‘We’re definitely going to grow’
Pelley thinks big as he steps into ‘dream’ CEO job
Long-time employees knew something had changed around Maple Leaf Sports & Entertainment this past week when they walked into a staff meeting and saw who’d shown up.
There, among a high-spirited gathering at Real Sports Restaurant populated by about 700 staff members, were some of the organization’s highest-profile executives. Maple Leafs president Brendan Shanahan was on hand. Ditto Raptors boss Masai Ujiri, who’d flown in especially from New York. Not since the days of long-departed CEO Tim Leiweke had those two been bankable fixtures at such events. But it would have amounted to an act of career sabotage to miss this meeting, seeing as it coincided with the first days on the job of newly inserted CEO Keith Pelley. Pelley, the 60-yearold Toronto-born executive who most recently ran golf’s DP World Tour, figures to have a lot to say about who leads the Maple Leafs and Raptors in the years to come.
And considering the state of the company’s two biggest franchises — Ujiri’s Raptors are in the early stages of a rebuild while Shanahan’s Leafs have managed one playoff series win during his 10-year tenure — let’s just say both Ujiri and Shanahan would be wise to use whatever means necessary to make Pelley a friend.
“(The meeting) was incredible,” Pelley was saying this past week. “Brendan and Masai were the last two to leave … I’ve heard (Shanahan and Ujiri) don’t come to a lot of (MLSE) functions. They’re now going to be part of all of our executive team meetings. Connecting the teams is something I think is really critical.”
Connecting MLSE’s teams, expanding MLSE globally, the importance of employing executives who know how to win — they were all recurring themes in a wide-ranging interview with Pelley. But let’s start with how Pelley got here. As recently as a few months ago, Pelley assumed his London-based post as head of the DP World Tour would usher him into retirement. That’s a big part of the reason why, just recently, he and his family were sworn in as British citizens.
Pelley said he and his wife, Joan, will always keep a residence in the London area, and dual Canadian-British citizenship will give their
two children “optionality” going forward.
When Pelley left his job at Rogers Media in 2015 for the golf life, he said he told Edward Rogers, the company’s chair and an MLSE board member, that he would only be tempted to return to Toronto by one of two job opportunities. One was CEO of a Toronto NFL team.
“Which does not exist,” Pelley said with a laugh.
The other: CEO of MLSE. If he had to leave family behind in London to take the gig — well, it was a family connection that drew him to what he has called a “dream job.” Pelley’s late father, Walter, was a “hard-core Leaf fan,” to the point that he took considerable pride in the origins of the family automobile. The big green boat of a Lincoln Continental, where Keith Pelley spent a good chunk of his childhood, was previously owned by Börje Salming.
“My dad told everybody, ‘I bought Börje Salming’s car,’ ” Pelley said. “True story.”
When Pelley attended last Monday’s Leafs-Panthers game at Scotiabank Arena, his first as CEO, he pressed a photograph of his dad up against the rinkside glass, as if to share the view with the man who took him to games at Maple Leaf Gardens.
“I said, ‘This is a little closer than we used to sit, Dad,’ ” Pelley said. “You know, I took this job partially because of my dad.”
He took the job, too, because the current trend among the world’s top sports organizations is global growth. And “globality,” Pelley will tell you, is the only way forward. Fenway Sports Group, for instance, has its roots in Boston, where it owns baseball’s Red Sox. But it now includes among its portfolio Liverpool FC of the English Premier League, the Pittsburgh Penguins of the NHL and a recent $3-billion (U.S.) partnership with the PGA Tour. One assumes Pelley, a part owner in second-tier British soccer club Birmingham City who spent the past handful of years rubbing shoulders with some of the richest sports people on the planet as golf was lit ablaze by an infusion of Saudi billions, has an idea or two about where MLSE might plant flags beyond the GTA.
“We’re definitely going to grow,” Pelley said. “What exactly that means, I’m still determining.”
Pelley said he recently lunched with Leiweke, and acknowledged the outsized legend of the former CEO credited with instilling a winning-is-everything ethos at the company — a top-down push that wasn’t in evidence during the tenure of Leiweke’s successor, the publicity-averse Michael Friisdahl, and Friisdahl’s interim replacement, Cynthia Devine, MLSE’s chief financial officer.
But if Pelley is possessed of Leiweke-esque energy and motivational acumen, he’s no carbon copy.
“I don’t have any (Stanley Cup) parade route planned,” Pelley said, referencing Leiweke’s infamous introductory claim. “I don’t have that, and I’m not making any promises or wild proclamations … Tim just explained to me what he did and how he did it. I was grateful for the time. Listen, I’ve got a lot to learn.”
Longtime observers of MLSE will tell you Pelley won’t be pleased to learn about the less-than-optimal boardroom dynamics, with ownership equals Bell and Rogers doubling as sworn corporate enemies and Larry Tanenbaum deep into the back nine of his run as the chair and face of ownership. Pelley said he’s unconcerned.
“The one thing I’m not worried about is ownership alignment,” Pelley said. “They have alignment on investment. They have alignment on being world class. And they have alignment on winning.”
Ah, winning — something the company’s teams have avoided since the Raptors’ epochal title run in 2019.
“Look, we’re rebuilding with the Raptors. We’re competing at the highest level with the Leafs and we need to win. I know that. Brendan knows that,” Pelley said.
There’s plenty more to be excited about, Pelley said. There’s an upcoming $350-million reimagination of Scotiabank Arena. There’s the six games Toronto will host at the 2026 FIFA World Cup, “an unbelievable opportunity” that’s possibly been underestimated locally, Pelley said.
All that, and “we’re going to have a lot of fun,” Pelley said. Upon arrival this past week Pelley, a consummate jock who played soccer and football at Martingrove Collegiate Institute and varsity hockey at the post-secondary institution formerly known as Ryerson University, talked of potentially reviving the MLSE staff shinny game, or perhaps a regular pickup basketball run.
“If we do that, we’ll have to have a height restriction: no one over six feet,” deadpanned Pelley. Not to say the new CEO is short. But he doesn’t exactly tower over Argos president Pinball Clemons, a wellestablished five-foot-six. Of course, a six-foot-and-under pickup game would exclude Shanahan and Ujiri, both 6-3. They’ll no doubt have plenty of other opportunities to make Pelley a friend. But the way Pelley was talking, winning might be the only way to ensure he stays their boss.
“It’s a privilege to run this organization. It’s a privilege to have this responsibility. And that’s what I think it is — I think it’s a responsibility, I truly do,” Pelley said. “I think it’s a responsibility to the city. And it’s also something I need to deliver on, and I need to be held accountable for. And I know there’s one thing I’ll be held accountable for, and that’s winning in every possible way. And I think that’s fair. And if I can’t deliver, I’ll be back where it’s raining, not snowing.”