The Pittsburgh Penguins are entering a fascinating crossroads as the organization balances its aging core with the need to build toward the future. With Sidney Crosby and Evgeni Malkin still leading the way, the window to contend hasn’t fully closed — but it’s narrowing.
That’s why the idea of the Penguins emerging as a destination for either Auston Matthews or William Nylander, should the Toronto Maple Leafs pivot their core, is gaining traction. It’s bold, headline-grabbing, and complicated — but not impossible.
At the center of it all is one key figure: Kyle Dubas.
Dubas’ history with both Matthews and Nylander is what elevates Pittsburgh from a hypothetical landing spot to a legitimate one. As the former general manager in Toronto, Dubas was instrumental in building around that core and maintaining strong relationships with both players.
That familiarity matters. There’s already an established level of trust, particularly between Dubas and Nylander, who has long been viewed as one of Dubas’ biggest internal supporters during their time in Toronto. Matthews, as the franchise centerpiece, also worked closely with Dubas throughout contract negotiations and roster construction.
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If either player were to become available — whether through trade demands or organizational direction — the Penguins would likely be on the short list of teams those players would consider.
If the Penguins are serious about acquiring a player of this caliber, it won’t come cheap — and it shouldn’t. Any conversation with Toronto would almost certainly begin with Rutger McGroarty.
McGroarty represents exactly the type of asset the Maple Leafs would demand in a blockbuster deal: a high-end young forward with upside, cost control, and the ability to step into a larger role relatively quickly. Given Toronto’s need to reshape its roster and potentially get younger and more flexible, McGroarty would be non-negotiable in discussions.
From Pittsburgh’s perspective, that’s a steep price. McGroarty is viewed as part of their future, especially as they prepare for life after Crosby and Malkin. Moving him would signal a clear “win-now” push — one that aligns with acquiring a superstar like Matthews or Nylander.
One of the biggest reasons this conversation isn’t purely hypothetical is Pittsburgh’s projected financial flexibility.
The Penguins are expected to have roughly $46 million in cap space next season. That kind of room gives them the ability to absorb a major contract, whether it’s Matthews’ steep cap hit or Nylander’s long-term deal.
But just because it’s doable doesn’t mean it’s simple. The Penguins would need to carefully structure their roster to ensure they remain competitive across multiple lines. Adding a superstar is one thing — maintaining depth afterward is another. Toronto would likely want additional assets beyond McGroarty, including picks and possibly roster players, which could thin out Pittsburgh’s lineup.
It’s a balancing act: star power versus depth.
Let’s be clear — the Penguins are not getting both.
Even with significant cap space, acquiring both Matthews and Nylander would be unrealistic from both a financial and asset standpoint. The cost in futures, roster players, and long-term cap commitments would be overwhelming.
So, if Pittsburgh goes down this path, they’ll need to choose. And while both players bring elite talent, they offer very different impacts.
On paper, Matthews is the more attractive option — and likely the Penguins’ first choice.
He’s a generational goal scorer, a dominant two-way center, and a player capable of redefining a franchise’s identity. Slotting Matthews into Pittsburgh’s lineup would give them a legitimate successor to Crosby down the middle, something few organizations ever get the opportunity to do seamlessly.
Imagine a transition where Crosby passes the torch to Matthews — it’s the kind of move that keeps a franchise competitive while also setting up its next era.
However, there is one factor that cannot be ignored: health. Matthews has dealt with injuries throughout his career, and while he remains elite when on the ice, availability is always part of the equation. For a team investing heavily in both cap space and trade assets, durability becomes a critical consideration.
Still, if the Penguins believe Matthews can stay healthy, he’s the swing-for-the-fences move.
If Matthews is the blockbuster, Nylander might be the smarter fit.
The Penguins have long needed to improve their wing depth, particularly alongside their top centers. Nylander brings elite scoring ability, playmaking, and consistency on the wing — all areas Pittsburgh could immediately benefit from.
He’s also proven he can drive offense independently, making him a strong fit regardless of line combinations.
Adding Nylander wouldn’t just strengthen the top six — it would create a more balanced offensive attack throughout the lineup. That’s something Pittsburgh has struggled with in recent seasons, often relying too heavily on its aging core.
From a risk standpoint, Nylander may also present fewer concerns than Matthews, particularly when it comes to durability.
Ultimately, any move for Matthews or Nylander would represent a major philosophical shift for the Penguins.
This wouldn’t just be about adding talent — it would be about redefining the team’s trajectory.
With Crosby and Malkin still producing, Pittsburgh isn’t in full rebuild mode. But they’re also not the dominant force they once were. Acquiring one of Toronto’s stars would be a way to bridge the gap between eras — staying competitive now while building toward the future.
Dubas is in a unique position to make that happen. He knows the players, understands their value, and has the organizational backing (and cap flexibility) to explore bold options.
The idea of the Penguins landing Matthews or Nylander is far from guaranteed — and it would take a perfect storm of circumstances to materialize.
Toronto would need to decide to move one of its core pieces. Pittsburgh would need to be willing to part with significant assets, starting with McGroarty. And both sides would need to align on value.
But if it does happen, it would be one of the most impactful moves in recent NHL history.
Between the Dubas connection, the Penguins’ cap space, and their need to plan for the future, don’t be surprised if Pittsburgh is firmly in the mix should the Maple Leafs explore that path.
And if they do — expect them to aim high, with Matthews likely at the top of their list.
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