Damon went from being loathed to loved by New York fans during his four years as a Yankee, helping lead the team to a 2009 World Series Championship. He has since relocated from Detroit to Tampa.

Damon grew up in Orlando and was drafted by the Kansas City Royals straight out of high school. After six seasons with the Royals and one with the Oakland Athletics, in 2001 he signed with the Red Sox and became one of the most popular members of the team, helping guide them to a World Series victory in 2004, a run that included a shudder-inducing victory over the Yankees in the League Championship Series—he hit two home runs, including a grand slam in Game 7 of the ALCS to clinch the victory over New York. In 2005, the Yankees signed him, prompting Beantown fans to view him as a traitor. Just four years later, and after helping the Yankees to a World Series Championship in 2009, Damon was back on the move. He signed with the Detroit Tigers and then was bounced to the Tampa Bay Rays in 2011.

It's unlikely that any team in history was as overexposed as the 2004 Boston Red Sox, and it's unlikely that any player on that team was as overexposed as Damon. His zany persona and caveman looks quickly went from cute to irritating, and after the World Series win he cashed in with a slew of off-field ventures. He's the co-author, along with Peter Golenbock, of the autobiography Idiot: Beating "The Curse" and Enjoying the Game of Life. And his onscreen appearances have included the movie Fever Pitch, Saturday Night Live, and Queer Eye for the Straight Guy.

He was married to Angela Vannice from 1992 to 2002; the couple had twins in 1999. Damon has admitted to philandering and having a drinking problem during the marriage. He married Michelle Mangan in 2004, and the couple had a daughter named Devon in January 2007. His second marriage has been dogged by rumors that Michelle is a former stripper, a charge the couple angrily denies. [Image via Getty]