3. Terrell Owens
An obnoxious teammate but an excellent player, Owens was a superb wide receiver. Sure, he hated almost every quarterback he lined up beside him but he still made the Hall of Fame after a brilliant career. The six-time Pro Bowler was as flamboyant on the field as he was off it. Meanwhile, he made a massive fortune including an estimated $80 million in salaries from six NFL teams.
However, Owens lost almost all of his massive fortune after living too large. He spent so much money on properties that he ended up paying $750,000 per month on mortgages alone. When the housing market crashed, he couldn’t find renters. Then there was a disastrous entertainment complex in Alabama that was a hammer blow. Owens also made all of the mistakes involving jewelry and fancy cars, but high-risk investments were his biggest problem.