The Toronto Maple Leafs are in a tailspin, and the timing couldn’t be worse. A brutal 0-4-1 homestand has pushed their already fragile playoff hopes to the brink.
As of January 28, their postseason chances sit at just 4.5% according to MoneyPuck - a staggering drop for a team that’s been a springtime fixture for the better part of a decade. Unless something dramatic shifts, Toronto could be looking at a very different kind of deadline than they’re used to: one where they’re sellers, not buyers.
That possibility opens the door to some tough conversations - and potentially even tougher decisions. Pending unrestricted free agents like Bobby McMann, Scott Laughton, and Troy Stecher are likely to generate interest.
But if the Leafs are serious about shaking things up, the conversation might not stop at depth players. It could reach the core.
And yes, that includes William Nylander.
Now, let’s be clear: no one’s expecting a Nylander deal before the March 6 trade deadline. But the topic is bubbling beneath the surface. TSN insider Darren Dreger recently joined OverDrive and didn’t shy away from the idea that Nylander’s future could be up for discussion this offseason.
When host Bryan Hayes floated the idea of Nylander being part of a summer trade to spark change, Dreger didn’t dismiss it. His response? “In the offseason, yep.”
That’s not nothing.
Nylander, 29, is in the second year of an eight-year, $92 million extension he signed in 2024 - a deal that comes with a full no-movement clause. And even with injuries limiting him to just 37 games this season, he leads the team in scoring with 48 points (17 goals, 31 assists). He’s been one of the few bright spots in what’s quickly becoming a lost year.
So, should the Leafs trade William Nylander?
There’s no easy answer. It depends entirely on where the franchise sees itself going.
If the plan is to keep building around Nylander and Auston Matthews, then moving him makes little sense. But if the front office believes this core has hit its ceiling - if they think it’s time to shake the foundation - then it’s a conversation worth having.
Nylander’s name has surfaced in trade rumors before, but it’s usually more smoke than fire. This time feels different.
If Toronto misses the playoffs, the pressure to make a bold move will be immense. And Nylander, despite his production and contract status, could be a piece that brings back a significant return - one that potentially reshapes the team’s identity.
There’s also the question of who will be making those decisions. GM Brad Treliving’s seat is heating up, and it’s hard to imagine him returning if the Leafs flame out this badly. Before any major roster decisions are made, the organization will need clarity on its leadership - and its direction.
If the Leafs do explore a Nylander trade this summer, they’ll have to weigh the offers carefully. They may not like what’s on the table. But they could also stumble into a deal that brings back multiple impact players - the kind of move that doesn’t just shake things up, but finally pushes this franchise past the playoff wall it’s been banging on for years.
For now, the Maple Leafs are staring down a harsh reality. The postseason is slipping away, and with it, the sense of stability this team has enjoyed for nearly a decade. What comes next could define the future of the franchise - and Nylander might be right at the heart of it.