If it’s not the Leafs this season, which teams have the best (worst?) shot at passing the Rangers 54-year Cup futility?

The record-setting 24-time Stanley Cup champs are the last Canadian team to have claimed hockey’s grail, back in 1993. This is the longest the Habs have ever gone without winning a Cup, and they haven’t even been to a Final since that series against Wayne Gretzky and the Kings. Still, it’s hard to imagine that it will take another 26 years for Montreal to get back to the top of the sport. Of course, who would’ve thought they’d go this long?

After entering the league in the fall of 1993, the Panthers made it to the Stanley Cup Final in 1996, only to be buried by the Colorado Avalanche. They’ve only made the playoffs in back-to-back years once, not counting last year’s four-game ouster in the qualifying round. With Joel Quenneville coaching, the Cats have their best chance to be relevant in years, and definitely have to be considered on the rise — but if it doesn’t happen in the next couple of years, another long spell of darkness has to be considered likely.

The original Sens won the Cup 11 times, last in 1927. These Sens have been in the NHL since 1992-93, and… nothing. A big part of the problem is having one of the worst owners in sports in Eugene Melnyk, who definitely should not be trusted to see through the current rebuild to its fruition without sabotaging the franchise with some kind of shenanigans. Still, Ottawa will get to build around Tim Stützle and Brady Tkachuk in the coming years, and the city can be a really good place to play when things are going well. Now if they can get Melnyk out of the picture at some point.

Once they get out of salary cap hell from having gone all-out to try to win a Cup in the mid-2010s, things should get better for San Jose, where it’s mostly been “close but no cigar,” rather than flat-out trash hockey since the Sharks entered the league in 1991-92.

The task doesn’t seem that hard: put some semblance of a defense and a league-average goalie behind Connor McDavid, the best player of his generation. Of course, any task for the Oilers that isn’t “step on a series of rakes” seems like it’s borderline impossible (see, Playoffs, NHL, 2021). Still, Edmonton could just luck into having a trash goalie go on a playoff heater to win their first Cup since 1990. It worked well enough for the Blues.

It’s not just that the Flames haven’t won the Cup since 1989, it’s that they’ve won one playoff round since making the 2004 Final, and have had only two 100-point seasons since then. While Darryl Sutter is capable of taking a mediocre regular-season team on a deep playoff run, last summer’s bonkers decision to give goalie Jacob Markstrom a six-year deal with a no-move clause is going to ensure that any such run under Sutter won’t be too deep. The Flames are at 32 years and counting now — it’s going to take a lot just to break free from their current state of everlasting purgatory, if they ever do.

With a blossoming superstar in Mathew Barzal and a goalie in Ilya Sorokin who looks like he can be a legit No. 1 for years to come, the window is open for the Islanders, who haven’t won since capping their four-in-a-row dynasty with Denis Potvin (above) in 1983. They also will benefit from moving into a new arena next season.

Officially, the franchise is now at 41 years, because their history includes the original Winnipeg Jets, even though the current Winnipeg Jets are… an actual team. Whatever. That’s a never-settled matter to fight about another time. What’s important is whether you call it 41 years or just the 25 they’ve been in the desert, the only way you’re going to see the Coyotes win a Cup is on your PlayStation.

It’s weird, but going back and forth every year between “maybe this is the season!” and “we’d all be better off if the team folded” is a lot better than perpetual mediocrity. The Flyers have alternated playoff and non-playoff seasons every year since 2012. Time is running out — Philly’s streak is now at 46 years and counting since the 1975 Broad Street Bullies with the toothless Bobby Clarke (above)— but they’ve also been to the Final six times since that last Cup, because that’s kind of how the Flyers are… (almost) all or nothing.

The last time the Sabres went to the playoffs was 2011, and next year they’ll become the first NHL team to go 11 straight seasons without a postseason appearance. Buffalo has been to the playoffs twice since its last series win in 2007, and of course, the Cup has eluded the franchise for its entire history since 1970-71. They’ve broken Jack Eichel’s spirit, and there’s no reason whatsoever to believe that a franchise that leads the league in five-year plans is going to do anything of note in the next three seasons other than pass the Rangers on the all-time list of years without winning a Cup.

Having been to the Stanley Cup Final three times since entering the NHL in the fall of 1970, the Canucks know pain. Lately, they’ve known a different sort: Missing the playoffs six of the past eight years, including their ludicrous completion of this season after a team-wide COVID outbreak. Maybe they get into the mix again in the next three years and Thatcher Demko stands on his head? Probably not.

This is year 54. The Leafs have to win the Cup this year to avoid tying the Rangers, or next year to avoid holding the drought record on their own. They have a legitimate chance to do that! Especially this season, as Toronto should be able to handle Winnipeg in the second round and advance to the league semifinals at the very least — which would be the Leafs’ deepest advance since making the 2002 Eastern Conference Finals. And as hard as it still will be to win the Cup within the next 12 months, the chance is still better than other teams have over several more-upcoming seasons.