Curt Schilling
Source: The Daily Signal
Curt, a former Boston Red ace helped his team erase an 86-year old championship drought which led him to accumulate a lot of money. He didn’t waste away his fortunes from baseball; in 2004, he invested in the state of Rhode Island to the tune of $75 million. Curt also founded a game development company in 2006 known as 38 studios. This was after he retired from baseball. Unfortunately, 38 studios didn’t grow due to poor management. It even failed to service its loans which sparked years of litigation which left Schilling financially crippled. Although he was reluctant to declare personal bankruptcy, his reputation was seriously ruined. According to the Toronto Star, his net worth of $50million at the time he retired shrunk to less than $million, and he had to sell some of his valuable possession to finance his lifestyle.