Connor McDavid signed a two-year contract extension with the Edmonton Oilers to extend his stay through the 2027-28 season. But this only increases the speculation among Toronto Maple Leafs fans that the best player on the planet is coming back home to sign with his childhood team.
THE CAPTAIN 🫡
— Edmonton Oilers (@EdmontonOilers) October 6, 2025
The #Oilers have signed forward Connor McDavid to a two-year contract extension with an AAV of $12.5 million! pic.twitter.com/UYpGe4NKkx
While every single member of Leafs Nation hoped for McDavid to walk right to free agency and sign with Toronto next summer, it looks like we might just need to put that thought on pause rather than throw it completely away.
With McDavid's new contract just being two years, he is set to hit unrestricted free agency in the summer of 2028. And if that sounds familiar for everyone in Toronto, it's because Leafs captain Auston Matthews is also set to hit the open market that very summer.
Two of the best forwards of their generation are going to hypothetically be free to sign wherever they want at the exact same time. And while we don't want to think about any possibility of Matthews leaving Toronto and how much it would hurt us to see him eventually move on from the team that drafted him first overall in 2016, there is a scenario where with all of Matthews's $13.25-million cap hit coming off the books that it is extremely easy to see McDavid come home and sign with the Toronto Maple Leafs.
We don't want to sound like we have our head in the clouds or are just trying to always bring it back to the Leafs, but it is pretty interesting that McDavid is essentially giving the Oilers three more years to not mess it up and get him his Stanley Cup in Edmonton before being able to sign elsewhere. He signed for the exact same cap hit as his previous deal to really make it easy on Oilers management for them to find adequate enough talent and get him that ring.
And to make it even more interesting, McDavid and Matthews share the same agent in Judd Moldaver. Of course it's not hard to find exactly when contracts expire, but having some more internal knowledge and making a decision to re-sign in Edmonton right up until the Maple Leafs just happen to have a lot of cap space available and a hole to fill at first-line centre, feels more than just a coincidence.
We can all put on our tinfoil hats to look at PuckPedia and see the contracts align for just a little bit longer until we get more breadcrumbs that this is a true possibility.
Welcome home, Connor (in 2028).