Top 15 Most Lopsided Trades In NHL History

Trades are always a risk in sports. If done correctly, you can add that missing ingredient you need to make your team a winner and take off wonderfully for long-term success. Do it badly and you suffer big time with someone who drags the team down. And if you do it very badly, you suffer while the other team ends up becoming a massive winner. Sports history is built upon teams who, with one trade, either soared to the heights or sank to the depths. Look at the Red Sox giving away Babe Ruth and thus allowing the Yankees to build their dynasty. Look at the Vikings thinking they got the better of a trade for Hershel Walker only to watch the Cowboys use it to become three-time Super Bowl champions. Every sport runs these risks and hockey is no different.

The NHL rarely does one-on-one trades, preferring to ship players off in multiple numbers and thus the risk is a bit lowered. But it’s still there, as a high-profile guy who should be a major contender just doesn’t work in his new surroundings. Or a “can’t miss” prospect that does, in fact, miss quite a bit. Too many times, teams give away slews of guys to get their hands on this talent and that ends up hurting them as rarely is one guy worth so much. There have been slews of cases in the NHL and these are the toppers. The 15 trades were one team made off like a bandit and the other gave too much for too little and showing why these are a risk.

16 Alek Stojanov for Markus Naslund


15 Marcel Dionne for and Bart Crashleyto the Kings for Terry Harper, Dan Maloney, and a 2nd round pick


While the Red Wings were already struggling since their glorious run in the 50s, this trade led to the dark 'Dead Wings' era in Detroit. Due to a contract dispute with their young star Marcel Dionne, the Wings traded Dionne and Bart Crashleyto to the Los Angeles Kings for Terry Harper, Dan Maloney and a 2nd round pick.

14 Jaromir Jagr for Kris Beech, Michal Sivek and Ross Lupaschuk


13 Ron Francis & Ulf Samuelsson for John Cullen, Zarley Zalapski & Jeff Parker


Want to know why the Hartford Whalers aren’t around anymore? Here’s a key reason. Despite some good play, the Whalers were unsure of Samuelsson as an enforcer and so decided to ship him and Ron Francis to Pittsburgh in exchange for John Cullen, Zarley Zalapski, and Jeff Parker. The latter three did almost nothing as Hartford would sink further and further until finally being sold and moved to Carolina.

12 Roberto Luongo for Todd Bertuzzi

Anne-Marie Sorvin-USA TODAY Sports

After inheriting the hard-luck Vancouver Canucks, Dave Nonis was determined to put the team back on top. As such, he instigated a trade with Florida that sent faded Todd Bertuzzi to Florida along with Alex Auld and defenseman Bryan Allen in exchange for Roberto Luongo, Lukas Krajicek, and a sixth-round pick (Sergei Shirokov). Luongo became the top-notch goalie Vancouver needed and kept them in serious contention while the Panthers didn’t click at all with their guys.

Luongo as earned himself a gold medal in the Olympics and led Vancouver to a Stanley Cup Final while Bertuzzi has been with five teams since, showing one time the Canucks came out ahead in a deal.

11 Patrick Sharp for Matt Ellison

Kim Klement-USA TODAY Sports

10 Phil Esposito


This is an interesting case as not once but twice, as this guy was at the center of trades that didn’t turn out as expected. He was a rising star in Chicago, doing a great job with his hard hitting style but made the mistake of getting drunk at a party and bad-mouthing GM Tommy Ivan. Naturally, Ivan decided to get rid of Esposito trading him (along with Ken Hodge and Fred Stanfield) to the Bruins in exchange for Gilles Marrote, Pit Martin and Jack Norris. Once in Boston, Esposito proceeded to become a major star, averaging 130 points a season, winning the Hart Memorial Trophy twice and the Bruins winning two Stanley Cups.

9 Max Bentley for “Flying Forts”


You can forgive the Chicago Blackhawks for thinking they were getting ahead in this 1947 deal, the biggest of its time. They were gaining Gus Bodnar, Bud Polie, Gaye Stewart, Ernie Dickens and Bob Goldham, who had formed the famed “Flying Forts” frontline for the Toronto Maple Leafs. It was basically an entire startling lineup that should have led to massive success in Chicago. However, combinations of injuries and bad coaching kept that lineup from turning the Blackhawks into the dynasty expected.

8 Eric Lindros for Peter Fosborg, et al.

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Breaking out majorly in junior, Lindros was hailed as “the next Gretzky” and only natural the Quebec Nordiques would draft him. There was a snag in that Lindros hated Quebec (both the team and city) and refused to play and the NHL had to step in to basically force the Nordiques to trade him. They did to the Flyers in a massive deal that included Peter Forsberg, Tony Amonte, three other players, three first round picks and $15 million. One would think that was a high price but the Flyers really thought they came out ahead in the deal…at the time.

The next season, Quebec went from the second-worst team in the league to the playoffs and with their new standing, were able to be sold to investors in Denver to become the Avalanche. In their very first season in their new home, the Avalanche won the Stanley Cup with nine players of that team having been acquired thanks to the Lindros deal. Lindros himself was good but never on Gretzky’s level and only got the Flyers to one Cup final, which they lost. The Avalanche would go on to further success with Forsberg ending up being the true star of that trade and showing how one man is very rarely worth parting with so much.


6 Scott Niedermayer for Tom Kurvers


Oh, Toronto, how this hurts. Thinking Tom Kurvers was going to be the must-get player to lead them to glory, the Maple Leafs went ahead and gave up their first-round draft pick to the New Jersey Devils in order to get their hands on him. Kurvers played 89 games total and scored 55 points for Toronto, not exactly stellar numbers.

5 The Trade


4 Brett Hull for Rob Ramage and Rick Wamsley


In 1988, still trying to keep themselves in contention, Calgary decided to get some new blood in a trade with the St. Louis Blues. In exchange for Rob Ramage and Rick Wamsley, the Flames gave up Brett Hull, a promising rookie but they figured worth dropping. Ramage was skilled but just not breaking out and he and Wamsley both fading into obscurity.

3 Patrick Roy


This is the trade that makes Montreal fans grit their teeth. Roy was a skilled goalie, never comfortable with the Canadians, having grown up in Quebec but did his best, helping Montreal with two Stanley Cup victories. However, he clashed constantly with his coaches and after Mario Tremblay left him in a game where he gave up 9 goals, Roy skated right up to President Ronald Corey and told him he was done. Days later, Roy and captain Mike Keane were traded to the upstart Colorado Avalanche for Jocelyn Thibault, Martin Rucinsky and Andrei Kovalenko.

2 Mark Messier for Louie DeBrusk, Steven Rice and Bernie Nicholls


Having apparently learned nothing from giving away one icon, the Oilers decided to follow up Gretzky in 1991 by trading Mark Messier away. Right with Gretzky, Messier had been key to the Oilers dynasty, a five-time Cup winner and fantastic on offense, still young with plenty in the tank and his departure was literally front page news in Canada. But Edmonton decided to let him go in exchange for three members of the New York Rangers they hoped would give them a “youthful spark.”

1 Doug Gilmour


One of the biggest trades in NHL history, the Calgary Flames decided they needed a big overhaul in 1992 and so engaged in a massive trade with the Toronto Maple Leafs that involved ten players in all. At the center of it was Doug Gilmour, a seasoned player who’d been part of the Flames’ Stanley Cup championship team in 1989. None of the guys they got put Calgary really fired that team up but Gilmour turned into one of the best players in Leafs history, a respected Captain scoring 452 points in his seven seasons, keeping them in serious playoff contention and loved by the fans. So many players involved but Gilmour helped Toronto be the real winner in this deal by far.

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Top 15 Most Lopsided Trades In NHL History