A Hockey Vacation With The Habs

Why a lifelong Leafs fan is finding a refreshing change of pace in Montreal—for now.

So, here is the deal.

It is April 5, 2026, Easter Sunday. The Blue Jays have officially kicked off their season, and the Toronto Maple Leafs are winding down a disappointing regular-season campaign.

Go Jays Go

Before I dive into the hockey talk, I have to give a quick shout-out to the Jays. For the first time, I watched the first three games of the season in their entirety, a thrilling three-game sweep of the visiting Oakland Athletics. It felt as though they picked up exactly where they left off after last year’s postseason run, which ended in that crushing Game 7 defeat to the Dodgers in the Championship Series. I truly hope they get another crack at the Commissioner’s Trophy this year.

Now, Back to the Rink

As a diehard Leafs fan, I’ve learned to keep expectations low. I’ve been a supporter for far too long to get sucked into the delusional dream of a Stanley Cup. If they manage to survive a round or two, I consider it a successful year. A Cup win remains on my bucket list, but I hope I have plenty of time left to see that actually happen.

Usually, once Toronto is out of the picture, my loyalties shift to whichever Canadian teams are still in the hunt. This year, something very strange has happened: I have, heaven help me, become a Habs fan.

I’ll say it one more time just so it can sink in: I am currently a Montreal Canadiens fan (though special terms and conditions definitely apply).

I’m not running out to buy a Montreal Canadiens ball cap, and a team jersey is out of the question, but I am cheering for them. And why not? They are a pleasure to watch. They play the game the right way, structured, hardworking, and with a “team-first” approach that is refreshing to witness.

An All-Canadian Final - Bettman Would Cringe

But imagine the absolute spectacle if we ended up with an all-Canadian final: the Montreal Canadiens versus the Edmonton Oilers. After years of the Cup residing in the States, having the championship decided on Canadian ice between two of our most iconic franchises would be a dream come true for the entire country.

However, if that dream scenario does become reality, my brief “playoff fling” with Montreal would have to come to a respectful end. In a Canadiens-Oilers final, my heart would pull me toward Edmonton. I want to see Connor McDavid hoist that elusive trophy before he retires. He is the most determined, hardworking player I’ve seen in years, a true force of nature once he laces up the skates. He has earned his place among the greats, and a Stanley Cup ring is the final piece of that puzzle.

For now, I’m enjoying this short-term change of scenery. No pressure, no decades of emotional baggage; just good, honest hockey. This is a temporary arrangement, a playoff vacation of sorts

At the end of the day, I know exactly who I am: a Leafs fan cautiously exploring other options. But for this spring, I’m trading my cynicism for a bit of Canadian flair. Whether it’s Montreal’s disciplined team effort or McDavid’s sheer brilliance, I’m just happy to see a team that remembers the season doesn’t have to end in April.

Go Habs Go (so weird to say that)

Happy Easter, Everyone.

Stay safe. Stay well. Have fun.

Richard