Year: 2004, 2006

This isn't the type of list that you want to be distinguishing yourself on, but Neagle takes the dubious honor by being the only athlete to have two separate incidents to his name. In the final year of his contract with the Colorado Rockies, Neagle was caught trying to receive oral sex from a prostitute, prompting the Rockies to void the final year of his contract, and his wife to leave him. Two years later, unsigned and out of the league, a similar incident occured, and Neagle was slapped with 40 hours of community service. Some guys can just never learn, right?