Top 15 Worst NHL Player/Team Breakups

Bad breakups. We’ve all had them. Sometimes, it’s a result of hanging on to something for too long that just wasn’t there. Other times, an isolated incident can result in a huge blowup, forever applying bitter resentment to your memories of that relationship and person.

Ugly breakups occur in professional relationships as well, and that applies to sports perhaps more than any other industry. Professional sports are obviously a very competitive market place to begin with. When you throw in the large egos and high levels of testosterone, it’s understandable that sometimes things boil over between an individual and an organization.

In the NHL there have been countless bad breakups between a team and a player. Most recently, we can point to Phil Kessel and the Toronto Maple Leafs. It wasn’t the most volatile of public spats if you can even consider it a spat at all, but I think we can all agree that Kessel won’t be sending the Maple Leafs organization a Christmas card this year.

The Kessel/Toronto divorce was actually pretty docile, though, if you compare it to some of the other breakups the league has witnessed in the past. Here are the top-15 worst player/team breakups in the history of the NHL:

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15 Chris Chelios - Montreal Canadiens

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Chris Chelios was a member of the Montreal Canadiens from 1984 until 1990. He was happy in Montreal for the most part, but when he left it wasn’t on the best of terms. Chelios was traded to the Chicago Blackhawks just one day after challenging a few of Montreal’s finest to a fight outside a bar. Apparently, the officers were trying to arrest Chelios for public urination.

This situation came amid rumors that Chelios was sleeping with team president Ronald Corey’s wife. Needless to say, it was time for Chelios to put the Montreal chapter of his life behind him, and the feeling was mutual with the organization.

14 Evander Kane - Winnipeg Jets

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Winnipeg Jets fans had been waiting for the maturation of Evander Kane ever since the franchise moved to Manitoba in 2011. Fans truly hoped that 2014-15 would be the year Kane took that next step; unfortunately, they were disappointed in the end.

Kane was constantly making headlines during his stay in Winnipeg for all the wrong reasons. It’s reasonable to believe that his teammates were a little fed up with Kane’s antics. About a week before he was dealt to Buffalo, there were reports that an unnamed player (rumored to have been defenseman Dustin Byfuglien) tossed Kane’s tracksuit in the showers. Kane didn’t take too kindly to this move, and the organization finally gave up and moved on from the enigmatic winger.

13 Pavel Bure - Vancouver Canucks

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Pavel Bure was the fan favorite in Vancouver for pretty much the entire time he was there, so it came as a surprise to most when he refused to play out the final year of his contract with the Canucks in the summer of 1998.

Bure cited “personal reasons,” and he even sat out a good chunk of the 1998-99 season while GM Brian Burke tried to find a dance partner in a trade. Bure was eventually sent to Florida, and although the sides have since reconciled their differences, it’s safe to say there was bad blood at the time of the incident.

12 Mark Messier - Vancouver Canucks

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The city of Vancouver pretty much hated Mark Messier (because of 1994) even before he came to play for the Canucks in 1997. When he stole the captaincy from fan favorite Trevor Linden upon arrival and demanded that he wear no.11 even though it was unofficially retired in honor of Wayne Maki (who died of brain cancer at the age of 29 as a member of the Canucks in 1974), the fans turned on him early.

The city never warmed up to Messier, and he played out his contract in Vancouver with underwhelming results. He wasn’t offered an extension, and fans in Vancouver still hate Messier to this day.

11 Darryl Sittler - Toronto Maple Leafs

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Darryl Sittler was granted the captaincy of the Toronto Maple Leafs in 1975, but it wasn’t until 1979 when his relationship with owner Harold Ballard started to go downhill. When Ballard hired Punch Imlach as the new GM, Sittler wasn’t too thrilled on the basis of Imlach having a very strained relationship with the NHLPA.

Sittler stripped the C off his own sweater amid the 1979-80 season, citing a lack of communication with management as the culprit. A long, drawn-out process followed, until and the Leafs eventually struck a deal with the Philadelphia Flyers.

10 Sheldon Souray - Edmonton Oilers

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Sheldon Souray played parts of three seasons with the Edmonton Oilers, but it wasn’t until the 2009-10 season when things started to go sideways. Not having fully recovered from offseason hand surgery, Souray was pushed into the lineup early by management and never really found his footing that year.

Souray simply couldn’t stay healthy throughout the season, and he ended up playing just 37 games. He requested a trade the following offseason, citing team management as the main reason for his desire to leave. The divorce got a little messy from there, as GM Steve Tambellini had a tough time finding a satisfactory return for his star defenseman. Souray spent some time playing for the AHL's Hershey Bears before the Oilers bought out the final year of his contract.

9 Bobby Hull - Chicago Blackhawks (and the NHL)

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The WHA was really a nothing league in its infancy. Founded in 1971, it couldn’t compete with the well-established NHL, and no matter how hard it tried it struggled to attract high level NHL talent. That was until it threw a $1.75 million, 10-year contract (unprecedented at the time) at The Golden Jet.

Bobby Hull, of course, signed the deal and made the move, but it was much to the chagrin of the Chicago Blackhawks and the entire National Hockey League. There was a silver lining to this, however; the move gave the WHA the credibility it needed to compete with the NHL, and negotiations of a merger began just a few years later.

8 Ilya Kovalchuk - New Jersey Devils

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A 17-year contract worth $102 million for a 27-year-old who’s secretly planning on retiring in a few years. What could go wrong?

The NHL stepped in and made a few necessary amendments to this ridiculous deal, but the changes weren’t drastic enough (15-year, $100 million). A few years after signing this ridiculous extension, Kovalchuk retired from the NHL to play in his homeland in the KHL.

Devils GM Lou Lamoriello, at least in the public eye, was royally pissed at this decision by Kovie, but something tells me it was all an act on Lou’s part. It came a little earlier than he probably wanted, but an early retirement was the only way out of that offensive contract for the franchise, really.

7 Martin St. Louis - Tampa Bay Lightning

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When Tampa Bay Lightning/Canadian men’s Olympic team GM Steve Yzerman passed over Martin St. Louis when compiling the 2014 Sochi Olympics roster, St. Louis didn’t hide his disappointment. Shortly after the snub, he requested a trade.

In a twist of irony, teammate Steven Stamkos wasn’t able to attend the tournament in Russia thanks to the broken leg he suffered in November, and St. Louis was named as his replacement. The damage to the relationship had been done, though, and St. Louis was sent to the Rangers at the trade deadline in March 2014.

6 Paul Kariya - Mighty Ducks of Anaheim

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Following the 2003 Game 7 Stanley Cup Final loss to the New Jersey Devils, Paul Kariya became a UFA. He was initially an RFA, but then-GM Bryan Murray chose to release Kariya since his qualifying offer would have to have been minimum $10 million.

Kariya was upset by this, seeing it as an insult of sorts. While Murray remained committed to renegotiating a long-term deal with Kariya at a lower price tag, Kariya instead opted for a one-year deal with the Colorado Avalanche for a paltry $1.2 million, below the league average.

Ducks fans saw this as a slap in the face, as he could have signed for much more than that to stay in Anaheim long term. When Kariya finally played a game at Arrowhead in enemy colors, he was booed every time he touched the puck.

5 Roberto Luongo - Vancouver Canucks

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Ah, yes. The Roberto Luongo debacle in Vancouver.

This could have been way higher on the list if Luongo hadn’t handled it all with such class, but I refuse to believe there isn’t some bad blood there.

It’s hard to point out exactly when the mistreatment of Luongo began in Vancouver, but the 2012 playoffs is a good guess. The Canucks faced the eventual champion Kings in the first round that year, and Luongo lost the first two games, despite solid play. Head coach Alain Vigneault chose to switch starters to Cory Schneider, and the goaltending controversy was in full swing.

The following season (the lockout shortened 2012-13), Luongo split the crease with Cory Schneider, including again in their first round playoff exit vs. the San Jose Sharks (each lost a pair of games). Surprisingly, Schneider was the one dealt at that year’s draft, and Luongo remained with the squad.

Perhaps the last straw was when head coach John Tortorella (who replaced Vigneault before the 2013-14 season) chose to start backup Eddie Lack for the Heritage Classic at BC Place on March 2, 2014. Luongo admitted major disappointment in this, as he said was looking forward to that game. He was traded to the Florida Panthers two days later, finally ending the madness.

4 Chris Pronger - Edmonton Oilers

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Chris Pronger’s first season in Edmonton was a dream come true for most hockey players; a fairytale run to Game 7 of the Stanley Cup Final in which Pronger played nearly 30 minutes a night and led his team in points. Needless to say, the city of Edmonton was shocked when it learned of Pronger’s trade request on June 23, 2006, just four days after the heartbreaking loss to the Hurricanes.

Pronger was more or less a savior in Edmonton during his short stay, so his trade request out of town sent ire throughout Oil Country. The official reason for his request was “personal reasons.” Some suggest his wife, Lauren, wanted out. Others suggest that the only reason Lauren wanted out was because of a certain someone’s affair with a local media “celebrity.”

Whatever the case, Pronger was dealt to Anaheim for Ladislav Smid and Joffrey Lupul, as well as a bevy of draft picks (one of which turned into Jordan Eberle).

3 Eric Lindros - Philadelphia Flyers

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Late in the 1999-00 season, Eric Lindros suffered his second concussion of the season. This prompted him to publicly criticize the Flyers’ training staff for not properly identifying and treating his head injuries. Looking back, this was a pretty fair point made by Lindros. Nonetheless, GM Bobby Clarke chose to strip him of his captaincy for his remarks.

Lindros eventually returned for Game 6 of the Eastern Conference Finals against the Devils. He scored the lone goal for the Flyers in the 2-1 loss, but in Game 7 he was leveled with an open-ice Scott Stevens hit, and that would be the last game Lindros played for the Flyers.

Lindros wasn't cleared for contact until December of the next season, but he had no contract at the time and ended up sitting out the entire season as a result, not wanting to re-sign with the Flyers, who still owned his rights. The following summer, Lindros was dealt to the Rangers, and the bad blood between Clarke and “The Next One” wasn't resolved until well after no.88's retirement.

2 Dany Heatley - Ottawa Senators

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At the end of the 2008-09 season, Dany Heatley had just completed the first year of his six year contract extension with the Ottawa Senators. Heatley was coming off his worst season from a points perspective since his rookie year, and he was unhappy with the way he was being utilized by new coach Cory Clouston.

Heatley requested a trade on June 9, 2009, infuriating Sens nation. That wasn’t all, though; GM Bryan Murray had a deal in place that would have sent Heatley to Edmonton in exchange for Andrew Cogliano, Dustin Penner and Ladislav Smid. Heatley went on to reject the trade, refusing to waive his no-trade clause to go play in Northern Alberta.

Murray was able to eventually strike a deal with the Sharks, but the package coming back was viewed as inferior to the deal he made with Edmonton, causing Ottawa (and Edmonton) to hate Heatley even more.

1 Patrick Roy - Montreal Canadiens

It was the most public (and somewhat awkward) of spats, and it immediately led to the trade that sent Patrick Roy to Colorado.

On Dec. 2, 1995, Roy was in net as the Habs hosted the Red Wings. It was the worst home loss in team history, 11-1, and Roy was kept in net for an unprecedented nine goals before he was finally pulled.

When Roy got to the bench after finally being pulled midway through the second period, he walked right past head coach Mario Tremblay and told team president Ronald Corey “it’s my last game in Montreal.”

Roy, who butted heads with coach Tremblay, felt that he was kept in net beyond the first period in order to humiliate him. Tremblay downplayed the incident to the media after the game, insisting they’d be able to settle the dispute the next morning after the sides had time to cool off.

Well, that never happened, and four days later Roy was sent to Colorado along with Mike Keane for Jocelyn Thibault, Martin Rucinsky and Andrei Kovalenko. Thus began the darkest period in the history of the Habs' storied franchise, while Roy went on to win two more Stanley Cups in Colorado.

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