In the middle of October, The Athletic’s Pierre LeBrun caught up with Keith Pelley, the president and CEO at Maple Leaf Sports and Entertainment, at the NHL Board of Governors meeting in New York.
The Maple Leafs had beaten the Nashville Predators in Toronto the night before. “The vibe around the team is positive,” Pelley said. “There’s a lot of optimism.”
Pelley said he was enjoying working more closely with Brad Treliving, the general manager, and Craig Berube, the head coach (also known as “Chief”), in the months since Brendan Shanahan was let go as team president.
“It’s go time,” said Pelley. “And I think we have two leaders, in Brad and Chief, to hopefully take us to the promised land.”
Three and a half months later, it’s definitely not “go time” anymore. And it’s become clear the new leadership structure isn’t working. With Pelley in charge minus Shanahan, the Leafs will very likely miss the playoffs for the first time in 10 years and end the NHL’s longest playoff streak.
The decision to move on from Shanahan after 11 years was warranted, but not hiring a replacement for him was questionable at the time. It’s beginning to look like a big mistake.
What it did was eliminate one crucial, experienced voice from atop the Leafs’ front office. Instead of leaning on Shanahan, who won three Stanley Cup championships as a player and oversaw the best decade of Leafs hockey since the franchise last won Stanley Cups in the ’60s, Treliving has had Pelley, whose resume includes 8 1/2 years of leadership at the European Tour Group in golf, five years as the president of Rogers Media and three years as a top executive at CTV.
For most of his 11 years running the Leafs, Shanahan was around all the time. He was there at most morning skates, most practices and most games studying his team alongside his various management groups. And while his tenure was obviously far from perfect, he clearly knew the Leafs inside and out.
Does Pelley?
The scope of his very large job — which includes overseeing the Raptors, Argos and Toronto FC — means he can’t be around anywhere near as much. And even if he were, his level of insight obviously doesn’t compare to that of Shanahan or whoever might have replaced him as president had MLSE chosen to go down that path.
Why they didn’t remains a mystery. The result has been a season largely characterized by inaction from the front office, when action, of varying degrees, might have saved the season. It’s hard not to wonder now how much more a new voice behind the bench might have gotten out of this group, or whether even one upgrade could have helped in the face of injuries and underperformance.
“We definitely have flexibility,” Pelley told LeBrun in October.
The only moves of any consequence: terminating forward David Kämpf’s contract, claiming defenceman Troy Stecher off waivers and firing Marc Savard — instead of Berube — from the coaching staff.
It wasn’t nearly enough. What’s the plan now?
How deep will the team’s apparent sell-off before the March 6 trade deadline go? How many assets, and of what quality, can Treliving bring in for the likes of Bobby McMann and Scott Laughton? And what does a sell-off mean, if anything, for the first-round pick in June that’s conditionally owed to the Boston Bruins thanks to the Brandon Carlo trade?
Keeping the pick, if it falls in the top five, would obviously be a good thing for the Leafs. But it wouldn’t be without the potential for major downside as the Bruins and Philadelphia Flyers would hold the rights to the Leafs’ 2027 and 2028 first-round picks, both effectively unprotected.
Assuming there’s no change in leadership at the Olympic break, what does the future hold for Treliving after this season’s looming failure? Does Pelley still believe he’s the right person to get this team to the “promised land” after the way things have panned out? Does Pelley give him a fourth offseason to retool the roster with how poorly things went last summer?
In other words, is it still “go time”?
Is MLSE prepared to hire a president to work with and advise the GM — and if so, is that GM still Treliving?
And what does this season mean, mind you, for Berube? The Leafs are tied for the third-most goals allowed on average in the league this season and have spent the third-least time in the offensive zone. Those are coaching issues that Pelley, a Berube backer, could choose to dismiss on account of injuries — even if the Leafs are hardly alone in that department.
But maybe the biggest question of all is this: Is Pelley up for what lies ahead?
The next few months are pivotal and will determine whether this team slides backward into the abyss that came before Shanahan or back onto a path where Cup contention becomes viable again.
Will the Leafs hold on to Oliver Ekman-Larsson through the trade deadline? (John E. Sokolowski / Imagn Images)
Thoughts on every player on the roster heading into the break
Simon Benoit: His first season with the Leafs, when he performed surprisingly well next to Jake McCabe, has proven to be the outlier. Will the team keep him through the deadline? He has one year left on his contract.
Brandon Carlo: From a poor start to a foot injury (and surgery) that kept him out nearly two months to a bumpy return, it’s been a rough season for the 29-year-old.
Easton Cowan: It sure looks as if he’s hit the rookie wall. A solid year, though, all in all. His 82-game pace right now: 13 goals, 32 points.
Max Domi: More effective in recent weeks, but still miscast in a top-line role.
Oliver Ekman-Larsson: An intriguing potential trade chip, but also someone the Leafs might want to keep for next season. Are the two remaining seasons on his contract a positive or negative for the trade value of a defenceman who turns 35 in July?
Calle Järnkrok: Can the Leafs turn him into a late-round pick at the deadline?
Dakota Joshua: The two years still left on his contract ($3.25 million cap hit) aren’t looking great at the moment.
Matthew Knies: The Olympic break should benefit him as much as anyone given the mysterious injury he’s played through all season.
Scott Laughton: He’s been good for the culture and mighty effective on the ice in two particular places: winning draws and killing penalties. A clear candidate to move at the deadline and someone the Leafs should bring back in the offseason only if it’s on the cheap. Laughton turns 32 in May and has only two assists in 37 games.
Steven Lorentz: The offence has ticked up from last season, and he’s been effective next to Laughton on the PK. His nightly impact hasn’t felt as pronounced, though.
Matias Maccelli: The Leafs are crushing it when he plays with William Nylander and John Tavares, winning over 60 percent of expected goals. Ultimately, he’s still overexposed in a top-six role, and his future with the team remains uncertain.
Auston Matthews: Has cooled off again of late, but is still scoring at a 55-goal pace since Christmas — and doing so with Domi and Bobby McMann by his side.
Jake McCabe: The Leafs gave up 41 five-on-five goals with McCabe on the ice all of last season. This season, after just 55 games: 40. McCabe has obviously missed Chris Tanev.
Bobby McMann: One of the few players exceeding expectations this season — and doing so at $1.35 million on the cap. A contract bet that worked out great for the front office and adds to his trade value.
Philippe Myers: In and out of the press box all season, Myers still has another year left on his contract at $850,000.
William Nylander: It’s felt like a disappointing and unusually injury-plagued season for him. He’s still producing at a 104-point pace.
Morgan Rielly: While reasonable to wonder about his future in Toronto, it’s also reasonable to wonder what kind of interest there would be in a soon-to-be 32-year-old with four more years on his contract at a cap hit of $7.5 million — who also has a full no-move clause.
The longest-serving member of the Leafs, Morgan Rielly, has struggled this season. (Ron Chenoy / Imagn Images)
Nick Robertson: He’s taken steps to make those around him better, already setting a career high for assists. Will he ever play more than the 12 1/2 minutes he’s drawing now? Is he someone the team can flip at the deadline? He’s a restricted free agent this summer.
Nic Roy: Probably better suited for the fourth-line centre role he largely had in Vegas and not the third-line gig he’s had with the Leafs. Roy scored only his fifth goal all season over the weekend.
Troy Stecher: A really nice story and find for the Leafs. Still best suited to being a sixth or seventh defenceman on a good team. Is he flipped before March 6?
Anthony Stolarz: The four-year extension he got before the season looked risky at the time and like a mistake now amid another injury-plagued season.
Chris Tanev: A huge wild card heading into next season. Can he get back to what he was in his first year as a Leaf? Or was his scuffling start before the injuries the first sign of his decline?
John Tavares: No Leaf figures to benefit more from the break than Tavares, who has just seven goals and 17 points in his last 30 games.
Joseph Woll: He had a .907 save percentage in his first full season (2023-24), a .909 save percentage last season and a .907 save percentage so far this season. A solid tandem goaltender appears to be his destiny.
