THE CORPORATE LIBRARY

Related Party Transactions and Outside Related Director Information

Affirmative Insurance Holdings, Inc. (AFFM)

5/1/2006 Proxy Information

Mr. Kalichstein serves on the board of managers of New Affirmative, which is a majority stockholder of Affirmative Insurance Holdings, Inc.

Mr. Ryan serves on the board of managers of New Affirmative, which is a majority stockholder of Affirmative Insurance Holdings, Inc.

New Affirmative LLC

New Affirmative LLC, owner of 50.9% of our stock as of the Record Date made changes in the composition of our Board on November 9, 2005 by nominating for election and voting for Kevin R. Callahan, Nimrod T. Frazer, David L. Heller, Avshalom Y. Kalichstein and Michael J. Ryan as members of the Board. Each of Messers Heller, Kalichstein and Ryan have disclaimed beneficial ownership. Further, each of Messers Frazer, Heller, Kalichstein and Ryan have directed that all compensation received for their service as a director be paid directly to their respective related employers. Finally, each of Messers Callahan, Frazer, Heller, Kalichstein and Ryan have opted to reject the stock options as automatically awarded as initial inducement and annual incentive awards as provided in the Company’s Amended and Restated 2004 Stock Incentive Plan.