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Larry Tanenbaum controlled the remaining 25 per cent during Leiweke’s tenure — a number that’s now down to 20 per cent after Tanenbaum’s 2023 indirect sale of five per cent to a pension fund. For Leiweke, navigating the boardroom triumvirate added untold “tension� and “stress� to a CEO’s day.

“You had to balance out Bell and Rogers. And remember — Bell and Rogers got up every morning trying to figure out how to kill each other. You had to balance out Larry. And I had a good relationship with Larry, but we had our moments,� said Leiweke, now chair and CEO of the Oak View Group. “So it was an interesting board.�

That’s not to say Leiweke’s job was untenable; he is still considered a civic hero of sorts for a successful recruitment of Masai Ujiri that led to a Raptors championship in 2019, all with MLSE’s three-pronged ownership in charge. But on Wednesday, Leiweke sounded somewhat envious of current MLSE CEO Keith Pelley for the opportunity presented by the newly streamlined reality of MLSE ownership

“This is fantastic for Keith,� Leiweke said. “Now you have one majority owner, and that allows you to have a sole vision, a sole purpose, a sole decision … I think this will be highly predictable, less drama. And Keith as the CEO is now in an amazing position to spend the majority of his time implementing a plan to win and to grow, and less time on votes, drama, politics and getting everyone to sign off on decisions.�

That’s one way of looking at the new monopoly on ÎÚÑ»´«Ã½ sports. Certainly there are less charitable views. Edward Rogers’ run as solo owner of the Jays, after all, has largely fallen short of expectations beyond spectacular stadium renovations.

And Edward is so relatively anonymous, and so untested in public, that the corporation he controls didn’t hold a press conference to hail his arrival as the reigning monarch of ÎÚÑ»´«Ã½ sports. Instead, he was introduced in a stilted, scripted, state-TV production that ran on a loop on the Sportsnet website. Poor Ron MacLean did about as well as you could do interviewing the folks who employ you. Edward managed to expel a boilerplate commitment to winning, but he didn’t exactly exude swashbuckling, Wolf of Bay Street charm. Let’s just say Rogers CEO Tony Staffieri carried an awful lot of water for his boss. MacLean could have lobbed a thousand more softballs in Edward’s direction, but there was no rhetorical home run in the offing.

Which would have surprised exactly nobody who knows Edward Rogers.

“You won’t see Edward out front. He’s not that kind of guy; he’s never going to be that kind of guy,� Leiweke said.

As Brian Cooper, the chair of Canada Basketball and MKTG Canada, was saying on Wednesday: “Edward is a passive owner, but better that than Jim Dolan (the bombastic and frequently cringe-inducing owner of the New York Knicks and Rangers).�

The corporate facelessness of Rogers and Bell is at least part of the reason why Tanenbaum, under the ownership structure that existed before Wednesday, was the human face of MLSE’s franchises. When players on the Leafs or Raptors made mention of ownership, they invariably mentioned Tanenbaum, never Rogers and Bell. Though Tanenbaum has never been an attention-seeking presence, he is immensely well liked in NHL and NBA circles. He counts commissioners Bettman and Silver as confidants. He was recently re-elected as chair of the NBA board of governors. And that’s why, for those who have appreciated Tanenbaum’s contributions to MLSE, Wednesday was a lamentable day.

Tanenbaum, who found a frequent boardroom ally in Bell’s representatives, a relationship that gave him considerable sway, is no ally of Edward Rogers. Insiders indicated Tanenbaum was essentially blindsided by the seismic news.

Not that change wasn’t in the offing. MLSE’s current shareholder agreement includes a sunset clause that will give Rogers the option to buy Tanenbaum’s shares as soon as the summer of 2026, although on Wednesday sources with knowledge of the organization were speculating that the two parties may come to a parting before then. Not that it’s simple. MLSE is now valued at $12.5 billion. The Rogers deal gobbled up 75 per cent. Buying out the remaining 25 per cent would require another $3 billion-plus — not exactly pocket change.

Still, as a release from Rogers indicated, the deal was financed with the help of private investment, a growing trend in pro sports. As Leiweke said Wednesday: “I’m at a CEO conference today. I’m sitting across from five people that would write that cheque tomorrow. There will be no end of people who’ll invest (in pro sports) … It’s a hell of an investment. There’s nothing like it, and it’s going to continue to grow, and it’s going to continue to prosper.�

If a new faceless pile of money just bought a big chunk of ÎÚÑ»´«Ã½â€™s most beloved sports teams, Tanenbaum, whose Kilmer Sports Group is bringing a WNBA team to ÎÚÑ»´«Ã½ that will begin play in 2026, has been a boots-on-the-ground, face-in-the-dressing-room staple of the ÎÚÑ»´«Ã½ sports scene going back to the mid-1990s, when he bought 25 per cent of the Leafs. So as much as Wednesday marked the beginning of a new era, it also signalled the coming end of a widely admired one.

“If and when Edward says goodbye to Larry, he is losing so much goodwill and so much expertise,� Richard Peddie, the former MLSE CEO, said in an interview. “That’s difficult to replace.�

Maybe so. But as Peddie or any other veteran executive will tell you, the moneyed allure of pro sports makes it, above all things, a cutthroat business. And in ÎÚÑ»´«Ã½ now, suddenly one man holds the only knife in town.

“Give Larry his credit. He built a culture there and he wanted to win. But you evolve as an organization, and this is the next step in that process for MLSE,� Leiweke said. “If I’m a Raptors fan or a TFC fan or a Maple Leafs fan, it’s a good day … If you look around sports, the most successful organizations, they speak with one voice. When it’s all said and done, this is the right outcome. This is a good outcome. This is what the outcome should be.

“You look at the Jays, the Leafs, the Raptors, TFC — that is the crown jewel of sports. I think it’s the most important sports organization in the world. I firmly believe that.�