The Worst Trades in NHL History

Every NHL general manager wants to succeed. They want to build a roster that competes night in and night out. They want to win and raise the Stanley Cup.

To that goal, they make trades to improve their respective squads. On most occasions, trades in the NHL work out well – both teams improve following the arrival of a new player(s) or assets. Weaknesses are addressed. Needs are fulfilled.

But there are times when trades are completely lopsided, leaving one team with prized assets and the other with nothing but remorse. Good players can flourish, becoming superstars while others flounder. Often the outcome of a trade isn’t known for a season or two.

Worst Trades in NHL History

Listed below are some of the worst trades to have taken place in NHL history.

New York Rangers Trade Rick Middleton to Boston Bruins

In 1976, the New York Rangers traded Rick Middleton to the Boston Bruins for veteran Ken Hodge, straight up. Middleton, seen as a bright and rising star, had scored 46 goals in his first two seasons on Broadway, though he was known to enjoy the New York scene a bit too much.

Rick Middleton Terry O'Reilly Ray Bourque Bruins 1980
Rick Middleton (L), Terry O’Reilly (C) and Ray Bourque (R) of the Boston Bruins accept three star awards in pre game ceremoney before game at the Boston Garden. (Photo by Steve Babineau/NHLI via Getty Images)

When Middleton arrived in Boston, he was coached by bombastic loudmouth Don Cherry, who wouldn’t accept nonsense behavior and such gallivanting from his players. As a result, Middleton spent more time in the gym than the party scene and developed into an explosive scorer. He scored 402 goals in 881 games in a Bruins uniform.

Meanwhile, Hodge’s career ended quickly. He scored 23 goals for the Rangers before retiring, having played only 96 games for the Blueshirts.

Montreal Canadiens Trade Patrick Roy

The Canadiens shipped Patrick Roy to the Colorado Avalanche with captain Mike Keane for Jocelyn Thibault, Martin Rucinsky and Andrei Kovalenko. The trade was a complete disaster for Montreal.

Patrick Roy of the Montreal Canadiens
Patrick Roy won four Stanley Cups, two with the Habs and two with the Avalanche. (Photo by Bruce Bennett Studios/Getty Images)

In Colorado, with Roy in net, the Avalanche became perennial Stanley Cup contenders. They won the Cup in 1996 and 2001. The Canadiens, on the other hand, went into a downward spiral and were not a competitive team for a several seasons.

Winnipeg Jets Trade Teemu Selanne to Anaheim Mighty Ducks

Selanne, is pure a goal scorer as the league has known, was traded with Marc Chouinard, and a fourth-round pick to the Anaheim Mighty Ducks on Feb. 6, 1996 for first-round draft picks Chad Kilger and Oleg Tverdovsky, along with a third-round pick at the 1996 NHL Entry Draft.

The deal changed Selanne’s life as well as the Ducks’ franchise.

The trade was a robbery. Selanne became the face of the franchise for many, many years, and still is to a certain extent. He’s the greatest Duck of all time.

Rangers Trade Jean Ratelle and Brad Park to Boston Bruins

After losing in the semifinal round of the playoffs to the Philadelphia Flyers in 1974 and in the first round in 1975 to the archrival New York Islanders, the Rangers felt the need to shake up their roster. In doing so, they made this list.

Brad Park #22 of the Boston Bruins
Brad Park played 17 season in his NHL career, eight of them for the Bruins. (Photo by Steve Babineau/NHLI via Getty Images)

The Rangers let netminder Eddie Giacomin go on waivers to the Detroit Red Wings, then traded center Jean Ratelle and defenseman Brad Park and Joe Zanussi to the Bruins for high-scoring Phil Esposito and defenseman Carol Vadnais.

Honourable Mention: Phil Esposito Makes His Way to Boston

The move was a disaster. Ratelle and Park played out terrific careers for the Bruins. While Esposito was still nearly a point-per-game player, he never quite had the same success in New York that he did in Boston.

Vancouver Canucks Trade Cam Neely and 1st-Round Draft Choice to Boston Bruins

In his first three seasons, Cam Neely scored 51 goals, posting a minus-56 plus-minus rating for the Canucks. He had also earned over 300 penalty minutes.

The Canucks then packaged Neely and a first-round draft pick (turned out to be defenseman Glen Wesley) to the Bruins for center Barry Pederson.

Cam Neely
Cam Neely was a premier power forward. (Photo by Steve Babineau/NHLI via Getty Images)

Neely played the rest of his career in Boston, playing 10 seasons and racking up 344 goals and 246 assists in 525 games. He was one of the league’s most-feared power forwards­ – a mix of pure strength and skill. If he didn’t beat you with his goal scoring, he did with his fists. He hit the 50-goal mark three times and was inducted into the Hall of Fame in 2005.

Related: Boston Bruins 50-Goal Scorers

Pederson’s career after Beantown fizzled. He only hit the 20-goal mark once with the Canucks and bounced around the NHL, playing for several teams.

New York Islanders Trade Zdeno Chara to the Ottawa Senators

In June of 2001, the New York Islanders made a disastrous deal.

Zdeno Chara had yet to pan out with the Islanders, and was traded to the Ottawa Senators alongside Bill Muckalt and a 1st-round draft pick in exchange for Alexei Yashin.

Zdeno Chara Bruins
Zdeno Chara (Icon SMI)

Yashin was a highly skilled, highly sought after player. Drafted second overall by the Senators in 1992, Yashin averaged just under a point per game during his seven seasons in Ottawa, scoring 491 points in 504 games before he was traded to New York.

Meanwhile, Zdeno Chara became one of the most intimidating, highly skilled defenders to play in the NHL. Averaging around 25 minutes per game, Chara found his scoring touch with the Senators, scoring 146 points in 299 career games in Ottawa.

And who did the Senators end up drafting with the pick they received from the Islanders; star player and former captain Jason Spezza.

Meanwhile, Yashin only played five seasons with the Islanders before his contract was bought out. During his time on the island, Yashin’s play deteriorated, scoring 290 points in 346 career games. The Islanders still pay Yashin $2.2 million this year, the last year of his buyout.

Calgary Trades Brett Hull to the St. Louis Blues

In March of 1988, the Calgary Flames made one of the worst trades in NHL history.

At the young age of 23, Brett Hull was in the middle of a great rookie season, having scored 50 points through his first 52 career games. It didn’t matter. The Flames traded Hull, alongside Steve Bozek in exchange for Rob Ramage and Rick Wamsley.

Brett Hull wrote the forward for 100 Things (David E. Klutho/Sports Illustrated)
Brett Hull (David E. Klutho/Sports Illustrated)

Of the two players the Flames received, Ramage was the most skilled. A strong defender, Ramage could also contribute offensively, yet he only played with the Flames for one full season before he was traded to the Toronto Maple Leafs. Goaltender Rick Wamsley was not a standout player either. Wamsley played parts of four seasons with the Flames as a backup before he too was traded to the Toronto Maple Leafs in a huge trade which also made this list.

In Brett Hull, the St. Louis Blues acquired one of the most dynamic goalscorers in NHL history. In his first season with the Blues, Hull scored 41 goals. He followed up this performance by posting totals of 72, 86 and 70 goals in his next three seasons in St.Louis.

All in all, Hull ended up playing in St. Louis for 11 years. In his 744 career games with the Blues, Hull scored 527 goals and 936 points.

He was inducted into the Hockey Hall of Fame in 2009.

Calgary Trades Doug Gilmour to the Toronto Maple Leafs

Doug Gilmour
Doug Gilmour of the Calgary Flames on the ice during a game against the New York Islanders (Bruce Bennett Studios/Getty Images)

In early 1992, the Calgary Flames completed a 10-player trade with the Toronto Maple Leafs centered around Doug Gilmour.

At 28, Gilmour was not an emerging young star, but an accomplished NHL player. Having split the first nine years of his career between the Flames and the St. Louis Blues, Gilmour was highly skilled offensively, having posted point-per-game numbers in his first 650 games.

The most notable player going the other way was Gary Leeman, a 50-goal scorer with the Leafs who managed only 11 goals in 59 games with the Flames before he was sent packing to the Montreal Canadiens.

Gilmour went on to become one of the most notable leaders in Maple Leaf history. His presence in the locker room is well documented, while his on ice abilities were also unique. Gilmour played a gritty style of hockey despite his small stature, yet was able to contribute offensively on a consistent basis. In his seven seasons with the Maple Leafs, Gilmour scored 452 points in 393 games alongside 386 penalty minutes.

He was inducted into the Hockey Hall of Fame in 2011.

Detroit Red Wings Trade Marcel Dionne to the Los Angeles Kings

Marcel Dionne’s illustrious career began with the Detriot Red Wings. In Motown, he scored 139 goals and added 227 assists for 366 points in 309 games. Very impressive by any metric.

Marcel Dionne Los Angeles Kings
Marcel Dionne was one of the best snipers of his era. (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images)

In 1975, the brilliant front office staff of the Red Wings then decided to trade Dionne to the Kings with defenseman Bart Crashley for Dan Maloney, Terry Harper and a second-round draft choice.

Related: Los Angeles Kings’ 50-Goal Scorers

Dionne went on to play 12 seasons for the Kings, putting up 1,307 points in 921 games. He had six 50-goal seasons with the Kings and holds several scoring records for the franchise. He was inducted into the Hall of Fame in 1992.

Edmonton Trades Mark Messier to the New York Rangers

In 1991, the Oilers made the second-worst trade in their franchise history, sending their heart and soul – Mark Messier – and future considerations (Jeff Beukeboom and David Shaw) to the New York Rangers in exchange for Louie DeBrusk, Steven Rice and Los Angeles Kings’ great Bernie Nicholls.

At the age of 29, Messier had already won five Stanley Cups with the Edmonton Oilers and certainly had plenty left in the tank.

Mark Messier of the New York Rangers
Canadian professional hockey player Mark Messier of the New York Rangers hoists the Stanley Cup (Photo by Bruce Bennett Studios/Getty Images)

For the Oilers, the return did not match the production and leadership leaving town. DeBrusk played parts of six seasons with the Oilers, yet was never a consistent threat at either end of the ice. Rice split parts of three seasons between the Oilers and the minors, failing to establish himself as an everyday NHL player. Nicholls was the biggest name returning to the Oilers, however he was traded to the New Jersey Devils after parts of two seasons with the Oilers.

Meanwhile, Messier poured in 107 points in his first season as a Ranger. He went on to win a sixth Stanley Cup with the Rangers in 1993-94 in which he famously guaranteed a win against the New Jersey Devils to tie the series before moving on and winning in the finals. Through 422 games in his first stint with the Rangers, Messier scored 515 points along with winning the Hart Memorial Trophy and Ted Lindsay Award.

Messier was inducted into the Hockey Hall of Fame in 2007.

Oilers Trade Wayne Gretzky to the Los Angeles Kings

In August of 1988, the Edmonton Oilers completed what is likely the most controversial trade in the history of the NHL. They sent Wayne Gretzky to the L.A. Kings in what turned out to be an eight-player deal.

At the age of 26, Gretzky had plenty of hockey ahead of him, yet due to rumoured financial difficulties with then Edmonton Oilers owner Peter Pocklington, the team was forced to trade the best player in NHL history.

In return, the Oilers received two players and three first-round draft picks. One of the picks was Jimmy Carson who posted a 100-point season with the Oilers, although he only played two seasons with the team. Martin Gelinas was not a spectacular player, as he only wound up playing with the Oilers for four years.

Wayne Gretzky, Edmonton Oilers
Wayne Gretzky brought one last glimmer of hope to the WHA but he was too young to save the league from financial woes. (Photo by B Bennett/Bruce Bennett Studios/Getty Images)

Of the three picks the Oilers received, Jason Miller played only six games while Nick Stajduahr played only two games in the NHL. Martin Rucinsky turned into a good player, however he only played two games with the Oilers.

As many know, Wayne Gretzky moved onto Los Angeles where he continued doing what he had done his entire career: dominating the NHL.

In his 539 games with the Kings, Gretzky scored an incredible 918 points. Although he was unable to lead the Kings to a Stanley Cup, Gretzky remained by far the best player in the NHL.

Inducted to the Hockey Hall of Fame in 1999, Gretzky scored 2,857 points in 1,487 career games and won four Stanley Cups.