Kawhi Leonard has always played it close to the vest, but when it comes to contract talks and off-court deals, things have gotten much louder. With eyes back on Leonard thanks to the NBA’s investigation into the Los Angeles Clippers, the stories swirling go way past the games. Now, fans are left wondering just how far those talks really went–and what the league will do next.
What Were Kawhi Leonard’s Eye-popping Demands to the Toronto Raptors in 2019 Free Agency?
Fresh off leading the Toronto Raptors to their first NBA title and grabbing the Finals MVP, Kawhi Leonard entered the 2019 offseason as the biggest name on the market. At just 28, he had the chance to stick with Toronto on a long-term deal, or head to California where both the Los Angeles Lakers and Los Angeles Clippers were interested.
However, according to The Star, Leonard’s camp didn’t hold back when telling the Raptors what it would take to keep him. The list was long and bold: a trade for Paul George, an extra $10 million in sponsorship income, partial ownership of the Toronto Maple Leafs, plus stakes in other businesses linked to Maple Leaf Sports & Entertainment.
Kawhi Leonard’s camp demands to the Toronto Raptors in 2019 free agency:
• A trade for Paul George
• An extra $10M in sponsorship income, bluntly stating: “We don’t want to do anything.”
• Partial ownership of the Toronto Maple Leafs
• Ownership stakes in other companies… pic.twitter.com/foMJ7AojzT
— NBACentral (@TheDunkCentral) September 9, 2025
The Raptors couldn’t meet those demands. Leonard ended up signing with the Clippers, who quickly traded for George–sending Shai Gilgeous-Alexander and a pile of draft picks to Oklahoma City in the process.
Meanwhile, the Raptors weren’t the only team hearing wild requests. Other reports say Leonard’s uncle, Dennis Robertson, put a different list in front of the Lakers. That included a private jet, a house, guaranteed sponsorship money, and partial team ownership. The league looked into it, but nothing came of those talks.
Now, years after those wild negotiations, Leonard finds himself tied to yet another controversy. According to reporting from Pablo Torre, Leonard signed a “$28 million no-show” endorsement deal with Aspiration, a financial firm backed by Clippers owner Steve Ballmer that is now bankrupt.
Plus, as reported by the Boston Sports Journal, Leonard allegedly received $20 million in company stock, bringing the total up to $48 million.
What’s the Latest on NBA Investigations into the Kawhi Leonard Scandal?
The salary cap accusations involving Leonard and the Clippers have pushed the NBA to launch a formal investigation. Ballmer has denied involvement, and the company’s co-founder has already pleaded guilty to fraud.
To show it means business, the NBA has tapped Wachtell, Lipton, Rosen and Katz–the same powerhouse law firm that oversaw cases against Donald Sterling and Robert Sarver –to dig into the facts.
On paper, the NBA’s rulebook makes salary cap cheating a risky game. If the Clippers are found guilty, the penalties could be stiff–a fine up to $7.5 million and the loss of draft picks. Leonard’s contract could be voided, as well as any extensions or changes tied to it.
Players can face fines of up to $3,50,000, and team officials could get suspended for a year. Any money or deals connected to violations might be canceled–unless Leonard can show he didn’t know what was happening.
Still, even with the league taking a hard look, ESPN’s Zach Lowe believes the punishment may not end up being major. Unless the investigation finds direct evidence linking the Clippers to the setup, Lowe expects something on the lighter side, like a second-round pick and a simple fine.
“I’m going to predict it finds no smoking gun,” Lowe said. “No email, no text, no nothing from anyone at the Clippers from Balmer on down to the equipment manager saying do this for this cap circumvention purposes.”
“And if that is in fact what they don’t find or what they find/don’t find, I’m going to predict that still because of the diligence and just appearance issues that you’re talking about, that they get a slap on the wrist,” Lowe continued. “Like a second-round pick and a million-dollar fine or something like that.”
Loaded new Zach Lowe Show! @McCannSportsLaw w/ expert legal analysis of Kawhi situation; reflecting on Melo/Dwight/Redeem Team w/ @HowardBeck; @AlanSiegelLA joins for some special Simpsons nostalgia:
Spotify: https://t.co/AFZGK8LW5N
YouTube: https://t.co/IFPBxKhnNj
— Zach Lowe (@ZachLowe_NBA) September 8, 2025
At the end of the day, Leonard’s history of eyebrow-raising free agency asks–now mixed with this $48 million endorsement mess–shows just how complicated things have gotten between him and the teams hoping to land him. No matter what the investigation turns up, it’s obvious that his negotiations off the court often bring as much drama as anything he does on it.
