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.