Sport: Baseball
Criminal History: Falsifying financial statements
Time Behind Bars: Currently serving a three-year sentence

Lenny Dykstra might be the worst person in the world. He's never done anything right. During an All-Star career with the Phillies, his high energy style of play was fueled by steroids. As a business person, he exaggerated his prowess by falsifying financial statements. Then, as just some asshole with a computer, he solicited a housekeeper on Craigslistallegedly told the woman the job required a massage, exposed himself during the act, and later held a knife to the woman's throat. Yikes, man.

The appropriately nicknamed Nails was able to build a reputation as a business guru. But when he fell behind on his $18M mansion and lot full of luxury cars, Dykstra was exposed for who he is: a fuck-up white collar criminal.

While he's currently serving a three year sentence for grand theft auto, Dykstra's biggest legal nightmare could come this winter. After pleading guilty to bankruptcy fraud, Dykstra's awaiting sentencing for allegedly hiding and destroying hundreds of thousands of dollars in property that should have gone to his creditors and then lying about it under oath.