Connor McDavid and Auston Matthews Predicted to Team Up in the Future

Connor McDavid and Auston Matthews’ current situations in Edmonton and Toronto are vastly different. However, one aspect that is similar is the uncertainty around both players’ long-term futures with their teams.

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McDavid is desperate to win a Stanley Cup, and he’s given the Oilers two more years of runway to ensure that happens in Edmonton. Matthews, on the other hand, hasn’t come all that close to winning with the Maple Leafs, and after such a disappointing 2025-26 season, he’s just trying to figure out what’s next in Toronto.

Because of that, speculation is always swirling, and on Thursday night, former NHLer turned analyst Keith Yandle threw out a wild potential scenario he could foresee happening if things break right—McDavid and Matthews joining forces in free agency in 2028.

Yandle said:

“I think him and McDavid, if McDavid doesn’t win this year, him and McDavid are going to join forces somewhere. They don’t need the money. They don’t need the money. They’ll do like a one-year deal. When they’re free agents, they’re both free agents the same summer,”

The 29-year-old McDavid and 28-year-old Matthews are, as mentioned, both slated to hit free agency in the summer of 2028, set to enter year one and year three of their respective two-year, $25 million, and four-year, $53 million contracts with the Oilers and Maple Leafs next season.

So much still has to play out before either player can hit the open market, but the timing of their contracts is absolutely something to keep in mind as we get closer.

If McDavid can’t find a way to get over the hump in Edmonton and Matthews decides it’s time for a fresh start away from Toronto, then it’s not all that far-fetched that we could see both players wearing different jerseys in a few years’ time. Whether a team would even be able to make it work and sign both superstars is a major question, but the rising salary cap makes such a scenario more plausible than ever before.

For now, though, this is just something lingering in the background. McDavid’s focus is on the Anaheim Ducks, while Matthews is trying to process the year that was while continuing to recover from knee surgery.

Next: Could the Golden Knights Try to Reunite Auston Matthews and Mitch Marner?