Toronto Maple Leafs' Biggest Questions Before the 2026-27 NHL Season

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On June 26, the Maple Leafs selected Gavin McKenna first overall during the 2026 draft at KeyBank Center, Buffalo. This is also the same place in which they called the name of Auston Matthews back in 2016, ten years earlier and following a long period without making it to the playoff finals, and this is the third time the franchise has selected first overall in its history.

Back in April, none of this seemed remotely possible. The team headed into the lottery with only an 8.5% chance of winning it, which is what online bookmakers like Melbet Canada thought, too.

Question 1: How Much Does McKenna Play?

McKenna, who will turn 19 over the course of the season, is set to make his debut with the team in the first game of the year. The year he had at Penn State was good enough that he was the overall first pick many days before the draft, although there does not seem to be a reason why new coach Jim Hiller would want to give an 18-year-old first-line minutes in October. 

Having the player on the team in an easier role would be a better course of action – it can be a starting role in the offensive zone, easier match-ups, and playing away from Matthews instead of playing alongside him. Toronto is also a city where patience with the first overall draft pick normally lasts until US Thanksgiving.

Question 2: Is Auston Matthews Staying?

Everything else hangs on this. Matthews carries a $13.25 million cap hit with a full no-movement clause and reaches unrestricted free agency in July 2028. Through the summer, reporting suggested Toronto would listen to any player on the roster except him.

John Chayka, hired on May 3 alongside Mats Sundin, has not behaved like a general manager tearing anything down. Whether that reflects a plan or a hope is what Canadian fans will spend the winter trying to read, and the Atlantic markets at Melbet Canada tend to price the answer before the club offers one.

Question 3: Was the Bottom Six Actually Fixed?

Chayka had the busiest July 1 in the league, and the logic behind it was not subtle: hand the defensive shifts to somebody other than the captain.

Move Player Terms
Trade with Tampa Bay F Nick Paul For Dennis Hildeby, a 2028 third, a 2027 fourth
UFA signing F Jack Roslovic Two years, $4M AAV
UFA signing F Colton Sissons Multi-year, depth centre
UFA signing F Teddy Blueger Multi-year, defensive centre
UFA signing D Darren Raddysh Right-shot top four
UFA signing G Sergei Bobrovsky Veteran starter

Under Craig Berube, Matthews' offensive-zone starts dropped from roughly 70 percent to about 55, mostly because the coach had nobody else he trusted with the hard minutes. Paul, Sissons, and Blueger were signed to take those shifts off him.

Question 4: Can the Defence Hold Up?

Losing Mitch Marner's 102 points hurt, but it does not explain 2025-26 on its own. Toronto allowed 299 goals, led the entire NHL in shots against, and watched its goal differential swing by 83 in a single year.

Raddysh improves the right side, and Bobrovsky is a real upgrade in net. Neither one fixes a team that spent long stretches of last season defending in its own end because it could not get out of it.

Question 5: What Happens in 2028?

Chayka committed roughly $16.5 million to depth on the opening day of free agency, which pushed Toronto up against the $104 million cap and left almost nothing for in-season additions. Nearly all of those deals expire in the summer of 2028 – the same summer Matthews can walk.

There is a case for that timing. No contract on the books becomes an anchor, and the roster can be reshaped in one go. The problem arrives with the bill. By 2028, the cap sits at $113.5 million, agents will be quoting the new number, and Toronto re-prices its entire supporting cast at once.

What a Successful Season Looks Like

Achieving a conference title is not a benchmark in this case, and neither is any playoff action. In order to achieve success in the upcoming season, the team must be able to undergo a transformation that would make McKenna an all-star by February, Matthews able to score consistently and secure victories, with the team’s total goals allowed decreased by 40. If this is achieved, Toronto will once again be able to fight for a playoff berth without surrendering any of its resources.

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