4. Jerome James

Year: 2005
Contract: $30 million/Five years
Team: New York Knicks
It's safe to say that no player in the history of pro sports has benefited from the contract year phenomenon quite like Jerome James. Hell, this dude didn't even put up a whole year (or half of one) of stellar stats in order cash in on a big contract. All it took for James was two playoff series. While with the SuperSonics, James tripled his regular season stats in the 2004 playoffs posting 12.5 points and 6.8 rebounds in series against the Kings and Spurs. After his signing, James showed up to the Knicks training camp out of shape and spent most of his first season injured or on the bench. Things never improved as James continued to show poor performance in the few minutes that he did play and a lack of conditioning during team practices. The low-point came in the 2007-08 season when James earned $5.8 million for a season in which he played in only two games for a total of five minutes. SMH, at least he lived up to the "Big Snacks" nickname.