1. Ricky Williams
Ricky Williams was known for being a great running back, but was also one big mess up. He was fond of using drugs which was well documented, and he was suspended from the NFL for long time, which at this point he took to doing a circus act for Toronto Argonauts as the CFL for the year.
There was no doubt of his class on this field, but distress always accompanied him. In 2014, he again filed lawsuit in Texas law courts against Peggy Fulford, a financial advisor. Ricky had always entrusted his financial verdicts to advisors. He made wrong financial judgements and his finances were absolutely in trouble.