Filed Pursuant to Rule 424(b)(3) Registration No. 333-44643 Prospectus Supplement (To Prospectus dated January 21, 1998) SYMONS INTERNATIONAL GROUP, INC. 1996 STOCK OPTION PLAN The purpose of this prospectus supplement is to provide updated information related to certain of the selling shareholders under the Symons International Group, Inc. 1996 Stock Option Plan. Name of Selling Common Stock to Percentage of Shareholder and Number of be Owned After Common Stock Position With the Shares Shares Subject Exercise of Option Owned After Company Owned(1) to Option Exercise of Option - ------------------------- ------------ ------------------- -------------------- ------------------------ G. Gordon Symons, Chairman 643,900(1a) 633,900 643,900 6.2% Alan G. Symons, CEO 383,400(2) 320,900 383,400 3.7% Douglas H. Symons, President and COO 201,300(3) 172,800 201,300 1.9% David L. Bates, Vice President, General Counsel and Secretary 23,750(4) 23,750 23,750 Less than 1% Gary P. Hutchcraft, Vice President, CFO and Treasurer 38,200(5) 34,500 38,200 Less than 1% Dennis G. Daggett, President, COO of IGF Insurance Company 66,500(6) 56,500 66,500 Less than 1% Thomas F. Gowdy, Executive Vice President, IGF Insurance Company 48,650(7) 46,000 48,650 Less than 1% The date of this Prospectus Supplement is January 22, 1999. Name of Selling Common Stock to Percentage of Shareholder and Number of be Owned After Common Stock Position With the Shares Shares Subject Exercise of Option Owned After the Company Owned (1) to Option Exercise of Option - ------------------------- ------------ ------------------- -------------------- ------------------------ Roger C. Sullivan, Executive Vice President, Superior Insurance Company 50,500(8) 48,000 50,500 Less than 1% Robert C. Whiting, Director 24,800(9) 10,000 24,800 Less than 1% James G. Torrance, Director 14,000(9) 10,000 14,000 Less than 1% David R. Doyle, Director 15,000(9) 10,000 15,000 Less than 1% John K. McKeating, Director 12,000(9) 10,000 12,000 Less than 1% Jerome B. Gordon, Former Director 5,000(21) 5,000 5,000 Less than 1% J. Ross Schofield, Director of Goran Capital Inc. 4,000(10) 3,000 4,000 Less than 1% David B. Shapira, Director of Goran Capital Inc. 4,000(10) 3,000 4,000 Less than 1% Ronald Chapman, Former Employee, Symons International Group, Inc. 1,665 1,665 1,665 Less than 1% Elizabeth N. Symons, Former Employee, Symons International Group, Inc. 3,333(10a) 5,000 3,333 Less than 1% Terry E. Diers, Vice President, Pafco General Insurance Company 3,500(11) 1,500 3,500 Less than 1% John L. Mason, Former Employee, IGF Holdings, Inc. 2,667 2,667 2,667 Less than 1% Name of Selling Common Stock to Percentage of Shareholder and Number of be Owned After Common Stock Position With the Shares Shares Subject Exercise of Option Owned After the Company Owned (1) to Option Exercise of Option - ------------------------- ------------ ------------------- -------------------- ------------------------ Carol Sorvik, Employee, IGF Holdings, Inc. 2,000(13) 2,000 2,000 Less than 1% Brian Donoho, Employee, IGF Holdings, Inc. 3,000(13) 3,000 3,000 Less than 1% Steven Wilson, Employee, IGF Holdings, Inc. 1,500(11) 1,500 1,500 Less than 1% Steve Griffin, Employee, IGF Holdings, Inc. 1,900(15) 1,200 1,900 Less than 1% Eric Pugh, Employee, IGF Holdings, Inc. 1,500(11) 1,500 1,500 Less than 1% Floyd Crain, Employee, IGF Holdings, Inc. 500(14) 500 500 Less than 1% Laura Britton, Employee, IGF Holdings, Inc. 200(16) 200 200 Less than 1% Debbie Rubadou, Employee, GGS Management, Inc. 2,000(13) 2,000 2,000 Less than 1% Jack Stone, Employee, GGS Management, Inc. 3,000(10) 3,000 3,000 Less than 1% Bob Collins, Employee, GGS Management, Inc. 1,000(20) 1,000 1,000 Less than 1% Doug Markel, Employee, GGS Management, Inc. 1,000(20) 1,000 1,000 Less than 1% Mark Gozdecki, Employee, Vice President, GGS Management, Inc. 6,000(17) 6,000 6,000 Less than 1% Name of Selling Common Stock to Percentage of Shareholder and Number of be Owned After Common Stock Position With the Shares Shares Subject Exercise of Option Owned After the Company Owned (1) to Option Exercise of Option - ------------------------- ------------ ------------------- -------------------- ------------------------ Gloria Valvasori, Employee, Goran Capital Inc. 2,150(18) 750 2,150 Less than 1% Carl Schnaufer, Vice President, Chief Information Officer 10,000(9) 10,000 10,000 Less than 1% Elise Quadrozzi, Employee, GGS Management, Inc. 2,000(13) 2,000 2,000 Less than 1% James J. Lund, Vice President, Chief Accounting Officer 2,300(13) 2,000 2,300 Less than 1% John Sheeley, Employee, IGF Holdings, Inc. 2,000(13) 2,000 2,000 Less than 1% Jim Petersen, Employee, IGF Holdings, Inc. 2,000(13) 2,000 2,000 Less than 1% Doug Burns, Employee, IGF Holdings, Inc. 2,000(13) 2,000 2,000 Less than 1% Mike Scott, Vice President, Pafco General Insurance Company 2,000(13) 2,000 2,000 Less than 1% Pat Pfeiffer, Employee, GGS Management, Inc. 1,000(20) 1,000 1,000 Less than 1% Karen Stroud, Employee, GGS Management, Inc. 1,000(20) 1,000 1,000 Less than 1% Daryl Mason, Employee, GGS Management, Inc. 1,000(20) 1,000 1,000 Less than 1% Name of Selling Common Stock to Percentage of Shareholder and Number of be Owned After Common Stock Position With the Shares Shares Subject Exercise Owned After the Company Owned (1) to Option of Option Exercise of Option - ------------------------- ------------ ------------------- -------------------- ------------------------ Susan Knotts, Employee, GGS Management, Inc. 500(14) 500 500 Less than 1% Robert Herzog, Employee, GGS Management, Inc. 1,100(14) 500 1,100 Less than 1% Henry Klosky, Employee, GGS Management, Inc. 500(14) 500 500 Less than 1% Brenda Armstrong, Employee, GGS Management, Inc. 800(14) 500 800 Less than 1% Brad Glenn, Employee, IGF Holdings, Inc. 5,000(21) 5,000 5,000 Less than 1% David Glenn 5,000(21) 5,000 5,000 Less than 1% Gary Dau, Employee, IGF Holdings, Inc. 5,000(21) 5,000 5,000 Less than 1% (1) Includes common shares subject to options some of which for certain individuals have not yet vested and therefore are not exercisable within 60 days of the date hereof, although such shares are not "beneficially" owned within the meaning of Section 13(3) of the Exchange Act. (1a) Includes 633,900 shares issuable upon exercise of options. (2) Includes 320,900 shares issuable upon exercise of options. (3) Includes 172,800 shares issuable upon exercise of options. (4) Includes 23,750 shares issuable upon exercise of options. (5) Includes 34,500 shares issuable upon exercise of options. (6) Includes 56,500 shares issuable upon exercise of options. (7) Includes 46,000 shares issuable upon exercise of options. (8) Includes 48,000 shares issuable upon exercise of options. (9) Includes 10,000 shares issuable upon exercise of options. (10) Includes 3,000 shares issuable upon exercise of options. (10a) Includes 3,333 shares issuable upon exercise of options. (11) Includes 1,500 shares issuable upon exercise of options. (13) Includes 2,000 shares issuable upon exercise of options. (14) Includes 500 shares issuable upon exercise of options. (15) Includes 1,200 shares issuable upon exercise of options. (16) Includes 200 shares issuable upon exercise of options. (17) Includes 6,000 shares issuable upon exercise of options. (18) Includes 750 shares issuable upon exercise of options. (20) Includes 1,000 shares issuable upon exercise of options. (21) Includes 5,000 shares issuable upon exercise of options. An aggregate of up to 1,500,000 shares of Common Shares may be offered and sold pursuant to this Prospectus by the selling shareholders.