Connor McDavid's Current & Complicated Legacy

Earlier this morning, I went over to a friend’s house at 5 a.m. to watch Team Canada and Team USA battle it out for Olympic gold at the Milano Cortina 2026 Olympic Games. It was probably one of the greatest hockey games I’ve ever watched, and unfortunately, the team I was cheering for, Team Canada, is leaving Italy with silver as opposed to gold.

That said, there’s no denying that this was hockey being played at the highest possible level. There was so much talent on the ice, and even sitting in the press boxes for both sides. This was a game that Team Canada largely dominated, and they looked like the better team throughout most of the game, but ultimately, that’s not how sports always work. Even when you play better, you can lose. Even when you are the better player, you can lose. It's not always going to be sunshine and rainbows, even when you feel like you deserved better.

Which brings me to the subject of this post.

For the third straight calendar year, I've watched Connor McDavid lose a championship-level game or series, and he’s now entering unprecedented territory for me during my sports-watching life as someone who may end up with one of the most complicated legacies I've ever seen at this point in a career.

In 2024, McDavid finally broke through and reached the Stanley Cup Final with the Oilers. They lost the first three games, all hope felt lost, and then they won three straight to force a Game 7, where McDavid and the Oilers came up just short. The next year wasn’t as dramatic. They still reached the Stanley Cup Final, but while it did go six games, it didn’t feel particularly close after Game 2. Florida was the better team, and once again, the Oilers lost in the championship round to the same team.

Now, this time around, with his idol Sidney Crosby sidelined and unable to go, McDavid wore the “C” for Team Canada. Where, once again, while it wasn’t his fault, a team he led fell short.

McDavid is, without a doubt, in my opinion, one of the top five most skilled players to ever play the game. Hell, he might even be the most talented player ever to play hockey. But I can’t say he’s one of the five greatest players ever without one of those defining accomplishments. While an Olympic gold medal wouldn’t have done as much for his legacy as a Stanley Cup, the fact that he has neither right now is troubling as he enters the final year of his 20s at age 29.

At this point in the NHL season, the Oilers have failed at any point to win three straight games, and sure, they could flip a switch come playoff time. But, based on their play to this point, I don’t see a scenario where McDavid and the Oilers win a Stanley Cup this year. That would mean he goes through his entire 20s without winning a Stanley Cup or an Olympic gold medal. It’s just so rare for a player of his calibre not to have one of those etched next to his name already.

What makes it even stranger is that he plays well for the most part in these championship games and series, as he is a Conn Smythe and Olympic MVP winner despite not winning the cup or gold medal when he got those honours, but when it becomes a winner-take-all scenario, or when his team needs him most, he can’t seem to find his way onto the scoresheet. He still passes the eye test, and he’s clearly not folding under pressure in terms of effort or presence. But there's no denying he has to start finding a way to capitalize and cross that finish line.

At this point, I genuinely don’t know what to think of Connor McDavid’s legacy. Is he one of the greatest players ever? Yes. Is he slowly turning into the best to never do it, or, not to be harsh, perhaps the greatest loser in hockey history? It’s certainly starting to trend that way if this pattern keeps up.

Saying that brings me no joy. I’ve written multiple times that he’s my favourite hockey player ever. The way he plays the game has been transformative. His speed, his skill, and the way it all comes together are unreal to watch in real time and are a joy every single time he steps on the ice.

And to be frank, aside from seeing my Montreal Canadiens win the Stanley Cup, I want to see Connor McDavid hoist the Stanley Cup one day more than anything. I want him to leave a lasting mark on the hockey world that includes championships.

If he doesn’t get it done this year and he leaves his 20s without being a champion on either the NHL or Olympic stage, then I really do have concerns heading into his 30s about how his career will end and what his legacy will ultimately be.

He should be remembered as one of the great players of this generation, and he will be remembered that way. But the question remains, will we remember him as a champion... Or as the guy who could never quite get it done?