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
This trade was the very definition of lopsided, as Alek Stojanov was shipped to Pittsburgh, with whom he would score just six points in 45 games. The Penguins thought Markus Naslund was too soft of a player and felt Stojanov would give them more punch in their linup. The most lethal punch is points though, and Naslund provided a lot of that, becoming Vancouver's all-time leading scorer (he was recently passed by the Sedin twins). Between trading Naslund and losing Lemieux to retirement in 1997, the dominant Penguins teams of the early 90s soon became a distant memory.
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.
Dionne would score 592 goals and 813 assists while playing 1,039 games for the next 14 seasons, while the Wings limped through the 80s. So essentially one of the greatest scorers in NHL history was traded for a journeyman defenceman and a second line winger.
14 Jaromir Jagr for Kris Beech, Michal Sivek and Ross Lupaschuk
After helping the Penguins to back-to-back Stanley Cups, Jagr decided he’d had enough of Pittsburgh and started making noises about being traded. The Penguins, feeling Jagr’s best days were behind him, agreed and shipped him to Washington for Kris Beech, Michal Sivek, and Ross Lupaschuk. Combined, those three scored 13 goals for Pittsburgh while Jagr went on to score more than 500 points. After two years, the Capitals traded him to the Rangers for Anson Carter. Carter lasted just 19 games while Jagr became New York’s captain and scored 123 points in his first year there. He still plays today, showing both teams foolish in thinking his time was passed.
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.
Meanwhile, Ulf would become key to the Penguins winning back to back Stanley Cups and one of the most feared enforcers on the ice, not making friends but earning plenty of points and awards. Francis would continue to dominate in the league and proved to be the most effective no.2 centre in the league, playing behind Lemieux. He would finish his career with the second most assists in NHL history, only trailing Wayne Gretzky. This pretty much doomed the Whalers while boosting Pittsburgh to massive heights.
12 Roberto Luongo for Todd Bertuzzi
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.
The Panthers have since re-acquired Luongo and find themselves in contention.
11 Patrick Sharp for Matt Ellison
If not for this trade, the current NHL landscape might look a lot different. Wanting to spark up the Flyers, GM Bobby Clarke decided to ship Sharp and Eric Meloche to the Blackhawks in exchange for Matt Ellison and a third round draft pick. Ellison would play just seven games in his two years with the Flyers and the draft pick was wasted. Sharp, meanwhile, would become a key component to Chicago’s revival and helping lead the Blackhawks to three Stanley Cup victories. So a lot of Blackhawks fans give thanks to Clarke for the free gift he sent them.
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.
Despite all that, in 1975, the Bruins decided to drop a guy who was the backbone of their team and gave him to the Rangers for three players. Esposito helped lead the Rangers to the Cup finals in 1979 and remained one of the best players on the ice. Two teams made the mistake of not realizing how skilled this guy was and both paid for it.
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.
Instead, Bentley would end up leading Toronto to three Stanley Cups in four seasons, one of the more revered players in their history and showcasing how sometimes one man really can be the bigger steal than an entire team.
8 Eric Lindros for Peter Fosborg, et al.
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.
Meanwhile, the Devils would use that draft pick to get Scott Niedermayer, who would become one of the best defensemen around. He would go on to win three Stanley Cups with the Devils and played in five All-Star Games. He would later lead the Anaheim Ducks to another Cup and a two-time gold medal Team Canada Olympic hockey team. All that could have been Toronto’s but for one horrific trade.
5 The Trade
It’s the trade that transformed the entire NHL. Hands-down the greatest player of the time (and some might argue, of all time), Gretzky had led the Edmonton Oilers to four Stanley Cups, numerous awards, not just a hero but an icon for Canada. So it was shocking that just after leading the Oilers to the Cup in 1988, Gretzky was already being shopped by the team wanting some new shifts and somehow thinking Gretzky’s time might be done. In the news that shocked a nation, the Oilers traded their biggest player (along with long-time allies Marty McSorley and Mike Krushelnyski) to Los Angeles in exchange for two players, $15 million and three first-round draft picks. While they would win a Cup in 1989, most agree the Oilers were never the same as Gretzky would keep to his winning ways to keep Los Angeles into contention and turning Los Angeles into a successful hockey town and pave the way for more franchises in “warm weather” cities. It was truly a change and L.A. got ahead on the deal as “The Great One” was worth any price paid.
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.
Hull, of course, would become one of the greatest scorers in NHL history, racking up 527 goals and 936 points in his 11 seasons with the Blues. He would go on to lead both the Stars and the Red Wings to Stanley Cup victories and easily elected to the Hall of Fame, showing one of the greatest dropped balls in the Calgary franchise history.
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.
Every Canadians fan cites this as the end of the franchise’s glory as all three of the newbies faltered and Montreal hasn’t been to the Cup since. Meanwhile, Roy would become a Colorado favorite, a multiple All-Star and Conn Smythe winner and helping the Avalanche to two Cups, finally retiring as one of the greatest goalies in history. Yet another blow to the Montreal fandom.
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.”
Nicholls only lasted two years before traded to the Devils and neither of the others would be notable. Messier, meanwhile, would thrive in New York, winning the Hart Memorial Trophy, scoring 515 points and leading the Rangers to their Stanley Cup victory in 1994. Once more, the Oilers dynasty is only matched by how fast they took it apart.
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.