1. Johnny Unitas
Source: Iconosquare
This three-time MVP NFL star is said to be one of the best quarterbacks in the world. Johnny was interested in trying his hand in many different business niches, such as restaurants, bowling, circuit board and air freight. After many attempts at success other than on the football field, none prevailed. Unitas and his wife sadly filed for bankruptcy in 1991. There was more than $3.2 million in debt.