TORONTO — William Nylander was hanging out up top in a private suite. The Maple Leafs winger’s brother and the Toronto Marlies were battling in an American Hockey League playoff game on the ice below. It was early May. The NHL draft lottery was set for that night. Nylander and the rest of his teammates had just endured a miserable, playoff-less season — the club’s first in a decade — and owned a meagre 8.5-per-cent chance of earning the No. 1 pick. The odds were not in Toronto’s favour. A single ping-pong ball changed everything. The Original Six franchise beat the odds and won the right to select winger Gavin McKenna with the first overall selection in June. That lucky break shifted the vibes around the organization overnight. “A game-changer,” Nylander said. “The team has been rebuilt in a different way (with) a little different thought behind it. I’m super excited.” That favourable lottery bounce removed angst about the immediate future of captain Auston Matthews — two seasons remain on his contract coming off a serious knee injury — and an underperforming core that failed to deliver in 2025-26 despite being among the early favourites. Newly-hired general manager John Chayka, alongside senior executive adviser of hockey operations and franchise legend Mats Sundin, then went about a roster and organizational reload. Toronto inked two-time Stanley Cup winner Sergei Bobrovsky to patrol the crease with Anthony Stolarz after Joseph Woll was dealt. The Maple Leafs also nabbed defenceman Darren Raddysh in a sign-and-trade swap with an eye toward adding speed and offensive flair to an aging blue line. The forward group’s supporting cast was also reimagined with the arrivals of Jack Roslovic, Colton Sissons, Nick Paul, Brandon Duhaime and Teddy Blueger. “Every day we’re looking to earn it,” Chayka said. “If we can do that, we’re going to have a good season, but it’s definitely not going to be easy.” Jim Hiller, meanwhile, was hired as head coach following Craig Berube’s dismissal. “You just start to really appreciate the mix that’s in place,” he said. “It gives us a really good opportunity to see what we can get out of them.” Matthews took a wait-and-see approach with his future back in the spring, but was encouraged by a summer push that also included plenty of backroom change. “You know never (if) they may think something different or they may have different plans or different visions,” he said of Chayka and Co. “I thought it was just appropriate to take a step back, see what happens, and go from there.” The rest of the veteran holdovers, meanwhile, are equally keen to make amends. “Clearly we weren’t very good (last season) and it’s resulted in a lot of change,” Maple Leafs centre John Tavares said. “Take responsibility and look forward, learn from it and embrace what’s ahead. “Hopefully things can get trending back in the right direction.” McKenna, who’s living with Tavares and his family, comes in with high-level pedigree following two seasons in the Canadian Hockey League before spending 2025-26 in the NCAA at Penn State. The 18-year-old from Whitehorse is keenly aware of what’s waiting for him in hockey’s biggest media market — one that hasn’t tasted glory since 1967. “Some people might not like it, but for me, I see it as a blessing in disguise,” McKenna said of the attention. “Had a bit of a slow start to (last season) and then heard all the noise and started to work harder. I want to obviously start the year as best as I can and hopefully not have to hear that noise. “But if I do, I think it’s a good motivator for me.” Bobbing for pucks Bobrovsky has turned heads for all the right reasons since arriving in town. “If there’s a flaw, we’re still looking for it,” Chayka said of the 38-year-old signed for the next three seasons. “He’s the first guy to come to the rink, last guy to leave, and there’s purpose. There’s a real intent to his work. He’s crafted a program for himself — mentally, physically — that’s led him to the top of the mountain. “That stuff wears off.” The Maple Leafs were on the wrong side of playoff losses to Bobrovsky in the Florida Panthers’ title runs in 2024 and 2025. “It’s an absolute treat,” Matthews said of having the netminder in the fold. “The stories, the hype around him and just the professional that he is, how he looks after himself, his focus — it’s extremely impressive.” Joining forces Raddysh and Paul, who both arrived from Tampa Bay, and Bobrovsky are now on the same side after a string of heated playoff meetings between their former clubs. “We’ve exchanged a couple of words,” Bobrovsky said with a laugh of Panthers-Lightning history. “(About) the fighting matches, not the hockey matches.” Paul, meanwhile, has fond memories of the rivalry — and is eager for what comes next in his new blue-and-white gear. “The Battle of Florida was definitely fun,” the 31-year-old forward said. “Bob was super dialled in coming to the rink. He’s a true professional.” This report by The Canadian Press was first published Sept. 28, 2026. Joshua Clipperton, The Canadian Press
