UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 13F Form 13F COVER PAGE Report for the Calendar Year or Quarter Ended: September 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 November 11, 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: 101 Form 13F Information Table Value Total: $1,146,846 (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 09/30/08 COLUMN 1 COLUMN 2 COLUMN 3 COLUMN 4 COLUMN 5 COLUMN 6 COLUMN 7 COLUMN 8 ---------------------------- -------------- --------- --------- ------------------- --------------- -------- -------------- INVESTMENT VOTING DISCRETION AUTHORITY MARKET --------------- -------------- 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 21,057 845,000 SH X 2 X NABORS INDUSTRIES LTD SHS G6359F103 3,988 160,000 SH X 3 X WEATHERFORD INTERNATIONAL LT COM G95089101 3,817 151,840 SH X 2 X WEATHERFORD INTERNATIONAL LT COM G95089101 4,525 180,000 SH X 3 X AT&T INC COM 00206R102 1,117 40,000 SH X 3 X ABBOTT LABS COM 002824100 518 9,000 SH X 3 X AGILENT TECHNOLOGIES INC COM 00846U101 955 32,200 SH X 3 X ALEXANDER & BALDWIN INC COM 014482103 881 20,000 SH X 3 X AMERICAN EXPRESS CO COM 025816109 1,485 41,900 SH X 3 X ANADARKO PETE CORP COM 032511107 10,405 214,500 SH X 2 X ANADARKO PETE CORP COM 032511107 3,202 66,000 SH X 3 X APACHE CORP COM 037411105 12,409 119,000 SH X 2 X APACHE CORP COM 037411105 4,849 46,500 SH X 3 X APPLIED MATLS INC COM 038222105 757 50,000 SH X 3 X AUTODESK INC COM 052769106 1,007 30,000 SH X 3 X AUTOMATIC DATA PROCESSING IN COM 053015103 855 20,000 SH X 3 X BAKER HUGHES INC COM 057224107 5,146 85,000 SH X 2 X BAKER HUGHES INC COM 057224107 3,657 60,400 SH X 3 X BERKSHIRE HATHAWAY INC DEL CL B 084670207 1,758 400 SH X 3 X BOEING CO COM 097023105 860 15,000 SH X 3 X BURLINGTON NORTHN SANTA FE C COM 12189T104 354,007 3,830,000 SH X 1 X CABLEVISION SYS CORP CL A NY CABLVS 12686C109 209 8,300 SH X 3 X CAMECO CORP COM 13321L108 1,740 78,000 SH X 2 X CAMECO CORP COM 13321L108 1,049 47,000 SH X 3 X CATERPILLAR INC DEL COM 149123101 894 15,000 SH X 3 X CHESAPEAKE ENERGY CORP COM 165167101 1,793 50,000 SH X 2 X CHESAPEAKE ENERGY CORP COM 165167101 6,276 175,000 SH X 3 X CHEVRON CORP NEW COM 166764100 20,620 250,000 SH X 2 X CHEVRON CORP NEW COM 166764100 4,479 54,300 SH X 3 X CHICAGO BRIDGE & IRON CO N V NY REGISTRY SH 167250109 9,235 480,000 SH X 2 X CHICAGO BRIDGE & IRON CO N V NY REGISTRY SH 167250109 3,656 190,000 SH X 3 X CHUBB CORP COM 171232101 1,647 30,000 SH X 3 X COCA COLA CO COM 191216100 1,370 25,900 SH X 3 X COMCAST CORP NEW CL A 20030N101 665 33,900 SH X 3 X CONOCOPHILLIPS COM 20825C104 23,440 320,000 SH X 2 X CONOCOPHILLIPS COM 20825C104 29,945 408,800 SH X 3 X COSTCO WHSL CORP NEW COM 22160K105 1,948 30,000 SH X 3 X DARWIN PROFESSIONAL UNDERWRI COM 237502109 291,535 9,371,096 SH X 3 X DEERE & CO COM 244199105 1,485 30,000 SH X 3 X DELL INC COM 24702R101 227 13,800 SH X 3 X DEVON ENERGY CORP NEW COM 25179M103 36,708 402,500 SH X 2 X DEVON ENERGY CORP NEW COM 25179M103 25,080 275,000 SH X 3 X DISNEY WALT CO COM DISNEY 254687106 1,381 45,000 SH X 3 X DOMTAR CORP COM 257559104 2,006 436,000 SH X 2 X DOMTAR CORP COM 257559104 754 164,000 SH X 3 X DU PONT EI DE NEMOURS & CO COM 263534109 1,411 35,000 SH X 3 X EOG RES INC COM 26875P101 5,636 63,000 SH X 2 X EOG RES INC COM 26875P101 9,572 107,000 SH X 3 X EXXON MOBIL CORP COM 30231G102 2,330 30,000 SH X 3 X FPL GROUP INC COM 302571104 9,507 189,000 SH X 2 X FPL GROUP INC COM 302571104 3,823 76,000 SH X 3 X FEDEX CORP COM 31428X106 1,186 15,000 SH X 3 X FIDELITY NATL FINANCIAL CL A 31620R105 3,584 243,800 SH X 2 X FIDELITY NATL FINANCIAL CL A 31620R105 735 50,000 SH X 3 X FLOTEK INDS INC DEL COM 343389102 2,530 230,000 SH X 2 X FLOTEK INDS INC DEL COM 343389102 1,650 150,000 SH X 3 X GENERAL ELECTRIC CO COM 369604103 1,775 69,600 SH X 3 X GLAXOSMITHKLINE PLC SPONSORED ADR 37733W105 300 6,900 SH X 3 X GLOBAL INDS LTD COM 379336100 20,195 2,910,000 SH X 2 X GLOBAL INDS LTD COM 379336100 7,565 1,090,000 SH X 3 X HOME DEPOT INC COM 437076102 518 20,000 SH X 3 X INTEL CORP COM 458140100 1,311 70,000 SH X 3 X INTERNATIONAL BUSINESS MACHS COM 459200101 1,474 12,600 SH X 3 X INTUIT COM 461202103 632 20,000 SH X 3 X ISHARES INC MSCI JAPAN 464286848 988 92,700 SH X 3 X 1 SECURITIES AND EXCHANGE COMMISSIONS FORM 13F INFORMATION PREPARED FOR ALLEGHANY CORPORATION AS OF 09/30/08 COLUMN 1 COLUMN 2 COLUMN 3 COLUMN 4 COLUMN 5 COLUMN 6 COLUMN 7 COLUMN 8 ---------------------------- -------------- --------- --------- ------------------- --------------- -------- -------------- INVESTMENT VOTING DISCRETION AUTHORITY MARKET --------------- -------------- 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) ---------------------------- -------------- --------- --------- ---------- --- ---- ---- ---- ----- -------- ---- ---- ---- ISHARES TR S&P 500 INDEX 464287200 759 6,500 SH X 3 X JOHNSON AND JOHNSON COM 478160104 1,787 25,800 SH X 3 X KELLOGG CO COM 487836108 1,122 20,000 SH X 3 X KEY ENERGY SVCS INC COM 492914106 5,742 495,000 SH X 2 X KEY ENERGY SVCS INC COM 492914106 2,378 205,000 SH X 3 X KOHLS CORP COM 500255104 387 8,400 SH X 3 X LAUDER ESTEE COS INC CL A 518439104 1,248 25,000 SH X 3 X LEGG MASON INC COM 524901105 335 8,800 SH X 3 X LILLY ELI & CO COM 532457108 1,541 35,000 SH X 3 X LINCOLN NATIONAL CORP IND COM 534187109 769 17,963 SH X 3 X MANPOWER INC COM 56418H100 647 15,000 SH X 3 X MARRIOTT INTL INC NEW CL A 571903202 913 35,000 SH X 3 X MCDERMOTT INTL INC COM 580037109 4,344 170,000 SH X 2 X MCDERMOTT INTL INC COM 580037109 2,427 95,000 SH X 3 X MEDTRONIC INC COM 585055106 1,844 36,800 SH X 3 X MICROSOFT CORP COM 594918104 2,269 85,000 SH X 3 X MILLIPORE CORP COM 601073109 1,376 20,000 SH X 3 X MOTOROLA INC COM 620076109 311 43,500 SH X 3 X NEWFIELD EXPL CO COM 651290108 230 7,200 SH X 3 X NEWS CORP CL A 65248E104 839 70,000 SH X 3 X NOBLE ENERGY INC COM 655044105 1,668 30,000 SH X 3 X NORDSTROM INC COM 655664100 865 30,000 SH X 3 X NOVARTIS AG SPONSORED ADR 66987V109 1,321 25,000 SH X 3 X NUSTAR ENERGY LP UNIT COM 67058H102 5,564 131,000 SH X 2 X NUSTAR ENERGY LP UNIT COM 67058H102 2,505 59,000 SH X 3 X OLD REP INTL CORP COM 680223104 21,038 1,650,000 SH X 3 X PETROLEO BRASILEIRO SA PETRO SPONSORED ADR 71654V408 7,846 178,500 SH X 2 X PETROLEO BRASILEIRO SA PETRO SPONSORED ADR 71654V408 3,142 71,500 SH X 3 X PFIZER INC COM 717081103 12,447 675,000 SH X 2 X PFIZER INC COM 717081103 5,993 325,000 SH X 3 X PLAINS EXPL& PRODTN CO COM 726505100 2,408 68,500 SH X 2 X PLAINS EXPL& PRODTN CO COM 726505100 1,108 31,500 SH X 3 X PROCTER & GAMBLE CO COM 742718109 2,335 33,500 SH X 3 X SPDR TR UNIT SER 1 78462F103 766 6,600 SH X 3 X SPDR GOLD TRUST GOLD SHS 78463V107 587 6,900 SH X 3 X SANOFI AVENTIS SPONSORED ADR 80105N105 214 6,500 SH X 3 X SCHLUMBERGER LTD COM 806857108 1,952 25,000 SH X 3 X SIEMENS A G SPONSORED ADR 826197501 1,174 12,500 SH X 3 X SIGMA ALDRICH CORP COM 826552101 1,048 20,000 SH X 3 X SONY CORP ADR NEW 835699307 772 25,000 SH X 3 X STATE STR CORP COM 857477103 853 15,000 SH X 3 X STATOILHYDRO ASA SPONSORED ADR 85771P102 2,916 122,500 SH X 2 X STATOILHYDRO ASA SPONSORED ADR 85771P102 1,011 42,500 SH X 3 X SYSCO CORP COM 871829107 925 30,000 SH X 3 X TARGET CORP COM 87612E106 383 7,800 SH X 3 X TEXAS INSTRS INC COM 882508104 495 23,000 SH X 3 X 3M CO COM 88579Y101 1,503 22,000 SH X 3 X TIME WARNER INC COM 887317105 468 35,700 SH X 3 X TIME WARNER CABLE COM 88732J108 632 26,100 SH X 3 X TRICO MARINE SERVICES INC COM NEW 896106200 5,337 312,500 SH X 2 X TRICO MARINE SERVICES INC COM NEW 896106200 2,349 137,500 SH X 3 X US BANCORP DEL COM NEW 902973304 245 6,800 SH X 3 X UNITEDHEALTH GROUP INC COM 91324P102 239 9,400 SH X 3 X VALERO ENERGY CORP NEW COM 91913Y100 5,151 170,000 SH X 2 X WAL MART STORES INC COM 931142103 2,695 45,000 SH X 3 X WASHINGTON POST CO CL B 939640108 835 1,500 SH X 3 X WELLS FARGO & CO NEW COM 949746101 1,464 39,000 SH X 3 X WEYERHAUSER CO COM 962166104 1,212 20,000 SH X 3 X WYETH COM 983024100 7,019 190,000 SH X 2 X WYETH COM 983024100 3,140 85,000 SH X 3 X XTO ENERGY INC COM 98385X106 6,652 143,000 SH X 2 X XTO ENERGY INC COM 98385X106 8,932 192,000 SH X 3 X ZENITH NATL INS CORP COM 989390109 4,250 116,000 SH X 3 X GRAND TOTAL 1,146,846 31,059,199 2