TORONTO - William Nylander was hanging out up top in a private suite.
asserted
Nylander → hang → 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.
uncertain
It → battle → ice
The NHL draft lottery was set for that night.
asserted
lottery → set → 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.
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Nylander → endure → pick
A single ping-pong ball changed everything.
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ball → change → everything
The Original Six franchise beat the odds and won the right to select winger Gavin McKenna with the first overall selection in June.
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franchise → beat → June
That lucky break shifted the vibes around the organization overnight.
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break → shift → organization
“A game-changer,” Nylander said.
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Nylander → say → ?
“The team has been rebuilt in a different way (with) a little different thought behind it.
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team → rebuild → it
I’m super excited.
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I → ’m → ?
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.
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that → remove → 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.
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Chayka → hire → roster
Toronto inked two-time Stanley Cup winner Sergei Bobrovsky to patrol the crease with Anthony Stolarz after Joseph Woll was dealt.
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Woll → ink → Stolarz
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.
asserted
Leafs → nab → 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.
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cast → support → Roslovic
“Every day we’re looking to earn it,” Chayka said.
asserted
Chayka → look → it
“If we can do that, we’re going to have a good season, but it’s definitely not going to be easy.”
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it → do → season
Jim Hiller, meanwhile, was hired as head coach following Craig Berube’s dismissal.
asserted
Hiller → hire → dismissal
“You just start to really appreciate the mix that’s in place,” he said.
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he → start → place
“It gives us a really good opportunity to see what we can get out of them.”
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we → give → 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.
asserted
that → take → 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.
uncertain
he → know → Chayka
“I thought it was just appropriate to take a step back, see what happens, and go from there.”
asserted
what → think → step
The rest of the veteran holdovers, meanwhile, are equally keen to make amends.
asserted
rest → 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.
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Tavares → result → change
“Take responsibility and look forward, learn from it and embrace what’s ahead.
“Hopefully things can get trending back in the right direction.”
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things → look → 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.
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who → live → 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.
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that → wait → 1967
“Some people might not like it, but for me, I see it as a blessing in disguise,” McKenna said of the attention.
uncertain
McKenna → like → attention
I want to obviously start the year as best as I can and hopefully not have to hear that noise.
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I → want → noise
“But if I do, I think it’s a good motivator for me.”
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it → do → me
BOBBING FOR PUCKS
Bobrovsky has turned heads for all the right reasons since arriving in town.
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Bobrovsky → bob → 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.
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Chayka → ’ → seasons
“He’s the first guy to come to the rink, last guy to leave, and there’s purpose.
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He → ’ → rink
He’s crafted a program for himself — mentally, physically — that’s led him to the top of the mountain.
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that → craft → mountain
“That stuff wears off.”
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stuff → wear → ?
“It’s an absolute treat,” Matthews said of having the netminder in the fold.
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Matthews → ’ → 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.”
asserted
it → look → himself
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.
asserted
who → join → clubs
“We’ve exchanged a couple of words,” Bobrovsky said with a laugh of Panthers-Lightning history.
asserted
Bobrovsky → exchange → history
…and 5 more, not listed.