McDavid Signing With Maple Leafs No Longer as Crazy as You’d Think

As soon as the Edmonton Oilers fell to the Florida Panthers in the Stanley Cup Final for the second-consecutive year, the immediate focus of the organization and fan base shifted towards Connor McDavid’s future. The 28-year-old had just wrapped up the second last season of his contract, and was eligible to sign an extension as of July 1. At the time, most were confident an agreement would be reached.

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There was plenty of reason for optimism regarding a McDavid extension. First of all, he’s playing on a team that has proven to be the best in the Western Conference. Not only have they played in two-straight Stanley Cup Finals, but they were able to advance to the Western Conference Final in 2022.

This current Oilers group is also still set to contend. Leon Draisaitl has been locked up long term, which to many suggested McDavid would be doing the same. They also have the likes of Zach Hyman, Ryan Nugent-Hopkins, Evan Bouchard, and Mattias Ekholm remaining in the fold, and have some young talent coming up in Matt Savoie and Isaac Howard. Even with all that, however, we are near mid September, and McDavid has yet to sign an extension. The question is, why?

McDavid May Be Wrestling With Maple Leafs Opportunity

It seems that since McDavid has joined the NHL, many out east have been counting down the days until he becomes a part of the Toronto Maple Leafs organization. Many, including myself, wrote that off as complete and utter garbage. After all, he wasn’t forced to sign an eight-year extension with the Oilers back in 2017. He did so because he wanted to remain in Edmonton and bring the city a Stanley Cup.

Fast forward, however, and that Stanley Cup win has yet to happen. They’ve come very close, but McDavid is smart enough to realize close doesn’t cut it when it comes to his legacy. In order to cement himself as the best player in NHL history, he needs to win, and he may not feel like he’s able to do so on an aging Oilers team.

Connor McDavid Edmonton Oilers
Jun 6, 2025; Edmonton, Alberta, CAN; Edmonton Oilers center Connor McDavid (97) reacts against the Florida Panthers during the first period in game two of the 2025 Stanley Cup Final at Rogers Place. Mandatory Credit: Walter Tychnowicz-Imagn Images

Though McDavid has said recently that his desire is to win in Edmonton, one can’t help but wonder if the idea of suiting up for his hometown Maple Leafs is lingering in the back of his mind. This is something that wouldn’t have been possible in years prior, but with Mitch Marner out of the picture, it’s a move that Maple Leafs general manager Brad Treliving may be able to pull off.

Seeing a player choose to go home to Toronto wouldn’t be a first for the NHL. In fact, we all saw it not too long ago. During his last season with the New York Islanders, John Tavares said over and over that he wanted to remain an Islander, only to depart the organization in free agency to instead join the Maple Leafs, a team he grew up idolizing.

Like Tavares, this isn’t to say McDavid is lying. There was likely a big part of Tavares who wanted to remain loyal to the team that took him first overall in the draft and made his life goals come true. Now, however, it’s clear that Tavares was likely torn between staying in Long Island or living out his childhood dream. It’s quite possible that McDavid is wrestling with the exact same decision.

McDavid’s Legacy Would Be Complete By Winning in Toronto

The fact that McDavid has yet to bring a Cup to Edmonton gives him plenty of reason to stick around, though at the same time, returning home to the Maple Leafs to end their lengthy Cup drought would only improve his legacy as one of the games best even further.

Many Oilers fans will say that the Maple Leafs aren’t as close to contending as the Oilers at this time, and they’re partially right. That said, if McDavid left the Oilers to join the Maple Leafs, the tides would change in dramatic fashion. With a forward group including the likes of McDavid, Tavares, Auston Matthews, and William Nylander, they would immediately become the favourite to win the Stanley Cup, not only in 2026-27 but years beyond.

Related: McDavid’s Future Will Be Negative Distraction for Oilers

To McDavid’s credit, he’s done a great job at keeping his thought process to only himself and those closest to him. It seems that no one in the hockey media landscape has the slightest clue as to what he’ll wind up doing, even with reports suggesting a wide variety of options. At this point, his mind likely isn’t made up yet, but seeing the NHL’s biggest talent join the Maple Leafs isn’t nearly as crazy of an idea as it would have seemed years ago.

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