The NBA’s probe into the Los Angeles Clippers and star forward Kawhi Leonard has expanded well beyond the recently uncovered Aspiration endorsement agreement, which could have delivered Leonard nearly $50 million. The deal, tied to a financial firm with business connections to Clippers owner Steve Ballmer, has placed renewed focus on the team’s handling of Leonard’s contracts and his longtime representative, Dennis Robertson.
Robertson, Leonard’s uncle, has drawn attention for years with his unconventional negotiating tactics. During Leonard’s 2019 free agency, Robertson asked the Los Angeles Lakers, Toronto Raptors, and Clippers for benefits that went far outside the collective bargaining agreement. Requests reportedly included unlimited private jet access, a house, guaranteed endorsement income, and even a stake in a franchise, per The Athletic. The Lakers declined repeatedly, and Leonard ultimately signed with the Clippers after they acquired Paul George in a trade. The NBA investigated but initially found no evidence that those perks had been granted.
Now, the league has authorized law firm Wachtell, Lipton, Rosen & Katz to revisit those negotiations. However, the investigation is not restricted to Aspiration. Any evidence suggesting the Clippers violated salary-cap rules in 2019 or afterward could be re-examined. The Clippers and Ballmer have denied wrongdoing and pledged cooperation.
Multiple executives and agents described Robertson’s persistence as extreme compared to other player representatives. While unusual requests are not rare in NBA circles, Robertson’s repeated demands set him apart.
One executive likened the behavior to driving 75 mph in a 35 zone, while others pushed just 10 mph over. That relentlessness has given rise to lawsuits as well, as former Clippers trainer Randy Shelton alleged Robertson pressured him to pay 10% of his compensation, more than double the industry norm, in exchange for access to the team. Shelton’s case remains active.
Robertson’s influence has influenced Leonard’s career since his breakout Finals MVP performance with the San Antonio Spurs in 2014. His role intensified after disputes with Spurs medical staff over a quad injury led to Leonard’s 2018 trade to the Raptors. In Toronto, Robertson was heavily involved in load-management decisions during Leonard’s championship run and Finals MVP award in 2019.
Though Leonard keeps a low profile, Robertson’s actions have put him in the spotlight. His reputation now sits at the center of a potential salary-cap scandal, with the investigation set to decide if the Clippers crossed the line or if his tactics merely pushed league limits.
