27. Mark Ingram Sr.
The father of the Alabama Heisman Trophy winner was a great NFL player in his own right. Ingram Sr. played for the Giants for several years and scored the game-winning touchdown in Super Bowl XXV. That was way back in 1991, but it was all downhill from there for the former wide receiver. However, he didn’t manage his money properly and looked for other avenues to bring in dollars when he retired.
Unfortunately, he turned to crime. A combination of defrauding the IRS and money-laundering is definitely enough to land you several years behind bars. The law caught up to him when he was hiding out in a hotel room and was just about to watch his son play on TV in the Sugar Bowl. Furthermore, as well as the jail time, they handed him a massive fine.