Internal emails revealed Aspiration executives expressed concerns about Kawhi Leonard’s endorsement contract, which required minimal promotional work while allowing the Clippers star significant control over his obligations, according to documents obtained by The Athletic.
The deal specified Leonard would participate in one eight-hour production day, one four-hour PR session, two community service events, and weekly five-minute conversations with Ty Lue during his 2021-22 injury recovery. Leonard also agreed to provide “five organic comments/likes/RTs as requested by Aspiration” and participate in three off-court projects.
However, the contract included provisions allowing Leonard to refuse requests “not consistent with his beliefs” and gave him sign-off authority on all activities. Aspiration could terminate the agreement if Leonard was no longer playing for the Clippers or for cause.
Aspiration marketing executives expressed frustration with the contract structure in internal communications. One executive noted the deal had “pretty big flags” and complained that Leonard’s limited social media presence would “significantly hamper” the company’s promotional efforts.
The executives initially considered marketing campaigns involving Leonard alongside Drake, a celebrity client and endorser. However, they ultimately decided against using Leonard as a spokesperson, with one executive believing the famously quiet star did not fit that role.
Andrei Cherny, Aspiration’s co-founder and CEO until 2022, disputed characterizations of the Leonard deal as problematic when contacted by The Athletic. He emphasized that celebrity endorsement contracts commonly include beliefs clauses and termination options for non-performance.
“In the months of discussion among our executives before signing the sponsorship, I don’t remember conversations about the NBA salary cap,” Cherny said. “I signed the contract shortly before I submitted my resignation, but before I left there were numerous internal conversations about the various things Aspiration was planning to do with Leonard once the 2022-23 season began, including emails from the marketing team about their plans in just the week before my last day.”
Three former Aspiration executives issued a joint statement responding to Cherny’s comments, claiming the Leonard contract was delivered already completed without proper review. The former chief legal officer, chief technology officer, and chief financial officer said they raised concerns about the deal’s cost and strategic value.
“The team expressed concerns at the time regarding the high cost of the agreement and its lack of alignment with Aspiration’s brand and business strategy,” the executives stated to The Athletic. “While subsequent marketing efforts were undertaken, they were ultimately discontinued and should not be interpreted as support for the deal itself.”
The Leonard contract reportedly exceeded Aspiration’s agreements with other celebrity endorsers. Leonardo DiCaprio and Robert Downey Jr. received less than $2 million in equity, while Drake invested $4 million but also received carbon offsets, according to a former executive.
Leonard never publicly promoted Aspiration during the contract period, despite the company’s initial marketing plans.