Rick DiPietro — Islanders 15-Year/$67.5M Deal

Rick DiPietro's 15-year, $67.5 million contract remains the NHL's longest and most catastrophic bet on a goalie, costing the Islanders $4.5 million annually for just 50 games in the final eight seasons. His career save percentage of .902 ranked dead last among starters over that span, while injuries—including concussions and hip surgery—sidelined him for 76% of possible games after year five. The 2000 first overall pick never matched his lone All-Star season (2006–07), when he posted a .919 save percentage. Compared to #7 Tobias Harris's deal, DiPietro produced 80% fewer minutes per dollar, making his buyout a $19.5 million sunk cost.