The Toronto Maple Leafs last hoisted the Stanley Cup in 1967, beating the Montreal Canadiens in six games with George Armstrong’s empty-netter and Dave Keon’s MVP swagger. It was their 13th championship, a golden memory so distant it’s practically a bedtime story for Leafs Nation. That was 58 years ago—long enough for the drought to have its own driver’s license, midlife crisis, and a mortgage it can’t afford.
Since then, the Leafs have stumbled into the playoffs 36 times, racking up a postseason record of 140-176. That’s a .443 winning percentage—worse than betting on a three-legged horse at Woodbine Racetrack. They’ve only won one playoff round since 2004, a 2023 first-round fluke against Tampa Bay that felt like the hockey gods accidentally hitting “undo” on a typo. Before that, they went 19 years without a series win, the longest stretch in franchise history, punctuated by eight straight losses in series-clinching games from 2013 to 2021. They even made history as the first team to drop winner-take-all games four years running (2018-2021). Toronto doesn’t just flirt with disaster—it sends it flowers and a mixtape.
This isn’t a talent shortage. Auston Matthews bagged 69 goals in 2023-24, Mitch Marner dishes passes like a Michelin-starred chef, and William Nylander’s hair alone deserves its own sponsorship deal. Yet in the playoffs, they turn into ghosts—scoring three goals or fewer in their last 11 postseason games, with two or less in 10 of them. The Leafs led the league with 3.63 goals per game in the regular season, but come spring, they play like they’re auditioning for a silent film. Maybe they’re saving their energy for the golf course.
What’s to blame? The fans, who pack Scotiabank Arena with the devotion of cult members, only to be repaid with heartbreak that could fill Lake Ontario? The revolving door of GMs who treat the roster like a fantasy hockey experiment? Or is it just Toronto’s cosmic role as hockey’s punching bag? In 1967, the NHL had six teams, and goalies faced pucks with their bare faces. Now, with 32 teams and a salary cap, the Leafs are a regular-season juggernaut that collapses faster than a cheap IKEA shelf.
They’re not cursed—they’re just masters of the choke, turning hope into a punchline with surgical precision. So here’s to the Maple Leafs: the team that keeps fans dreaming, betting, and screaming, only to remind us every May that “next year” is the most expensive lie in sports. At this rate, their next Cup parade might be a holograph.
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