The NBA’s investigation into Kawhi Leonard’s endorsement deal with Aspiration is raising broader questions about how players and teams navigate sponsorship arrangements.
According to Howard Beck of The Ringer, it is common for franchises to connect players with team sponsors or local businesses to facilitate endorsements. Examples include Stephen Curry’s commercials for Rakuten, a Golden State Warriors partner, and the San Antonio Spurs’ long-running ads with HEB supermarkets.
Beck reported that such deals typically pay in the hundreds of thousands, occasionally reaching the low six figures, and usually require commercials, appearances, or social media promotion. In contrast, Leonard’s $28 million partnership with Aspiration has drawn scrutiny for its unusual size and limited public promotion.
The arrangement became more concerning when documents revealed Leonard was prioritized for payment even as the company went bankrupt. He earned more than other high-profile endorsers, including Leonardo DiCaprio and Drake.
NBA spokesman Mike Bass confirmed the league is reviewing the deal for potential salary cap circumvention. The investigation is being handled by law firm Wachtell, Lipton, Rosen & Katz, which has overseen past high-profile league cases involving Donald Sterling and Robert Sarver.
Clippers owner Steve Ballmer admitted to holding a small stake in Aspiration, under three percent, but denied any involvement in Leonard’s endorsement or contract negotiations.
Zach Lowe reported that the likely outcome will fall into a gray area, making severe penalties such as the Minnesota Timberwolves’ 2000 punishment — which cost them multiple first-round picks — highly unlikely. Instead, the most probable penalties would be a fine or loss of a second-round pick.
Former players and executives told The Ringer that the scale of Leonard’s deal and its alleged “no-show” element are red flags. One former executive said the figures were “extreme,” while another called it a “huge red flag.”
Beck added that in some cases, teams have arranged local business deals worth around $150,000 to sway free agents, with players making promotional appearances to fulfill requirements. Leonard’s case differs significantly given the higher dollar amount and the lack of visible promotional activity.
League insiders, including Sam Amick of The Athletic, have suggested possible outcomes range from fines to suspensions if clear violations are proven. Still, most indications point to lesser penalties unless investigators uncover direct ties between the Clippers and Aspiration’s payments.
