What If "Tony O" Continued His Career as a Montreal Canadien?
The Beginning of an NHL Career That Slips Under the Radar
Here’s something that still surprises people: before Tony Esposito became a Chicago Blackhawk legend, he got his NHL start with the Montreal Canadiens. Thirteen games (5-4-4 record), his name engraved on the Stanley Cup, and a blink-and-you’ll-miss-it stint behind Gump Worsley and Rogie Vachon—that’s the quick snapshot. Most fans don’t associate “Tony O” with the Montreal Canadiens at all, which is part of what makes this whole scenario so much fun to revisit.
Montreal’s crease was crowded, and when protection lists rolled around, Esposito ended up exposed. Chicago took the chance, and suddenly “Tony O” is winning the Calder Memorial Trophy, earning 15 shutouts as a rookie, and building a career that turned into a highlight reel of hardware and unforgettable moments. It’s easy to take that path for granted now, but the turning point was razor-thin as a result of the NHL Intra-league Draft.
Cool Fact: One of the most consequential selections in the NHL Intra-league Draft occurred in 1969 when Chicago selected Tony Esposito from the Montreal Canadiens; “Tony O” played the rest of his NHL career with Chicago (which included three Vezina Trophies).
Imagining a Different Call from the Canadiens
So let’s play out the alternate version. Maybe Montreal reads Esposito’s potential a little differently. Maybe the organization decides they can’t risk losing a young, athletic goalie who played with a style people didn’t fully understand yet. Esposito’s mix of quick pads, smart positioning, and calm under pressure may have meshed perfectly with the team’s identity. Would that tweak have swung a playoff round or two? Maybe. And would Montreal fans still talk about him the way Chicago fans do now? Hard not to imagine.
Legacy: A Career in Different Colours
That’s the other angle—legacy. If Esposito stays in Montreal, he probably becomes woven into that familiar Canadiens goaltending lineage we all know by heart. Picture his mask in red, white, and blue and celebrated as a legendary goalie in the richness of Montreal Canadiens history—instead of being the superstar who “got away”. For younger fans, the idea of Esposito in a Montreal Canadiens jersey wouldn’t be a trivia surprise; it would be part of the standard story you hear growing up around the rink.
A What-If Story Worth Chatting About
And that’s the charm of this little detour through hockey history. It’s not an attempt to rewrite anything—just a chance to appreciate how a tiny fork in the road can shape decades of fandom. If Chicago legend “Tony O” had stayed in Montreal, both franchises would feel just a little different today. So here’s the question to kick around with fellow hockey fans: How differently would the hockey world look if Tony Esposito had remained a Montreal Canadien?