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Why it’s harder than ever for Canadian teams to win Stanley Cup
Deputy NHL Commissioner Bill Daly prepares to present the Colorado Avalanche with the Stanley Cup trophy after defeating the Tampa Bay Lightning in Game 6. Mark J. Rebilas-USA TODAY Sports

It is, as we are seeing, a short trip from O Canada to Woe Canada.

It’s not necessarily a new phenomenon but, as we watch the Calgary Flames quickly disintegrate from legitimate Stanley Cup contender to, well, not exactly sure what, in a matter of weeks, it is yet another reminder that, as much as hockey is life in Canada, the game sometimes doesn’t love its Canadian NHL franchises back unconditionally.

It’s always a mug’s game to feel sorry for millionaire players and billionaire owners, but I still have felt an inordinate amount of pathos for fans of the Calgary Flames if not the organization itself in recent days.

The Flames under GM Brad Treliving seem to have hit if not all the right notes at least most of them. They have drafted and developed well. They have made good, smart acquisitions. They hired a smart, veteran coach in Darryl Sutter who seems a perfect fit for a team with high aspirations. And while the team folded in a disappointing manner in the second round against Edmonton after running away with the Pacific Division crown with 111 points, the future as a legitimate Cup contender looked bright.

Looked. Past tense.

In spite of a whopper eight-year deal tendered to pending UFA Johnny Gaudreau, the team’s leading scorer coming off a 115-point season, tied for second in NHL scoring, he took a smaller, shorter deal to become a Columbus Blue Jacket, instantly turning optimism to disappointment and uncertainty in Calgary.

Then, after months of inertia vis a vis getting a contract extension done with the team’s electric star winger, Matthew Tkachuk, the team has taken him to arbitration, possibly signaling the beginning of the end for Tkachuk in Calgary.

Maybe the signals have been misconstrued, the team ends up bagging Tkachuk, a 24-year-old restricted free agent, on a nice extension, and the impact of the Gaudreau departure will be at least somewhat blunted. But many inside the business of hockey believe this is the Flames preparing to find a taker for Tkachuk so they don’t run into the same dilemma they faced with Gaudreau, having Tkachuk go through arbitration on a one-year deal that leads him to free agency next summer.

In fact, one veteran agent insisted Tkachuk is as good as gone unless the Flames shift gears and massively overpay, putting Tkachuk in Connor McDavid territory. Rock, meet hard place.

A longtime player and executive doesn’t believe there was anything Calgary could have done to change the script.

“Not good in Calgary,” he said. “They did all they could do, and to say they should have acted earlier with Gaudreau? I don’t think he was staying. His prerogative, and you can’t blame them.”

Worse?

“The trickle down could hurt more,” he added.

Another longtime NHL executive agreed that Tkachuk appears bound for points south. He thinks, like many, that Tkachuk hopes to play at or closer to his home in St. Louis, although this executive also pointed out that Tkachuk’s younger brother, Brady, signed a long-term deal to become a foundational piece in Ottawa where he is the captain.

“So maybe Matthew surprises me,” the executive said.

Is Calgary unique?

Hardly.

The Saddledome stinks, and the in-fighting in getting a new rink built is very Canadian. Just ask the Ottawa Senators. But the city is world class. The fan base is supportive without being manic. The media treatment of players is middle of the road, which is to say not particularly off-putting. Ownership is solid. You’re a short drive to the mountains. In short, what’s not to like about Calgary?

And with all due respect to Columbus, another market that has historically struggled to attract and keep top-level talent, it’s easy to see why Flames fans compare the two cities and wonder how in the hell Gaudreau ended up there.

Well, it’s really pretty simple isn’t it? One city is in the United States and the other is in Canada, and Gaudreau reached a point in his career where he can make these choices without having to answer to anyone but those closest to him.

It’s as simple and as complex as that. As our top agent told us, it’s not one thing, it’s all that goes with being a Canadian market: taxes, climate, size of the city, overzealous media attention. And while each of the seven Canadian markets face greater and lesser obstacles in building and maintaining a winner, all Canadian markets are at some disadvantage to most if not all of their American brethren.

“It’s death by a thousand cuts,” the agent said.

Winnipeg is the smallest Canadian market and, given its reality as a kind of prairie outpost, maybe it’s not entirely surprising the Jets have always struggled to attract and keep top-name talent. In recent years they were forced to trade sniper Patrik Laine to Columbus in exchange for hard-to-please center Pierre-Luc Dubois, who has already informed the Jets he’s not interested in extending long-term when he becomes a UFA — in two years. Two years.

All GMs must consider whether players will stay long term with their respective teams, and if they don’t believe they will, those GMs must consider moving them before they reach UFA status to protect the team’s storehouse of assets. That is league-wide. But it's fair to say that challenge is more acute for Winnipeg GM Kevin Cheveldayoff than any of his colleagues.

The same dynamic used to exist in Edmonton before the arrival of Connor McDavid and Leon Draisaitl, but Edmonton still remains a hard sell to some players given its climate and relative remoteness. That’s life.

Vancouver is as beautiful a city as any in the NHL but has housing costs that are astronomical plus the Canadian tax system etc. etc. The Canucks have been wrestling with what to do with star winger J.T. Miller for months now. It appears unlikely he will stay long term with Vancouver and the belief is he wants to return to a U.S. market. Which means that, entering his contract year on a team that looks to be back in the playoff hunt, Canucks management will have to move a key asset before the trade deadline or, like Calgary, watch a star player walk out the door leaving behind only cap space.

Montreal, with its unique language dynamics, has marched uphill for years in collecting and keeping top talent.

Ottawa has made news in recent days by actually attracting a star free agent in Claude Giroux, who has made his summer home in Ottawa for years, and adding burgeoning star Alex DeBrincat. But these signs of optimism are in stark contrast to much of the recent past for a small market with historically dysfunctional ownership and, outside of Arizona the worst rink placement in the league, though there is finally optimism for a new downtown arena in Canada’s capital now.

Toronto is the most immune to the factors the other Canadian teams face, but angst lives pretty much nonstop in the heart of all Leaf fans as they follow a team that hasn’t won a playoff round since before the 2004-05 lockout. Already Leaf fans are clenching for what will happen when Hart Trophy winner Auston Matthews reaches unfettered free agency in two years. This agent suggested Matthews is likely to depart to a market that could pay him the maximum contract (20% of the cap), something the Leafs — or any Canadian franchise really — can’t accommodate.

Some players, like Leafs captain John Tavares, bucked the trend coming from the New York area to sign a long-term deal as a UFA with his hometown Leafs. And there will always be players for whom playing in Canada will be attractive, especially in the larger Canadian markets. But as the agent pointed out, the game continues to become more and more international and less Canadian. And with the cap constraints all teams face, especially coming out of COVID, for many players it becomes a question of, why would you go to (or in the case of Gaudreau and perhaps Tkachuk) or stay in Canada if you don’t have to?

“Even Canadian players don’t want the pressure (of playing in Canada) and like the idea of playing in markets like Nashville, Dallas, Tampa,” the agent suggested. “It really is the thousand cut argument. No one big reason for it, just the multitude of factors making it harder to compete.”

Another longtime NHL executive familiar with the Canadian marketplace agreed that the Canadian conundrum is real, although he pointed out that the tax issue is more a regional one with New York and California also hitting players hard and that states like Texas, Nevada, Tennessee and Florida with modest or no state tax put NHL teams in those states at a distinct advantage.

“There are definitely players that don’t want to sign in Canada because of the factors you mentioned,” the executive said. “COVID restrictions have been a big one. We used to hear from agents all the time that their player would only stay south of the border or would only stay on the east coast.”

The other issue that affects all NHL teams but can compound issues for Canadian teams is that if you’re not a contender, how do you attract top free agents or keep your own players when they have an opportunity to hit the market?

“If the team is not poised to win, all of those factors are magnified, because who wants to deal with all of that stuff AND not win?” the executive said. “So unless the player is out of options, you have to be a team with a chance to be successful to even be in the running.”

Now, having McDavid and Draisaitl as Edmonton does or Matthews and Mitch Marner as the Leafs do can mitigate those Canadian issues. Maybe.

“If a team is good and has a chance to win, or if a team has elite players that will make the free agent look good and earn him more on his next deal, those other issues tend to fade away,” the executive added.

So if Tkachuk and Gaudreau both depart the Flames, where does that put them in pursuing another Stanley Cup, having won their first and only championship back in 1989? Square one or close to it.

Back in the day when the Canadian dollar was at rock bottom, trading at less than 30% of the U.S. dollar, NHL Commissioner Gary Bettman stepped in and created a fund that helped alleviate the disparity between the Canadian and U.S. franchises. It was critical to the health and survival of Canadian franchises. Is there a way for the league to help level what is clearly an unlevel playing field now?

With the salary cap and the homogenization of the league that has come with the cap system, it’s hard to imagine other teams would sign up for any kind of options that would give any of the Canadian teams any kind of break. Which means that, as much as the game continues to run like an electric current through the psyche of an entire nation, the chance that a Stanley Cup drought that dates back to Montreal’s 1993 win will end anytime soon becomes more remote with each passing day.

O Canada. Or is that woe Canada?

This article first appeared on Daily Faceoff and was syndicated with permission.

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