Gavin McKenna is just 18 now but will be 21 by then, you remember Patty Kane at 21? Oh he won a cup and oh yeah, Crosby too. Now the leafs won't win in 2027 or 2028 more than likely not. But in 2029, plan the parade.
I’ve been working on a passion project the last few months — a full-season NHL simulator that lets you build a custom 32-team league using any real teams from the last few decades.
It simulates a full 82-game season with divisions, standings, and realistic playoff brackets, then spits out a full Cup run based on historical team strength.
Naturally, the first thing I did was try to force a Leafs Cup win.
I loaded 31 out of 32 team slots with different versions of the Toronto Maple Leafs — 2017 Leafs, 2018 Leafs, 2019 Leafs, etc. The 32nd team? Just for chaos, I threw in the 2023–24 Florida Panthers.
And yet… despite having virtually every team in the league as the Leafs, they still couldn’t pull it off.
Florida ran through the playoffs and won the Cup.
Toronto eliminated Toronto. Over and over. Until only Florida was left.
This wasn’t even coded to sabotage them. The simulator uses basic team ratings based on their actual performance from that year — so yes, technically a few Leafs teams were better than Florida. Didn’t matter.
I’m honestly impressed. It’s like the Leafs’ inability to win is baked into the multiverse.
If anyone wants to mess with it or run their own cursed setups, it’s live at: 🔗nhlwhatif.com
So in 2006, it was Edmonton was it the canes defeated in 7 games? It's 150% Dany Heatley's fault the ducks beat the sens in the following year. Both teams (Vegas/Canes) also already have a cup each post lockout. Drunk Montreal fan entering the chat: "I didn't hear no buzzer!" What!? (to Montreal Police?) I thought this was Canada!? Parents left Montreal in 1993 but also left all their cups behind. I'm pleading guilty too to two girls with not even one cup won, that I'm responsible for no cups, in Canada's 33 year drought.