Sport: Baseball
Team(s): New York Mets (1986); New York Yankees (1996, 1998, 2000)
Champion: World Series (1986, 1996, 1998, 2000)
Offense(s): Drug possession and solicitation of prostitution
Sentence: 18 months. Initially suspended in 1999, but reinstated following 2002 probation violation.

Darryl Strawberry and Doc Gooden were supposed to be the New York Mets saving grace, and at the beginning it looked like the duo would be. They were the essential pieces in the '86 Mets World Championship team. Then everything went to hell from there. 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.

Then, in 1995, 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. In 2012 Strawberry reportedly owed the IRS $500K in back taxes and another million to his ex-wife in child support.