Sports figure(s) involved: Brett Favre
Year: 2010

The nerve of Brett fucking Favre. During his '08 season with the Jets, the old gunslinger allegedly left a string of humiliating voicemails and ridiculously unimpressive dick pics to team sideline reporter Jenn Sterger. Favre's moves were especially weird because, by all accounts, Sterger was unreceptive to the quarterback's early advances. That means that this dude was rejected (or at least brushed over) and just started asking her to his hotel room and firing off pictures of his dork *cough* allegedly *cough*. The NFL launched an investigation of misconduct and fined Favre, who was uncooperative with the case, $50,000.