A lot of bad contracts to choose from but the worst of the bunch has got to be Rick DiPietro. Giving any player a 15 year deal is absolute lunacy, but to give a goaltender that takes it to another level altogether. The fact they had to buy him out and are still paying him through 2029, 23 years after signing it is just icing on the cake. No other contract in the history of the NHL will ever top Rick DiPietro's deal. Just the worst of the worst.