1. Terrell Owens

Terrell Owens is the winner of this list and you will find out why…

Terrell Owens played 15 seasons in the NFL. He is seen as a Hall of Famer by many. He amassed a fortune worth $80 million (more than anyone else featured on this list). Yet he has no money today. Reason? That is a series of misfortune, blunders and bad decisions.

PHOTO: Wikipedia

Let’s begin with his personal reasons first. He has fathered four children with four different women. In 2012, he was paying more than $50,000 monthly on child support. That coupled with a partying lifestyle and a series of bad investments caused the NFL star to fall flat. He has tried getting coaching and commentating roles since 2012, but to no success.