This article was originally written in November, 2014.
Every year in the NHL, trades take place between teams in order to improve their respective squads. On most occasions, trades in the NHL work out well, in which both teams improve following the arrival of a new player(s) or asset which addresses a weakness or need a team may have.
On other, less common occasions, trades in the NHL are completely lopsided and work out terribly for one team involved in the deal.
Listed below are five of the worst trades to have taken place in NHL history.
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 age of 23, Brett Hull was in the middle of a great rookie season, having scored 50 points through his first 52 career games with Calgary. Yet the Flames decided to trade Hull, alongside Steve Bozek in exchange for Rob Ramage and Rick Wamsley.
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 stand out 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 goal scorers 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 to the Hockey Hall of Fame in 2009.
New York Islanders Trade Zdeno Chara to the Ottawa Senators
In June of 2001, the New York Islanders made a disastrous deal.
6 foot 9 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.
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 on the ice 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 dollars this year, the last year of his buyout.
Calgary Trades Doug Gilmour to the Toronto Maple Leafs
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 a 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 Toronto 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 to the Hockey Hall of Fame in 2011.
Edmonton Trades Mark Messier to the New York Rangers
In 1991, the Oilers made the second worst trade in their franchise history, sending Mark Messier to the New York Rangers in exchange for Louie DeBrusk, Steven Rice and Kings great Bernie Nicholls.
At the age of 29, Messier had already won 5 Stanley Cups with the Edmonton Oilers and certainly had plenty left in the tank.
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. Steven rice split parts of three seasons between the Oilers and the minors, failing to establish himself as an everyday NHL player. Bernie 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 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 onto and winning in the finals. Through 422 games in his first stint with the Rangers, Messier scored 515 points alongside winning the Hart Memorial Trophy and Ted Lindsay Award.
Messier was inducted to the Hockey Hall of Fame in 2007.
Edmonton Trades 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, sending 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 which 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. Of the three picks the Oilers received, Jason Miller played 6 games while Nick Stajduahr played 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 2857 points in 1487 career games and won four Stanley Cups.