When Kawhi Leonard was on the verge of becoming the NBA’s most sought-after free agent in the summer of 2019, his camp, led publicly by his uncle and longtime business manager, Dennis Robertson, presented a shopping list of demands that went far beyond the standard contract terms, sources told Baxter Holmes of ESPN.
Those requests, as reported, came during intense negotiations with multiple teams. Robertson reportedly made similar overtures to the Los Angeles Lakers and the Toronto Raptors before Leonard ultimately chose the Clippers.
According to those accounts, Robertson pressed potential suitors for more than just money and minutes: he allegedly sought part ownership stakes, a private plane, guaranteed off-court endorsement money, a house, and other bespoke perks that would give Leonard and his inner circle significant control and comfort off the court.
Some of the asks, such as equity stakes in outside companies or sponsorship guarantees that required little or no active work by Leonard, stretch well past what the collective bargaining agreement contemplates and would be highly unusual for typical player-team negotiations.
The Toronto Star has also reported that Robertson pursued ownership stakes and corporate sponsorship arrangements that would benefit Leonard without demanding corresponding performance or appearances.
The Clippers publicly declined to approve every item on that list.
But multiple people familiar with the talks told ESPN the organization agreed to several demands that shaped Leonard’s experience in Los Angeles: he was initially permitted to live in San Diego and commute by helicopter rather than relocate immediately to L.A.
The team consented to limited media obligations and scaled-back community appearances. The Clippers committed to marketing Leonard as an individual brand, and they allowed certain personnel from Leonard’s camp to be integrated into team operations.
Perhaps most consequential was the insistence on a near-complete media blackout: Robertson required strict protocol about public commentary on Leonard, essentially instructing team staff and spokespeople to say as little as possible about his health or availability. Rival coaches called that last demand unusual but not unheard-of for a superstar.
That same climate of personalized deals and opacity has heightened scrutiny in recent months as a separate controversy has swirled around Leonard’s off-court earnings. Podcast reporting and document disclosures have focused attention on a sizable endorsement relationship Leonard had with Aspiration, a now-bankrupt environmental and financial firm.
Pablo Torre’s reporting has alleged timing and transactional links between Aspiration payments to Leonard and investments from a Clippers minority owner. Hours after those allegations circulated, the NBA announced a formal investigation.
Soon afterward, reporting surfaced that Clippers minority owner Dennis J. Wong wired roughly $1.99 million into Aspiration in December 2022, just days before the company made a $1.75 million payment to Leonard, a transfer that raises questions about whether external endorsement money was being used to materially benefit a player in a way that might affect the team’s salary-cap accounting.
What has become clear, however, is that the Leonard era in Los Angeles was built on unusually expansive demands from his camp and a team prepared to meet many of them a dynamic that has had long-term consequences on internal culture, public perception, and now league scrutiny.
