While Leafs Nation would prefer to forget, the Toronto Maple Leafs failed to advance to the Stanley Cup playoffs for the first time since 2016. However, with the departure of former general manager Brad Treliving and the arrival of new Leafs GM John Chayka, the Leafs have been busy this offseason through the draft, free agency, and the trade market.
There will surely be more tweaks and moves by the Leafs and the other 31 NHL teams as the 2026–27 regular season draws near, but that won’t stop us from looking ahead and predicting whether the Leafs will flip the script this season and advance to the playoffs. To form our conclusion, we will look at the key moves, draft picks, and acquisitions Chayka has made thus far, along with the state of the other teams the Leafs will have to battle with in the Atlantic Division.
Here we go.
New look, similar parts
The big question heading into the 2026 offseason for Toronto was whether they would keep their core group together or opt for a rebuild around their 2026 No. 1 overall draft pick, Gavin McKenna. For now, Auston Matthews, William Nylander, John Tavares, Matthew Knies and Morgan Rielly remain Leafs, but Chayka has made some impactful moves around the edges, the first of which saw the Leafs deal goaltender Joseph Woll and defenceman Simon Benoit to the Flyers. In return, the Leafs got a 2026 third-round pick, goalie Samuel Errson and defenceman Emil Andrae, although the Leafs later traded Errson to the Ottawa Senators for a 2027 fifth-round pick.
The next big move the Leafs made was one I actually predicted in an article on the Leafs’ defensive pairs for the coming season: a sign-and-trade deal with the Tampa Bay Lightning for elite D-man Darren Raddysh. Raddysh will undoubtedly strengthen Toronto’s defensive corps, and he is also on an eight-year deal, but he isn’t the only former Lightning player who will be joining the Leafs, as the team also dealt backup goalie Dennis Hildeby, along with picks, to Tampa for Mississauga-born left winger Nick Paul.
In addition to other smaller moves, the Leafs also added a formidable replacement for Woll in the crease by signing free-agent netminder Sergei Bobrovsky to a three-year deal, bringing additional championship pedigree to the Leafs’ back end. And let’s not forget the Leafs snagged McKenna in the draft, so if all goes as planned, he should have an immediate offensive impact. So while the Leafs didn’t deal any of their core, they did make some moves that should allow them to be at least better than a season ago, if not far better.
The competition in the Atlantic
The Leafs finished at the bottom of the Atlantic Division last season, meaning they will have to improve quite a bit if they want to make a true run at playoff contention. It will be no easy task, as the division remains one of the toughest in the league.
To start, the Leafs, apart from a miracle, likely won’t finish as the top team in the division, and they may not even finish in the top three. Teams like the 2026 Atlantic Division champion Buffalo Sabres, the Tampa Bay Lightning and the Montreal Canadiens showed incredible improvement last season, and even though the Lightning lost Darren Raddysh, they added forwards Ilya Mikheyev and Jeffrey Viel, and replaced Raddysh with D-man John Carlson. Being able to compete with these teams will really depend on whether the Leafs existing core can click with McKenna and the new pieces, like fans are hoping.
In all likelihood, the Leafs will be battling for a wild-card spot in the Eastern Conference, but even that won’t be an easy task with a team like the Florida Panthers looking to reclaim their contender status, and the Cats are honestly looking pretty scary. Not only did the team acquire star left winger Brady Tkachuk from the Ottawa Senators, but they will also have their captain, Aleksander Barkov, back on the ice after missing the entire 2025–26 season with an ACL tear.
The thing the Leafs have going for them is that the division is very top-heavy at the moment, so if they can crack even the top five of the division, there is a chance they could sneak into the postseason, and as we know, anything can happen come playoff time. And despite the Leafs never advancing to a conference final in the Core Four era, the core members of the current roster do have a plethora of both regular-season and playoff experience. With solid additions to their defensive core, in net, and, of course, on the front line, with McKenna hopefully next in line for an elite rookie-of-the-year-level season, there is a very good chance the Leafs can get back to the playoffs in 2027.
So, with that in mind, yes, the Leafs will make the playoffs in 2027; just don’t be surprised if it ends up being through a wild-card berth, given the solid cores already present at the top of the Atlantic.
