What is the worst contract in sports history?

Bob Loblaw: That's an awful lot of words to defend a player (DiPietro) who has played 164 games since signing that deal in 2006. I don't think Risk/Reward is a valid take on a question like this. These are 100 million dollar franchises. Yashin, Kovalchuk, Hossa, Werth, Jones, they all have WINNING in common. DiPietro was given this contract based on a small sample of minor league/NHL body of work. He was guaranteed pay with the assumption that he could bring wins to the Islanders for a decade and then some. The outcome is unarguable. Cap hit or not, they are paying $4.5 million per year to a player who can't keep his pads on.