15. Mike Vrabel
As a three-time Super Bowl winner with the New England Patriots, Vrabel was extraordinarily successful. With an estimated $11 million in earnings from his playing career, he was flush with cash. Meanwhile, if he went bankrupt for some reason, he could always sell one of his Super Bowl Rings. According to the Sportster, they’re worth between $30,000 and $50,000 dollars, depending on the athlete and the game.

What we are building up to is this: there was no need for Vrabel to steal a couple of bottles of liquor from a deli in 2011. He could have bought the deli if he wanted to. Las Vegas police arrested him for his shenanigans, which he labeled a misunderstanding. They released him on a bond of $600 which was obviously more than the cost of the alcohol. All in all, it was extremely foolish.