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He said: Roy didn’t get along with newly appointed Habs coach Mario Tremblay, and there’d even been unconfirmed rumors of physical altercations. Then, one December night in 1995, the Red Wings came to town … 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. Meanwhile, Michalek remains a relatively useful piece for 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. They later went to court to try to get that bonus money back, in a case that wasn’t resolved until 2013. 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. 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. They struck a deal with the Oilers, only to have Heatley use his no-trade clause to kill the transaction. They said: The Senators chafed at Heatley’s insistence on picking his destination. Oh, and he also intended to use his no-trade clause to force a deal to a team he liked. Either way, he was adamant that he’d played his last game in Ottawa.
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. 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. 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. (And don’t worry if I somehow left your favorite player off the list and you’re not sure you can ever forgive me. And a few even eventually ended with everyone agreeing to stay friends. Some fell apart over the course of a few hours. Some of these relationships were in trouble for years. Today, let’s look back at 10 of the worst breakups in NHL history. 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. 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. A player walking out on his team because players threw his tracksuit in the shower is not one of them. In any relationship, there are some moments you can still recover from. 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. OK, so Evander Kane and the Jets were a week early. What would Valentine’s Day be without an ugly breakup?