3. Michael Vick
In 2005, Michael Vick signed for Atlanta Falcons to a 10-year deal that was worth $130 million. This deal made him the record of richest contract in NFL time. Nevertheless, in 2007, Vick pleaded guilty to some criminal concerns related to dog fighting. He lost all the deals.
Furthermore, Michael Vick had to repay the Falcons for around $20 million of his original $37 million authorization bonus. In 2008, he lost his NFL contract and all his million dollar certification deals. Vick then filed for bankruptcy.