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10 worst trades in NHL history

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There are many big trades that occur throughout an NHL season, but what are the worst NHL trades ever? Some of the worst trades in NHL history looked bad from the start, while others took years to realize the mistakes that were made.

Worst NHL trades

The worst NHL trades are the ones that set teams back for years. They are not easily forgotten and can cost a general manager their job.

Whether it was due to injuries, a steep decline in performance, or simply giving away too much for little in return, these 10 trades turned out to be the worst trades in NHL history.

10. Adam Oates traded to the Blues (1989)

Detroit made a terrible trade in 1989 that gave the St. Louis Blues Adam Oates.

Oates, along with Paul MacLean, was traded to the Blues in exchange for Bernie Federko and Tony McKegney.


Federko and McKegney were well past their primes and near the end of their careers. Each ended up lasting a single season in Detroit and had 60 combined points. Oates on the other hand scored 102 points in his first season with the Blues and put up big numbers all three seasons he was there.

MacLean scored 34 goals and racked up 33 assists in his first season with St. Louis, making the trade look even worse for Detroit.

9. Alexei Yashin traded to the Islanders (2001)

The Islanders did not get the Alexei Yashin they hoped for in 2001 when acquiring him from Ottawa.

Yashin was traded from the Senators to New York in exchange for Zdeno Chara, Bill Muckalt, and a first-round draft pick. That pick ended up being Jason Spezza, who turned out to be a star for the Senators.

Chara would find his footing in Ottawa, as he scored 146 points in just under 300 games with the team. Yashin had back-to-back 85+ point seasons prior to the trade but never had more than 75 points in a season after being traded. Ottawa got a return far better than first expected, while the Islanders missed on their only piece in the deal.


8. Wayne Gretzky traded to the Kings (1988)

Trading the best player to ever play was not a smart move by the Oilers in 1988.

Wayne Gretzky was traded to the Kings along with Marty McSorley in exchange for Jimmy Carson, Martin Gelinas, three first-round picks, and $15 million.

The Edmonton Oilers needed money, but it shouldn’t have led to trading the best player in the sport. The Oilers also did not get much in return. Most of the draft picks led to players who barely played for the team, while Carson only played two seasons in Edmonton. It goes without saying that you shouldn’t trade the greatest player of all time in their prime.

7. Phil Esposito traded to the Bruins (1967)

The Chicago Blackhawks made one of the worst NHL trades ever with the Boston Bruins in 1967.

Chicago shipped Phil Esposito, Ken Hodge, and Fred Stanfield to Boston in exchange for Jack Norris, Pit Martin, and Gilles Marotte.

Esposito would go on to have six seasons of 100+ points with the Bruins, while Hodge would go on to have two such seasons. Even Stanfield was a success in Boston, making it one of the most one-sided NHL trades in history.

6. Marcel Dionne traded to the Kings (1975)

Marcel Dionne was already a star early in his career with Detroit, yet that didn’t stop the Red Wings from letting him go.

Dionne and Bart Crashley were traded to Los Angeles in exchange for Dan Maloney, Terry Harper, and a second-round pick. The trade was a complete disaster for Detroit, as they had to watch Dionne score 1307 points in 921 games with the Kings.

Harper would go on to last only four years in Detroit, while Maloney only lasted three seasons. Maloney’s highest point total in a season with the Red Wings was 66. On the other hand, Dionne scored at least 74 points in all 12 seasons with the Kings.

5. Cam Neely traded to the Bruins (1986)

Cam Neely did not have a great start to his career in Vancouver, but things quickly changed after he was traded.

The Canucks traded Neely and a first-round pick to the Bruins in exchange for Barry Pederson. Neely went from scoring under 40 points in his last two seasons with Vancouver to scoring at least 69 points in his first five seasons with Boston.

Pederson had a good start with Vancouver, but after two seasons his level dropped drastically. If that wasn’t all, the Bruins selected Glen Wesley with Vancouver’s draft pick, who turned out to play seven seasons with Boston.

4. Patrick Roy traded to the Avalanche (1995)

Trading one of the best goalies of all-time definitely puts the Canadiens high on this list of worst NHL trades.

Montreal sent Patrick Roy and Mike Keane to the Colorado Avalanche for Andrei Kovalenko, Martin Rucinsky, and Jocelyn Thibault. The trade marked the end of Montreal’s winning ways, while the Avalanche were just getting started.

Colorado went on to win the Stanley Cup with Roy in 1996 and 2001. Roy was named the Conn Smythe Trophy winner in 2001 for his stellar play throughout the playoffs. Montreal on the other hand has not won the Stanley Cup since 1993 when Roy was still in net for the team.

3. Rick Middleton traded to the Bruins (1976)

The Rangers made a huge mistake in 1976 when they traded away a young star for a veteran player.

New York sent Rick Middleton to the Boston Bruins for Ken Hodge. Hodge was nearing the end of his career, while Middleton was just beginning.

Hodge would go on to last just 68 games across two seasons with the Rangers before his NHL career was over. Middleton ended up playing 12 seasons with the Bruins and scored at least 20 goals in 10 of those seasons. He also reached the 100-point mark twice with the team, making it one of the worst NHL trades ever for the Rangers.

2. Markus Naslund traded to the Canucks (1996)

The Pittsburgh Penguins made one of the worst NHL trades in history at the 1996 trade deadline.

Pittsburgh gave away a future star in Markus Naslund, and in return got Alek Stojanov. If you don’t know who Stojanov is, you aren’t alone, as he only played 45 games with the Penguins.

Naslund turned out to be way more than the Canucks had hoped at the time. He would go on to play over 800 games with Vancouver and rack up more than 750 points. Naslund was named an All-Star five times with the Canucks and won the Ted Lindsay Award in 2003.

1. Brett Hull traded to the Blues (1988)

Shipping Brett Hull to the St. Louis Blues couldn’t have turned out worse for the Calgary Flames, making it the worst trade in NHL history.

The Flames sent Hull and Steve Bozek to the Blues in exchange for Rob Ramage and Rick Wamsley. Ramage lasted only one full season with the Flames, while Wamsley was a backup goaltender for parts of four seasons with Calgary.

Hull would turn out to be one of the best goal scorers of all time while playing with St. Louis. He scored over 50 goals five times with the Blues, which included three straight seasons of 70 or more goals. Hull played 11 seasons with St. Louis, collecting over 500 goals and 900 points with the team.

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