Alex Rodriguez, New York Yankees
The embattled former Yankee should get on his hands and knees everyday to thank his lucky stars for the negotiating skills of superagent Scott Boras. That's because over the course of his turbulent career, Boras successfully netted $448 million for the former star; $317 million from the Yanks alone, including one of the richest contracts in baseball history. While the team did score a World Series ring in 2009 with A-Rod in tow, the majority of the slugger's twelve seasons as a Bronx Bomber was spent embroiled in scandal or marred by underperformance, ending with the player departing the team last summer with little notice and no fanfare. Oddly enough, A-Rod fired Boras in 2010.