One of the worst contracts that comes to mind is the Rick DiPietro contact, which was a 15 year - $67,500,000 contract, which after signing it, DiPietro only played 175 games. That's $385,714 per game! This contract was later bought out on Jul. 3, 2013, which the Islanders are still paying DiPietro $1,500,000 in buyout fees until the end of the 2028-29 season.