Newly minted Toronto Maple Leafs GM John Chayka will have plenty on his mind right off the bat. While it seems he’ll be just taking orders (more on that in another conversation), he’ll have one major priority early on: Keeping Auston Matthews in the fold.
Matthews’ representation will likely want to sit down with Chayka and Mats Sundin as well, to talk shop. The likeliest outcome will be both sides agreeing to buy each other some time. Then, the pressure will be on Chayka to do something, anything, to improve the team.
The hope is that Chayka still has some of his wunderkind acumen left in him. By now, his seemingly visionary skills are yesterday’s news. But there is the hope that an older, more mature Chayka can figure out how to turn things around for next season.
But there’s also the possibility that the Maple Leafs’ 2026-27 season quickly goes ca-ca. If that’s the case, Chayka may have to deal with the hardest task of his tenure: Trading Matthews.
It’s not that Matthews will come bearing down the door, demanding a trade. It’s that he, as Quinn Hughes did in Vancouver, will politely tell the organization he won’t be re-signing. When that happens, the Maple Leafs will have no choice. They’ll either run out the clock on this contract or trade him.
That’s where Chayka may have no other choice but to end up pulling the trigger on the franchise’s biggest trade ever.
Timeline for Matthews Trade written on the wall for Maple Leafs
The timeline for a Matthews trade is written on the wall. The Maple Leafs can extend Matthews on July 1, 2027. That’s the official deadline. That’s why the organization will want to negotiate with Matthews’ camp well in advance, so that a deal could be in place by then.
However, should the Maple Leafs find themselves off to a horrid start next year, the club will need to make a major decision quickly. As the Canucks did with Hughes, the Leafs will want to move Matthews while he’s still got a year and a half on his contract. That situation would maximize the return.
Of course, that largely depends on Matthews waiving his no-trade clause, and his chosen destination being able to pay up.
The bifurcation facing the Leafs at this point is simple. A quick turnaround and return to the playoffs could buy the Leafs another couple of seasons, much the same way Connor McDavid did with the Oilers. That’s about another three seasons to take the Maple Leafs from Eastern Conference also-rans to Stanley Cup contenders.
The other path is the utter destruction of the roster and the current core in place. At that point, Matthews and Nylander, for that matter, will see the impending rebuild looming. And that’s when the organization will have no choice but to pull off a trade.
You would think that with such a complicated scenario unfolding, the Maple Leafs would have brought in a much more seasoned and respected GM. But there could be something else afoot. Time will tell.
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