Top 15 NHL Trades That Should Have Never Been Made

There's nothing worse than watching your favorite team ship away a talented player only to watch them flourish with their new club. In a fair deal, both teams win and the players involved in the transaction contribute equally to their new organizations. Let's be honest, fair deals are boring. They usually involve sub-par players and mostly meaningless draft picks. Gone are the days of good blockbuster deals that flipped the NHL on its head.

Too many trades ended so one-sided that it changed the face of some organizations forever. It's not knowing how valuable that 1st round pick will be, or how quickly a young player might turn around their game that's keeping the owners and management of a lot of teams, at bay. Remember when you looked forward to the trade deadlines? The last few years have seen a handful of big moves well before the final day, leading to a few meaningless pawn moves by the time we're all paying attention. But why are teams being more conservative than ever?

It could have something to do with a number of huge trades that should have never happened in the past. I'm talking about moves involving players like Wayne Gretzky, Eric Lindros and Jaromir Jagr to name a few. Others seemed innocent at the time, but ended up costing teams franchise players and arguably, Stanley Cup championships.

Rarely, but every now and then we still witness a move we'd never thought we'd see. Some make no sense at all until you read about a disgruntled player and a locker room scandal. Some of these moves are so fresh we can't yet see how they will play out. Others, we're all too familiar with.

Here are the top 15 NHL trades that never should have happened.

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15 Brett Hull to St. Louis

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On March 7, 1988, the St. Louis Blues acquired Brett Hull from the Calgary Flames in one of the most iconic one-sided trades in NHL history. Hull scored a game winning goal for Calgary in his first regular season game. He went on to dominate in the AHL for a season before being recalled by Calgary. Hull had 50 points in 52 games for the Flames before he was traded to St. Louis and became the prolific goal-scoring machine we know him as today.

The Flames did use the pieces of the Hull deal to win a Stanley Cup but by the late 90s, would embark on a seven-year playoff drought. Calgary should’ve seen what was in front of them at the time. A Brett Hull trade never should have happened.

14 Patrick Roy to Colorado

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Can you imagine Carey Price being left out to dry for nine goals on a bad night? Or being mocked by his own home crowd? Montreal Canadien fans would love to forget that fateful night when Patrick Roy experienced just that, before letting then team president, Ronald Corey know he would never play for Montreal again.

Had the coach pulled Roy after the 4th, maybe even the 5th goal, it's possible Roy would have put the bad night to rest and come focused for the next game. The rout and poor support from fans left an irreparable impression on Roy who moved to Colorado and solidified his Hall of Fame career.

13 Dion Phaneuf to Ottawa

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Trading the captain of your team to your biggest rival is something we never expect to happen in any sport. When Dion Phaneuf was traded to the Ottawa Senators in an unusual nine-player deal, it sent the hockey world into a frenzy.

While there was no immediate impact on the ice and the move couldn't help the Senators squeak into the playoffs. The Phaneuf trade may be the strangest and most obvious trade that never should have happened.

12 Evander Kane to Buffalo

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Evander Kane hasn't budded into the franchise player he was believed to be when he was drafted by the Winnipeg Jets. Analysts believed frustrations boiled over and left Kane on the outside looking in from the locker room with is teammates. Kane, who should have been one of the main Jets building blocks with Mark Scheifele, Dustin Byfuglien, and Blake Wheeler was traded to Buffalo which saw a return for Tyler Myers.

Unfortunately, personalities can be hard to predict. In a perfect world, Kane would have swallowed his pride and helped Winnipeg compete with the NHL's elite.

11 Tyler Seguin to Dallas

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We could have used Toronto as a great example, but the Phil Kessel fiasco has finally passed us. Now, we can pick on the Boston Bruins, who were quick to dispense a rowdy and recklessly young Tyler Seguin early in his career. Seguin's numbers exploded to career bests when he landed in Dallas and quickly made the Bruins look silly for sending the talented forward packing. Now considered one of the best in the game, Seguin and Jamie Benn have provided the Stars with some serious firepower to make a deep playoff run.

10 Roberto Luongo to Vancouver

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Luongo ultimately struggled to break into the league. It led to his first move to the Florida Panthers from the New York Islanders after the Islanders drafted DiPietro 1st overall in the 2000 NHL entry draft. Luongo was surprised by the move but the Panthers welcomed him with open arms, stating he would be their franchise goalie.

Unfortunately Florida couldn't put their money where their mouth was and traded Luongo to the Vancouver Canucks in a package deal that saw them land Todd Bertuzzi, Bryan Allen and Alex Auld in return. The Canucks inked Luongo immediately and held on to the netminder through his best years before eventually sending him back to Florida in 2014.

9 Mark Messier to New York

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It took a few more years, but Messier realized that the Edmonton Oilers were not going to be the same team without Wayne Gretzky. He made the decision to move and Edmonton subsequently traded the last piece of their 80s dynasty to the New York Rangers. Without Messier, Gretzky, Fuhr, and Kurri, the Oilers went on a five-year playoff drought as they worked to rebuild a competitive team. While they've mustered a handful of 1st round playoff appearances and one finals appearance, the Oilers still struggle to this day and never should have traded their stars away.

8 Joe Thornton to San Jose

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When Mike O'Connell, the then GM of the Boston Bruins called Thornton with the news of a trade to San Jose, Joe was stunned. He knew changes were coming because of the adversity the team had been facing but the changes should have been made upstairs, not on the ice. Thornton had this to say at the time of the trade, "Obviously [the Bruins] believe in their coach and their general manager, and I'm next in line, so I've got to move on. ... I came back here to win, and we haven't been winning. Whose fault is that? I'm not sure, but I'm out of here, so it must be mine."

Thornton reveled in the fresh start and quickly found success with the Sharks, forming a dominating duo with Patrick Marleau.

7 Tuukka Rask to Boston

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One of the worst trades in Toronto Maple Leafs history was trading their 2005, 1st round pick, Tuukka Rask to the Boston Bruins for Andrew Raycroft. Rask had not played a single NHL game before being shipped to Boston in what shaped out to be catastrophically lopsided trade as Raycroft immediately declined with his new club and Rask, slowly grew into a strong starting goaltender for the Bruins. The Maple Leafs wanted a veteran goalie to fill that role, and regrettably threw away the best goalie they never had.

6 Kris Draper to Detroit

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Back when you were child, $1 could buy you a lot more than it could today, but did you know in 1993 it could buy you a future Selke trophy winner? Neither did the Winnipeg Jets who infamously gifted the Detroit Red Wings with Kris Draper for exactly that.

Draper would go on to win four Stanely Cups, a 2004 Frank J. Selke trophy, and play over 1,100 games with the Red Wings before retiring in 2011. The only part of this trade that never should have happened were the laughable terms.

5 Phil Esposito to Boston

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One of the most famous moves in Boston Bruins history was the acquiring of Phil Esposito, Ken Hodge, and Fred Stanfield from the Chicago Blackhawks. In return the Blackhawks received an above average player in Pit Martin, an average at best defenseman in Gilles Marotte, and below-average goaltender in Jack Norris.

The Blackhawks truly believed they won this deal, claiming Esposito was too slow and a bad leader while getting Gilles Marotte from the Bruins was an absolute steal in their eyes.

If the NHL's large six-team expansion wasn't on the horizon, the Blackhawks wouldn't have been so eager to move their pieces around. The Bruins turned their entire franchise around on a deal that never should have happened.

4 Jaromir Jagr to Washington

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The Pittsburgh Penguins needed to trim up their salary cap to re-sign a large number of players to the team in 2001. Jagr was set to make about $20 million in the next two years and was ultimately the salary they chose to cut. The result would be one of the most lopsided trades in NHL history. In return, the Penguins would receive three players by the names of Beech, Sivek, and Lupaschuk. Beech was the only one who spent much time in the NHL but was quickly bounced around the league. Sivek and Lupaschuk would both play a handful of NHL games before heading overseas. Washington undoubtedly robbed the desperate Penguins.

3 Eric Lindros to Philadelphia

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Eric Lindros redefined the power forward role in the NHL. He was as big and mean as an enforcer, while possessing the finesse and scoring touch of a sniper. What should have been the cornerstone for Quebec's team, turned out to be a very controversial situation when Lindros announced prior to the 1991 NHL Entry Draft that he wouldn't play for the Nordiques. Committed to their game plan, Quebec drafted him anyway and Lindros, true to his word, refused to play. Quebec would eventually trade him away to Philadelphia, notably getting the rights to Peter Forsberg in the deal.

Lindros and the NHL put Quebec in a tough position and forced their hand in a trade that never should have happened.

2 Guy Lafleur to Montreal

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One of the most iconic Canadiens of all-time was famously acquired through two trades, one being very timely in solidifying the draft of Montreal's legend.

Sam Pollock, the GM mastermind, convinced a very bad California Golden Seals team to give Sam their first overall pick in the 1971 NHL Draft. It's arguable Pollock was just looking to take advantage of the Seals and hadn't quite set his sights on Lafleur just yet. It was a lot more obvious when Pollock traded a talented veteran in Ralph Backstrom in a one-sided deal to Los Angeles to ensure they wouldn't finish last, that he wanted to retain 1st overall pick. If the Seals or Kings had done any homework at all neither trade would have happened, and hockey history would have been written much differently.

1 Wayne Gretzky to Los Angeles

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It's hard to justify any other move in this list over the monumental trade of the greatest hockey player the world has ever seen. Wayne Gretzky was the main piece of the Edmonton Oilers dynasty years. In a trade that would alter the hockey universe forever Gretzky was shockingly traded to the Los Angeles Kings for reasons that are still not completely understood today. Arguably, the deal came down to money, $15 million of it. It was a deal that was very slowly constructed behind the scenes for years before the fateful press conference at Molson House in 1988.

With that, Gretzky moved to Hollywood and changed the landscape of the hockey world, forever.

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