Following up on Pablo Torre’s report on the possibility of salary cap circumvention involving the Clippers and star forward Kawhi Leonard, John Karalis of Boston Sports Journal provides some fascinating additional details, citing a “high-level” source who says Leonard made a side deal with the company Aspiration to receive an additional $20MM in company stock on top of the $28MM from his original endorsement agreement.
Co-founder Andrei Cherny didn’t run the $28MM endorsement deal Leonard signed by the company’s board of directors, according to Karalis, who says the agreement was presented to Aspiration’s executive team “as is,” without consulting them or giving them an opportunity to be involved in negotiations. If the executive team had been privy to the talks, it would have advised against the deal, Karalis explains, since management viewed it as a “poor use of cash resources.”
While Cherney signed the deal against the wishes of management, Aspiration’s marketing and management teams saw “no brand synergy” with Leonard and and opted against using his services, preferring to work with climate-focused influences, Karalis continues.
Regarding the $50MM that Clippers owner Steve Ballmer invested in Aspiration, Karalis says that investment was described as having been made with “light-to-no diligence” and came at a rate higher than the one Oak Tree Capital Management had paid during the company’s rounds of fundraising. As Karalis observes, it wouldn’t have been unusual for a well-known investor like Ballmer to be offered a discounted share price, since his involvement would create positive buzz for the company. Instead, the $11 he paid per share was a dollar higher than what Oak Tree paid.
Here’s more on the Leonard situation:
- Although the Clippers asserted in a statement on Wednesday night that there’s “nothing unusual or untoward about team sponsors doing endorsement deals with players at the same time,” rival executives who spoke to Sam Amick of The Athletic pointed out that Ballmer’s investment in Aspiration and the size of Leonard’s endorsement deal are red flags on their own, even before taking into account the fact that the star forward did no promotional work for the company. “This (sort of endorsement deal) does not happen,” one general manager told Amick.
- Executives who discussed the issue with Chris Mannix of SI.com conveyed a similar sentiment. “If this is what it looks like, I think (commissioner) Adam (Silver) has to make an example of them,” one team executive said.
- It’s worth noting that the Clippers were previously investigated in 2019 due to rumors that Leonard’s uncle Dennis Robertson was asking teams for improper benefits during Kawhi’s free agency negotiations that summer. John Gambadoro of Arizona Sports 98.7 (Twitter link) hears that Leonard was seeking an extra $15MM in endorsement money from the Raptors that offseason, while Bruce Arthur of The Toronto Star cites sources who say “Uncle Dennis” was asking for an ownership stake in the NHL’s Toronto Maple Leafs during talks with the Raptors.
- Nate Jones, who works as an agent and marketer at Goodwin Sports, shared some insights into the situation in a Twitter thread, explaining why the Clippers, Ballmer, and Leonard may all have plausible deniability if there’s no smoking gun laying out a quid pro quo arrangement. Still, as Kurt Helin of NBC Sports relays, citing Zach Lowe’s podcast, the NBA’s Collective Bargaining Agreement allows for cap circumvention to be proven by circumstantial evidence if the terms of a deal “cannot rationally be explained in” another way.
In a 
Toronto was well on its way to a lottery finish in 2024/25 when the front office swung a deal to acquire Pelicans forward 
Perhaps most pressingly, the Raptors are currently operating over the luxury tax line, which presumably isn’t the end goal for a team coming off a 30-win season. They also find themselves above the first tax apron due to the incentives in the