Jason Robertson’s next contract could reshape the Maple Leafs’ plans without forcing them to part with Matthew Knies.
The Dallas winger’s one-year, $12-million deal has quieted the immediate noise around his future, but it also leaves the door open for a much bigger market down the line. If Robertson does not sign beyond this season, he would move into unrestricted free agency in 2027, and that would instantly make him one of the headliners of that class.
For Toronto, that matters. The Leafs were already being floated as a possible landing spot, with some speculation that Knies could have been part of a trade package to get Robertson out of Dallas.
That kind of move would have been costly, even if the appeal was obvious. Robertson, 27, scored 96 points last season with 46 goals, added a plus-22 rating, posted a 58.6% CF rating, and finished with a 67% xGF percentage.
He has already established himself as one of the league’s best two-way forwards, and he is still in his prime years.
If he reaches the open market, the price tag figures to be massive. Robertson could land somewhere in the $14-15M range per season, but free agency would give Toronto a way to chase him without giving up Knies or a package built around prospects such as Easton Cowan or Ben Danford.
The catch is money. Toronto is projected to have just $6.7M in cap space for 2027-28, which means the Leafs would need to clear room before they could even think about making a real run.
That could mean moving on from Morgan Rielly, if he waives his NMC, as well as Dakota Joshua and Max Domi. With no free agents in 2027 and everyone else already locked up, a trade would not just help Toronto’s case - it would be the only way to make it work.
The key date on Toronto’s calendar is January 1. That is when Robertson becomes eligible to extend, giving both sides a few months to see where things stand. He can get a feel for the direction of the team, and the Maple Leafs can judge their own season before the real decisions start to come into focus.
If Toronto makes the playoffs but exits early, it could leave John Chayka considering one more major swing in Auston Matthews’ final year while still keeping Robertson in play alongside McKenna, Knies and Nylander.
There is also the family factor. Nick Robertson’s view matters here, too.
He knows the organization, has dealt with tension there, and was traded away, so he could try to steer his brother toward another destination. The two are close, and there will be plenty of time for those conversations.
Robertson’s fit is about more than dollars. He is not going to chase money alone, and he is not looking to land somewhere he does not believe can win, which is part of why the Seattle deal was rejected.
Whether Toronto can sell him on its own path is up to Robertson. If he decides the fit is right, the Maple Leafs will need to have the cap space ready to make it happen.
In Other News...
Maple Leafs Still Have 3 Free Agent Decisions To Make
Even after a busy stretch of signings, the Maple Leafs still have a few free-agent possibilities left on the board if they want to keep tinkering with the roster. The names being floated are familiar in different ways: Eeli Tolvanen as a scoring winger with some upside, Michael Bunting as a former Leaf who did some of his best work in Toronto, and Nick Blankenburg as a right-shot defense option who could come cheaply and fill a depth role.
Tolvanens appeal is obvious if the Leafs are still looking for another forward who can push into the top six, while Bunting would give them another middle-six winger with a track record in this market. Blankenburg is the quieter fit, but the kind of low-cost defenseman teams often circle back to late in the process, which is why Torontos remaining decisions feel less about headline moves now and more about whether there is still one more useful piece to add. [Read more 🡒]
Leafs Just Made Quiet Changes Fans Have Been Waiting On
With the NHL arbitration calendar now wrapped up without a single hearing, the attention around the league has started to shift from contract disputes to the quieter roster-building work happening behind the scenes. Torontos latest move falls into that category, with the organization making official changes to its Marlies hockey operations and coaching staff as it continues to shape the support system around the big club.
Chris Bourque has been named assistant GM to Ryan Hardy, while Jeremiah Crowe joins as director of player personnel. The Marlies bench is also getting new faces, with Denver Manderson and Greg Moore added as assistant coaches for Steve Sullivan and Mark Giordano, a set of moves that suggests the Leafs are still fine-tuning the pipeline even as the offseasons louder headlines play out elsewhere. [Read more 🡒]
Leafs Defensive Logjam Could Force Another Painful Roster Decision
Torontos defense picture has changed again this summer, and the additions of Emil Andrae and Darren Raddysh, along with Troy Stechers return and Simon Benoits departure, have left the Maple Leafs with more bodies than clear openings. That kind of depth can be useful in camp, but it also means someone on the fringe is going to feel the squeeze as the team tries to sort out its blue line and make room for younger options.
Philippe Myers is the name most likely to be caught in the middle of that logjam after a difficult season following his 2024 free-agent signing. Toronto still has to decide how it wants to handle the roster and cap space issue, and the path forward could affect whether prospects such as William Villeneuve and Ben Danford get a real chance to push for jobs. If Myers stays put, the Leafs may have to find another way to trim the group. [Read more 🡒]