The Toronto Maple Leafs enter 2026-27 with a completely different look, and that alone makes them one of the league’s biggest draws. After missing the playoffs in 2026-27, MLSE president and CEO Keith Pelley brought in a new front office, hiring general manager John Chayka and senior advisor Mats Sundin. From there, Chayka and Sundin reshaped the organization on and off the ice, then kept the momentum rolling after the club won the NHL Draft lottery and landed the top pick.
That lottery win changed everything. The Leafs used the No. 1 selection on Gavin McKenna, the Whitehorse phenom who now steps into a roster already featuring Auston Matthews, William Nylander, Matthew Knies, and John Tavares.
In theory, that should take some of the pressure off McKenna. In reality, being the top pick in Toronto comes with a spotlight that never really turns off.
How he handles that stage will be one of the season’s most closely watched stories.
Matthews remains the biggest reason the Leafs can’t be ignored. Two years ago, he was being talked about alongside Connor McDavid as one of the NHL’s most dominant players.
But injuries and poor play have dragged him down over the past two seasons, leaving him with 60 goals combined. That falls well short of the standard he set when he scored 60 goals twice in a single season, won multiple Rocket Richard trophies, and captured a Hart Trophy for MVP.
His 2025-26 season was so rough that he was noncommittal about his future in Toronto.
He has stayed quiet through the offseason, as usual, but the questions around him are loud. Has he fully recovered from his injuries?
Can he stay healthy? Can McKenna help him get back to his old goal-scoring level?
This season could shape what comes next for Matthews, who has two years left on his current deal. If he and the Leafs click, a contract extension could follow.
If he goes through another injury-hit, underwhelming year, the relationship could end.
Toronto’s new arrivals add even more fuel to the fire. Goaltender Sergei Bobrovsky and defenseman Darren Raddysh both came over from division rivals, with Bobrovsky arriving from the Florida Panthers and Raddysh from the Tampa Bay Lightning.
The Panthers were unwilling to pay up for the decorated Bobrovsky, and he’s coming off a career-worst season, which only adds to the intrigue. Raddysh brings a heavy shot from the blue line, giving the Leafs something they haven’t had in a long time: a real threat from back there.
The returning cast has its own storylines, too. Chris Tanev, the team’s most important defenseman, is coming back at age 36 after serious injury issues.
Matthew Knies spent most of the offseason in trade rumors, which makes his response this season worth watching. And the Leafs’ longest-serving player looked like he might be starting 2026-27 somewhere else, only for a move never to happen.
He’s still in Toronto, and now the question is whether he can restart his career with a fresh beginning under new leadership.
There’s also a new voice behind the bench. Jim Hiller takes over as head coach, with Daniel Alfredsson joining as an assistant after Chayka pulled him away from the Ottawa Senators. Chayka also rebuilt much of the rest of the front office.
Other teams will have plenty of attention, including McDavid and Leon Draisaitl chasing a championship with controversial former Leafs coach Mike Babcock, plus the rising San Jose Sharks. Still, the Maple Leafs bring together too many moving parts, big names, and unresolved questions to look away from. Love them or hate them, they’re the NHL’s must-watch team this season.
In Other News...
Maple Leafs Could Face One Tough Decision With Reilly Smith
The Maple Leafs are weighing a professional tryout for Reilly Smith, a veteran forward whose rsum still carries plenty of value for a team looking to deepen its options. With more than 575 points and approaching 1,000 NHL games, Smith would bring experience, versatility and another layer of depth to a Toronto forward group that is always under the microscope.
The catch is roster math. Toronto already has a full contract roster, so inviting Smith in on a PTO is the easy part compared with what comes next if the fit is right. Before any deal could become real, the Leafs would have to clear space, and that is where a seemingly straightforward veteran addition can turn into a tougher decision than it first appears. [Read more 🡒]
Maple Leafs Prospects Have A Real Chance To Shake Up Camp
The NHL Prospect Showcase on Sept. 12-13 will give a group of Maple Leafs prospects an early chance to separate themselves before training camp opens. For players like Ben Danford and Tinus Luc Koblar, this is more than a tune-up, because the organization will be watching closely to see who looks ready for a longer look and who can start building a case for a depth role.
For a Toronto team that always has a few open questions at camp, these kinds of weekends can matter more than they seem. A strong showing does not guarantee anything, but it can shape who gets extra attention once the real battles begin and help nudge the early depth chart in one direction or another. [Read more 🡒]
Leafs Just Closed Off One Offseason Option Fans Wanted
The Maple Leafs have hit the NHLs 50-contract limit, a notable early-fall checkpoint that leaves the organization with no room to simply add another player without first making a corresponding move. As of Sept. 7, Toronto was the only team in the league sitting at that ceiling, and the recent addition of Brendan Brisson helped push the club into that fully booked position.
For a fan base still hoping for one more offseason swing, the timing matters because it likely shuts the door on any straightforward signing, including professional tryouts, unless the Leafs clear space through a trade or another roster move. Trades are still on the table, so the front office is not out of options, but the path to any further additions just got a lot narrower. [Read more 🡒]