McDavid, Matthews’ agent speaks about potentially playing together in 2028: ‘What the future holds, I don’t know’

While the summer of 2026 was long anticipated as the hottest upcoming free agency market, that notion began to cool last week as Connor McDavid and other league superstars signed extensions.

Now, with McDavid on a new two-year deal starting next season, attention has shifted to July 1st, 2028, when McDavid will hit free agency. Set to hit the market at the same time will be Toronto Maple Leafs captain Auston Matthews, currently on the second year of a four-year pact worth $13.25 million annually.

With these two offensive powerhouses set to hit free agency the same summer, keen fans have begun to wonder about the possibility of seeing Matthews and McDavid play join forces somewhere (in Toronto, perhaps?). Both are represented by Wasserman’s Judd Moldaver, who spoke about the future of the two top forwards on Sportsnet’s 32 Thoughts podcast Monday with Elliotte Friedman and Kyle Bukauskas.

“I know it’s a two way street when they’re competing against each other, either internationally or in (NHL) games, it’s all about winning,” Moldaver said. “And yet I’m just proud of the respect they have for each other. That’s just too far in the future, you know. It so happens that they’re all UFA the same summer. What the future holds, I don’t know.”

Moldaver’s comments also refer to another big client he represents in Columbus Blue Jackets defenceman Zach Werenski.

“I think I can clearly say for all three of them, they love their organizations, the Leafs, the Jackets, the Oilers, respectively. And for them, it’s winning where they’re at and in all three cases, they’ve only played for one organization.”

While it would be intriguing to see Matthews, McDavid, and even Werenski team up somewhere, Moldaver’s comments seem to allude that, at least for now, it seems unlikely, considering the commitment each has to the market in which they’ve built their career.

That being said, the even clearer point from Moldaver’s comments are that this is well down the road. With McDavid contract speculation finally put to bed last week, let’s not that re-open that can of worms until we have to. In the meantime, the player agent gave kudos to how McDavid and Matthews in particular have carried themselves through any extension rumours.

“I know they have a tremendous respect for one another, both as people and players,” Moldaver said. “I think it shows my clients. I’m proud of them. They have an understanding of how things work, how the business works, and respect. Everyone’s in their own situation, as Auston mentioned. And I thought it just showed a lot of class in his comments.”

Matthews previously went to bat for McDavid, after the Oilers’ star signed his extension on October 6. Two years can be an eternity, but it won’t stop fans and media alike from wondering what could be, especially if the Oilers fail to win the Cup during McDavid’s tenure.