Charlie Batch
Charlie Batch had a moderately successful career in the NFL, but he won two Super Bowls during his time with the Steelers. Though he made a decent amount of money while in the NFL, he filed for bankruptcy in 2011 and nearly had to sell off his Super Bowl rings. He made several bad real estate investments that caused him to reach $8.3 million in debt. However, he managed to pull it together while working on NFLPA as a broadcaster.
Charlie Batch
Shawn Kemp
Shawn Kemp played for the SuperSonics and went on to six All-Star games and led the SuperSonics through a title run in 1996, though they ultimately lost to the Bulls. He made over $91 million during his career, but by 2022, he was broke after dealing with money-draining legal issues and having to keep up with child support for six different families.
Shawn Kemp
