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We have seen this before, although perhaps not on this scale and not all at once.

The general manager of a Canadian NHL team, in pursuit of the old-school hockey ideal of grit or size or some other intangible, moving key pieces and/or salary-cap space out in order to change the mix.

This was the way in Toronto for years. One GM called it "truculence." The next branded it "leadership." What it really was was folly: Elevating Mike Komisarek, Dion Phaneuf, David Clarkson and many others into more than they ever were on the ice because of their good-in-the-room-ness.

Wednesday was a particularly brutal example of this. The Edmonton Oilers dealt Taylor Hall, one of the best five (and probably three) left wingers in the game, to New Jersey for Adam Larsson, a solid yet unremarkable 23-year-old defenceman who has nine career goals and has yet to live up to being drafted fourth overall five years ago.

The Montreal Canadiens, meanwhile, moved P.K. Subban to Nashville for the Predators long-time captain, Shea Weber, who is four years older and, to most discerning eyes, four years slower.

And Steven Stamkos opted to stay in the Sun Belt, signing a bargain eight-year extension in Tampa despite the interest of three Canadian teams: Toronto, Montreal and Vancouver.

There has been a lot of hand-wringing about the seven Canadian NHL teams this season after every one of them missed the playoffs for the first time in 45 years. But the truth is, issues were there long before 2015-16.

Edmonton is the worst team in the NHL in its salary cap era, averaging 32 wins per 82 games over the past 11 years despite drafting at the top of the heap again and again.

Toronto is 29th in wins over that span. Calgary has missed the playoffs in six of the past seven seasons. Ottawa has advanced past the first round once since being embarrassed in the finals nine years ago and is under some of the tightest budgetary restrictions in the league. Vancouver, after years of competence under other management teams, now looks anything but, with the GM struggling to follow even basic principles such as anti-tampering rules.

It is, in short, a mess.

Why this is happening isn't complicated, either. It's not the pressure of the market, the media, the league conspiring against them or the fact that players don't want to play here. (Hall and Subban certainly did.)

The Canadian NHL teams have been, by and large, horribly mismanaged. They are, generally speaking, not progressive organizations, not adept at change and not finding ways to outmanoeuvre their competition. Most are well behind in areas such as analytics.

Contrary to what many seem to believe, the reason the Chicago Blackhawks, Pittsburgh Penguins and Los Angeles Kings have been the best teams of this generation is not because they've won draft lotteries and drafted elite players. It's because they're run by better people who have found ways to keep their elite talents and complement them with other good players.

Stamkos surely realized that as he did his brief tour of his options over the past week. His best chance to win was with the Lightning, a well-run franchise with a wonderful owner who doesn't meddle and a GM who is about as calculated and cutthroat as they come. (Appropriately, the top advisor in Steve Yzerman's managerial entourage, Julien BriseBois, was hired away from the Canadiens.)

They are miles closer to winning the Stanley Cup than any of the Canadian teams.

The trades Edmonton and Montreal made on Wednesday are not defensible ones. They could set those franchises back for years because in both cases they subtracted one of the best assets they had on the roster for an inferior replacement. Neither deal added much in the way of cap space, the NHL's other key currency.

Neither deal was made for purely hockey reasons, either. Rumours have swirled all season about both players' personalities and fit "in the room," with Hall blamed for getting "used to losing" and Subban for being an oversized character in a staid organization.

Hall was shopped around the league for defencemen of varying quality. (Larsson was one of the weaker options pursued.) Teams had quietly been offered Subban going back to at least January. His no-movement clause – which begins on Friday – loomed large in the mind of Canadiens GM Marc Bergevin.

Granted, sometimes trades have to be made for off-ice or fit issues. But you should never be this far on the losing end of them, not with how hard it is to accumulate elite talent in the NHL.

Edmonton and Montreal will try to patch up this shoddy work in free agency, but July 1 is where most of the NHL's biggest mistakes happen. That appears to be what's next.

The Oilers are likely to make former Boston Bruins baddy Milan Lucic incredibly wealthy with a long-term deal, ostensibly to make them bigger. (Not better.) The Habs have plenty of cap space and only secondary offensive weapons are available for purchase. None will bring the dynamism they shipped to Nashville.

"That team is like a video game now," one rival executive said after the Predators acquired Subban. "It's going to be so exciting there."

And good for the Music City.

But as Nashville and Tampa and New Jersey all took steps forward, it wasn't hard to see the symmetry of it all on a more macro scale. Talent – Canadian-born-and-bred talent – was going (or staying) south, where the Cup has lived now for 23 years. All of the best teams next season will, again, be American.

While there are signs of life in some Canadian markets – Winnipeg, Toronto and Calgary have growing stables of promising prospects and some bright lights in the front office – the overall trend has been in the wrong direction for a long time now. Even the teams headed in the right direction are playing from behind, trying to catch the Tampas and Nashvilles.

Days like Wednesday are why.