Dan Marino
Easily one of the greatest quarterbacks the NFL has seen. He will always be remembered for his quick release and powerful arm, for leading the Dolphins to the playoffs 10 times in his 17 season career. The Pro Football Hall of Famer also had his Miami Dolphins No. 13 jersey retired. Currently, he ranks 5th, behind behind Brett Favre, Peyton Manning, Tom Brady and John Elway, on the list of most wins by a starting QB, with 147. Unfortunately he’s also remembered for investing a whopping $14 million with the entertainment company named Digital Domain – who created the first ever Tupac Shakur hologram at Coachella. The company ended going belly up not long after Marino’s investment, which caused the QB to lose everything.
Warren Sapp
When Sapp retired, he was just one of eight defensive players in NFL history to make the Pro Bowl, be named Defensive Player of the Year and win a Super Bowl or pre-Super-Bowl NFL title. His career was also clouded with controversy due to his hard-hitting style of play and verbal outbursts, both on and off the field, some of which resulted in fines, and once he was kicked out from a game for unsportsmanlike conduct. And since retiring, he’s had his own series of problems. He bought into some poor real estate, had troubles with child support and alimony, and then ran into issues with the law. Sapp’s $82 million earned during his NFL career is basically all dried up now.