Worst Team-and-Player Breakups in the NHL

It doesn’t happen very often, but it makes for some great news headlines when it does.
Team drafts/trades for player, team is excited, player is excited. Fans go nuts.
And then all hell breaks loose.
The most recent example was Evander Kane leaving the Winnipeg Jets (for Buffalo of all places), then we the sports fans, get to sit back and poke fun at whoever got the worst of it.
That’s the best part of the breakup, somebody has to lose. Sometimes nobody gets the better of it, but in every single case, somebody loses either money, respect, pride, or a fun mix of both.
Here are some of the worst (best) that I could find online:

-Evander Kane and the Jets, 2014 
The long and short of it saw Kane show up to a team meeting. Apparently everybody else was dressed in a suit (hockey players at almost every level are required to look good, even at Pee Wee, so what Kane may have been thinking, I do not know). Some players did not take this too well. One of them was the big guy on the team, Dustin Byfuglien.
Byfuglien then proceeded to throw some of Kane’s clothes in a shower stall. When Kane realized this, apparently he went home and the team could not reach him until about an hour prior to game time. Not cool, Kane. This may have not been quite so bad had Kane not been photographed from a hotel room in Las Vegas pretending to talk to Floyd Mayweather on a phone made of 100 dollar bills.

Who won? Right now, the Jets won because they no longer have to deal with this clown, I have trouble believing that Kane wins because now he is stuck in Buffalo, one of the worst franchises in the league. And to further the problem, they just traded their starting goaltender (Michal Neuvirth) for the NYI backup goaltender (Chad Johnson). Don’t see this as a win for Kane; at least the Jets will probably make the post season; plus they got Tyler Myers and Drew Stafford in the deal.

-Dany Heatley and the Senators, 2009
This is the spoiled brat story for the ages. This is the dude that killed a past teammate (unintentionally we hope) while speeding in a Lamborghini) then got traded to Ottawa where he became a flat-superstar, scoring 50-goals in two seasons and establishing himself as one of the most unstoppable forces in the game. He also scored 4 times in the all-star game one year.
Then all hell broke loose.
The team struggled, and then Heatley decided that he did not like the team’s new head coach, Corey Clouston.
Then, because of the no-trade clause in his contract, Heatley got to choose the team he would be dealt to.
Ottawa then had a deal worked out with the Oilers (of all teams) as a destination, however that was not good enough for Heater either. Plus, the dilemma dragged out for so long that the Sens were forced to pay out a $4 million roster bonus even though the sniper wasn’t playing.
Ottawa wound up granting Heatley’s request, sending him to San Jose in a deal that fetched Milan Michalek as the main component in return; Jonathan Cheechoo and a draft pick were also in the package. At the time, it was seen as a lopsided win for the Sharks. The Senators eventually took Heatley to court in attempt to win their bonus money back.
According to the Ottawa Sun in a story dated Oct. 22, 2013, the Senators were able to get some of the money back.

Who won? The Senators, easily. Heater had one strong season in San Jose. He was there for a total of 2 seasons. He played injured a lot, despite a trip to the Conference Finals in 2010 where the Sharks were swept by the Blackhawks. The following season was his worst. He was dealt to the Minnesota Wild and has been bouncing around ever since.
Heater is now signed with the Florida Panthers; Milan Michalek, on the other hand, remains a relatively strong part of the Senators.

-Ilya Kovalchuk and the Devils,  2013
Three years into this 15-year deal, Kovalchuk decided that he would rather go back home and play in the KHL. I think that tells you who won the conflict right there. Now we should all be wondering at what point Kovy decides to try and make a return to the NHL.

-Paul Kariya and the Mighty Ducks,  2003
Kariya was the first draft pick of the then-Anaheim Mighty Ducks. He did everything for them except win the Stanley Cup in 2003 (they came up one game short to be exact). The team owed him a qualifying offer at that point, for the value of his contract ($10M). They decline to make it. Kariya did not like that. Not one bit. Kariya had been the face of the franchise for 10 years in Anaheim.
This made him an unrestricted free agent and could go anywhere he chose.
He signed a contract, and shocked everybody in the process. It was worth only $1.2M with the Colorado Avalanche.

Who won? Kariya did not win. He didn’t win anything. He had his first disappointing year in the NHL. The Avalanche were already heavily loaded with offensive stars, expected to win the Stanley Cup; and the following season was wiped out by the lock out.
Kariya wound up spending the next 5 seasons between Nashville and St. Louis and did not regain that superstar status. As for the Ducks, they missed the playoffs without Kariya in 2004, rebuilt themselves, and actually won the Cup 3 years later.

-Eric Lindros and the Flyers,  2001
Eric Lindros won the Hart Trophy and took his team on a hell of a ride to the Stanley Cup final in 1997…all this came after all the craziness of the draft which saw the Flyers outbid the entire league to acquire Lindros since he had refused to play for the team that drafted him originally, the Quebec Nordiques.
In my mind, he was doomed from that very day. Great player (for awhile). Bad attitude.
Come 2000, he started falling victim to the deadly concussion, and other health problems. Then he attempted to make a heroic return to the conference finals but was sent right back to the hospital after Scott Stevens nailed him near the blueline, and he was done like dinner, completely.
The ‘fun’ part began when he refused a two-way qualifying offer from the Flyers. He told GM Bobby Clarke that he wanted to be traded to one team, and one team only, that was the Toronto Maple Leafs.
Furthermore, if Clarke could not make a deal with the Leafs, Lindros would sit out the entire season; he ended up doing that.
The Leafs nearly had him on 2 separate occasions, both times missed so Lindros gave Clarke more destination teams to which he would accept a trade.
Finally they found a deal with the Rangers, but all that arguing probably cost Lindros his entire career, he never dominated. He was granted his original wish, to play for the Leafs, but that didn’t go well, either.
He is probably sitting at home somewhere right now as I write this.

-Chris Pronger and the Oilers,  1999
Pronger had arrived in Edmonton and in his first year with the Oilers, the team went on a wild playoff run that saw them lose in the Stanley Cup final to the Carolina Hurricanes.
Once that playoff run ended, he said he wanted out.
Nobody has a clue why he made that decision. My guess is his wife decided that she was sick of Oil town (remember another NHL superstar that put Edmonton back on the map then asked for a trade because his wife wasn’t from town???).
Edmonton sent Pronger to Anaheim (big surprise-it isn’t cold down there), in exchange for Joffrey Lupul, Ladislav Smid and draft picks.
Sadly for Canadian hockey fans (and Oiler fans), the superstar won a Stanley Cup down in Anaheim in 2007. The Oilers had to do what they could with what they got (Jordan Eberle) but their franchise has looked like a cyclone hit it, ever since. Not good.

Who won? Ducks of course.

-Pavel Bure and the Canucks,   1999
One of the least-known breakups in pro hockey was between Pavel Bure (the Russian Rocket) and the Vancouver Canucks. Bure was one of the most electrifying hockey players during the 1990s. He could dipsy-doodle around everybody the same way Patrick Kane does today. Bure had a pair of 60-goal seasons and he led the Canucks to the 1994 Stanley Cup final which they came up short in 7 to the Rangers.
Bure made 5 all-star teams too. It wasn’t all fun and games, though. There were contract disputes and a rumoured threat of a holdout during the playoffs.
After the 1997-98 season, Bure informed the team that he would not report the following seasons, saying he was unhappy with the organization. Bure remained in Moscow during training camp.
Vancouver finally traded the unhappy superstar to the Florida Panthers.

Who won? Hard to argue against Bure. He had 98 points in the first season (1999-2000) and was league scoring champ, the following year he scored 59 goals. Vancouver got Ed Jovanovski in the Bure deal so they did not get completely ripped off.

-Patrick Roy and the Canadiens , 1995
Nobody on the Montreal Canadiens roster in the early 1990s had a stronger impact on the team than goaltender Patrick Roy.
That all changed one night in December of 1995 when the Detroit Red Wings rolled into town.
They absolutely destroyed Patrick Roy. Absolutely destroyed him. He had nothing that night and it wound up being his last with the Habs.
The Wings beat Roy 9 times on 26 shots and the Canadiens’ ‘faithful’ gave it to him too.
That was end of Roy in Montreal. He got suspended after he told team president Ronald Corey that he played in his last game for Montreal. He was traded to the Avalanche. Roy hadn’t gotten along with the new coach hired in Montreal Mario Tremblay, but the 11-1 loss was clearly what moved him.

Who won? The Avs won, big time. Roy led them to their first Stanley Cup that year (if you are a Habs fan, that had to hurt), and Colorado won another Cup in 2001.
The Habs were roasted like Charlie Sheen on Comedy Central, for not getting anything back for Roy. Montreal hasn’t returned to the Cup since Roy played for them.