLOBAL INDS LTD COM 379336100 5,827 325,000 SH X 3 X HOME DEPOT INC COM 437076102 468 20,000 SH X 3 X INTEL CORP COM 458140100 1,504 70,000 SH X 3 X INTERNATIONAL BUSINESS MACHS COM 459200101 1,482 12,500 SH X 3 X INTL PAPER CO COM 460146103 11,068 475,000 SH X 2 X INTL PAPER CO COM 460146103 4,078 175,000 SH X 3 X INTUIT COM 461202103 551 20,000 SH X 3 X ISHARES INC MSCI JAPAN 464286848 258 20,700 SH X 3 X JOHNSON AND JOHNSON COM 478160104 1,383 21,500 SH X 3 X KELLOGG COM 487836108 960 20,000 SH X 3 X KEY ENERGY SVCS INC COM 492914106 8,739 450,000 SH X 2 X KEY ENERGY SVCS INC COM 492914106 3,884 200,000 SH X 3 X KRAFT FOODS INC CL A 50075N104 8,413 295,700 SH X 2 X 1 SECURITIES AND EXCHANGE COMMISSIONS FORM 13F INFORMATION PREPARED FOR ALLEGHANY CORPORATION AS OF 06/30/08 COLUMN 1 COLUMN 2 COLUMN 3 COLUMN 4 COLUMN 5 COLUMN 6 COLUMN 7 COLUMN 8 ---------------------------- -------------- --------- --------- ------------------- --------------- -------- -------------- INVESTMENT VOTING MARKET DISCRETION AUTHORITY VALUE SHRS OR SH/ PUT/ SOLE SHRD OTHER SOLE SHRD NONE NAME OF ISSUER TITLE OF CLASS CUSIP (X 1000) PRIN AMT PRN CALL (A) (B) (C) MANAGER (A) (B) (C) ---------------------------- -------------- --------- --------- ---------- --- ---- ---- ---- ----- -------- ---- ---- ---- KRAFT FOODS INC CL A 50075N104 2,134 75,000 SH X 3 X LAUDER ESTEE COS INC CL A 518439104 1,161 25,000 SH X 3 X LEGGETT & PLATT INC COM 524660107 28,257 1,685,000 SH X 2 X LEGGETT & PLATT INC COM 524660107 10,314 615,000 SH X 3 X LILLY ELI & CO COM 532457108 1,385 30,000 SH X 3 X LINCOLN NATIONAL CORP IND COM 534187109 814 17,963 SH X 3 X MANPOWER INC COM 56418H100 874 15,000 SH X 3 X MARRIOTT INTL INC NEW CL A 571903202 918 35,000 SH X 3 X MCDERMOTT INTL INC COM 580037109 5,261 85,000 SH X 2 X MCDERMOTT INTL INC COM 580037109 2,475 40,000 SH X 3 X MEDTRONIC INC COM 585055106 1,646 31,800 SH X 3 X MICROSOFT CORP COM 594918104 2,124 77,200 SH X 3 X MILLIPORE CORP COM 601073109 1,357 20,000 SH X 3 X MOTOROLA INC COM 620076109 83 11,300 SH X 3 X NEWS CORP CL A 65248E104 1,053 70,000 SH X 3 X NOBLE ENERGY INC COM 655044105 3,017 30,000 SH X 3 X NORDSTROM INC COM 655664100 909 30,000 SH X 3 X NOVARTIS AG SPONSORED ADR 66987V109 1,376 25,000 SH X 3 X NUSTAR ENERGY LP UNIT COM 67058H102 1,478 31,190 SH X 2 X NUSTAR ENERGY LP UNIT COM 67058H102 1,592 33,600 SH X 3 X OLD REP INTL CORP COM 680223104 16,576 1,400,000 SH X 3 X PHH CORP COM 693320202 2,184 142,300 SH X 3 X PETROLEO BRASILEIRO SA PETRO SPONSORED ADR 71654V408 10,164 143,500 SH X 2 X PETROLEO BRASILEIRO SA PETRO SPONSORED ADR 71654V408 4,002 56,500 SH X 3 X PFIZER INC COM 717081103 11,792 675,000 SH X 2 X PFIZER INC COM 717081103 5,678 325,000 SH X 3 X PLAINS EXPL& PRODTN CO COM 726505100 3,904 53,500 SH X 2 X PLAINS EXPL& PRODTN CO COM 726505100 2,299 31,500 SH X 3 X PROCTER & GAMBLE CO COM 742718109 1,879 30,900 SH X 3 X SPDR TR UNIT SER 1 78462F103 307 2,400 SH X 3 X SCHLUMBERGER LTD COM 806857108 2,686 25,000 SH X 3 X SIGMA ALDRICH CORP COM 826552101 1,616 30,000 SH X 3 X SONY CORP ADR NEW 835699307 1,094 25,000 SH X 3 X STATE STR CORP COM 857477103 960 15,000 SH X 3 X STATOILHYDRO ASA SPONSORED ADR 85771P102 4,579 122,500 SH X 2 X STATOILHYDRO ASA SPONSORED ADR 85771P102 1,589 42,500 SH X 3 X SYSCO CORP COM 871829107 825 30,000 SH X 3 X TESORO CORP COM 881609101 8,402 425,000 SH X 2 X TEXAS INSTRS INC COM 882508104 597 21,200 SH X 3 X 3M CO COM 88579Y101 1,531 22,000 SH X 3 X TRICO MARINE SERVICES INC COM NEW 896106200 10,835 297,500 SH X 2 X TRICO MARINE SERVICES INC COM NEW 896106200 4,279 117,500 SH X 3 X VALERO ENERGY CORP NEW COM 91913Y100 12,766 310,000 SH X 2 X VALERO ENERGY CORP NEW COM 91913Y100 6,589 160,000 SH X 3 X WACHOVIA CORP 2ND NEW COM 929903102 627 40,400 SH X 3 X WAL MART STORES INC COM 931142103 2,529 45,000 SH X 3 X WASHINGTON POST CO CL B 939640108 880 1,500 SH X 3 X WELLS FARGO & CO NEW COM 949746101 603 25,400 SH X 3 X WEYERHAUSER CO COM 962166104 1,023 20,000 SH X 3 X WYETH COM 983024100 9,112 190,000 SH X 2 X WYETH COM 983024100 4,077 85,000 SH X 3 X XTO ENERGY INC COM 98385X106 2,364 34,500 SH X 2 X XTO ENERGY INC COM 98385X106 1,062 15,500 SH X 3 X ZENITH NATL INS CORP COM 989390109 20,178 573,879 SH X 3 X GRAND TOTAL 1,377,600 31,857,568 2