Sports figure(s) involved: Michael Jordan
Year: 2002

Karla Knafel was one of (likely) many Michael Jordan mistresses, but she must have been special because No. 23 offered her $5,000,000 after he retired to stay silent about their affair. Knafel sued Jordan in 2002 claiming that MJ reneged on his bizarre offer and told the court that he confided in her that his marriage to now ex-wife Juanita was calculated to "maintain his favorable public image." Jordan won the case, but has seemingly been the target of a paternity suit every year since and divorced Juanita in 2007, a separation that cost a Jordan a reported $168,000,000 settlement. You can't win them all, MJ.