John Chayka’s offseason work has made the Maple Leafs’ timeline crystal clear: this is a two-year push built around Auston Matthews.
Matthews asked the front office to add more bite, and Toronto answered by bringing in Nick Paul, Colton Sissons, Teddy Blueger, Jack Roslovic, and Brandon Duhaime. The club also added insurance behind Anthony Stolarz by signing Sergei Bobrovsky.
On paper, the collection makes sense. The bigger point is harder to miss: these moves were made to help Matthews win, and there doesn’t seem to be a plan that stretches much beyond that.
That urgency lines up with Matthews’ contract, which expires in 2028. Chayka appears to be betting heavily on the next two seasons because that’s the window Toronto has before everything gets much more complicated.
If it works, great. If it doesn’t, the reset comes fast.
The Leafs’ new bottom-six pieces fit that same clock. Toronto added:
- Nick Paul ($3.15M AAV, Exp. 2029)
- Jack Roslovic ($4M AAV, Exp. 2028)
- Teddy Blueger ($2.5M AAV, Exp. 2028)
- Colton Sissons ($4.25M AAV, Exp. 2028)
- Brandon Duhaime ($2.6M AAV, Exp. 2029)
- Sergei Bobrovsky ($7M AAV, Exp. 2029)
There’s also a wider wave of contracts that land in 2028. Max Domi, Steven Lorentz, Dakota Joshua, and Zack MacEwen are all on deals that expire that year too.
In total, that gives Toronto 10 players whose contracts run out in the same year as Matthews, including eight in 2028. That’s basically three full lines the team may need to sort out.
One deal sits outside that two-year frame: Darren Raddysh’s eight-year contract at $8.5-million AAV. That move wasn’t only about Matthews. It was also meant to change a blueline offense that had been stagnant for years, and it stands as one of the last eight-year contracts a player can sign under the new CBA.
The pressure on Chayka is obvious. If he wants the best shot at keeping Matthews, these additions have to do exactly what they were brought in to do.
If Toronto still hasn’t figured things out by 2028, Matthews leaving becomes the more likely outcome. It’s not just about making the playoffs.
The bar is higher than that. The Leafs would need to get to a Conference Final or a Cup Final to give him real confidence in the direction of the team.
If that doesn’t happen, the path forward is simple: Matthews walks.
It wouldn’t be a small loss. By then, he would have been Toronto’s greatest player with nothing to show for it. Records won’t matter much if the Cup never comes.
And 2028 could be loaded. Matthews, Connor McDavid, and Zach Werenski could all be available, making it one of the most elite free agent classes ever. Edmonton or Columbus could chase Matthews to replace their stars, and Los Angeles is also preparing for a major signing, which opens the door for another possible destination.
Matthews has already given Toronto his time, dedication and loyalty. The question now is whether the next two years finally bring the winning to match it.
In Other News...
Morgan Rielly Trade Twist Just Changed The Leafs Conversation
Morgan Riellys name has quietly become part of a broader Maple Leafs conversation after reports surfaced that his trade preferences were not as geographically limited as first believed. Toronto had been operating under the idea that his list pointed only to Western Conference destinations, but the latest chatter has opened the door to a much different kind of discussion, one that reaches beyond the usual framework of a veteran defensemans movement.
Philadelphia has now been mentioned as a possible Eastern Conference fit, adding another layer to a situation that is still very much unsettled. Rielly also holds full trade protection for the next two seasons, so nothing can move without his say, and Toronto has not confirmed any expanded list of options. For now, it remains a rumor-driven story with no deal in hand, but it is the kind of wrinkle that can change how the Leafs are viewed around the league. [Read more 🡒]
Leafs Missed Out On A Forward They May Not Have Fit
Vitali Pinchuks move out of the KHL had him on the radar for a few NHL teams, including the Maple Leafs, but the fit in Toronto always looked tricky. The Leafs have already added multiple forwards this offseason, and with the roster and cap picture tightening, the kind of opening Pinchuk would need was never going to be easy to find.
Nashville ended up being the landing spot, but even there the path has gotten crowded fast. Recent offseason additions have pushed Pinchuk further down the depth chart and left his roster spot in question, which only underscores the bigger issue for Toronto: this is the sort of player the Leafs could have considered, but not necessarily the sort they had room to keep. [Read more 🡒]
Two Returning Marlies Are Running Out Of Time To Matter
The Marlies have brought back a pair of depth pieces who spent much of last season in the ECHL, giving the organization a couple of familiar names to sort through as camp and roster decisions loom. One is coming off a productive offensive run in Cincinnati, while the other handled the bulk of the work in net there, and both now get another shot to show they can be more than short-term insurance for Torontos AHL club.
For players in that spot, the margin for error is thin. They need to prove they can help the Marlies right away and, just as important, make themselves useful enough to stay on the radar for future NHL opportunities. The challenge is not just earning a place in the lineup, but doing it quickly enough to matter before the roster picture tightens. [Read more 🡒]