13. Vince Young – $33 Million

Vince Young made a name for himself before even starting a professional career. His 2006 Rose Bowl rush was hailed as “the single greatest individual performance” in the history of College Football. Needless to say, he was a first-round NFL pick and the 2007 Rookie of The Year.

The quarterback was also a 2-time Pro Bowl Pick, earning him the nickname “inVINCEable.” After six seasons, his earnings totaled $33,000,000.

His spending habits give some insight into how Young lost his fortune. As a rookie, he spent $5,000 a week at Cheesecake Factory. During his superstar years, Vince picked up the tab (around $6,000 according to an employee) for everyone at a local TGI Fridays, where the team hung out after practice. And after each home game, he’d down $700 shots of ‘Louis XIII’ at a Nashville bar.

To fly home from a 2007 game, VY bought out every seat on a Southwest Airlines plane – that’s 120 seats for a 2-hour flight. And, in 2010, his credit card issuer denied a 1:00a.m. request for $8,000 in singles. Young probably just shrugged and decided to use $20’s to ‘make it rain’ at the club instead.

Someone should have told Vince that being inVINCEable on the field didn’t mean his career was too. After multiple injuries received in 2011, no one was willing to sign him. Young filed for bankruptcy in 2014, claiming assets worth one million and a debt of over $10,000,000.