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The Raptors' home opener against Milwaukee on Friday was moved from 7:30 p.m. to 6:30, and the Maple Leafs' game against Buffalo on Saturday was moved from 7 p.m. to 5.
As president and CEO of MLSE, a role he assumed in April 2024, Keith Pelley is responsible for establishing a winning culture at the top of an empire that includes the NHL’s Toronto Maple Leafs, NBA’s Toronto Raptors, MLS’s Toronto FC and CFL’s Toronto Argonauts. Put simply, he’s trying to recreate the spirit he found in the European team room at the Ryder Cup. There’s no mystery for Pelley in how they’ve managed to win five of the past seven matches despite being perennial underdogs against the powerhouse Americans — a place Europe finds itself again entering this weekend’s event at Bethpage Black.
What Pelley hopes to recreate, though, is an environment where the Leafs and Raptors can tap into the kind of “magic” that Europe’s Ryder Cup team seems to find when the competition is at its fiercest. “I look at the Raptors now, I look at the Leafs, culture and chemistry still (matters),” he said. “You can’t put a number on it, but it makes a difference. You get chemistry and culture and momentum, and that can take you to spots that you didn’t think you could get to.”
Multiple sources with knowledge of Toronto’s contract negotiations with Kawhi Leonard in 2019 told the Star that Leonard’s uncle and representative, Dennis Robertson, made demands that line up almost perfectly with what Leonard reportedly got from Aspiration. According to those sources, who were granted anonymity in order to speak freely about the negotiations, Robertson’s list was long, and absurd. It included a trade for George, which featured an exorbitant price tag. It included a slice of ownership of the Toronto Maple Leafs, which Robertson was told was impossible.
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Two details stand out, in retrospect. One, Robertson asked for ownership stakes in outside companies: not just the Leafs, which he seemed to believe was separate, but with other companies with whom MLSE had a relationship. And two, the Raptors were told they needed to match at least $10 million per year in extra sponsorship income. Teams are allowed to introduce players to team sponsors; teams cannot negotiate deals, and MLSE was aware of that fact.
Sources in Toronto say, in one meeting, Uncle Dennis asked for an ownership stake in the Toronto Maple Leafs, because that way he wasn’t asking for a piece of the Raptors. It was politely explained to him that both teams were owned by the same company, and that the request was impossible.
Raptors general manager Bobby Webster and assistant GM Dan Tolzman recently received contract extensions that were not announce until Friday and now assume day-to-day control of basketball operations while MLSE conducts a search for Ujiri's replacement. We'll have to see to what lengths MLSE is prepared to go in terms of hiring a successor when the significant annual salaries held by Ujiri and former Maple Leafs president Brendan Shanahan are believed to have factored in strongly to the dismissals of both lead executives in the space of the past five weeks.
Michael Grange: Rogers has received all league approvals — NBA, NHL, MLS and CFL — to take 75% ownership of MLSE and Raptors, Leafs, TFC and Argos etc. Last step for deal to close is approval from CRTC on indirect ownership of NBA Canada.
“Two years ago, you weren’t really thinking about this,” said Rob Tilliss, chief executive officer of Inner Circle Sports, a boutique investment bank that works within the sports and entertainment spheres. The company has worked with several professional sports teams, including the Ottawa Senators and Montreal Canadiens. “Now (as a business executive with a Canadian team) you’re thinking about hedging strategies. You’re thinking about how much of my revenue is contractual season tickets versus day-of-game tickets. “As the Canadian dollar declines, you have to adjust your budget. They’re all probably reassessing their budgets for the next year or two.” This might be a particular issue for the Toronto Raptors, the lone Canadian NBA team. Rogers’ purchase of Bell’s shares in Maple Leaf Sports and Entertainment, the group that owns the Raptors, Maple Leafs, Toronto FC, among other teams and facilities, is expected to close in the middle of this year. That deal will give Rogers 75 percent control of MLSE. Rogers also owns the Toronto Blue Jays, although not under the MLSE umbrella. Rogers is a publicly traded company, and its stock price has fallen from more than $50 in December, to currently being under $40. Raptors president Masai Ujiri has never complained about MLSE’s financial support for the team, but these are unfamiliar, if not unprecedented, times.
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Rogers signed a deal to purchase Bell’s 37.5 percent ownership stake in Maple Leaf Sports & Entertainment (MLSE), which owns the Toronto Maple Leafs and Toronto Raptors, for $4.7 billion Canadian dollars ($3.46 billion USD), making it the majority owner of the sports entertainment company.
MLSE’s primary assets are the NBA’s Toronto Raptors, NHL’s Toronto Maple Leafs, MLS’ Toronto FC, CFL’s Toronto Argonauts and their respective venues. Tanenbaum owns 25% of MLSE; it is unclear how much of his stake he is selling.
The league announced a new team in the Bay Area on Thursday, with The Athletic reporting the league is also strongly considering awarding an expansion team to Portland. The Toronto Star reported that, among other factors, Edward Rogers’ poor relationship with Ujiri played a part in MLSE’s decision. Rogers is the chairman of Rogers Communications, one of the three major stakeholders in MLSE, along with Rogers’ main telecom competitor in Canada, Bell, and construction magnate Larry Tanenbaum. The latter is the chairman of MLSE’s board of directors, but reports surfaced in the summer that Tanenbaum is close to selling a portion of his stake to OMERS — the Ontario Municipal Employees Retirement System. (Bell and Rogers have reportedly expressed concern about Tanenbaum selling a portion of his share.) Tanenbaum headed up a group that originally tried to bring an expansion NBA team to Toronto in the early ’90s, eventually working his way to the Raptors when the Maple Leafs purchased the basketball team and the arena then known as Air Canada Centre in 1998.
Maple Leafs Sports and Entertainment — owner of the Toronto Maple Leafs and the Toronto Raptors, among other pro sports franchises — has been named one of Toronto's largest property tax debtors, with an unpaid bill of roughly $1.18 million, dating back to the 2019 tax year.