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:
15 15. Chris Chelios - Montreal Canadiens
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.
14 14. Evander Kane - Winnipeg Jets
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.
13 13. Pavel Bure - Vancouver Canucks
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.
12 12. Mark Messier - Vancouver Canucks
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.
11 11. Darryl Sittler - Toronto Maple Leafs
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.
10 10. Sheldon Souray - Edmonton Oilers
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.
9 9. Bobby Hull - Chicago Blackhawks (and the NHL)
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.
8 8. Ilya Kovalchuk - New Jersey Devils
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.
7 7. Martin St. Louis - Tampa Bay Lightning
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.
6 6. Paul Kariya - Mighty Ducks of Anaheim
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.
5 5. Roberto Luongo - Vancouver Canucks
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.
4 4. Chris Pronger - Edmonton Oilers
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.”
3 3. Eric Lindros - Philadelphia Flyers
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.
2 2. Dany Heatley - Ottawa Senators
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.
1 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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