The New York Islanders selected Rick DiPietro with the first overall pick in the 2000 NHL Entry Draft.
He was only the second goaltender ever to be taken in the prestigious spot and first since Michel Plasse in 1968 by the Montreal Canadiens.
The Islanders traded away a future Hall of Famer to select DiPietroDiPietro’s mobility and puck-handling skills convinced Islanders general manager Mike Milbury to trade Hall of Fame goalie Roberto Luongo and go all in on the prospect.
Despite playing sparingly over the next six years, more history followed with an incredible 15-year contract — the longest in NHL history.
Per ESPN, only Magic Johnson‘s 25-year Los Angeles Lakers deal from 1981 was longer in US Sports at the time.
Worth $67.5million, the groundbreaking offer was supposed to set the franchise up for glory.
Instead, it turned into probably the worst contract disaster in hockey history.
“I guess it’s pretty beneficial to be a goaltender on Long Island right now,” DiPietro said as the ink dried just a week before his 25th birthday
“Well, 15 years seems like a long time,” he added. “It is a long time.”
“This is not a big deal,” late owner Charles Wang said at the time. “You have to have a commitment to who you’re working with. I’ve done this all my business career. Now I’m doing it in sports and everybody is like, ‘Oh my God. How could he do that?'”
DiPietro was supposed to be paid $4.5million each season until 2021.
“I hope at some point I’m underpaid,” he said. “That means I’m playing really well and becoming an elite goaltender.”
GettyDiPietro’s contract was bought out by the Islanders after injuries derailed his career[/caption]“Clubs are free to make their own decisions within the rules. Time will tell whether this will be a good decision or a bad one for the Islanders,” then-NHL deputy commissioner Bill Daly added ominously
Things initially got off to a decent start as DiPietro broke the Islanders franchise with 56 saves in a loss to the New York Rangers in 2007.
But eight days later he suffered a concussion — the first in a series of injuries that destroyed a promising career and earned him the unfortunate nickname ‘Rickety.’
Named as a starter in his first — and only — All-Star Game in 2008 after an injury to New Jersey Devils goaltender Martin Brodeur, DiPietro injured his hip during the shootout competition a day before taking the ice.
He played on until the Islanders were out of playoff contention before undergoing surgery.
After managing 63 and 62 games in the two seasons following the contract, the goalie played just 50 over the next five campaigns.
GettyDiPietro is being paid until 2029 as part of the buyout[/caption]The Islanders bought out DiPietro’s contract on July 3, 2013.
The terms of the deal saw the All-Star receive two-thirds of the remaining $36 million he was due as a $1.5 million payment every year until 2029.
DiPietro could have put his feet up and watched the money roll in but tried to keep his hockey career going.
He signed a professional tryout contract on October 25, 2013, with the Carolina Hurricanes‘ AHL affiliate, the Charlotte Checkers, but was cut a month later.
The former pro currently hosts ESPN 98.7 FM New York’s DiPietro and Rothenberg with Dave Rothenberg.
He has been working as an analyst for ESPN’s NHL coverage since the 2021-22 season.
DiPietro wanted to be an Islander for life but injuries turned him into a costly mistake that the current regime is still paying for.
Unsurprisingly, his lengthy contract has not been repeated since, although Ilya Kovalchuk had a 17-year deal rejected by the league.
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