What would Valentine’s Day be without an ugly breakup?

OK, so Evander Kane and the Jets were a week early. And technically, they haven’t officially broken up yet — that will come when Kane is traded, either in the next few weeks or during the summer. But it’s over. In any relationship, there are some moments you can still recover from. A player walking out on his team because players threw his tracksuit in the shower is not one of them.

So Kane and the Jets are done. But as they sob into their pillows over what might have been, it’s worth pointing out that this isn’t the first nasty breakup the NHL has ever seen. In fact, Kane and the Jets barely rate a mention when you consider some of the superstars who’ve seen things end badly with the team they were supposed to be meant for.

Today, let’s look back at 10 of the worst breakups in NHL history. Some of these relationships were in trouble for years. Some fell apart over the course of a few hours. And a few even eventually ended with everyone agreeing to stay friends.

(And don’t worry if I somehow left your favorite player off the list and you’re not sure you can ever forgive me. It’s not you, it’s me.)

1. Dany Heatley and the Senators, 2009

Happier times: Heatley had played four seasons in Ottawa, scoring 50 goals twice and establishing himself as one of the most productive wingers in the game. But the team was struggling, having missed the playoffs for the first time in 13 years, and Heatley didn’t get along with new coach Cory Clouston.

He said: Heatley wanted out because … well, we’re not quite sure, although the most likely explanation seems to be the simplest one: He just didn’t like Clouston. Either way, he was adamant that he’d played his last game in Ottawa. Oh, and he also intended to use his no-trade clause to force a deal to a team he liked.

They said: The Senators chafed at Heatley’s insistence on picking his destination. They struck a deal with the Oilers, only to have Heatley use his no-trade clause to kill the transaction. To make matters even worse, the situation dragged on long enough that the team ended up having to pay Heatley a $4 million roster bonus.

How it ended: The Senators eventually gave Heatley his wish, sending him to San Jose in a deal for Milan Michalek and others that most agreed was a lopsided win for the Sharks. They later went to court to try to get that bonus money back, in a case that wasn’t resolved until 2013.

Who won? The Senators. Heatley had one decent season in San Jose but has bounced around the league with several teams since then and is currently in the minors. Meanwhile, Michalek remains a relatively useful piece for the Senators.

2. Patrick Roy and the Canadiens, 1995

Happier times: Roy had almost single-handedly won two Cups in Montreal to go along with three Vezinas and the consensus “best goalie in hockey” title, making him the latest in the franchise’s long line of French Canadian superstars. Then, one December night in 1995, the Red Wings came to town …

He said: Roy didn’t get along with newly appointed Habs coach Mario Tremblay, and there’d even been unconfirmed rumors of physical altercations. In that infamous Red Wings game, the Canadiens were blown out 11-1, and Tremblay left Roy in for nine goals before finally pulling him. Feeling as if he’d been intentionally humiliated, Roy arrived at the bench, pushed past Tremblay, and told team president Ronald Corey that he’d never play another game for Montreal.

They said: “If there’s any problem, we’re going to solve it tomorrow,” Tremblay said. Spoiler alert: Nope.

How it ended: The team suspended Roy, and four days later it traded him to the Colorado Avalanche.

Who won? Roy, who led the Avalanche to their first Stanley Cup that year and won another in 2001. The Canadiens were roasted for not getting much of anything back for a future Hall of Famer, and they haven’t been back to the Stanley Cup final in the nearly two decades since.

3. Eric Lindros and the Flyers, 2000

Happier times: Well, “happier” may be pushing it here, since the relationship between Lindros and the Flyers always seemed strained. But there had been good times, including a Hart Trophy win in 1995 and a trip to the Stanley Cup final in 1997. But by 2000, Lindros had suffered several concussions and other health problems, and when his attempt to make a heroic return in the conference finals was cut short by Scott Stevens, he’d played his last game as a Flyer.

He said: Lindros refused to accept the Flyers’ two-way qualifying offer and told GM Bobby Clarke he wanted to be traded and would only accept a move to one team: the Toronto Maple Leafs. If Clarke couldn’t get the deal done, Lindros said, he’d sit out the entire season to force it.

They said: The Flyers were happy to move Lindros but refused to do it at a discount. They seemed to be on the verge of a trade with Toronto on multiple occasions, but the two sides could never finalize a deal, and Clarke made it clear he’d let Lindros sit out all year if he couldn’t get fair value for him.

How it ended: Lindros did indeed miss the entire 2000-01 season. After one last near-miss with the Leafs, he backed down and gave Clarke an expanded list of possible destinations. Clarke found a deal with the Rangers, and the saga was mercifully over.

Who won? Nobody. In hindsight, the Flyers didn’t get much for their one-time franchise player. And while Lindros was reasonably productive in his first season in New York, he never dominated. He’d stick around the league until 2007 (including a one-year stint with the Leafs) before retiring at the age of 34.

4. Darryl Sittler and the Maple Leafs, 1982

Happier times: Sittler was arguably the greatest Maple Leaf of all time, sitting as the franchise’s leader in goals and points.¹ He’d also been captain for six seasons, kind of.

He said: Sitler ripped the “C” off his jersey in 1979 after a dispute with management. He eventually took the captaincy back, but by 1981 his relationship with the front office had soured so badly that he asked to be traded. Several teams were interested, but the Leafs took nearly two months to finalize a deal.

They said: “Hi, we’re the Maple Leafs and we’re owned by Harold Ballard, so we will never do anything right, ever.”

How it ended: In January 1982, Sittler walked away from the team, citing doctor’s orders that he take a break from hockey. Two weeks later, the Leafs finally pulled the trigger on a trade, sending Sittler to the Flyers.

Who won? Sittler was past his prime by this point, but he played well for the Flyers. Meanwhile, the Maple Leafs looked ridiculous throughout the ordeal, cementing their Ballard-era reputation as the league laughingstock.

5. Paul Kariya and the Mighty Ducks, 2003

Happier times: Kariya was the first draft pick in Mighty Ducks’ history and had emerged as the face of the franchise over the course of nearly a decade in Anaheim. In 2003, he led the team on a Cinderella playoff run that ended just one win short of a Stanley Cup.

He said: Kariya made a hefty $10 million in 2003, and at the end of the season the Ducks owed him a qualifying offer for the same amount. They declined to make it, and Kariya wasn’t happy with that. An unrestricted free agent, he decided to see what he could get on the open market.

They said: Ducks GM Bryan Murray simply didn’t feel like he could afford to commit a quarter of his roughly $40 million payroll to one player. But despite the temporary bad feelings, it was widely assumed that Kariya would return to Anaheim on a long-term deal with a slightly lower annual salary.

How it ended: Kariya shocked the hockey world by signing in Colorado for a paltry $1.2 million. It was a move designed to reunite him with close friend and fellow free agent Teemu Selanne, and it made the already offensively loaded Avalanche the prohibitive Stanley Cup favorite.

Who won? Certainly not Kariya, who left a ton of money on the table and then had a disappointing year. The Avalanche didn’t win the Cup, and the next season was wiped out by the lockout. When the league resumed, Kariya played five more seasons in Nashville and St. Louis, but he battled injuries and never really regained his superstar status. Meanwhile, the Ducks missed the playoffs without Kariya in 2004 but rebuilt quickly and won the Stanley Cup in 2007.

6. Chris Pronger and the Oilers, 2006

Happier times: Pronger had arrived in Edmonton via trade the previous offseason. In his first year as an Oiler, he led the team on an inspiring playoff run that saw it nearly win the Stanley Cup, finally putting the franchise back on the NHL’s map after a decade of irrelevance.

He said: We’re not really sure. Once the playoffs ended, Pronger told the Oilers he wanted out, but he’s never publicly explained his reasoning.²

They said: The Oilers spent several days trying to convince Pronger to stay, but it became evident he wasn’t changing his mind.

How it ended: The Oilers sent Pronger to Anaheim in exchange for Joffrey Lupul, Ladislav Smid, and draft picks.

Who won? Pronger and the Ducks, who went on to win the Stanley Cup in 2007. The Oilers had their hand forced and got what they could, including the pick they used to take Jordan Eberle, but they haven’t been back to the playoffs since.

7. Pavel Bure and the Canucks, 1999

Happier times: Bure may well have been the most entertaining player of the ’90s. He’d had a pair of 60-goal seasons, made five All-Star teams, and led the Canucks to the 1994 final. There had also been bumps in the road, including various contract disputes and a rumored holdout threat during the playoffs, which Pat Quinn firmly denied.

He also had plenty of injury troubles. But when he played, man, he was unstoppable.

He said: After the 1997-98 season, Bure informed the Canucks he would not report the following season, citing various complaints about his treatment by the organization and the pressure of playing in Vancouver. He was true to his word, remaining in Moscow when training camp opened.

They said: The Canucks GM at the time was Brian Burke, who wasn’t about to roll over to accommodate his superstar. He told fans he didn’t buy Bure’s reasons for wanting out, and he let the Russian star sit at home for four months.

How it ended: In January 1999, Burke finally signed off on a trade that sent Bure to the Florida Panthers.

Who won? Bure led the league in goals in each of his first two full seasons in Florida, but injuries forced him out of hockey by the age of 31. The Canucks didn’t hit a home run on the trade, but they did get Ed Jovanovski in the deal, so they extracted some value. Call this one even. (And in a nice touch, the two sides eventually reconciled.)

8. Ilya Kovalchuk and the Devils, 2013

Happier times: Kovalchuk was one of the league’s top goal scorers despite playing his early years for the woeful Thrashers. He became an unrestricted free agent in 2010, and the Devils signed him to a stunning 17-year, $102 million deal. The league rejected that contract for circumventing the salary cap but approved a revised 15-year, $100 million version.³

He said: Just three years into the deal, Kovalchuk decided he’d rather head home to Russia to play in the KHL.

They said: Have you ever wanted out of a relationship and been delighted when the other side broke up with you first? That was the Devils here.

How it ended: Kovalchuk announced his retirement from the NHL, voiding the 12 years left on his massive contract.

Who won? The Devils were the big winners, getting three good seasons out of Kovalchuk before he turned 30, then escaping the massive commitment they’d made to a player who was likely on the verge of declining. As for Kovalchuk, he seems happy enough in the KHL, although we’ll probably periodically hear rumors of an NHL return.

9. Brendan Shanahan and the Whalers, 1997

Happier times: Shanahan was considered one of the league’s best power forwards when the Whalers acquired him in 1996 in a deal for Chris Pronger. He had one good year in Hartford, scoring 44 goals and being named team captain while also making the All-Star team.

He said: Shanahan requested a trade during the offseason, citing the Whalers’ lack of stability and rumors of a franchise move. When a deal hadn’t been reached before opening night, Shanahan remained with the team and played in its first two games, but he resigned his captaincy and made it clear he wanted out.

They said: With the threat of Shanahan walking out on the team hanging over them, the Whalers didn’t have much choice.

How it ended: The Whalers traded Shanahan to the Red Wings for a decent package that included Keith Primeau and Paul Coffey.⁴ It was a big deal — here’s a Detroit TV station breaking into coverage of a Tigers game to announce it.

Meanwhile, Shanahan is considered one of the most hated players in Whalers history.

Who won? Hmm, let’s see. Shanahan went on to win three Stanley Cups in Detroit and was inducted into the Hall of Fame in 2013. Meanwhile, the Whalers moved to Carolina a few months after this deal. Also, nobody outside Hartford even remembers that this all happened. Yeah, I’m going to go ahead and say Shanahan won.

10. Bobby Hull and the Blackhawks (and also the entire NHL), 1972

Happier times: Hull had spent 15 seasons with the Blackhawks, establishing himself as one of the greatest goal scorers in league history. He led the league in goals seven times, setting the single-season record along the way, and by 1972 his 604 career goals was the most among active NHLers.

He said: When the World Hockey Association arrived in 1972, there was talk the upstart league could try to poach established stars from the NHL. Hull suggested it would take millions to get him to jump ship. When the Winnipeg Jets shocked the hockey world by offering him just that, Hull signed a 10-year deal. Other players soon followed.

They said: The NHL went to court to try to block the defections, and the Blackhawks filed a restraining order against Hull.

How it ended: In November 1972, the court ruled against the NHL, and Hull was free to join the WHA. He scored at least 50 goals in each of his first four seasons in the league, including a ridiculous 77 in 1975.

Who won? Hull’s bank account. While the WHA earned some much-needed credibility from the signing, the league only lasted until 1979. Meanwhile, the NHL’s iron grip on players was weakened significantly, helping to lay the groundwork for the salary explosion of later years.

1. Since surpassed in both by Mats Sundin.

2. Most in Edmonton blame his wife.

3. It also punished the Devils with the loss of a first-round pick, then changed its mind because Lou Lamoriello growled at them.

4. Coffey also didn’t want to play in Hartford, but that’s another story.