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.

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.

14 Patrick Roy to Colorado


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.

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.

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.

11 Tyler Seguin to Dallas

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10 Roberto Luongo to Vancouver

Anne-Marie Sorvin-USA TODAY Sports

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.

9 Mark Messier to New York


8 Joe Thornton to San Jose

Marc DesRosiers-USA TODAY Sports

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."

7 Tuukka Rask to Boston

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6 Kris Draper to Detroit



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.

5 Phil Esposito to Boston


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.

4 Jaromir Jagr to Washington


3 Eric Lindros to Philadelphia


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.

2 Guy Lafleur to Montreal


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.

1 Wayne Gretzky to Los Angeles


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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Top 15 NHL Trades That Should Have Never Been Made