Terrell Owens
T.O. could have one of the NFL’s most endearing stars, but instead, he’s now on the outside trying to find his way back in. For over 15 years, he was known for his lavish touchdown celebrations and made more than $80 Million.
Now, he’s got very little to show for it. Between child support payments, numerous fines and some bad investments, he’s broke. His biggest mistake was investing in a large entertainment complex in Alabama that was not only illegal in the state, it violated the NFL’s policy on players investing in gambling. That mistake cleaned him (and numerous other NFL players) out. He should have checked the rules first.