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The Maple Leafs' bleak outlook leaves John Chayka with a massive challenge

On TSN's That's Hockey, Craig Button revealed the Maple Leafs' bleak offseason priorities, exposing the gigantic front-office task now facing new GM Chayka.
May 4, 2026; Toronto, Ontario, CANADA; Toronto Maple Leafs general manager John Chayka speaks to the media during an introductory news conference at Real Sports Bar. Mandatory Credit: Dan Hamilton-Imagn Images
May 4, 2026; Toronto, Ontario, CANADA; Toronto Maple Leafs general manager John Chayka speaks to the media during an introductory news conference at Real Sports Bar. Mandatory Credit: Dan Hamilton-Imagn Images | Dan Hamilton-Imagn Images

One can safely assume that new Toronto Maple Leafs general manager John Chayka likes a challenge.

The marquee GM position of the Original Six team became available following a deflating, underachieving season that resulted in a franchise-worst year-to-year drop in points, leaving many to question the organization's direction.

While the immediate euphoria of winning the NHL Draft Lottery and the right to make the first overall selection briefly injected hope into the fan base, it has quickly been replaced by a daunting, high-stakes "to-do" list for Chayka and his senior advisor of hockey operations, Mats Sundin.

The true scale of this rebuild was laid bare when the Leafs became the first of seven Canadian franchises to be dissected on TSN's That's Hockey. A deep dive into their offseason priorities revealed the herculean effort and gigantic front-office task now required of Chayka in his first summer in Toronto.

TSN exposes the scale of the Leafs' rebuild

TSN's NHL analyst Craig Button was a guest with host Gina Reda and gave a breakdown of the Maple Leafs' offseason priorities. To offer some perspective on the job ahead, the Leafs' current coaching search and its obstacles didn't even make Button's list.

Nailing the coaching hire and the No. 1 overall pick are Chayka's most important imminent jobs to get Toronto back on track. He, himself, has stressed the importance of choosing the right coach.

The Leafs overall roster was graded respectfully by the former Calgary Flames GM. Auston Matthews, William Nylander, and Matthew Knies were given first-line grades. The Maple Leafs' upcoming draft pick and John Tavares were handed a second-line ranking.

Button graded the team's defense as its weakest area. Chris Tanev was the only blueliner given a top-pairing rating. Morgan Rielly, Jake McCabe, and Oliver Ekman-Larsson were ranked as second-pairing defenseman. Brandon Carlo was rated third-pairing. Phillippe Myers and Simon Benoit were given 6/7 spare part designations. Both of the goaltenders, Joseph Woll and Anthony Stolarz, were handed 1B ratings in net.

Despite the decent talent rankings, mentioning the specific Leafs' priorities demonstrated the challenge in front of Chayka. While it didn't make Toronto's final checklist of objectives, Button acknowledged the importance of the coaching position, saying the Maple Leafs need to understand their players and what they require when choosing a new bench boss.

The TSN analyst stressed that Toronto must ideally get the best player in the draft while picking first, since that player will likely outlast the new coach. Whoever they pick should be a player "that can establish themself as a contributor."

The next item on the Maple Leafs' checklist was to set a franchise path and let Matthews decide his future. Button suggested the center is still a "first-rate superstar in the National Hockey League."

Button said it is not necessary to "put a stake in the ground in that regard" about giving an ultimatum to Matthews to address his future intentions. He explained Chayka's actions are paramount in convincing the Leafs' captain to stick around, that it is about "showing," not "telling," Matthews your plans for the team.

"I don't know if you have to put a stake in the ground in that regard"
Craig Button on Matthews' future

The last two items mentioned were finding a play-driving second-line center and a puck-moving defenseman. When prompted by Reda, Button agreed that Tavares would be better suited to the wing at this stage of his career to lessen his burden, but the biggest obstacle is that "about twenty teams are looking for a play-driving second-line center."

A puck-moving defenseman, either left or right-handed, was the final need listed for the Maple Leafs. Button noted the Leafs have too many second-pairing defensemen and lack someone to carry the "archetype of a top-pair number-one defenseman."

Chayka is stepping directly into the fire for his first offseason as general manager in Toronto. Despite boasting high-level core talent, the current roster suffers from massive deficiencies in critical areas. Before Chayka can even look at the on-ice product, two monumentally historic decisions await his front office: hiring a franchise-altering head coach and selecting the absolute best player available with the coveted first-overall pick in the upcoming NHL Draft.




Before Chayka can even look at the on-ice product, two monumentally historic decisions await his front office: hiring a franchise-altering head coach and selecting the absolute best player available with the coveted first-overall pick in the upcoming NHL Draft.

Establishing a clear, sustainable future direction for the Maple Leafs will require navigating an absolute minefield of major challenges, leaving no doubt that Chayka's Herculean task is only just beginning.

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