Sports figure(s) involved: Rick Pitino
Year: 2009

In 2003 Rick Pitino had sex with the soon-to-be wife of his equipment manager at an Italian restaurant after closing. According to his testimony in court, the woman whispered something in his ear, unzipped his pants, and initiated intercourse. Six years later, Pitino began receiving threatening calls and letters demanding millions of dollars in cash to stay silent about the tryst. The Louisville coach reported the extortion attempt to the FBI and in 2011 Karen Cunagin Sypher was sentenced to seven years in prison for extortion, lying to the FBI, and retaliation against a witness.