Breaking Down the Maple Leafs' Busy 2026 Offseason

The Toronto Maple Leafs entered the 2026 offseason knowing change was necessary after missing the Stanley Cup Playoffs for the first time since the 2015-16 season. Under new general manager John Chayka and senior executive advisor Mats Sundin, the organization has wasted little to no time reshaping the franchise in all facets of the game.

Here's a complete look at everything the Maple Leafs have done so far to begin the 2026 offseason.

A new era begins in the front office

The first major change came before the offseason truly got underway, when MLSE CEO Keith Pelley hired John Chayka as general manager and Mats Sundin as senior executive advisor of hockey operations.

The duo immediately made it clear that the organization was entering a new era, promising a thorough evaluation of every aspect of the franchise after a disappointing season.

One of Chayka's first major decisions was moving on from head coach Craig Berube after just two seasons behind Toronto's bench.

Calling it an "organizational shift," Chayka began a lengthy coaching search before eventually hiring former Los Angeles Kings head coach Jim Hiller. Hiller, who previously served as a Maple Leafs assistant from 2015-19, was viewed as the right fit to lead Toronto back into playoff contention.

Winning the Draft Lottery changes everything

Perhaps the biggest turning point of the offseason came when Toronto won the NHL Draft Lottery, earning the first overall selection.

The Maple Leafs used the pick to draft Gavin McKenna, widely considered one of the top prospects to enter the NHL in recent years. Landing a potential franchise player immediately changed the long-term outlook of the organization and gave Toronto a new centrepiece to develop alongside superstar forward Auston Matthews.

Major changes within the lineup

The Maple Leafs' first trade of the offseason included netminder Joseph Woll, who was sent to the Flyers.

The Maple Leafs dealt Woll, which signalled a major change as they traded him along with Simon Beniot to the Flyers in exchange for young puck-moving defenceman Emil Andrae, Samuel Ersson and a third-round pick. The moves did not stop there, as on July 1st, they signed Sergei Bobrovsky to a three-year $21 million deal, rekindling the duo from the Stanley Cup Champion Florida Panthers.

Toronto also began reshaping its defence core.

The Maple Leafs went after the top free agent on the market, acquiring Darren Raddysh from the Tampa Bay Lightning in a sign-and-trade where they signed the Caledon native to a monstrous eight-year $68 million deal. The acquisition makes the Maple Leafs a much stronger team from the backend, adding something they have been missing over the Auston Matthews era: a true number one right-handed defenceman who can move the puck and be a factor offensively.

The Maple Leafs also moved on from Brandon Carlo, who never truly found his footing within the lineup. Shortly after, Chayka re-signed Troy Stecher to a two-year contract, retaining an affordable depth option who impressed after arriving during the season.

The Maple Leafs also addressed their forward depth by acquiring veterans Colton Sissons, Jack Roslovic, Teddy Blueger, and Brandon Duhaime during free agency, and Nick Paul via trade from the Lightning.

Meanwhile, Nick Robertson's tenure in Toronto officially came to an end after he was traded to the Pittsburgh Penguins for a future fourth-round pick, ending years of speculation surrounding his future with the organization. Matias Maccelli also departed from the organization as he was not tendered a qualifying offer.

The Maple Leafs' roster remains a work in process

Although the Maple Leafs have already undergone one of the busiest off-seasons in franchise history, Chayka has repeatedly emphasized that the roster remains a work in progress.

From a new front office and coaching staff to drafting Gavin McKenna and completely reshaping the roster, the Maple Leafs have made it clear they are committed to turning the page after last season's disappointment.

Whether these moves are enough to return Toronto to playoff contention will be one of the biggest storylines heading into the 2026-27 NHL season.