Kawhi Leonard’s contract negotiations with the Toronto Raptors in 2019 included demands similar to those recently under investigation by the NBA involving his Aspiration endorsement.
According to the Toronto Star, Leonard’s uncle and representative, Dennis Robertson, requested a long list of items, including a trade for Paul George and ownership stakes in the Toronto Maple Leafs.
Sources said Robertson also sought stakes in companies affiliated with Maple Leaf Sports & Entertainment and asked the Raptors to generate at least $10 million per year in sponsorship income for Leonard.
The Raptors were reportedly surprised when Leonard’s camp refused to engage with Toronto’s corporate partners, effectively asking for “no-show” sponsorship arrangements and no-investment investments. MLSE ultimately rejected the proposals.
The NBA’s current probe into Leonard’s $28 million deal with now-bankrupt Aspiration may result in only minor penalties, according to Zach Lowe. A Timberwolves-style punishment involving multiple draft picks is considered unlikely.
Documents obtained by The Athletic showed Leonard was prioritized in payments over other high-profile endorsers, including Leonardo DiCaprio, Drake, and Robert Downey Jr., raising questions about potential salary cap circumvention.
League spokesman Mike Bass confirmed the Aspiration arrangement is under review. The NBA has engaged Wachtell, Lipton, Rosen & Katz, the law firm behind prior cases involving Donald Sterling and Robert Sarver, to conduct the investigation.
Clippers owner Steve Ballmer acknowledged holding a small personal stake in Aspiration but denied involvement in Leonard’s NBA contract, emphasizing it was less than three percent and unrelated to player negotiations.
Sources suggest the investigation could result in fines, minor suspensions, or loss of second-round picks if direct links to the Clippers are found. Extreme sanctions remain possible but are considered unlikely.
