Bernard Kerik
A former chauffeur for Rudy Giuliani who rose to become police commissioner of New York City and later a security consultant in Iraq, Bernard Kerik seemed like am eminently justifiable pick to be Secretary of Homeland Security in 2004. But just a week after President Bush announced the nomination, Kerik withdrew his name from consideration, citing problems with the immigration status of a former housekeeper. As other allegations against Kerik surfaced, including tax fraud and corruption, it became increasingly apparent that he would have had trouble clearing the vetting process for a member of the cabinet. The saga is ongoing — in December 2008, Kerik pleaded not guilty to the most recent set of tax fraud charges filed against him, and faces trial on charges of lying to investigators when he was in the running for the Homeland Security position.