15 NHL Trades That Came Back to Haunt Teams Almost Immediately
Trading away a superstar is always a gamble. Usually, teams are forced into it by contract disputes or internal tension, or it’s just a poor read on talent and a short-sighted attempt to shake up the roster. And when those deals go wrong, they go really wrong. Here are times NHL franchises shipped out stars and quickly realized they made a big mistake.
Chicago Blackhawks Trade Phil Esposito (1967)
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Chicago misjudged Phil Esposito’s potential and sent him to Boston in a multi-player deal. The Bruins gave him a prime role, and he became the league’s leading scorer multiple times and rewrote franchise records.
Edmonton Oilers Trade Wayne Gretzky (1988)
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As one of the best hockey players, Wayne Gretzky became the Oilers’ identity. However, financial pressure led Edmonton to send him to Los Angeles. The Kings became a must-watch team overnight, while Gretzky’s star grew even brighter.
Montreal Canadiens Trade Patrick Roy (1995)
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Patrick Roy’s departure began with one brutal game against Detroit and ended with him hoisting the Stanley Cup for Colorado just months later. The Canadiens received three players who never became difference-makers. In Montreal, the netminder carousel spun for years. Roy, meanwhile, added to his legend, and Avalanche fans got the star their new franchise needed.
Calgary Flames Trade Brett Hull (1988)
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Brett Hull was only starting to show his potential when the Flames sent him to St. Louis. They wanted to balance the roster, but they gave away a pure scorer. Hull erupted with the Blues, eventually scoring 86 goals in a season.
Vancouver Canucks Trade Cam Neely (1986)
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The Canucks had doubts about Cam Neely’s development and sent him to Boston along with a high draft pick. In a Bruins jersey, Neely became one of the league’s most intimidating forwards. Barry Pederson, the player Vancouver acquired, showed flashes of skill but never returned to form.
Winnipeg Jets Trade Teemu Selanne (1996)
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Even though he was the face of the team, Teemu Selanne got moved as Winnipeg prepared to relocate. Anaheim picked him up and watched him thrive immediately. His chemistry with Paul Kariya became the stuff of highlight reels.
New York Rangers Trade Rick Middleton (1976)
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Rick Middleton showed promise but had a reputation for partying, which made the Rangers uneasy. They traded him to Boston for Ken Hodge, a player near the end of his career. Under Don Cherry’s guidance, Middleton transformed into a consistent top scorer.
Edmonton Oilers Trade Mark Messier (1991)
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Mark Messier left Edmonton after expressing frustration with the team’s direction. The Rangers were happy to take him, and it paid off. Messier won the Hart Trophy and helped New York snap its championship drought.
Montreal Canadiens Trade Chris Chelios (1990)
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Concerned about the wear on Chris Chelios’ knees, the Canadiens sent him to Chicago. The return was Denis Savard, who still had name value but had already peaked. Chelios went on to play into his late 40s while capturing awards and championships along the way.
Ottawa Senators Include Zdeno Chara in Yashin Deal (2001)
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Ottawa packaged Zdeno Chara and a top draft pick to get Alexei Yashin. It didn’t take long to see where things went wrong. Yashin never reached elite status again and was eventually bought out. Meanwhile, Chara emerged as one of the game’s premier defensemen.
Calgary Flames Trade Doug Gilmour (1992)
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Following a bitter contract dispute, Doug Gilmour left Calgary in a massive trade. He landed in Toronto and immediately became their heart and soul by delivering the most productive season in team history.
Boston Bruins Trade Joe Thornton (2005)
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Boston grew impatient with Joe Thornton’s playoff struggles and dealt him to San Jose. He responded by leading the league in points and taking home the Hart Trophy. He became the face of the Sharks, and the Bruins spent the next few years regrouping.
Edmonton Oilers Trade Chris Pronger (2006)
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Just weeks after leading Edmonton to the Final, Chris Pronger requested a move and was traded to Anaheim. He joined an already strong roster and helped them win it all the next season. Edmonton’s return featured promising names, but none filled the void.
New York Rangers Trade Pavel Buchnevich (2021)
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While facing cap space issues, the Rangers moved Pavel Buchnevich to St. Louis. He quickly became a top-line fixture and produced career-best numbers. In return, New York got a depth forward who didn’t stick and a pick that didn’t solve their scoring depth. Buchnevich’s breakout in another jersey turned a salary decision into a costly miscalculation.
Calgary Flames Trade Matthew Tkachuk (2022)
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When Matthew Tkachuk made it clear he wouldn’t re-sign, Calgary pulled off a blockbuster with Florida. Jonathan Huberdeau came over with high expectations, but his production dropped off. Tkachuk, meanwhile, helped lead the Panthers to a championship.