Mookie Blaylock
Mookie Baylock was one of the best defensive players of his time, which helped him earn about $31 million during his career. However, he struggled with alcohol and substance abuse, so a lot of his money was drained due to that along with court troubles. In 2013, he was in a car accident in which he was driving, ending in a fatality. He plead guilty and served 3 years along with 8 years of probation, leaving him without any funds at all.
Terrell Owens
Terrell Owens made about $80 million while playing in the NFL. However, his spending was out of control, and along with having to pay $45,000 a month in child support, he reached the end of his funds, his net worth dwindling down to half a million dollars. He nearly went to jail for avoiding child support payments, but he managed to get work in the CFL and Fan Controlled Football to avoid more issues.