Rick DiPietro signed a 15-year $67.5 million deal with the Islanders back in 2006. After successful campaigns in his first two seasons under the new contract, the goalie began a long bout with injuries to his head, hips, knees, and groin. DiPietro has found many unique ways to get injured including the NHL skills competition and a goalie fight. Over the last four seasons, DiPietro has started just 43 games.
The Islanders could buy DiPietro's contract out for $27 million, which would be the biggest buyout in NHL history. He is signed with the team through 2021.
Remarkably, DiPietro came in at second on Grant's list, behind Montreal's Scott Gomez. Gomez's seven-year $51.5 million contract is not nearly as long as DiPietro's, but it is far more costly per season.