If Larry Tanenbaum sells his MLSE stake, what will he spend his $3 billion on? Experts offer two possibilities

Are you ready for some football?
No, not necessarily the NFL. But Toronto businessman Larry Tanenbaum could soon have more than $3 billion burning a hole in his pocket, and sports industry experts say he’s likely looking to buy a professional soccer team in England’s Premier League, or a chunk of an NFL franchise.
“He’s going to have a lot of money to spend. I don’t know what it will be net of taxes, but it will be a substantial amount,” said Richard Peddie, longtime sports executive and former CEO of Maple Leaf Sports & Entertainment.
In mid-September, Rogers Communications announced it had agreed to acquire the 37.5 per cent stake of MLSE currently owned by BCE, for $4.7 billion. If that deal is approved by regulators and league officials at the NHL, NBA, MLS and CFL, it would give Rogers a total of 75 per cent in MLSE, which owns the Toronto Maple Leafs, the NBA’s Raptors, MLS’s Toronto FC, and the CFL’s Argonauts, as well as the AHL’s Toronto Marlies.
The other 25 per cent of MLSE is owned by Tanenbaum-controlled Kilmer Sports Ventures. (The Ontario Municipal Employees Retirement System, in turn, owns 25 per cent of Kilmer Sports.) Kilmer has the right to sell its stake in MLSE to Rogers by July 2026, but stock analysts who cover Rogers think the telecommunications giant might look at buying Kilmer out sooner than that. At the same overall company value as the BCE-Rogers deal, Kilmer’s stake would be worth roughly $3.1 billion.
Both Kilmer and Rogers declined to comment for this article.
While Peddie doesn’t know exactly what Tanenbaum intends to do with the potential windfall, he said the real estate industry mogul would be welcomed by other NFL or Premier League owners, because of his long track record with MLSE and strong relationships with league officials in the NBA, NHL and MLS.
“The man has got an outstanding reputation. He’s liked by three leagues. He’s a great guy, and he’s got a track record,” said Peddie. Tanenbaum isn’t, in other words, just some guy with a big bank balance, said Peddie. “He gets the sports, and that’s important. Some of these rookies come in, they’ve got billions, but then they fall flat on their face because they do stuff that just doesn’t make sense.”
While Kilmer has already announced it’s bringing a WNBA expansion franchise to Toronto in 2026, there would still be plenty of ammunition left in Tanenbaum’s financial arsenal, Peddie said. Kilmer is spending roughly $150 million (U.S.) bringing the WNBA to town, including a $50-million expansion fee, as well as building a new practice facility.
In March, Tanenbaum might have tipped his hand on his next step when he hired veteran soccer executive Ivan Gazidis as president of Kilmer Sports.
In June, Kilmer announced it had bought AS St-Étienne, a team in the second tier of French professional soccer. The deal was announced the day after St. St-Étienne clinched a spot in the top division Ligue 1 for next season. Kilmer also announced that Gazidis would serve as president of St-Étienne. The price Kilmer paid wasn’t announced.
As the former CEO of English Premier League giants Arsenal, Gazidis is already a well-known figure in the European and U.K. soccer industry, said Kieran Maguire, a soccer finance specialist at the University of Liverpool’s Centre for Sports Business, and author of “The Price of Football.”
And having an experienced, respected CEO is the most important step in operating a Premier League club, said Maguire.
“Having somebody that knows the pitfalls of the industry, knows where the bodies tend to lie, in my view, is worth their weight in gold,” said Maguire. “I’d always be willing to pay top dollar for a chief executive who you can trust, as an owner. And there aren’t that many people you can trust in football.”
While only one team in the Premier League turned an operating profit last year, Maguire said there are other reasons potential owners look at buying in, including growth of franchise values and, well, ego.
“You can buy some fine art and stick it on your wall, but how many people are going to come and see it? … You buy a Premier League football club? The Premier League is broadcast to 197 countries each week,” said Maguire, who also suggested some potential buyers see the success of American investors Fenway Sports Group and hope to duplicate it.
“There is a view that it’s undervalued, and if you buy in at right time, and buy the right club, you can do a fantastic deal,” said Maguire, noting that Fenway bought Liverpool Football Club for $400 million (U.S.) in 2009, then sold a 10 per cent stake in the club for the same price in 2022.
“So they own 90 per cent of Liverpool Football Club for nothing,” said Maguire. Nothing, that is, except hundreds of millions in salaries and other expenses every season. “The two best days are the day you buy it and the day you sell it, with a football club. And the bits in between, you’re just losing money left, right and centre.”
Maguire said there are several Premier League clubs on the market at any given time, and that some could be purchased for a fraction of the price of an NFL franchise.
“If I were a North American investor, I’d probably be looking at somewhere in London, because London’s really a separate market to the rest of the U.K.,” said Maguire, who pointed to Tottenham Hotspur, Crystal Palace and West Ham United as potential London-based targets for Tanenbaum. Of those three, Tottenham would be the priciest, at anywhere from $4.5 to $5.4 billion (Canadian), while West Ham could go for $1.4 billion.
NFL franchises, however, range anywhere from $5 billion (U.S.) to over $10 billion. And bidding wars have been known to happen, said David Carter, a professor at the University of Southern California’s Marshall School of Business, and the founder of the Sports Business Group, a sports business consultancy.
“Nobody knows what a franchise is ultimately going to go for. It’s a function of how many franchises or partial shares are available at any given time,” said Carter, who poured cold water on the hopes of Toronto football fans hoping they’d get to see an NFL team locally.
Three-quarters of NFL teams have to approve any ownership change, or the potential granting of an expansion franchise. Expansion means the owners would have to divvy up league revenues even further, and the league might already have enough fans in Canada that putting a team here wouldn’t result in any more attention, Carter said. As for relocation, there really aren’t any teams with a pressing need, he added. There’d also be potential opposition from the Buffalo Bills and owner Terry Pegula to a team in Toronto.
“You’ve got to have the votes to move forward and you could probably suggest that the Pegula family might be one of those that will … not vote affirmatively,” said Carter.
Ultimately though, said Peddie, buying part of an NFL team could still be tempting for Tanenbaum.
“It’s closer to home. He kicked the tires with Buffalo. He knows a lot of the owners. It’s a well-run league. He hired someone who knows soccer. But what’s in your backyard might be a little more familiar,” said Peddie, adding that the salary and transfer spending of some teams in English and European soccer might also put Tanenbaum off.
“He’s a sports fan but still a businessman,” said Peddie.
This article was edited from a previous version to include additional information about Kilmer Sports and its purchase of AS St-Étienne, a second tier French professional soccer team.