12. Mark Brunell
A true Jacksonville Jaguars’ legend, Brunell spent six seasons with the franchise and led them to their first-ever championship game. Furthermore, he won a Super Bowl with the New Orleans Saints in 2009. The three-time Pro Bowler passed for over 32,000 yards in his spectacular career. When you’re as brilliant as Brunell was, then you’ll make millions of dollars in salary and endorsements.
Brunell’s career ended in 2011 and he ran out of money very soon after. He was down to just over five million dollars but owed $25 million in debts. In total, he lost about $50 million including several spectacular real estate busts. It turns out that plunging your cash into mansions isn’t always a good idea. Meanwhile, his Whataburger franchise also failed.