TORONTO — John Chayka and Mats Sundin, you are on the clock.
The worlds start next week. The combine lies around the bend. The draft and free agency are mere weeks away. And those intriguing UFA coaches won’t stay unemployed forever.
The Toronto Maple Leafs’ new executives have been thrown directly into a task firestorm, charged with making the NHL’s 28th-place team competitive come fall.
“We are trying to catch a moving train here,” GM Chayka admitted. “There are just a lot of ways in which we can improve the team — team speed — but ultimately, we’re sitting here in May. It is a long off-season. It is my job to go out and make some moves to make the team better.”
Here are the six big-picture boxes Chayka and Sundin must check on this summer’s critical to-do list.
And we don’t mean Yakupov.
Thanks to Tuesday’s lottery luck, the spendy Maple Leafs have a full complement of draft picks for the first time in a long time.
The safest choice at No. 1 would be to select dynamic Canadian winger Gavin McKenna (Mitch Marner replacement, easy?), but Sundin has been watching Option B, Ivar Stenberg, with a keen eye. And so will Leafs Nation when the two-way Swedish star takes to world championships ice next week.
The idea of getting cute, trading down for a blue-chip defenceman, and adding another asset might be tempting. But, boy, would that be a bold first swing for a new executive regime already facing intense scrutiny.
Not since the Marc-Andre Fleury draft of 2003 has the top pick been traded away, and we don’t see it here.
“We all want the smartest, fastest, most skilled, best scorer you can get. But when you trade things off, certainly I value hockey sense and competitiveness,” Chayka said. “In terms of trading up and trading down, I’ve done both. I think it just matters how things fall and how you value the players and what the opportunities are and what teams are willing to offer candidly.
“I’m always open to everything. But I do think when you get a chance to draft first overall, it’s obviously a special opportunity.”
Stenberg is viewed as more NHL-ready and defensively responsible, and the Leafs aim to jump right back into the playoffs. McKenna comes with the higher superstar, game-breaking, replay-that-clip upside.
2. Determine Craig Berube’s fate.
The Maple Leafs have a pattern.
They hire a general manager with a head coach already in place. The new GM resists temptation to expend a bullet early and tries to win with his inherited bench boss.
Kyle Dubas bet on Mike Babcock and his ginormous contract. Brad Treliving met with Sheldon Keefe for 17 hours and decided not only to keep but extend him. So, “of course,” Chayka says, the new guy is open to retaining the old guy.
Craig Berube is the 2025-26 Maple Leafs’ Neo. He Matrix’d his way out of a bullet that took out assistant coach Marc Savard midseason and another that eliminated boss Treliving in March. Atrocious defensive metrics and lack of buy-in to the Berube Way be damned.
Now Chayka and Sundin must decide if Berube, who has two more seasons on his contract, is the man to run training camp.
In back-to-back years, the good hockey man has overseen both the most successful and least successful campaigns of the Matthews-Nylander era. So … which was the fluke, 2024-25 or 2025-26?
Having already spent its first-round picks in 2027 and 2028, Toronto is in go-for-it mode, and there is another (expensive) Cup-winning head coach just sitting out there on the open market: Bruce Cassidy.
Is it possible that the final shift of the greatest goal scorer in Maple Leafs history ended with him crumpled on the ice from a greasy hit and no one immediately sticking up for him?
Is it possible the captain feels encouraged by Tuesday’s monstrous lottery fortune, becomes intrigued by the Chayka-Sundin vision, and gets sold on this summer’s acquisitions in free agency and trade?
There is a third option here: Matthews simply lets this breathe a minute. He’s under no deadline.
Remember, Matthews and management began preliminary discussions two years out from his first UFA summer. That’s where they’re at now, the spectre of July 2028 looming large in three Canadian markets.
But the landscape has changed drastically since 2022. Both superstar and team are coming off their most disappointing showing yet (Olympics notwithstanding), and the captain’s injury history has grown more complicated.
Matthews will be 29, with a well-rested back and rehabilitated knee, when the puck drops again. Milan gave him a taste for championships. Surely, seeing Marner thrive in Vegas’s post-season is a reminder that he has options.
No doubt, Toronto will do everything in its power to keep its captain happy. That’s a top-down mandate.
But Chayka & Co. also need an offensive rebound from 34, who finished 67th in points per game this season (minimum 20 games played), and must also consider what the next wave will look like.
4. Hit on multiple free agents.
It’s impossible to view Toronto’s 2025 free agency as anything but an unmitigated failure. The previous regime put all its eggs into the Brad Marchand basket, then watched their playoff nemesis re-up with those dastardly Florida Panthers until his age Gordie Howe season.
Treliving took flyers on depth pieces Michael Pezzetta, Dakota Mermis, Travis Boyd, and Bo Groulx. All of whom spent way more time with the Marlies than the Leafs.
As was the case with Treliving last July 1, Chayka will have gobs of cap space but few difference-makers to spend it on.
Toronto-born Darren Raddysh (if not re-signed by Tampa) will be an obvious target, but the data-crunching Chayka must uncover a couple of value gems and get lucky the way, say, Pittsburgh’s Dubas did with Anthony Mantha. Easier said than done.
5. Be smart with restricted free agents.
The Maple Leafs poured years of development into late-blooming forwards Pontus Holmberg and Alex Steeves. But when those players had a smidge of leverage as RFAs, Toronto let them walk for nothing to divisional rivals.
Holmberg (in Tampa Bay) and Steeves (in Boston) may not be world-beaters, but they are useful, reasonably priced role players — and regular reminders of poor asset management.
Chayka must quickly figure out what he has in Matias Maccelli, Nick Robertson, Jacob Quillan, Ryan Tverberg, and William Villeneuve. All five pending RFAs are armed with arbitration rights and due qualifying offers next month.
The Leafs can’t simply hand out raises across the board. Who’s a must-keep? Who’s tradeable? Who’s expendable? Choose wisely.
6. Get crafty on the trade market.
Chayka has a mix of options and obstacles here.
The Maple Leafs have three good but flawed goalies on one-way deals, plenty of NHL-calibre defencemen with cost certainty, and a plethora of bottom-six forwards — too many with trade protection, though.
“I think you’d be really hard-pressed to do better than Matthew Knies,” Chayka told us Monday.
The GM’s priority is to inject mobility and playmaking into his blueline. He also needs a legitimate top-six winger, if not two. A middle-six centre couldn’t hurt either, considering neither Nicolas Roy nor Scott Laughton were replaced.
It’s unrealistic to fill all those holes in one summer, and internal growth will be critical (Quillan? Groulx? Bueller?).
But if Chayka can tick one box in free agency, one at the draft, and one via trade … well, that desired momentum the executive spoke of at his introductory press conference can get rolling for real.
Chayka’s history suggests a willingness to pull the trigger. Back in Arizona, he hit his mark on trades for Lawson Crouse and Nick Schmaltz, both of whom are key contributors in Utah to this day.