September is here, and the NHL preseason is about to get rolling. For the Toronto Maple Leafs, there’s a different kind of buzz around camp this year after a frustrating finish to the 2025-26 season. The organization went through a major overhaul in both the front office and the roster over the summer, and GM John Chayka spent the offseason reshaping the team with an eye on getting back to contender status.
Some of those moves were practical. Some were bold.
And a few could end up mattering for a long time. Here are the three best decisions Chayka made this offseason.
The first big swing came when Toronto sent promising rookie Dennis Hildeby to the Tampa Bay Lightning, along with a couple of draft picks, in exchange for Nick Paul. It was a calculated move, and an important one.
The Leafs were never going to carry three goaltenders into the regular season for 2026-27, and Hildeby would have needed waivers if Toronto tried to send him back to the Marlies to start the year. Given how well he played in limited action last season, there was a real chance another team would have taken him, leaving the Leafs with nothing.
Instead, Toronto turned that asset into a useful NHL piece. Paul gives the Leafs a player who can move all over the lineup and still bring value in different ways.
He has the potential to score 20 goals, but he can also grind out tough minutes in defensive situations and on the penalty kill. That kind of flexibility can quietly change games over the course of a season.
Another move that stands out is the acquisition of Darren Raddysh from the Tampa Bay Lightning. Toronto has gone a long time without a true booming shot from the blue line to run the power play. Jake Muzzin was the closest thing they had this decade, though most of his time with the club was spent in a defensive role.
Raddysh gives them something they’ve been missing. His shot adds a new layer to a power play that had become strong but increasingly easy to read.
Opponents knew Morgan Rielly wasn’t likely to fire from the point, and even Toronto’s five-forward looks didn’t offer the same kind of threat from the back end. That changes now.
Raddysh comes off a breakout year in Tampa Bay, where he scored 22 goals, including 10 on the power play, and that kind of production from the blue line should give Toronto another weapon to work with.
The biggest move of all came at the 2026 NHL Draft, when Chayka took Gavin McKenna first overall. It might have looked like the obvious call, but it still mattered that he made it. Toronto could have gone another direction, with Ivar Stenberg or one of the elite young defensemen available, but Chayka stuck with McKenna, the choice most Leafs fans wanted.
That decision could shape the franchise for years. The Leafs could have tried to fill a future need on defense, or added the polished all-around game of Stenberg, but McKenna offers something different.
He has been described as a potential generational talent, the kind of player who could become the next Patrick Kane or even Sidney Crosby. Defense can be developed.
Elite vision and playmaking like McKenna’s are much harder to find. His hockey IQ and creativity give him a ceiling that feels enormous, and that’s why this was not just Toronto’s best move of the summer, but one that could end up defining the franchise.
In Other News...
Maple Leafs May Regret Letting A Defense Prospect Help Tampa Bay
Nathan Mayes, a defenseman originally drafted by the Maple Leafs, is now getting a look in Tampa Bay after being added to the Lightnings Prospect Showcase roster. It is a small roster move on paper, but for Toronto it is one of those reminders that player development does not stop at the draft table, especially when a prospect keeps moving and another team is willing to take a closer look.
Toronto did not offer Mayes an entry-level contract, which opened the door for Tampa Bay to evaluate him without surrendering a draft asset. The Lightning are now weighing whether his development in the WHL has put him on a path to help at the AHL or NHL level, and that kind of opportunity is exactly the sort of thing that can sting when a former pick starts to find traction elsewhere. [Read more 🡒]
Leafs Forward Depth Issue Could Open Door For An Unexpected Prospect
The Leafs have spent plenty of time this season trying to sort through their forward depth, and that has naturally put a few younger names back on the radar. Among them is Miroslav Holinka, whose recent development has stood out enough to keep him in the conversation for a possible call-up. He has handled both junior and professional levels well, which is the kind of progress that can move a prospect from long-term project to something a little more immediate when a roster needs an extra body up front.
For Toronto, the appeal is straightforward: when depth becomes an issue, the organization wants options that have shown real growth rather than just emergency insurance. Holinka has given the Leafs reason to keep watching closely, especially with the kind of opening that can appear when injuries or lineup turnover start to pile up. The question now is less about whether he belongs on the radar and more about how quickly the team is willing to test him if the need gets serious. [Read more 🡒]
Barkovs Bobrovsky Message Should Have Maple Leafs Fans Paying Attention
A former teammates praise can carry extra weight this time of year, and Aleksander Barkovs words about Sergei Bobrovsky should resonate in Toronto. The Panthers captain spoke glowingly about the goaltender the Maple Leafs brought in, pointing to Bobrovskys work ethic, his leadership and the kind of presence he brought every day over their seven seasons together in Florida.
For Maple Leafs fans, the more relevant part is how Barkov framed what Bobrovsky still brings now. He said the veteran remains in excellent shape and continues to operate with the professionalism that has defined his career, which is a useful reminder that Toronto is getting more than just another name in net. Florida will miss him, Barkov said, and for a Leafs team looking for stability at a critical position, that kind of endorsement is hard to ignore. [Read more 🡒]