10 times an NHL team instantly regretted trading a superstar

May 12, 2025, 10:30 EDT

10 times an NHL team instantly regretted trading a superstar

The Colorado Avalanche understood the risk of trading Mikko Rantanen. He was a Stanley Cup champion, a second-team all-star, a 50-goal scorer, a two-time 100-point scorer and a future Hall of Famer. But even by that standard, what has transpired since they parted ways in a Jan. 24 blockbuster is the stuff of nightmares for GM Chris MacFarland.

It didn’t look that way at first. Martin Necas, the key piece coming from the Carolina Hurricanes in the tree-team trade including the Chicago Blackhawks, instantly gelled in Colorado. Rantanen wasn’t a fit with Carolina and wound up dealt to the Dallas Stars six weeks later after he and the Canes couldn’t agree on a long-term contract. Even as a Star, the fit was awkward at first. But something clicked in the playoffs, against his old teammates and close friends in the Avalanche, no less. He buried them with a third-period hat trick in Game 7 of the first round. He opened Round 2 against the Winnipeg Jets with a second consecutive hat trick, becoming the third NHLer ever to accomplish that feat in the postseason. Factoring in the eight-year deal he signed to play for Colorado’s division rival, the Rantanen trade threatens to become an all-time sliding door moment for the franchise.

It wouldn’t be the first. The Avs have even been on the right side of history for a trade of this magnitude before. What are some other examples of an NHL team trading a superstar at the peak of his powers and quickly regretting it?

Consider these 10 examples. To qualify, the deal had to come when the player was an established superstar still at his best. The Boston Bruins trading Ray Bourque at the end of his career, for example, does not qualify. Nor does the New York Islanders trading Zdeno Chara when he was still a young project. Cam Neely? He was coming off a 14-goal season when the Vancouver Canucks traded him to Boston. Even Phil Esposito wasn’t yet an elite player when the Blackhawks dealt him. We’re looking for situations in which a team said goodbye to one of its established icons.

1988: Edmonton Oilers trade Wayne Gretzky

In the discussion for the most seismic blockbuster in sports history. Oilers fans’ hearts are forever broken by the trade to the Los Angeles Kings, which occurred a couple months after Edmonton won its fourth Stanley Cup in a five-year stretch. Gretzky had already won seven of this 10 Art Ross Trophies and eight of his nine Harts at that point, but he was only 27, still playing at generational superstar level. The trade brought a package including promising young scorer Jimmy Carson, multiple first-round picks and Martin Gelinas, but it was a sell-off from financially desperate owner Peter Pocklington, plain and simple. Gretzky won the Hart in his debut season with the Kings, eliminating the Oilers in Round 1 of the playoffs, too. He also took L.A. to the Stanley Cup Final in 1992-93 and put the Sun Belt on the map for NHL hockey. Expansion wouldn’t have played out the same way without the trade.

1990: Montreal Canadiens trade Chris Chelios

Chelios was a Stanley Cup champ and Norris Trophy winner, still in his 20s, by the summer of 1990. But then-GM Serge Savard was worried about a knee injury Chelios sustained in the 1989-90 season. The medical expertise suggested to the Habs that Chelios’ career could be finished in a couple more campaigns. Oops. Little did they know, he’d play in the NHL until he was 48 years old, snagging two more Norrises and two more Cups. The Habs got future Hall of Famer Denis Savard in the deal, but he was on the downside of his career and was merely a depth piece by the time Montreal won the Cup in 1992-93. Who knows much longer they could’ve stayed competitive if Chelios was patrolling their blueline for the balance of his prime?

1991: Hartford Whalers trade Ron Francis

Francis was the Whalers’ long-serving captain and a 100-point scorer when the immortal Trade Deadline deal went down in March of 1991. But here’s the thing: it wasn’t declared a mistake that day. Francis went to the Pittsburgh Penguins along with Ulf Samuelsson and Grant Jennings for John Cullen, Zarley Zalapski and Jeff Parker. Cullen was fifth in the NHL in points at the time. But the Penguins understood they needed to insulate superstar Mario Lemieux up the middle, and adding Francis paid instant dividends. They won the Stanley Cup that spring and the following season. Francis was an integral part of the team’s borderline dynastic run, especially because he jumped up to be an elite first-line center whenever health problems got the better of Lemieux. The Whalers franchise did get Francis back, but not until it had relocated to Carolina, of course. As for Cullen? He only played 109 games in a Whaler uniform before they traded him in fall 1992 for a second-round pick.

1991: Edmonton Oilers trade Mark Messier

Messier was ultimately another casualty of penny pinching in Edmonton. He’d given everything to the franchise, leading them to five Stanley Cups – the most notable coming post-Gretzky in 1989-90. But he was disgruntled in the 1991 offseason at the fact the Oilers wouldn’t renegotiate his contract and that they were allowing such a huge exodus of talent from their dynastic years. They sent him to the New York Rangers Oct, 4 1991. He instantly transformed the Broadway Blueshirts into a contender, winning the Hart Trophy that season. After their step back the following season, he famously helped them end their 54-year championship drought in a memorable 1993-94 campaign that included his Guarantee Game, a hat trick in the Eastern Conference Final after he’d promised a victory over the New Jersey Devils. The key component of the Oilers’ return in the deal was Bernie Nicholls, who did help them reach the final four in 1991-92. But Messier’s impact in New York was legendary. He remains the only player to captain two different Stanley Cup winning franchises.

1992: Calgary Flames trade Doug Gilmour

See a trend here? It’s amazing how many of the ill-fated superstar trades involved money. Gilmour, part of the Flames’ 1988-89 Stanley Cup team, was mired in a squabble over his next contract and accused the Flames of tampering in the arbitration process. He walked out on the team Jan. 1, 1992 and was sent to the Toronto Maple Leafs the next day in an epic 10-player trade: Gilmour, Jamie Macoun, Ric Nattress, Kent Manderville and Rick Wamsley for Gary Leeman, Michel Petit, Alexander Godynyuk, Craig Berube and Jeff Reese. Gilmour helped a bad Leafs team show promise in the stretch run of that season and, by 1992-93, gave them their best shot at the Stanley Cup since 1967. His 127 points that year still stand as the franchise record. He won the Selke Trophy that season and was the Hart runner up. He helped Toronto reach consecutive Conference Finals with back-to-back 100-point campaigns. The trade sent each franchise in a completely opposite direction.

1995: Montreal Canadiens trade Patrick Roy

The image of Roy on the Habs bench after being left in for nine goals, telling the team president Ronald Corey he’d never play for them again, is burned into many of our brains. The Canadiens dealt their superstar, who’d won multiple Vezina Trophies, Stanley Cup and Conn Smythe Trophies with them, along with Mike Keane to the Colorado Avalanche for Andrei Kovalenko, Martin Rucinsky and Jocelyn Thibault. Talk about instant revenge; Roy backstopped the Avs to the Stanley Cup later that season and did so again in 2000-01, becoming the first player to win the Conn Smythe three times. The pieces Montreal recouped never became anything close to stars in the NHL, merely serviceable veterans.

1996: Winnipeg Jets trade Teemu Selanne

Money determined this deal too, but the player didn’t want out. Selanne, who exploded onto the scene with an NHL record 76 goals as a rookie in 1992-93, was incensed when the Jets, months away from relocating to Phoenix, dealt him to the Anaheim Ducks for prospects Oleg Tverdovsky, Chad Kilger and a third-round pick. The Jets were trying to keep costs down with Keith Tkachuk and Alexei Zhamnov on their payroll, too. And they paid dearly for the move. Selanne forged legendary chemistry with Paul Kariya and continued a superstar trajectory – for two stints in Anaheim, one during his prime years, the other when Selanne defied his age in his twilight years and helped them win the Stanley Cup in 2006-07.

2005: Boston Bruins trade Joe Thornton

The Bruins’ return alone made the trade tough to stomach. Thornton at the time was 25 and two years removed from delivering a 100-point season during the Dead Puck Era. To acquire him, the San Jose Sharks surrendered no picks, just Brad Stuart, Marco Sturm and Wayne Primeau. Stuart and Primeau were gone in another trade the following season. Thornton became the first and only player to win the Hart and Art Ross Trophies in a season during which he was traded. He’s arguably the greatest player in Sharks history, too.

2007: Edmonton Oilers trade Chris Pronger

Edmonton’s hand was forced. Pronger had completed a phenomenal season, helping the Oilers reach Game 7 of the 2005-06 Stanley Cup Final. He was so dominant that spring that he might have deserved the Conn Smythe Trophy even in a losing cause. But he requested a trade the ensuing offseason for family reasons. The Oilers swung the best deal they could at the time with the Anaheim Ducks, snagging Joffrey Lupul, Ladislav Smid and a pick package that eventually netted them Jordan Eberle. But Pronger formed an all-time great pair with Scott Niedermayer and led the Ducks to the Stanley Cup the following season. It’s tough to call the deal a full blunder went it wasn’t in then-GM Kevin Lowe’s control to keep Pronger, but no return justified what he brought to the Ducks.

2022: Calgary Flames trade Matthew Tkachuk

We can all agree MacKenzie Weegar has done a fine job patrolling the Flames’ blueline since coming over from the Florida Panthers along with Jonathan Huberdeau in the century’s biggest trade. But the consequences of dealing Tkachuk were instant and painful, even if then-GM Brad Treliving was handcuffed knowing Tkachuk wanted out. He was a Hart finalist and tallied a career-best 109 points in his debut season with Florida. He took the Panthers to the Stanley Cup Final in each of his first two seasons with the team, winning it in 2023-24. Meanwhile, Huberdeau, who was coming off a 115-point season at the time of the trade, has been a shell of what he was. The Flames haven’t made the playoffs since.

Honorable mentions: Canucks trade Pavel Bure, Blues trade Adam Oates, Nordiques trade Mats Sundin, Oilers trade Taylor Hall

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