Report: Kawhi Leonard’s 2019 Raptors demands included Maple Leafs ownership stake

Kawhi Leonard’s representation asked the Toronto Raptors in 2019 for an ownership stake in the NHL’s Toronto Maple Leafs and other unconventional compensation, according to a report that adds new detail to an ongoing NBA investigation into alleged “no‑show” endorsement deals.

The Toronto Star reported Tuesday that Leonard’s uncle and manager, Dennis Robertson, sought an ownership interest in Maple Leafs owner Maple Leaf Sports & Entertainment (MLSE) as part of free‑agency negotiations after the 2018‑19 season. The report said Robertson also requested stakes in outside companies with MLSE ties and pressed the Raptors to match at least $10 million a year in additional sponsorship income, while insisting the player would not be required to perform promotional duties.

The disclosures come as the NBA investigates whether Los Angeles Clippers owner Steve Ballmer and the franchise circumvented the salary cap by arranging a “no‑show” endorsement for Leonard with Aspiration, an environmental finance startup that was a Clippers sponsor. The alleged Aspiration deals were revealed in a lengthy investigation by journalist Pablo Torre and reported further last week.

Torre reported that Leonard signed a four‑year, $28 million endorsement agreement with Aspiration that required little or no promotional activity from the player. The report also said Aspiration co‑founder Joe Sanberg later pleaded guilty to two counts of wire fraud for allegedly defrauding investors and lenders of more than $248 million, a Justice Department announcement said in August. A separate report in the Boston Sports Journal said Leonard had a second "side deal" tied to Aspiration that involved roughly $20 million in company stock from Sanberg’s personal holdings.

The NBA has engaged the law firm Wachtell, Lipton, Rosen & Katz to investigate the allegations involving Leonard and the Clippers. Ballmer has denied any wrongdoing, telling ESPN last week that the Clippers did not violate salary‑cap rules.

According to the Toronto Star account, Leonard’s camp told the Raptors, “we don’t want to do anything,” in reference to promotional obligations tied to sponsorships. The team, the report said, pushed back that any outside deals would require appearances or participation in advertising shoots. Robertson reiterated to the Raptors that Leonard would not undertake promotional activities as part of proposed agreements.

The Raptors were Leonard’s team for the 2018‑19 season, when he led Toronto to its first NBA championship, before he signed with the Clippers in 2019. The reported 2019 negotiation posture described by the Toronto Star adds a new layer to questions about how elite players’ off‑court compensation and endorsement arrangements intersect with team salary‑cap accounting.

League officials have long scrutinized endorsement deals and outside income for potential impacts on team payroll calculations. The current investigation centers on whether any arrangements constituted sham endorsements or otherwise helped teams exceed the salary cap by shifting compensation outside standard player contracts.

MLSE, the parent company of the Raptors and the Maple Leafs, did not immediately respond to requests for comment. Representatives for Leonard and Robertson have previously defended legitimate business arrangements while disputing any suggestion of cap evasion. The Clippers have said they will cooperate with league inquiries.

The developments have drawn attention because of the scale and timing of the alleged deals, including the reported Aspiration agreements that came after Leonard signed a contract extension in August 2021. The NBA’s inquiry and related legal developments surrounding Sanberg’s guilty plea could affect league discipline or restructuring of past transactions, depending on investigators’ findings.

As the league’s review proceeds, the Toronto Star’s reporting underscores evolving tensions between player marketing, team revenue arrangements and salary‑cap integrity. The NBA and involved parties have not disclosed a timeline for the investigation’s completion or whether it will lead to penalties.