TORONTO — Minutes after the buzzer sounded on the Toronto Maple Leafs’ season, on a dark mid-April night on the outskirts of Ottawa, William Nylander was spotted in the bowels of Canadian Tire Centre sharing a laugh and a chat with another one of Sweden’s great offensive talents.
Daniel Alfredsson, then a member of the Senators bench and, seemingly forever, Toronto’s all-time enemy in the Battle of Ontario.
But with off-season upheaval aplenty in the province, those Alfie-Willy conversations will now be the norm.
In a head-spinning announcement Tuesday, the first modern-era Senator to have his number retired in Ottawa is taking his coaching talents westbound down the 401.
The 53-year-old Alfredsson — one of the 20-plus candidates who interviewed for the Maple Leafs’ head job — is joining Jim Hiller’s staff in Toronto as an associate coach.
John Gruden, hot off his Calder Cup championship with the AHL Marlies, and Brad Werenka, who most recently served as an assistant coach for the University of Calgary’s program, were named assistants.
Mike Van Ryn and Derek Lalonde will not be returning as assistant coaches next season. Steve Sullivan was not mentioned in the Leafs’ press release, but his name is no longer listed as a coach on the club’s website. Gruden’s promotion leaves a head coaching vacancy for the Marlies.
Hiller attempted to snatch friend D.J. Smith as his right-hand man on the bench but was outbid by Mike Babcock and the Edmonton Oilers.
Following a thorough search and interview process under GM John Chayka’s guidance, Hiller landed on Alfredsson, who had been rumoured to be open to a move after three years assisting the Senators.
“While I wish he wasn’t joining an arch rival, Alfie is forever an Ottawa Senator, and the door will always be open for his return. He has done so much for our organization and community, and he has my full respect,” Senators owner Michael Andlauer said in a statement.
Make no mistake: This is a tough look for Senators fans, a group still swallowing the exodus of captain Brady Tkachuk to another divisional foe in Florida.
For Chayka’s Leafs, the completion of an overhauled bench, as selected by Hiller, further enforces its off-season themes of top-down alignment and a training camp that should feel fresher, with faces and ideas, than it has in years.
Alfredsson is a direct line from the room to Sundin’s ear.
It’s no secret that Nylander and ex-coach Craig Berube saw the game differently. Alfredsson worked with the Leafs’ leading scorer as an assistant on Team Sweden’s 2026 Olympic bench. Ditto Swedish Leaf Oliver Ekman-Larsson.
The Hall of Famers and good friends captured Olympic gold as teammates in 2006, though.
And Toronto’s Swedish ties have long run deep. Newly acquired defenceman Emil Andrae is the latest member of what captain Auston Matthews once affectionately referred to as the room’s “Swedish mafia.”
We wonder: Could the respected Alfredsson get more out of franchise cornerstone Nylander, who looks to bounce back from an injury-plagued campaign?
In Ottawa, Alfredsson ran the forward group and oversaw a power play that ranked eighth (24 per cent) in the 2025-26 regular season but shrivelled in the Sens’ four-game playoff sweep by the eventual champion Hurricanes (1-for-21; 4.8 per cent).
Toronto’s power play rebounded when Sullivan was brought in mid-season, but finished a disappointing 15th overall (21.3 per cent).
Hiller’s Maple Leafs are depending on a rejuvenated man-advantage to drag them back into contention. Hence, the signing of quarterback Darren Raddysh and the acquisition of offensive minds like Hiller and Alfredsson.
“I’m incredibly excited to add Daniel, John and Brad to our coaching staff,” Hiller said.
“Daniel’s experience, leadership and understanding of the game speak for themselves. John has established himself as one of the top coaches in the American Hockey League and played an instrumental role in leading the Marlies to a Calder Cup championship last season. Brad brings a unique combination of NHL experience, player development and expertise in performance analytics. Together, they’ll be outstanding additions to our team.”
Alone, Alfredsson’s new job will be a thorn in the side of Senators.
Berube reflects on Toronto’s two big losses
Speaking of Leafs coaches…
In his most candid discussion yet of what went wrong as the Maple Leafs plummeted to 28th place last season, Berube explained to Rob Simpson that Mitch Marner was the club’s emotional centrepiece.
“Mitch brought the energy and the emotion to the game on a nightly basis — and to practice. Vocal guy. Chatted a lot on the bench. Chatted a lot in practice. Brought the energy. He’d come back to the bench and let guys know: Pick it up. Let’s go. He was great. I really enjoyed coaching him,” the ex-coach said during an appearance on Simmer’s Morning Skate.
“We lost our emotional leader, for sure. It was a big loss. Not only the player but that side of it, too — in the locker room, on the bench, in practices. He held guys accountable.”
A casualty of Toronto’s failings in 2025-26, Berube also mentioned goaltender Joseph Woll’s absence in training camp, Chris Tanev’s injuries, and the team’s flat performance out of the Olympic break as contributors to the Leafs’ dropoff.
But Marner’s departure was the biggie.
“Never really found that winger to play with Matthews, just the chemistry of your No. 1 line,” said Berube, who believes his roster was better than the results.
“It bothers me…. Just couldn’t catch a hold of anything.”