The Maple Leafs should be looking for a new president. Here's what they need

New York Times

27-05-2025

When Maple Leaf Sports & Entertainment hired Keith Pelley to be the organization's new CEO and president last year, he had a big decision on his plate with the group's flagship team.
The Toronto Maple Leafs were about to have yet another postseason disappointment — a first-round loss to the Boston Bruins — and the fan base was clearly getting restless. The question for Pelley was, with the head coach soon to be fired and a new one with a Stanley Cup pedigree brought in, was that going to be enough?
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With little time to bring in a high-profile new hire at the top, the options Pelley considered were threefold:
1. He could stick with the status quo, having then-president Brendan Shanahan run out the final year of his contract in 2024-25 and giving GM Brad Treliving a second season to prove his worth.
2. He could fire Shanahan, after 10 years on the job, and promote Treliving to president with one of his many underlings moving into the GM chair.
3. He could fire Shanahan and take a more hands-on approach, with Treliving reporting directly to him.
The problem for Pelley was that the timeline was condensed. He started the job on April 2, 2024. The Leafs were eliminated a month later on May 4. And after years working overseas as CEO of the PGA European Tour, he'd hardly gotten his feet wet in figuring out his new role managing one of the biggest sports organizations in the world.
Plus, MLSE ownership is in the midst of a massive transition, with Rogers set to become the sole owner after years with a three-headed monster in charge.
There was a lot going on in Toronto. There still is, a year later.
As we now know, Pelley punted on the decision, going with option one. A year later, with more information — some of it gleaned by sitting in the stands during an ugly Game 7 loss to the Florida Panthers, when fans booed and threw jerseys on the ice — he went with option three, letting Shanahan go last week.
Far more than last season, Pelley is now on the clock. And there's no buffer between Treliving and the big boss, whose stated goal is finally putting the Leafs 'on the pathway to winning the Stanley Cup.'
I saw some interpret Pelley's press conference on Friday as a significant endorsement of the current regime, but I don't think that's exactly right. Yes, if the Leafs are a huge success over the next six to 12 months, there's a world where Treliving gets a promotion and can pick his own GM and get some job security.
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But Treliving only has two years remaining on his contract and was hastily handpicked under strange circumstances in 2023 by the man just shown the door. The GM is believed to have less term on his deal than coach Craig Berube right now — an unusual situation — and he has to be feeling the pressure here with how complex the Leafs offseason is going to be.
Press conference platitudes or not, there's a very plausible scenario where Pelley wants to put his stamp on the team in 2026 with his own hire atop the Leafs. Someone with a deeper pedigree. Someone who has built a championship organization and who can clean up and bolster what's become a cluttered management group.
I'm not saying that's going to happen for certain at this point, but it would make a lot of sense. I know there's been a lot of talk lately about streamlining and efficiency around MLSE, and more cuts are definitely coming, but dropping Shanahan freed up more than $5 million in the annual budget.
With the Leafs' contention window open — potentially only for another two or three more seasons — it hardly makes sense for the richest franchise in the NHL to skimp on hockey operations talent, especially at the top.
What moving on from Shanahan allows Pelley to do is begin a search for an upgrade. Start doing some due diligence on which of the best management talents might be available, looking at the most successful franchises in the league. Rather than trying to mimic the Panthers' success — or the Lightning's, Avalanche's or Golden Knights' — by acquiring their depth players or overpaying their few stars who get to free agency, why not go to the top of the organization and see if they can pluck out the mastermind behind that rise?
St. Louis Blues president Doug Armstrong is one name that has long been connected to Toronto, although it appears that may be a pipe dream given his contractual situation there. But there are other strong candidates around the league, including among the four teams still playing right now.
MLSE should have the resources to offer a team president the highest hockey operations salary in the league. They're already paying Raptors president Masai Ujiri $15 million a season, which would blow every NHL exec salary around the league out of the water. If you can identify the right candidate, why not get similarly aggressive with the Leafs?
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Even with the usual playoff disappointments, the Leafs' annual revenues are approaching $350 million (U.S.), the highest in the league, giving them a considerable advantage (and profit margin) in a league with a $95.5 million salary cap.
Compare that to the Raptors, who bring in a similar figure thanks to the NBA's lucrative TV package but have a dramatically higher payroll than the NHL allows, including individual players making nearly $40 million a season.
Streamlining the Leafs front office is fine if what you're looking for is a better decision-making process and not to simply save money. That kind of penny-pinching shouldn't be on the agenda here, not with executive salaries one key area where MLSE can outspend the competition.
Maybe at the end of the day, Pelley decides the brain trust he wants running the Leafs is still Treliving supported by his handpicked lieutenants, Derek Clancey and Shane Doan. Treliving had a stronger second season in Toronto than his first, with key additions like Anthony Stolarz and Chris Tanev helping lead to a six-point improvement in the standings. But his tenure in Calgary was underwhelming at best, and even with the Leafs there have been contractual misfires (John Klingberg, Jani Hakanpää, David Kämpf, Ryan Reaves, Max Domi etc.), some of which need to be cleaned up this offseason.
We should get a pretty good idea of this front office's effectiveness over the next five weeks, which might be some of the most challenging this franchise has faced in quite some time given the likely exit of Mitch Marner in free agency.
If they fall short here in this pivotal window, Pelley needs to start exploring his options — if he isn't already.
(Photo of Keith Pelley and Craig Berube: R.J. Johnston / Toronto Star via Getty Images)