NBA Investigates Kawhi Leonard Raptors, Clippers 2019 Benefit Requests

In 2019, Kawhi Leonard's free agency negotiations with the Toronto Raptors included unusual and extravagant demands reportedly pushed by his uncle and representative, Dennis Robertson. These requests encompassed a trade for Paul George, ownership stakes in the Toronto Maple Leafs and other MLSE-affiliated companies, and at least $10 million annually in sponsorship income without any endorsement work, essentially no-show arrangements. Raptors executives rejected these demands, recognizing they extended beyond standard endorsements and involved impermissible benefits akin to no-show jobs. This pattern is strikingly similar to the current NBA investigation into a no-show endorsement deal Leonard allegedly received from Aspiration, a Clippers sponsor tied to owner Steve Ballmer, raising questions about potential salary cap circumvention. Despite the contentious negotiations and these demands, Leonard ultimately chose to sign with the Clippers, partly to avoid playing alongside LeBron James on the Lakers. The Raptors, meanwhile, maintained a strong position, having secured a championship with Leonard and avoided the questionable financial arrangements his camp sought.