Ex-NHL top draft pick securures post-retirement income, 16 years later, thanks to a disastrous $67.5 million contract - a deal only surpassed by Magic Johnson's.
The Long and Winding Road: Rick DiPietro's 15-Year NHL Saga
The New York Islanders shook the hockey world in 2000 when they drafted Rick DiPietro with the first overall pick. This move was historic as DiPietro, a goalie, became only the second to be chosen first, following Michel Plasse in 1968 by the Montreal Canadiens.
The Islanders' general manager, Mike Milbury, had a vision. Convinced by DiPietro's mobility and puck-handling skills, he traded away Hall of Famer Roberto Luongo to gamble on the young prospect.
Fast forward to 2006, and DiPietro signed a groundbreaking 15-year contract, valued at $67.5 million. At the time, only Magic Johnson's 25-year Los Angeles Lakers deal from 1981 was longer in US sports. This deal was meant to solidify the Islanders' future. Unfortunately, it turned out to be a roller coaster ride, fraught with injury and performance issues.
In essence, DiPietro's contract, despite its lofty ambitions, seems to rank as one of the most controversial in the history of the National Hockey League (NHL).
NHL's Longest Legacy: A Tale of Hiatus and Comeback
Historically, DiPietro's deal isn't alone in the annals of the NHL. Ilya Kovalchuk, another prolific player, inked a 17-year contract worth $102 million with the New Jersey Devils in 2010. However, the NHL later rejected this deal, citing circumventions of the salary cap rules.
These two contracts, while lengthy and impactful, serve as a cautionary tale for teams committing to long-term deals in the NHL, offering valuable lessons in salary cap management.
Despite the controversy, DiPietro has since refocused on his career as a sports analyst. He currently co-hosts ESPN 98.7 FM New York's DiPietro and Rothenberg with Dave Rothenberg and has been an analyst for ESPN's NHL coverage since the 2021-22 season.
Injuries may have marred DiPietro's career, but his resilience has ensured he remains a significant figure in the world of hockey. His story serves as a reminder that while long-term contracts can bring promise, they can also bear unforeseen challenges.
Sports managers in the NHL have often faced uncertainties with long-term contracts, as seen with Rick DiPietro's 15-year deal worth $67.5 million in 2006. Interestingly, Ilya Kovalchuk's 17-year contract worth $102 million with the New Jersey Devils in 2010 also encountered controversy due to salary cap rules. These incidents highlight the complexities of salary cap management in the NHL and underscore the importance of careful decision-making when committing to long-term contracts in boxing or hockey. Now, as a sports analyst for ESPN, DiPietro continues to contribute significantly to the world of sports, reminding us that even amid challenging circumstances, one can still make a lasting impact.


