In March 2023, LA Clippers owner Steve Ballmer made headlines with a significant investment of nearly $10 million into the financial technology and sustainability services company, Aspiration. This investment was revealed through legal filings reviewed by The Athletic and confirmed by a former executive of Aspiration. This lesser-known investment came about 18 months after Ballmer initially invested $50 million into Aspiration, a company currently facing an NBA investigation. The investigation centers around allegations that Clippers star Kawhi Leonard may have entered a side deal to bypass the NBA’s salary cap limitations, a story first reported by the “Pablo Torre Finds Out” podcast.
Ballmer’s latest investment seems to have been a lifeline for Aspiration, which was grappling with severe financial challenges at the time. The company was reportedly laying off employees and struggling to secure additional funding. This $10 million influx came just three months after Dennis Wong, Ballmer’s college roommate and Clippers vice chairman, invested $1.99 million into the firm. The podcast also highlighted that shortly after Wong’s investment, Aspiration made a $1.75 million payment to Leonard, who had previously signed a $28 million endorsement contract with the company in April 2022.
Aspiration aimed to raise $75 million during this fundraising round, but fell nearly $9 million short, primarily due to a lack of new investors. Most shares were purchased by Aspiration co-founder Joe Sanberg and board member Ibrahim AlHusseini, with Sanberg later agreeing to plead guilty to fraud charges filed by the Justice Department. Ballmer's first investment in Aspiration, the $50 million, took place in December 2021, shortly after Aspiration secured a deal to become a founding sponsor of the Clippers' new arena, valued at over $300 million.
As part of the partnership, the Clippers committed to paying Aspiration over $50 million for carbon offsetting initiatives, aiming for carbon neutrality. Seven months later, Leonard’s endorsement deal was established. However, Aspiration soon found itself struggling to meet its quarterly payment obligations to Leonard. When the company fell behind on payments, Leonard’s agent, Mitch Frankel, contacted Aspiration’s executives to address the delay.
According to sources, the endorsement deal with Leonard quickly became a source of confusion within Aspiration. A former executive revealed that the deal seemed to have little value to the company and appeared to materialize unexpectedly. Leonard's contract included provisions for his participation in various promotional activities, yet the lack of a strong social media presence from the player posed challenges for marketing efforts.
As the situation unfolded, Aspiration faced further scrutiny, with Leonard being listed as a creditor in Aspiration’s bankruptcy filings for $7 million, alongside two companies representing the Clippers for a combined total of $50 million. Following the investigation announcements, NBA commissioner Adam Silver stated that the league would assess whether the Clippers and Ballmer had indeed violated salary cap regulations. If the investigation finds wrongdoing, potential consequences could include fines, docking of draft picks, or even voiding Leonard’s endorsement deal.
Steve Ballmer’s significant investments in Aspiration, particularly against the backdrop of ongoing NBA investigations, raise questions about the integrity of these financial dealings and partnerships. While the Clippers have refrained from commenting on the March 2023 investment, the outcome of the NBA's investigation may have lasting repercussions for both the franchise and the players involved.
