On December 3, 2004, President Bush nominated Bernard Kerik to head the Department of Homeland Security, reportedly after Giuliani had repeatedly made a “personal pitch to the White House” on Kerik's behalf. Giuliani had appointed Kerik New York City Police Commissioner in 2000 -- even after Giuliani was reportedly briefed on Kerik's ties to what the Times described as a company “suspected of links to organized crime” -- and the two were reportedly “literally inseparable on 9/11 and in the months that followed.”

On December 10, 2004, Kerik withdrew his nomination. Bronx District Attorney Robert Johnson subsequently began investigating Kerik for corruption, resulting in Kerik's 2007 indictment on 16 counts. In 2009, Kerik pleaded guilty to eight felonies, including two counts of tax fraud, one count of making a false statement on a loan application, and five counts of making false statements to the government. The last charges “stemmed from statements Mr. Kerik made to the White House during the vetting process after the Bush administration nominated him to lead the Department of Homeland Security.” In 2010, Kerik was sentenced to four years in prison.