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The new Toronto Maple Leafs GM will have a major priority to clear off the board even before figuring out how to improve the team.

The Toronto Maple Leafs have turned the page on a significant offseason storyline by landing John Chayka as the team’s next GM.

With that out of the way, the real fun begins. Chayka will need to get down to business and sort out the organization’s most pressing concern: Assuaging captain Auston Matthews.

Now, it’s worth speculating that Matthews must have had some sort of input in the organization’s final call on Chayka. The Maple Leafs could not risk alienating their captain by hiring someone he didn’t like or get along with.

That’s not to say that Matthews decided who he wanted. But it is fair to assume the organization considered Matthews’ feelings.

That said, Chayka will now need to figure out how to reassure Matthews about the path forward. That means unveiling a plan that would lead the Maple Leafs back to prominence as soon as next season.

It has to be a tight turnaround. Matthews has two more years on his current contract. As such, Chayka and his administration can’t afford to dally around, hoping for a solution to fall out of the sky.

Sure, miracles happen, like Matthew Schaefer ending up in Long Island. But that’s not a viable strategy for the Maple Leafs moving forward. Chayka has to lay out a vision that could convince Matthews to continue being a marine, at least for the next couple of seasons.

Chayka Will Have to Deal with Matthews Extension

Assuming Chayka is someone Matthews can get along with, the new Maple Leafs GM will have to handle a potential contract extension. If Chayka were wise, broaching the subject would be among his first priorities this season.

While Matthews can’t technically sign an extension until July 1, 2027, talking about it could happen as soon as this summer.

After all, the Maple Leafs need to have clarity on where Matthews stands. Perhaps these last couple of weeks have given the 28-year-old a chance to think things over and decide he’d rather seek greener pastures elsewhere.

If that’s the case, Matthews’ representation would need to make it clear that an extension is not happening.

Chayka Could Deal with Maple Leafs Biggest Trade Ever

Let’s assume for a minute that Matthews sees the writing on the wall and makes it known he doesn’t want to re-sign.

At that point, Chayka might have to engineer the Maple Leafs’ biggest trade in franchise history. The newly minted GM would have to figure out where to send Matthews and what he could get in return for the team’s all-time leading goalscorer.

The likelihood of that situation seems low at this point in time. But it has to be something either discussed at one point during the hiring process. Perhaps that was a private conversation that only people in the know were privy to.

For everyone else, the situation seems pretty clear. Matthews is a core piece of the team. And anything to suggest the Maple Leafs are going to rebuild could lead the former first-overall pick to forego signing an extension.

It’s nothing personal, it’s just business.