Maple Leafs could consider blockbuster trade with Penguins this offseason

It should not be shocking that the Toronto Maple Leafs have several players on the trade block heading into the offseason, given how disappointing this season has been. What should be shocking to many is the players who are rumoured to be heading to a new destination for the 2026-27 season.

If the Toronto Maple Leafs truly want a shake-up to their roster -- and that all depends on the future front office hires and what they want to do -- then moves involving Auston Matthews and William Nylander make sense.

Could Matthews or Nylander be traded to the Pittsburgh Penguins?

If a deal were to transpire, the Pittsburgh Penguins are a team many see as attempting to acquire the Maple Leafs' stars. Josh Yohe of The Athletic explains why Pittsburgh could be a destination for the two.

"I think Nylander and Kyle Dubas do have a good relationship, and I think the Penguins would certainly be equipped to make such a deal, both financially and with the number of picks they have at their disposal. Yeah, and I mean the Penguins would be on the short list if Auston Matthews wants out, I don’t think there’s any question about that, so that’s something to consider." Yohe said on a recent podcast.

With Nylander having six years remaining on his contract, compared to Matthews' two, the Penguins may be more inclined to make a deal regarding the Swedish forward. If they strike a blockbuster deal for Matthews and, following the end of his contract, he decides to take his talents elsewhere, this could come back as one of the worst trades Kyle Dubas has ever made, including if the two seasons do not come with any success.

The familiarity between Dubas and the Maple Leafs forward could be a reason for these players to waive their no-movement clauses. As the former general manager of the Maple Leafs, he was a key factor in building the Maple Leafs core and the star players they would have to build around.

William Nylander confirms his desire to be with the Maple Leafs

William Nylander, in retrospect, has expressed his desire to stay with the organization, implying they are not heading into a rebuild. He recently spoke with The Athletic, saying, “Unless it was a full rebuild and we were going to get rid of everybody, then it’s a different story. Then you take that conversation then. But just to do a retool or whatever, I don’t even know, but I mean, I still want to be here, yeah."

At this current time, a trade regarding either Auston Matthews or William Nylander seems unrealistic as the Maple Leafs fill their general manager position; the hiree could make some tough decisions and expect Pittsburgh to emerge as a name in these trade talks.