Coming Up on 30 Years: Revisiting The Worst NHL Hire In History

In a few weeks will be the 30-year anniversary of one of the worst hires in league history, one so bad that nearly two decades after the two sides separated, the team is still feeling the effects of the decision to bring in someone who made some incredibly poor decisions.

Mike Milbury, a former NHL player and executive, is perhaps best remembered for his controversial and often criticized trades during his tenure as the general manager of the New York Islanders. Milbury’s run with the Islanders, which lasted from 1995 to 2006, was marked by a series of deals, player swaps, and bad signings that left a lasting impact on the franchise.

In fact, even today, the Islanders are still paying for his mistakes.

Milbury Had More Bad Trades Than Anyone

One of Milbury’s most infamous trades occurred in 2000 when he sent star goaltender Roberto Luongo, along with forward Olli Jokinen, to the Florida Panthers in exchange for forwards Mark Parrish and Oleg Kvasha. Luongo went on to become one of the best goaltenders in the league, while Parrish and Kvasha failed to make a comparable impact with the Islanders. Hilariously, Milbury thought it was a great deal. He noted, “We didn’t get chopped liver in return. We filled the holes we wanted to fill. It’s a win-win day for us. We’re doing a little dance over at the Islanders’ table.”

If that wasn’t bad enough, in the same year, Milbury made another questionable move. He traded away Zdeno Chara, Bill Muckalt, and the second overall pick in the 2001 NHL Draft (which turned out to be Jason Spezza) to the Ottawa Senators for Alexei Yashin. While Yashin had some productive seasons with the Islanders, his large contract and inconsistent performance became a burden on the team.

Milbury’s history of bad trades continued in 2001 when he dealt away future Hall of Famer Chris Osgood to the St. Louis Blues for goaltender Justin Papineau and a second-round pick. Osgood went on to win multiple Stanley Cups with the Detroit Red Wings, while Papineau failed to make a significant impact.

Milbury’s Biggest Whopper Wasn’t Even a Trade

Milbury’s most questionable decision was likely his drafting and signing of goaltender Rick DiPietro. They signed him to a 15-year, $67,500,000 contract on Sep. 12, 2006. Once touted as a future franchise goaltender for the Islanders, he faced a career marred by injuries and unmet expectations. His contract became an albatross, burdening the team’s salary cap. He was bought out on July 1, 2013, and his $1.5 million cost (not cap hit) is on the books for the team until the end of the 2028-29 season.

Despite his controversial tenure with the Islanders, Milbury’s impact on the team extended beyond just the trades. He served as the team’s head coach, and his dual role as both coach and general manager drew criticism for a perceived lack of separation between the two roles.

Was Mike Milbury the Worst Hire In NHL History?

Mike Milbury’s time as general manager of the New York Islanders should be a cautionary tale. It’s one that shows how poor decision-making in trades and management can negatively impact a franchise for years to come. His legacy is one marked by a series of trades that were among the worst in NHL history. A dynasty team at one time, the Islanders have never been close to really contending since.

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