The annual milestone passed without much fanfare this NHL season.

Perhaps that’s because, after all this time, it’s become a given. Perhaps it’s because the Montreal Canadiens made things interesting, with their surprising run to the Eastern Conference final.

Nonetheless, after the Canadiens were eliminated by the Carolina Hurricanes, Canada’s NHL teams officially extended their Stanley Cup drought to 33 years, meaning that a decent share of hockey fans have still never seen one hoist the trophy. It’s quite a contrast from the decades leading up to that last, distant title, when a plucky Habs team won in 1993 to cap a run of 35 championships in 50 years for teams from Montreal, Toronto, Edmonton and Calgary.

And then … nothing.

At the same time, the United States’ Sun Belt region remains on a heater. Since the Dallas Stars became the first warm-weather franchise to take the Stanley Cup in 1999, those clubs have won 11 of 27 championships, which will become 12 of 28 — including six of the past seven — after the 2026 Cup Final wraps up with either the Hurricanes or the Vegas Golden Knights winning for the second time. The pace of Sun Belt success seems to be accelerating, too: This year marks the NHL’s third all-Sun Belt Cup Final, with each having occurred in the past seven years.

This dichotomy between Canada’s now-massive drought and the Sun Belt’s remarkable rise is a constant hot-button topic in league circles. But the NHL’s mass-expansion beyond Canada and the northeastern U.S. that started in earnest in the early 1990s was inevitable and unquestionably successful, both from a business perspective and in terms of growing the sport.

A relatively small and regional league that generated $400 million in annual revenue as of 1992-93, the NHL is now poised to rake in upwards of $8 billion for the 2025-26 season, commissioner Gary Bettman told reporters before the start of the Stanley Cup Final. And, globally, more people are playing and watching the game than ever.

To me, that’s a win for anyone who loves hockey.

But there is also an undeniable malaise among many Canadian fans right now, especially after an awful year on the ice for all but the Canadiens. The Toronto Maple Leafs and Winnipeg Jets experienced two of the era’s bigger year-over-year drop-offs, and were this season’s only two teams to fall by 30-plus standings points from 2024-25. The Calgary Flames and Vancouver Canucks, meanwhile, both started to sell off talent and fell into the league’s basement as they enter prolonged rebuilds. And the Edmonton Oilers and Ottawa Senators both disappointed in the postseason, with decisive first-round eliminations.

The Canadiens are obviously the country’s next great hope to end the drought, but they were wiped out so convincingly by the Hurricanes that it feels like they may be a bit further away than their run suggested. Still, it’s easy enough to see a path for them to contend for years to come, especially with a smart management team in place and so much young talent, both on the roster and coming in the pipeline.

It’s hard to find that same optimism across the rest of the country. The Oilers, Maple Leafs and Jets all appear to be older teams on the decline, with only Edmonton — led by the star power of Connor McDavid and Leon Draisaitl — a decent bet to make a push to contend in 2026-27. Even there, dark clouds loom. Just as when Quinn Hughes asked out of Vancouver, McDavid’s and Auston Matthews’ uncertain futures (and pending unrestricted free-agent statuses in 2028) overshadow what’s next for the Oilers and Leafs. The Leafs and Jets are already tasting the hurt of watching a former star excel in the postseason, with Mitch Marner (Vegas) and Nikolaj Ehlers (Carolina) playing key roles elsewhere.

That southward talent drain isn’t entirely new — Wayne Gretzky was traded to Los Angeles in 1988, after all — but like the Sun Belt’s success on the ice, it seems to be accelerating. Few were surprised when Detroit Red Wings captain Dylan Larkin’s preferred destinations leaked out and two of the three reported markets were Florida and Vegas. In fact, it’s no longer uncommon for players to have no-trade clauses that forbid movement to all seven Canadian NHL teams and other Canada-adjacent markets such as Buffalo.

One NHL coaching staff member, who has worked for teams in both Canada and the U.S. Sun Belt, told me last week that he regularly hears from players who don’t want to suit up for Canadian teams, in large part because of the added attention placed on them there. Add in the fact that the nine Sun Belt teams include six of the NHL’s best 11 regular-season clubs over the past five years, and the existence of lower tax environments for many of them, and it’s easy to see why the idea of shifting markets holds significant appeal.

Other factors are potentially at play, too, including the NHL’s increasingly American player base — a record-high 30 percent of its players were born in the U.S. — and rising geopolitical tensions between the North American countries, especially with U.S. President Donald Trump calling for Canada to become the 51st state and an ongoing trade dispute. As a whole, NHL players skew more ideologically conservative than many counterparts in other North American leagues; some born and raised in the U.S. may simply want to stay in their home country.

Despite these headwinds, however, most of the agents, coaches and other league sources I spoke with on this subject believe that on-ice success will have the biggest impact on the ability of Canadian teams to recruit free agents and trade targets. While palm trees and lower state taxes can factor into players’ decisions, it’s also true that the seven Canadian teams haven’t been as well-run as the nine Sun Belt franchises under the NHL’s hard salary cap and revenue-sharing system since both were reintroduced in 2005.

Last season, when The Athletic ranked every NHL owner, the top four — and five of the top 10 — were located in warm-weather U.S. markets. Several Canadian owners, meanwhile, scored near the bottom, including Calgary, Edmonton, Toronto and Vancouver, receiving low marks from fans in categories such as organizational stability and franchise vision.

These are issues that ultimately impact teams’ success on the ice. And the reality is, most top players want to play for a winner, above all else.

Taken together, all these factors help explain where we are today and why Canadian teams have been unable to keep up.

Now, it’s possible that all this is cyclical, that the trend of Sun Belt success will simply play itself out in the years to come, as stars age out in those markets and rosters enter a period of decline. But it’s also not hard to spot aspects that could become ingrained, as the NHL’s player base becomes more American, no-trade clauses continue to proliferate and concerns about taxes and “noise” keep scaring players away from Canadian teams.

While I’ve seen some fans call for a league-mandated solution to this power shift, especially when it comes to the taxation issue, that feels unlikely given what we’ve heard from commissioner Gary Bettman on the subject. But the NHL should also be careful about taking Canadian markets and their fans for granted, given how much they contribute to the overall equation. Even though the seven teams make up only 22 percent of the league — and potentially less when expansion inevitably adds two more Sun Belt teams over the next five years — Canadian franchises are vital to its overall financial health.

The league’s new $7.7 billion Canadian national television rights deal could be worth as much as 7 or 8 percent of all NHL revenue next season, the equivalent of $92 million per Canadian team a season for the next 12 years. Unlike in the past, when the vast majority went to Canadian teams, TV revenue is more equally shared across the league — as American teams get a significant piece of the Canadian deal — and it’s a much higher per-team haul than what the U.S. deals are generating.

If you factor in what high-revenue teams such as the Leafs, Canadiens, Canucks and Oilers have put into the revenue-sharing pool in recent years, thereby helping lift smaller markets, the entire enterprise could start to feel like a raw deal for significant portions of the Canadian fan base. Especially if the talent drain continues.

From a league perspective, however, attempting to fix where players want to play feels like an even thornier issue than simply adjusting for taxation. But some sort of a limitation on no-movement and no-trade clauses could be a start, given that a ridiculous 56 percent of all eligible players now hold some form of contractual protection.

Barring outside help, however, the first step for Canadian franchises must involve following Montreal’s lead in improving on the ice. Stop hiring retread GMs and coaches and get the cream of the crop. Make smarter personnel decisions, build a strong internal culture and win more games through innovation and creativity. Challenges will always exist when recruiting in smaller centers such as Calgary or Winnipeg, but every NHL market has its pros and cons.

Ten years ago, the Panthers were viewed as an undesirable destination that would never succeed, annually missing the playoffs and frittering away talent. At that point, Florida was even frequently placed on players’ no-trade lists.

It took a new owner and a whatever-it-takes mentality to shift that perception and make South Florida a draw for talent, with high-profile players such as Matthew Tkachuk, Brad Marchand and now Larkin requesting to go there.

For teams that can’t pull in star free agents using the weather or tax situation as a draw, the entry draft remains one of the sport’s great equalizers, helping them lock up young, cost-controlled talent. Montreal has proven that savvy selections there can be part of a path up the standings, as they’ve gone from dead last to a contender in short order.

Perhaps the Canadiens will continue to lead the way on a national level, finally ending the Canadian drought and showing that the Stanley Cup can be won without any palm trees around.