The biggest douchebag in sports has also earned more money from professional sports franchises than any other athlete in history. The 10-year, $275,000,000 contract he got from the Yankees in 2008 is the largest contract in sports history. Guess who has the second-largest sports contract? Alex Rodriguez. The $252,000,000 deal he got from the Rangers in 2001 was the largest in history before his Yankees deal. Those are some serious Ms.