The Toronto Maple Leafs missed the Stanley Cup playoffs last season, a break from a run that had lasted since 2016. But with former general manager Brad Treliving out and John Chayka now running the show, Toronto has spent the offseason reshaping the roster through the draft, free agency and trades.
The biggest question around the Leafs entering the 2026 offseason was whether they would keep their core intact or start over around 2026 No. 1 overall pick Gavin McKenna. For now, Auston Matthews, William Nylander, John Tavares, Matthew Knies and Morgan Rielly are still in place, even as Chayka has worked aggressively around them.
One of the first major moves sent goaltender Joseph Woll and defenceman Simon Benoit to the Flyers. Toronto received a 2026 third-round pick, goalie Samuel Errson and defenceman Emil Andrae in return, though the Leafs later flipped Errson to the Ottawa Senators for a 2027 fifth-round pick.
Another notable deal came in the form of a sign-and-trade with the Tampa Bay Lightning for elite D-man Darren Raddysh. That move gives Toronto a clear boost on the blue line, and it also came with an eight-year contract. The Leafs also brought in another former Lightning player, sending backup goalie Dennis Hildeby and picks to Tampa in exchange for Mississauga-born left winger Nick Paul.
Toronto then addressed the crease again by signing free-agent goaltender Sergei Bobrovsky to a three-year deal, adding more championship pedigree behind the team. And with McKenna now in the organization, the expectation is that he can make an immediate offensive impact if everything breaks right.
Even with those additions, the road back to the postseason won’t be simple. The Leafs finished last in the Atlantic Division last season, and the division remains loaded. A jump from the bottom of the standings to a playoff spot will take a real step forward.
Toronto probably won’t challenge for first in the division, and even a top-three finish looks unlikely. The 2026 Atlantic Division champion Buffalo Sabres, the Tampa Bay Lightning and the Montreal Canadiens all took major steps last season. Tampa also managed to replace Raddysh with John Carlson and added forwards Ilya Mikheyev and Jeffrey Viel.
That leaves Toronto likely fighting for a wild-card position in the Eastern Conference, and even that path looks crowded. The Florida Panthers are trying to get back into contender form after acquiring Brady Tkachuk from the Ottawa Senators and getting captain Aleksander Barkov back after he missed the entire 2025-26 season with an ACL tear.
Still, the Leafs do have one thing working in their favor: the Atlantic is top-heavy. If Toronto can get into the top five in the division, there’s at least a path to the postseason. The current core brings plenty of regular-season and playoff mileage, and with upgrades on defense, in goal and up front - plus McKenna’s expected arrival - the Leafs have a real shot to get back in.
So yes, the Leafs should make the playoffs in 2027, even if the more likely route is through a wild-card berth.
In Other News...
Maple Leafs May Finally Have The Piece For A Real Top Six Trade
The Maple Leafs are still shopping for a top-six forward, and the search has only gotten trickier after they moved most of the pieces that would normally bring back real value. One asset they do have is a 2027 first-round pick acquired in the Nic Roy deal, and that kind of draft capital is the sort of thing that can at least get a serious conversation started if Toronto decides to push for help up front.
Pittsburgh, meanwhile, is in a position where it may have to weigh what its future roster looks like against the value of keeping veterans in place. Bryan Rust has come up as a name worth watching in that discussion, especially with his contract running through 2028 and no trade protection attached, but the cost to pry him loose would not be small. If the Leafs are going to make a real swing, they may need to decide whether to part with more than just a pick to get the kind of forward they have been missing. [Read more 🡒]
Maple Leafs May Finally Have A Shot At The Blue Line Fix
Alexander Nikishins situation in Carolina has quickly become one to watch for teams looking to reshape their blue line, and Toronto has naturally surfaced as a club with the kind of need that makes sense in that conversation. The young defenseman and Stanley Cup winner is reportedly seeking a significant contract extension, which has the Hurricanes at least considering trade calls, and that alone is enough to put the Maple Leafs on the radar as a possible partner.
For Toronto, the appeal is obvious: a chance to add a young, high-end defenseman without waiting for the market to dry up elsewhere. Nothing is official, and the talks remain firmly in the realm of possibility, but the fit is the kind that tends to linger around this time of year, especially for a team still searching for a cleaner answer on the back end. [Read more 🡒]
Blue Jackets Fans Wont Love Why Werenski Is Back In Trade Talk
Matthew Knies has become one of the more interesting names in the Maple Leafs orbit because his combination of age, role and contract control gives Toronto something every team wants and few are eager to move. Even with reports that the Leafs have at least listened on him, the asks they have been weighing have been substantial enough to show just how much value he carries, especially for a club that is always trying to balance present urgency with future flexibility.
That is why the speculative trade chatter keeps circling back to big names, from Dylan Larkin to Zach Werenski to Connor Hellebuyck, even if none of those possibilities is close to real. The Werenski idea, in particular, comes with its own obvious hurdle because Toronto would need more than just a willing trade partner, and the price would not be light. For now, Knies remains in Toronto, but the fact that he is still being discussed at all says plenty about how aggressively the Leafs are at least exploring their options. [Read more 🡒]