The 10 Worst NHL Trades of the Past Quarter Century
The NHL is filled with transactions that have changed the course of franchises, but not all trades are created equal. Some of the most regrettable deals in league history have left fans scratching their heads for years. Whether it’s due to a star player being traded away or the return being underwhelming, these trades stand out as some of the worst the NHL has seen over the past 25 years. Let’s take a look at 10 of the most head-scratching deals in recent NHL history.
1. Wayne Gretzky to the Los Angeles Kings (1988)
Although it happened just outside the 25-year window, it’s hard to discuss poor trades without mentioning this one. The Edmonton Oilers sent the Great One, Wayne Gretzky, to Los Angeles in exchange for a package of players, picks, and cash. While this trade is more known for the monumental shift it caused in the league, the Oilers’ return ultimately didn’t match Gretzky’s legendary status, and it marked the beginning of a decline for the Oilers.
2. Phil Kessel to the Toronto Maple Leafs (2009)
In a deal that saw the Boston Bruins send Kessel to Toronto in exchange for two first-round picks and a second-round pick, it’s clear who won. Kessel went on to have a successful tenure with the Maple Leafs, even leading them to the playoffs after years of mediocrity. The Bruins, meanwhile, saw their picks turn into Tyler Seguin and Dougie Hamilton, both of whom became integral parts of Boston’s future success, including a Stanley Cup championship.
3. Erik Karlsson to the San Jose Sharks (2018)
When the Ottawa Senators traded their franchise defenseman Erik Karlsson to San Jose for a hefty return, including draft picks and young players, it looked like a deal that could work for both sides. However, the Senators came away with little immediate benefit, while Karlsson’s time in San Jose was marred by injuries, and the Sharks did not make it to a Stanley Cup final during his tenure.
4. Ryan O’Reilly to the St. Louis Blues (2018)
The Buffalo Sabres traded Ryan O’Reilly, one of their top players, to the St. Louis Blues for a package that included young prospects and picks. O’Reilly immediately turned into a key piece of the Blues’ Stanley Cup run, winning the Conn Smythe Trophy as playoff MVP. Meanwhile, the Sabres saw little in return, and their rebuilding efforts were hampered by the trade.
5. Taylor Hall to the Arizona Coyotes (2020)
The New Jersey Devils traded Taylor Hall, the 2018 Hart Trophy winner, to the Arizona Coyotes in exchange for a conditional first-round pick and a few prospects. Arizona struggled with Hall’s fit, and the Devils received little for one of the league’s brightest stars. Hall would go on to sign with Buffalo and later Boston, but this trade remains a significant misstep for the Coyotes.
6. Joe Thornton to the San Jose Sharks (2005)
The Boston Bruins dealt Joe Thornton to the Sharks for a package that included Marco Sturm, Wayne Primeau, and Brad Stuart. While Thornton went on to become one of the best centers of his era with San Jose, the Bruins saw little immediate return. This trade was one of the worst in recent memory for Boston, as Thornton became a superstar, and the Bruins struggled to replace his production.
7. Jesperi Kotkaniemi to the Carolina Hurricanes (2021)
In one of the most bizarre restricted free-agent offer-sheet deals in recent memory, the Carolina Hurricanes signed Jesperi Kotkaniemi to an offer sheet, forcing the Montreal Canadiens to either match the deal or let him go. Montreal chose to not match the offer, and Kotkaniemi moved to Carolina, where he has yet to live up to his potential. Montreal’s loss here was compounded by the fact that they never truly received enough for a highly drafted prospect.
8. Zdeno Chara and Jason Spezza to the Ottawa Senators (2006)
The Ottawa Senators traded Zdeno Chara, a young defenseman, and Jason Spezza, a high-profile prospect, to the Toronto Maple Leafs for a collection of players and picks. Chara would go on to become one of the best defensemen in NHL history with the Boston Bruins, while Spezza blossomed into a star center. Meanwhile, the Leafs’ return never made a lasting impact, and this trade remains one of their most regrettable.
9. Dany Heatley to the Ottawa Senators (2005)
In a deal that sent Dany Heatley from the Atlanta Thrashers to the Ottawa Senators, the Thrashers received a package that included Marian Hossa. While Hossa would eventually be a key part of the Blackhawks’ dynasty, Heatley became a star in Ottawa, leading the team’s offense and becoming a fan favorite. The Thrashers’ long-term rebuild did not benefit from this deal, as Hossa was moved again, and the franchise ultimately struggled.
10. Mike Richards to the Los Angeles Kings (2011)
The Philadelphia Flyers traded Mike Richards to the Los Angeles Kings in exchange for a group of players and picks, hoping to shake things up. Richards went on to help the Kings win two Stanley Cups, becoming a key leader for the team. The Flyers never saw similar success with the return and ended up regretting the trade as they searched for stability in their lineup.
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These trades highlight how poor decision-making in the NHL can have long-term ramifications. Whether it’s trading away a franchise player or failing to get value in return, these trades stand as cautionary tales for general managers everywhere.
