The NBA’s probe into Kawhi Leonard’s endorsement deal with Aspiration and its potential ties to the Los Angeles Clippers could end with only minor penalties.
NBA insider Zach Lowe said the case is “likely” to land in a gray area, making a Timberwolves-style punishment — which cost Minnesota multiple first-round picks in 2000 — an unlikely outcome.
According to Lowe, second-round pick confiscation and a fine are the most probable penalties if no direct evidence emerges linking the Clippers to the $28 million deal.
The investigation stems from Leonard’s partnership with Aspiration, a now-bankrupt tree-planting company. Documents obtained by The Athletic’s Pablo Torre showed Leonard received more money than other endorsers, including Leonardo DiCaprio, Drake, and Robert Downey Jr., and was treated as a payment priority even as the company collapsed.
League spokesman Mike Bass confirmed the arrangement is under review for potential salary cap circumvention. The NBA has retained Wachtell, Lipton, Rosen & Katz — the same law firm that handled cases involving Donald Sterling and Robert Sarver — to conduct the investigation.
Clippers owner Steve Ballmer previously admitted to a small personal stake in Aspiration but emphasized it was under three percent and unrelated to player negotiations. He denied any wrongdoing and said Leonard’s NBA contract was handled independently.
The uncertainty lies in whether investigators uncover direct ties between Aspiration’s payments and the Clippers’ recruitment of Leonard in 2019. Lowe said both extreme outcomes — from no punishment to heavy sanctions — remain plausible, but the middle ground appears most realistic.
Other insiders, including Sam Amick, have noted potential penalties could include fines, suspensions, or voided contracts if violations are proven. However, most reporting indicates the league will stop short of severe measures unless stronger evidence surfaces.
