Sport: Baseball
Criminal History: Drug possession, domestic violence, soliciting a prostitute
Time Behind Bars: 11 months

Darryl Strawberry and Doc Gooden were supposed to be the New York Mets saving grace, the cornerstones of a dynasty. Instead, their brilliant careers were overshadowed by a series of off the field incidents that played out like a baseball crossbreed of Hard Knocks and Celebrity Rehab with Dr. Drew

Although no criminal charges were filed, Strawberry was arrested on at least three occasions for domestic violence. In one incident he was alleged to have threatened a woman with a .25 caliber handgun after hitting her in the face. He and his agent were indicted on federal tax evasion charges for failing to report some $500K in income. Later, he was arrested and charged with soliciting a prostitute and cocaine possession when he allegedly offered and undercover police officer $50 for sex.

Now, more famous for his arrest record than being a member of the 30-30 Club, Strawberry reportedly owes the IRS $500K in back taxes and another million to his ex-wife in child support.