10 Worst Trades in NHL History

It's a funny thing about trades.

When discussing the worst trades in NHL history, we could easily be discussing the best trades.

It all depends on the team's perspective.

However, when one team benefits so much from a trade and the other side fails to keep up, you have to question the thought process and perspective that led to the trade.

In some cases, good players became superstars in their new environment, while the players the opposing team received floundered or failed to make progress.

It may take a year or more for a bad trade to reveal itself. When these deals happen, one general manager will be taking pats on the back while his counterpart will be looking for a towel to wipe the egg off his face.

Oilers Trade Mark Messier to New York Rangers

It was the lead story in the evening news reports when the Edmonton Oilers traded their heart and soul, Mark Messier, to the New York Rangers prior to the start of the 1991-92 season.

The Oilers were going through continued difficulties as they moved their captain, who didn't want to be part of a sinking ship. Messier was traded with future considerations (who turned out to be Jeff Beukeboom and David Shaw) for Bernie Nicholls, Steven Rice and Louis DeBrusk.

Messier's trade created an instant leadership void in Edmonton and brought that commodity to New York. He also was a sensational clutch scorer for the Rangers. He scored 107 points in his first season with the Rangers, but his greatest achievements came in the 1993-94 season.

The Rangers had been without the Stanley Cup since 1940, and when the Rangers reached the sixth game of the Eastern Conference Finals trailing the New Jersey Devils three games to two, Messier guaranteed the Rangers would tie the series. He delivered a hat trick, and the Rangers won the game. They beat the Devils in the seventh game and would go on to win the Stanley Cup.

The Oilers have never fully recovered.

Flames Trade Brett Hull to St. Louis Blues

In the middle of his first full season in the NHL, Brett Hull was proving he belonged and that he was a lot more than just hockey legend Bobby Hull's son.

Through the first 52 games of the 1987-88 season, Hull had scored 26 goals and was putting his name into prime consideration for the Calder Trophy that goes to the NHL rookie of the year.

Nevertheless, the Flames traded this young stud to the St. Louis Blues with Steve Bozek for Rob Ramage and Rick Wamsley. Hull would go on to become a full-fledged superstar in St. Louis.

After scoring 41 goals in his first full season in St. Louis, Hull followed with three seasons that produced 72, 86 and 70 goals.

Good going, Calgary.

Rangers Trade Rick Middleton to Boston Bruins

It was a classic one-on-one trade when the New York Rangers traded young Rick Middleton to the Boston Bruins for veteran Ken Hodge in 1976.

Middleton scored 46 goals in two seasons with the Rangers, and he was looked at as a potential superstar. However, he was known to enjoy the New York nightlife and was not necessarily in the best of shape.

That changed when Middleton donned a Bruins uniform and started to play for head coach Don Cherry. Middleton matured, got himself in top shape and developed into an explosive scorer. He would go on to score 402 goals in a Bruins uniform, and many of them were spectacular and memorable.

Hodge was all but finished in the NHL. He scored 23 goals for the Rangers before his career came to an end.

Red Wings Trade Marcel Dionne to Los Angeles Kings

The Detroit Red Wings had a brilliant young star in Marcel Dionne. He had scored 366 points in his first four seasons.

But the Red Wings decided to trade Dionne to the Los Angeles Kings in 1975 with defenseman Bart Crashley for Dan Maloney, Terry Harper and a second-round draft choice.

Dionne would go on to play 12 seasons for the Kings and become a Hall of Fame player. He would have six 50-goal seasons with the Kings and become one of the most exciting players in NHL history.

Islanders Trade Zdeno Chara and First-Round Draft Choice to Ottawa Senators

You may ask why the New York Islanders are one of the tail-ending franchises in the NHL.

You can trace a large part of the answer to their 2001 trade with the Ottawa Senators. In that deal, they traded huge defenseman Zdeno Chara to the Ottawa Senators along with a first-round draft choice and Bill Muckalt for Alexei Yashin.

At the time, Chara was nothing but the biggest player in the NHL. He was a 6'9" defenseman who had not yet found his way. The first-round draft choice would be used to select Jason Spezza.

Chara would become a solid defender with the Senators before he signed with the Bruins as a free agent and became one of the best defensemen in the NHL. Spezza has been a dominant star with the Senators.

Yashin would score 119 goals in five seasons with the Islanders.

Canucks Trade Cam Neely and First-Round Draft Choice to Boston Bruins

At the end of the 1985-86 season, Cam Neely was a 20-year-old right wing with the Vancouver Canucks. He had scored 51 goals in three seasons and had a minus-56 plus-minus rating.

When the Boston Bruins came calling and dangled classy center Barry Pederson, the Canucks sent the Bruins Neely and a first-round draft pick who turned out to be defenseman Glen Wesley.

Neely would turn out to be one of the NHL's most explosive power forward in the history of the game. He would exceed the 50-goal mark three times in his career, and he would gain entry into the Hall of Fame.

Not only was Neely an explosive scorer, he was a willing and brutal fighter who could dominate with his fists.

Pederson had been a solid scorer with the Bruins, but he would only exceed the 20-goal mark once with the Canucks.

Flames Trade Doug Gilmour to Toronto Maple Leafs

If the Flames erred in trading Brett Hull to the St. Louis Blues in 1989, they compounded that error when they moved Doug Gilmour to the Toronto Maple Leafs in 1992

Gilmour would go on to become the heart and soul of the Leafs. It was a huge deal that saw Calgary send Jamie Macoun, Ric Nattress, Kent Manderville and Rick Wamsley along with Gilmour for Gary Leeman, Alexander Godynyuk, Jeff Reese, Michel Petit and Craig Berube.

Leeman had been a 50-goal scorer for the Leafs, but he was ineffective with the Flames.

Gilmour would go on to have a Hall of Fame career. His 1992-93 and 1993-94 seasons were the best of his career. He scored 127 points in '92-93 and had 111 points the following year.

Gilmour was far more than a scorer. Despite his 5'11", 177-pound frame, he was a hard-nosed physical player who was one of the top locker room leaders the Leafs have ever known.

Rangers Trade Jean Ratelle and Brad Park to Boston Bruins

In 1975, the New York Rangers were cleaning house.

They had lost in the semifinal round of the playoffs to the Philadelphia Flyers in 1974. Then they inexplicably lost a first-round matchup with the neighboring New York Islanders in 1975.

Management decided to change the team's culture.

After letting goaltender Eddie Giacomin go on waivers to the Detroit Red Wings, the Rangers followed that disaster by trading classy center Jean Ratelle and defenseman Brad Park along with defenseman Joe Zanussi to the archrival Boston Bruins for high-scoring Phil Esposito and defenseman Carol Vadnais.

The jaw-dropping trade turned out to be brilliant for the Bruins and a disaster for the Rangers. Ratelle and Park would have many great years for the Bruins, while Esposito never had the same success on Broadway that he did in Boston.

The Rangers not only strengthened the Bruins with the deal, they weakened their own on-ice performance.

Blackhawks Trade Phil Esposito, Ken Hodge and Fred Stanfield to Boston Bruins

Phil Esposito had three productive seasons with the Chicago Blackhawks when the team was preparing for the 1967-68 season.

The Bruins were clamoring to make a deal with the Blackhawks. The Bruins had a phenomenal young defenseman in Bobby Orr, but they didn't have enough talented players around him. They saw Chicago's lumbering center as a player who might complement Orr and wanted him.

The Bruins sent goalie Jack Norris, defenseman Gilles Marotte and forward Pit Martin to Chicago for Esposito, Ken Hodge and Fred Stanfield.

The deal proved to be a disaster for Chicago. Martin was a solid player, and Marotte was a hard-hitting physical defenseman, but while Norris was a washout in goal.

Esposito would go on to become the top scorer in the league and a perfect 1-2 punch with Orr. Hodge would go on to exceed the 50-goal mark while Stanfield was a versatile performer who could play the point on the power play and play a fine all-around game.

They still shake their heads in Chicago at the mention of this disastrous trade.

Oilers Trade Wayne Gretzky to Los Angeles Kings

While the trade of Wayne Gretzky to the Kings is often credited with making hockey a major league sport in Los Angeles and other non-traditional U.S. markets, it was an unmitigated disaster for the Edmonton Oilers.

Financial difficulties for Edmonton owner Peter Pocklington were reportedly at the root of the Gretzky trade. By moving him to Los Angeles, the Oilers traded either the best (or second-best behind Bobby Orr) player in hockey history and stripped their team of the greatest offensive force in the history of the game.

The Oilers had won the Stanley Cup in 1988, and there were no signs that they were slowing down. After the trade, the Oilers would also win the Stanley Cup in 1990.

However, losing Gretzky robbed the Oilers of their identity and swagger.

The Oilers traded Gretzky, center Mike Krushelnyski and Marty McSorley for Jimmy Carson, Martin Gelinas, three first-round draft choices and cash.

The Oilers have never come close to putting the same kind of explosive team on the ice they had when Gretzky wore his famous No. 99 uniform in Edmonton.