The Toronto Maple Leafs are in a precarious position this offseason.
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Mitch Marner is likely headed elsewhere, there are major holes on the roster (Marner and otherwise), the free-agent class (save for Marner) is blah, and the pressure on the franchise is as high as ever after another early playoff flameout and the subsequent exit of Brendan Shanahan as team president.
Add it all up and the Leafs could stumble into some decisions they come to regret.
They should think bigger. They need to think bigger. To the long term. To next summer when there may be a chance to lift the franchise in a way that has no parallel. It’s July 1, 2026, that Connor McDavid could become an unrestricted free agent, the greatest unrestricted free agent, potentially, in the history of the NHL.
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In everything they do this offseason, the Leafs need to be thinking about that, about McDavid, about the chance to bring home the NHL’s best player and reset the franchise for the long haul.
It’s possible, of course, that McDavid isn’t even available.
He can sign an extension with the only NHL team he’s ever known, the Edmonton Oilers, as soon as July 1. His pal, Leon Draisaitl, committed to the franchise for eight seasons last offseason.
McDavid may decide to join him.
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The two have wreaked havoc on the league together. He may have no desire to exit that partnership.
But if he is at least willing to contemplate leaving, perhaps by playing out the last remaining year of his contract next season only to hit free agency next summer, the Leafs need to be well-positioned to strike.
Which means making shrewd decisions this summer that won’t cost them that chance, if not for McDavid than for Jack Eichel, Kirill Kaprizov or Kyle Connor, all of whom could become free agents in the summer of 2026.
Marner’s apparent desire to play elsewhere this summer could actually be fortuitous in that it leaves the Leafs with a massive chunk of money, potentially, to play with next summer.
The salary cap is expected to hit $104 million for the 2026-27 season. At the moment, the books are in pretty good shape. The Leafs have about $60 million already committed. That includes only four forwards, two of whom are David Kämpf and Max Domi, one or both of whom could be dealt this summer.
Which leaves just under $44 million in cap space, not including whatever number the Leafs end up at with Matthew Knies this summer.
Anthony Stolarz will be a free agent after the coming season, as will Bobby McMann and Calle Järnkrok.
Depending on what they do this offseason, the Leafs will need a new goalie in the summer of 2026 (it might just be Stolarz) and some forwards. The defence wouldn’t require any change unless the front office wanted it to change.
McDavid’s next deal figures to come with a cap hit that exceeds Draisaitl’s $14 million as the largest in the league.
Mitch Marner and Connor McDavid could potentially become the top free agents available in back-to-back years. (Dan Hamilton / Imagn Images)
What makes this offseason tricky is the urgent need to improve, both for the franchise and for the GM.
Taking what might feel like a gap year might not be tenable for all kinds of reasons.
For one thing, Keith Pelley, the head of MLSE, recently suggested that anything but a Stanley Cup would no longer be deemed acceptable. Which means that losing in the second round again, for instance, won’t be tolerated and could cost Treliving — set to enter the third year of what is, according to The Athletic’s Pierre LeBrun, a four-year contract — his job.
Precarious job security might embolden the Leafs GM to take big swings this offseason, summer of 2026 be damned. Maybe that means paying whatever it takes (i.e., too much) to bring pending UFA Sam Bennett to Toronto.
There’s also this: Auston Matthews has only three years remaining on his contract and will turn 28 later this fall.
The Leafs are on the clock to make every year count.
The Leafs are also an older team. The list of players who will be younger than 28 at the start of next season is short: Knies (22), Pontus Holmberg (26), Simon Benoit (27), Joseph Woll (27), and Nick Robertson (24) — and Robertson is likely headed elsewhere this summer.
Prioritizing for 2026, gambling even on the allure of that summer, doesn’t mean punting the year.
It just means not spending recklessly by handing out (or trading for) a number of big and bloated contracts.
Treliving could take a more prudent approach, which sees the Leafs target a handful of veteran forwards on one-year deals, such as Matt Duchene, Brad Marchand, Jamie Benn, Claude Giroux, Patrick Kane or Kyle Palmieri. He could seek out potential bargains to fill out the roster otherwise rather than splurge on the likes of Bennett, Brock Boeser and Nikolaj Ehlers — the kind of players that are destined for pricey long-term deals.
Some holes on the roster could also be filled through trade.
And if McDavid re-ups in Edmonton this Canada Day? The Leafs still need to exercise caution, particularly in free agency, and not splurge just for the sake of it.
To not be equipped to take a swing at McDavid, if he becomes available, because the team has over-committed to good but not great players — not McDavid — would be bordering on organizational malpractice.
Whether McDavid would a) leave Edmonton and b) desire the chance to play at home (he hails from the Toronto suburb of Richmond Hill) are obviously huge unknowns. His intentions could become clear in the coming weeks.
McDavid shares the same agent (Judd Moldaver) as Matthews. He and the Leafs captain are pals and would form a mean 1-2 punch down the middle. McDavid would be the best insurance possible in the event that Matthews is injured and/or leaves as a free agent in the summer of 2028.
McDavid would transform the franchise.
But that’s all jumping the gun.
Point is, this is not the summer to spend foolishly. The Leafs need to think bigger.
— Research courtesy of PuckPedia
(Top photo of Connor McDavid and Oliver Ekman-Larsson: Dan Hamilton / Imagn Images)