Worrying Warning Given To Maple Leafs Despite Offseason Moves

Toronto Maple Leafs Introduce New Manager
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TORONTO, ONTARIO - MAY 4: Mats Sundin speaks at a press conference where he was announced as Senior Executive Advisor of Hockey Operations and John Chayka was introduced as General Manager of the Toronto Maple Leafs at Real Sports Bar & Grill on May 4, 2026 in Toronto, Ontario, Canada. (Photo by Michael Chisholm/Getty Images)

Among the busiest teams in the NHL so far this offseason have been the Toronto Maple Leafs, who not only made monumental changes to their roster, but to their front office and coaching staff.

The Leafs, who missed the Stanley Cup Playoffs for the first time in a decade, lucked out by winning the NHL Draft Lottery and earning the right to select phenom forward Gavin McKenna from Penn State University. They’ve also made several additions to their roster with the likes of Sergei Bobrovsky and Nick Paul, along with Darren Raddysh, among others.

But have the Maple Leafs done enough to ensure that missing the postseason in 2025-26 was an anomaly?

NHL Insider Has Worrying Prediction For The Toronto Maple Leafs

In the mind of NHL Insider Harman Dayal of The Athletic, the Maple Leafs are one of a handful of clubs that are stuck in, as he put it, the “mushy middle” of the League, thanks in large part to the presence of other strong clubs in the heavily competitive Atlantic Division.

He wrote:

“Toronto’s back end could be significantly better with the addition of Darren Raddysh and a healthy Chris Tanev (who only played 11 games last season), and moving Simon Benoit out and bringing Emil Andrae in should result in a third pair that’s much better at breaking the puck out. Gavin McKenna should give the team’s top-six and first-unit power play a big jolt. The new coach bump going from Craig Berube to Jim Hiller could be meaningful; the bottom six is upgraded (Nick Paul, Jack Roslovic, Colton Sissons, Brandon Duhaime, Teddy Blueger) and Auston Matthews should rebound after arguably the worst season of his NHL career.

However, the issue is that even if they make the playoffs, the path to a deep run feels quite unlikely in a stacked Atlantic Division. The Montreal Canadiens, Florida Panthers and Buffalo Sabres are all stronger teams than the Leafs on paper. Their future outlook also faces several question marks.”

Dayal continued by noting the age of players like Bobrovsky and John Tavares, while also noting that William Nylander is already 30, while Auston Matthews will be soon.

“Yes, McKenna has a good chance of eventually developing into a star, but the rest of Toronto’s core is aging. The Leafs’ five best defenders are all in their 30s, John Tavares will turn 36 and Sergei Bobrovsky will turn 38 before the season starts. Matthews will turn 29 in September and William Nylander is 30. They don’t have enough young pieces coming with a prospect pool that’s quite bleak beyond McKenna (ranked No. 29 by Wheeler in March) and they’re asset-poor as they don’t own their next two first-rounders.

There’s a path for the Leafs to be decent short-term, but a Stanley Cup run over the next few years feels like a long shot, especially since their best players have underwhelming playoff track records.”

Did The Maple Leafs Do Enough To Make The Playoffs In 2027?

As stated, the Maple Leafs have been among the busier teams in the NHL so far this offseason thanks to the moves by GM John Chayka.

But will it be enough to get them back to the postseason, especially considering how many other strong teams are in the Atlantic?

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Worrying Warning Given To Maple Leafs Despite Offseason Moves

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