John Chayka equated his first few weeks as general manager of the Toronto Maple Leafs to “trying to catch a moving train,” but even that might have been selling his challenge short.
This looks a lot more like “Mission: Impossible.”
Chayka’s surprising second chance in the NHL comes from an ownership group that has no interest in a rebuild and expects him to immediately rebound an aging 28th-place team back into its competitive window. This, while inheriting a cupboard woefully short on assets, in a year where NHL free agency leaves a lot to be desired, and at a moment where the future of franchise player Auston Matthews remains very much in question.
Matthews has two years remaining on his contract, but still isn’t sure if he’ll be back in Toronto in the fall, according to league sources.
At season’s end, the Leafs captain told reporters, “I can’t predict the future.” That remains the case after Chayka and Mats Sundin were hired to run a revamped front office.
This is unquestionably the lowest point the franchise has hit since Matthews was drafted No. 1 in 2016. The Leafs had a 30-point decline in the standings this season and will need a favorable bounce in Tuesday’s draft lottery just to find any silver lining in that ugly finish since the Boston Bruins own their first-round pick if it falls outside of the top five selections.
Top to bottom, they’ve dug a pretty big hole with no clear way out.
For Matthews, set to celebrate his 29th birthday in September, there are some understandable concerns about the direction things are headed. Athletes have finite careers and he’s never been further from the Stanley Cup. And while Chayka intends to pick the brain of the franchise’s all-time goals leader in short order, it’s safe to say the new GM might not like everything he hears when that happens.
“We’re going to get together in the next couple weeks and spend some time,” Chayka said after Monday’s introductory news conference. “I think he deserves some answers about where we’re at and where we’re headed, and (I’ll) give him a forum to provide feedback and ask questions and then take it from there.”
Chayka added that he wouldn’t place a timetable on when he needs an answer from Matthews regarding his own intentions.
That’s a smart way to approach a sensitive subject because the timing is definitely going to be tricky for the new Leafs front office to navigate.
The only sales pitch Matthews needs at this stage is real action, according to league sources. Before committing to another season in Toronto, he wants to see a roster that has been meaningfully upgraded through trades and free agency. This isn’t about selling him on a fancy 12-point plan or a bunch of vague promises. Seeing is believing.
Effectively, the Chayka-Sundin front office will be auditioning for the team’s most impactful player with their work around draft week in late June and the opening of free agency on July 1. As such, they shouldn’t expect any commitments from Matthews about his future until some point after that happens and he can evaluate where the team stands heading into 2026-27.
“Listen, I think Auston is the best goal-scorer in the league the last 10 years,” Sundin said. “He’s a superstar in his own right. Won Olympic gold. I think he’s a good leader, a great leader, and he captained the U.S. to the gold (in Milan). The Toronto Maple Leafs and the fanbase, I think, (are) very fortunate to have a player of that caliber.
“Let’s hope that he’s committed to lead this team through the next period as well.”
Chayka said he views the relationship with Matthews as a partnership.
“Auston’s the captain of the Toronto Maple Leafs, this is his team,” Chayka said. “He obviously lived it all year, so I want to get together with him and hear his thoughts on things, and that will kind of help sculpt our vision a bit as well. But certainly, as we think about communicating to him, you know, letting him know that there’s still a window here where we feel like he’s one of the best players in the world for a reason and we’ve got some good pieces, and we’ve got a lot of work to do. And kind of walk him through how we want to go about doing that.”
Keeping Matthews in the fold will be critical to delivering on the promise of an expedited retool, rather than entering a full-scale rebuild. With as great a player as the former MVP is, you’re simply not coming out ahead in the transaction if he wants to be traded.
In the event that were to happen, Matthews would have full control of where he goes courtesy of a full no-movement clause. That means Leafs management wouldn’t be able to drive up the price like they might if free market conditions were present, and the hand-picked acquiring team wouldn’t be shedding useful present-day assets that would make them less appealing as a destination.
At best, you’d be hoping for a multi-pronged package of future assets similar to what the Vancouver Canucks got back when they traded Quinn Hughes to the Minnesota Wild in December. A handful of magic beans for a proven game-breaking commodity.
That certainly doesn’t align with the vision Chayka shared in his first official day on the job in Toronto, where he spoke of needing to improve the Leafs’ blue line this summer in a bid to immediately improve the team’s fortunes.
“I think next year’s an important year to get some momentum back,” Chayka said. “Again, we’re in May. We’ve got a long offseason, depending on what moves are available and how we can execute and the hit rate of the moves we make, honestly. That’ll determine (if we consider a rebuild), but I’d rather answer that question in training camp when we have a full view of the roster.”
He certainly can’t be blamed for requesting more time to survey the situation.
Chayka’s only been here for a few minutes and already the clock is ticking.