Vince Young
Vince Young was once a star prospect on the Texas Longhorns who looked like he was on his way to being one of the top quarterbacks in the NFL. But, that never really materialized, and instead, he became a cautionary tale of how NOT to spend your career earnings.
Despite being hugely a disappointment, Vince Young still earned around $34 million during his time in the NFL and an additional $30 million from endorsements, much of which he has since spent on ridiculous purchases. Case in point, back in 2007, he reportedly wanted to have as much privacy as possible, so he bought out all the 120 tickets on his Southwest Airlines flight from Houston to Nashville.
In 2012, Young was facing financial problems, and in 2014, he filed for Chapter 11 bankruptcy.