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Kawhi Leonard allegations bring echoes of 2019 for Raptors fans

September 12, 2025
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TORONTO — The south end of the Thomas and Mack Center at Las Vegas Summer League is where the NBA goes to gossip every summer. There’s a school’s-out feeling to the early days of what is essentially a convention for NBA players, executives, media and league officials.

With the three major events on the league schedule — the NBA Finals, NBA Draft and the opening of free agency wrapped up in the space of a couple of weeks — there is a collective exhale, and those with stories to tell gather at the south baseline, near the locker rooms and exchange notes. 

It was in that context in the summer of 2019 that I first heard about some of the behind-the-scenes maneuvering that former Raptor and current Clippers star Kawhi Leonard’s camp — which boils down to his uncle, Dennis Robertson (who acts as the star forward’s agent, even if his certified agent, Mitch Frankel, is the person of record for league purposes) — was doing to leverage Leonard’s superstar talent for as much financial gain as possible. 

The pattern of asks are now well known: an ownership stake, guaranteed endorsement income, use of a private plane, the list goes on. I can’t claim the specificity that Bruce Arthur of the Toronto Star had in a recent column, where he reported Robertson asked for $10 million annually in “no-show” endorsement deals and an ownership stake in the Toronto Maple Leafs — this, above and beyond the expectation that changes would be made to the championship roster — but the broad strokes were known then, and given what we’ve learned from a pair of explosive podcasts from journalist Pablo Torre that has lifted the lid on one of the most far-reaching scandals in recent NBA history (business affairs division, at least), the details seem entirely plausible. 

Torre’s reporting has focused primarily on the events surrounding Leonard signing a four-year, $176-million contract extension with the Clippers in 2021. The gist: Torre has shown with an impressive amount of evidence that there are, at the very least, some extraordinary coincidences that could lead to the conclusion that Clippers owner Steve Ballmer allegedly used his business relationship with Aspiration Partners, a now-bankrupt environmental bank that has had two co-founders since pleading guilty to a $248-million fraud scheme, to funnel approximately $50 million to Leonard and his camp in an elaborate plan to circumvent the NBA’s salary cap. 

For Toronto Raptors fans, there are echoes of 2019 to the entire affair, given they watched Leonard sign with the Clippers as a free agent for three years and $104 million when the Raptors were prepared to sign him for five years and $190 million. There were reports then — some of which were based on the Summer League whispers at the Thomas and Mack Center — that Robertson was trying to shake down teams in free agency. But at the moment, the asks were so outlandish they seemed almost laughable. 

“Uncle Dennis was always knocking on doors and asking for stuff,” one person with knowledge of the Raptors negotiations told me. “He wasn’t shy and would try to talk to everyone. But no one was really taking him seriously. It almost seemed like a joke.”

Multiple sources have told me that the Raptors — who were led in the contract talks by then-president Masai Ujiri, current general manager Bobby Webster and minority owner Larry Tanenbaum — dismissed Robertson’s requests outright, understanding that they represented a clear and obvious case of salary-cap circumvention. 

“It was, like, why would you even suggest that?” said one source. 

The tone changed when Leonard ended up signing with Clippers and they were among teams that alerted the league office to the requests Robertson was making on behalf of Leonard. The 2019 NBA Finals MVP signing with the Clippers came on the heels of a season-long public courtship by the Los Angeles club, with Clippers officials in attendance at virtually every Raptors home game to prove their interest in and commitment to the then-pending free agent. 

A source close to the situation this week said that at the time, the Raptors were convinced the Clippers had bent to at least some of Robertson’s requests, in some shape or form: stock options or investments in companies that Ballmer, the NBA’s richest owner and one of the world’s wealthiest people, had relationships with; perhaps some kind of phony endorsement deal that has never been made public (some of the documentation that Torre has relied on became available when Aspiration filed for bankruptcy).

Now, they’re surer than ever that something fishy went down in 2019. 

The NBA did investigate allegations of tampering and salary-cap circumvention then but found no evidence of wrongdoing, but it will be fascinating to see if it digs a little deeper this time around, given what allegedly seems to be a pattern of behaviour by Robertson and Leonard and Ballmer. 

If the allegations levelled by Torre — and the latest, with documentation that late in 2022 Clippers minority owner and long-time Ballmer business partner Dennis Wong sent a one-time, $1.99-million payment to a then-financially distressed Aspiration just days before Leonard was due a $1.75-million installment on his “no-show” endorsement deal with the company, seems like a difficult coincidence to simply explain away. 

The joke is clearly over, and the Raptors may have the last laugh, of a sort. But losing out on the chance to defend their 2019 championship with Leonard in the lineup will be a sore spot for Raptors fans for generations. 

— There is a certain irony that for Tanenbaum, one of his last acts as chairman of the NBA’s Board of Governors will be helping decide the fate of Ballmer and the Clippers. The long-time Raptors owner is — by the terms of the ownership agreement — obligated to begin the process of selling his remaining 20 per cent stake in MLSE to Rogers Communications (which owns Sportsnet, and a 75 per cent share of MLSE) by July 7, 2026. 

There are rumblings that the sale of Tanenbaum’s interest could come sooner, but in the meantime, it will be Tanenbaum, who has led the NBA BoG since 2017, who will have a front-row seat into the investigation into the Clippers owner being conducted by a New York law firm at the behest of NBA commissioner Adam Silver. And it will be Tanenbaum who will presumably have a voice in what — if any — sanctions are levelled against Ballmer and the Clippers. 

The penalties can include steep fines, the forfeiture of future first-round draft picks and even voiding Leonard’s contract, though how that might work is anyone’s guess, given the Clippers star has signed a three-year, $150-million extension with the Los Angeles team subsequent to the deal he signed in 2021, the circumstances of which have been the subject of Torre’s reporting.

But the appetite around the league for significant sanctions is strong, with one league insider explaining to me that teams risk tampering charges because the penalties aren’t that severe: “It’s like, ‘it’s worth risking a second-round pick if we get the guy.’”

But if the NBA wants its carefully negotiated collective bargaining agreement between the players union and owners to serve its function for creating level playing field and ordered competition, Ballmer and the Clippers will need to be hit hard.

“Otherwise, it will be chaos,” the insider said. “If he gets away with this, what will stop anyone else from doing the same thing?” 

Having been the victim of the Clippers alleged subterfuge, chances are Tanenbaum will have some pointed questions as the league conducts its investigation and might be more than willing to drop the hammer if it comes to that. 

— A palate cleanser: All the Raptors have been back in Toronto this week, well in advance of the official opening of training camp on Sept. 29. Almost overnight, the OVO Athletic Centre went from having a quiet summer-campus vibe to all-day bustle with coaches, training staff, players and team staff back in their offices and on the floor, with the Raptors conducting individual workouts and scrimmages. 

The exception is free-agent signee Sandro Mamukelashvili, who helped lead Georgia to a surprising run to the quarterfinals at EuroBasket. The former Spur saved his best for last in a strong overall showing at the tournament, scoring 22 points on 8-of-15 shooting (2-of-5 from three) in a 39-minute outing in a loss to equally surprising Finland, which will play Germany in the semifinals Friday. Greece and Turkey are the other semi-finalists. 

— Palate cleanser II: I was able to catch up with former Raptor and current Indiana Pacers star Pascal Siakam recently. It was a short off-season for Siakam, who helped Indiana to a valiant run to the NBA Finals before losing in seven games to the heavily favoured Oklahoma City Thunder in late June, but Siakam still found the time to build on the work his charitable foundation — PS43 — started north of the border during his seven-year tenure with the Raptors and he’s continued even since he was traded to Indiana in January 2024. 

On Sept. 3, Siakam was in New Brunswick, making an appearance in rural Gagetown to meet with kids who were participants in his long-running Data Dunkers program, where students from Grade 5-12 develop their skills in data science through basketball statistics. Later, he was on campus at the University of New Brunswick in Fredericton to accept an honorary degree from the school in recognition of his charitable work and the scholarship program for Cameroonian students to attend UNB he’s been supporting. 

“You want to help kids all over the world, but if you have an opportunity to help someone from where you’re from, I think it makes it even, even more special,” Siakam told me. “And when we had an opportunity to create a scholarship with the University of New Brunswick, I mean, it was, it was so amazing. And we have a couple of kids (from Cameroon) already going through school and doing things that, without our help, they probably wouldn’t be able to do is just super awesome.” 

And as for Siakam’s ongoing Canadian connection? “It’s always amazing, like, the admiration and the love, like everywhere that I’ve been in Canada has always been good, you know?” said Siakam, whose long-term goal with his foundation is to build a school in his native Cameroon. 

“Canada feels like home for me because coming in as a young man, I learned literally everything here. I learned how to drive in Canada, and with us winning a championship and all the amazing things were able to do here, the bond will be there forever, I think.”



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Tags: allegationsbringechoesFansKawhiLeonardRaptors
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