Wong being the lone exception<\/a>. The company hoped to raise $75 million in fresh money but came up nearly $9 million short. A vast majority of the shares were bought up by Aspiration co-founder Joe Sanberg and Ibrahim AlHusseini, another Aspiration board member. Sanberg later agreed to plead guilty to fraud charges brought by the Justice Department.<\/p>\nBallmer\u2019s first investment into Aspiration \u2014 a $50 million infusion alongside $265 million from OakTree Capital, a prominent financial firm \u2014 came in December 2021, three months after Aspiration signed a deal with the Clippers worth more than $300 million to be a founding sponsor of the team\u2019s new arena and its jersey patch partner. The Clippers also signed an agreement to pay Aspiration more than $50 million for carbon offsetting toward the goal of becoming carbon neutral, according to multiple sources briefed on the deal.<\/p>\n
Seven months later, Aspiration inked Leonard to a four-year, $28 million endorsement contract. Almost immediately, Aspiration struggled to make its quarterly $1.75 million payments to Leonard, and when the company was late with a payment that fall, Leonard\u2019s agent, Mitch Frankel, reached out to company executives.\u00a0<\/p>\n
In December 2022, Wong invested almost $2 million in Aspiration through DEA 88 Investments LLP. Days later, according to reporting by \u201cPablo Torre Finds Out,\u201d Aspiration paid Leonard $1.75 million.<\/p>\n
Three months later, according to court documents in a civil suit, Ballmer invested $9,999,997.92 in the company. Aspiration had been struggling financially, with just $12.2 million in cash as of Feb. 17, 2023 and running through more than $2 million a week. The Clippers declined to comment on the March 2023 investment.\u00a0<\/p>\n
It\u2019s unclear if Aspiration continued paying Leonard, who is listed as a creditor in Aspiration\u2019s bankruptcy filings for $7 million, as are two companies representing the Clippers for a combined $50 million.<\/p>\n
Long before the relationship between Leonard and Aspiration fell under public scrutiny, it caused confusion within the company itself, according to ex-employees who spoke with The Athletic. After Sanberg introduced the idea, members of Aspiration\u2019s executive team believed Leonard\u2019s deal, which was never announced publicly, held little value to the company. A former Aspiration C-Suite executive said that the deal \u201cmaterialized essentially out of the ether.\u201d<\/p>\n
As part of the deal, Leonard also received $20 million in equity via Aspiration shares that came directly from Sanberg.<\/p>\n
\u201cI am personally contributing stock to Kawhi to make this partnership possible,\u201d Sanberg wrote members of his leadership team in a May 2022 email obtained by The Athletic. \u201cAspiration\u2019s CEO judged the deal to be not worth doing. For avoidance of doubt, any and all benefit to Aspiration from the Kawhi deal is being subsidized by my contributing my equity to make this happen.\u201d<\/p>\n
As part of the agreement, Sanberg also pressured the company to pay for fees incurred by Frankel, who did not respond to The Athletic\u2018s request for comment.\u00a0<\/p>\n
While Aspiration executives initially traded ideas on how to incorporate Leonard in marketing campaigns \u2014 including in collaboration with Drake, a celebrity client and endorser \u2014 it never did so. One executive believed the famously laconic Leonard did not fit as a spokesperson.\u00a0<\/p>\n
The contract specified that Leonard would, among other asks, participate in one eight-hour day of production, one four-hour day of public relations, two one-hour community service events, one five-minute segment per week \u201cin conversation with (Clippers) Coach Ty Lue\u201d while he sat out the 2021-22 season recovering from an injury, \u201cfive organic comments\/likes\/RTs as requested by Aspiration\u201d and three off-court projects.<\/p>\n
But the deal, which allowed Aspiration to terminate it for cause or if Leonard was no longer playing for the Clippers, also gave Leonard sign-off on the requests and allowed him to refuse to do anything \u201cnot consistent with his beliefs.\u201d<\/p>\n
Emails between Aspiration executives obtained by The Athletic reflected confusion and frustration with the contract. One marketing executive emailed that the deal had \u201cpretty big flags\u201d while bemoaning that it only guaranteed Aspiration one eight-hour production day, adding that Leonard\u2019s lack of social media presence would \u201csignificantly hamper\u201d the company\u2019s ability to extract value from the deal.<\/p>\n
When reached by The Athletic this week, Andrei Cherny, Aspiration\u2019s co-founder and CEO until 2022, disputed that Leonard had a no-show contract. He said the beliefs clause is standard for celebrity endorsements and that the company could end the agreement if Leonard didn\u2019t perform on his end.\u00a0<\/p>\n
\u201cIn the months of discussion among our executives before signing the sponsorship, I don\u2019t remember conversations about the NBA salary cap,\u201d Cherny said. \u201cI 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. I can\u2019t speak to what was done or not done after I left \u2014\u00a0or why.\u201d<\/p>\n
The contract was, however, much richer than Aspiration\u2019s deals with other endorsers, according to the former executive who related that Leonardo DiCaprio and Robert Downey Jr. both received less than $2 million in equity, while Drake invested $4 million but also received carbon offsets.<\/p>\n
Leonard never publicly promoted the company.<\/p>\n
In March 2025, Sanberg was arrested and Aspiration filed for bankruptcy. Sanberg has agreed to plead guilty to federal charges of defrauding investors for $248 million. His next plea hearing is next week. An attorney for Sanberg declined to comment.<\/p>\n
In August, the Securities and Exchange Commission alleged that Sanberg inflated the company\u2019s revenue and duped investors, using Aspiration shares to take out more than $100 million in personal loans. The SEC\u2019s complaint pointed specifically to two investors, including one who bought $50 million in shares between September and December 2021.<\/p>\n
Aspiration employees said that Sanberg built and maintained a relationship with Ballmer to convince him to invest in the company. During a deposition last October, when the Aspiration co-founder was asked whether he was the one who landed Ballmer as an investor, Sanberg invoked his fifth amendment rights.<\/p>\n
\u201cThey conned me,\u201d Ballmer told ESPN last week. \u201cI made an investment in these guys, thinking it was on the up and up, and they con me. At this stage, I have no ability to predict why they might have done anything they did, let alone the specific contract with Kawhi.\u201d<\/p>\n
Last week, the NBA announced it had hired law firm Wachtell, Lipton, Rosen & Katz, which has previously conducted league investigations into the Clippers and Phoenix Suns, to determine if Ballmer and the Clippers used Aspiration to circumvent salary cap restrictions. Ballmer has denied wrongdoing and said that aside from introducing Leonard to the company, he did not know anything about Leonard\u2019s endorsement contract.\u00a0<\/p>\n
If, after the investigation and a ruling by an independent arbitrator, NBA commissioner Adam Silver determines the Clippers broke league rules, he has the ability under the collective bargaining agreement to punish the team and Ballmer by docking draft picks, implementing fines and even voiding Leonard\u2019s deal.\u00a0<\/p>\n
At a news conference Wednesday following an NBA board of governors meeting<\/a>, Silver\u00a0 said he will look for more than the \u201cappearance of impropriety\u201d to penalize the team, adding that the burden of proof is on the league.<\/p>\n\u201cI think the goal of a full investigation is to find out if there really was impropriety,\u201d Silver said. \u201cIn a public-facing sport, the public at times reaches conclusions that later turn out to be completely false. I would want anyone else in situations Mr. Ballmer is in now \u2014 and Kawhi, for that matter \u2014 to be treated the same way I would want to be treated if people were making allegations against me. We\u2019re not a court of law at the end of the day, either.\u201d<\/p>\n
(Photo of Steve Ballmer by Jayne Kamin-Oncea-USA TODAY Sports)<\/p>\n","protected":false},"excerpt":{"rendered":"In March 2023, LA Clippers owner Steve Ballmer invested almost $10 million into financial technology and sustainability services…\n","protected":false},"author":3,"featured_media":222029,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[10],"tags":[3142,1260,62,67,132,68],"class_list":{"0":"post-222028","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-sports","8":"tag-los-angeles-clippers","9":"tag-nba","10":"tag-sports","11":"tag-united-states","12":"tag-unitedstates","13":"tag-us"},"share_on_mastodon":{"url":"https:\/\/pubeurope.com\/@us\/115193795320020893","error":""},"_links":{"self":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts\/222028","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/comments?post=222028"}],"version-history":[{"count":0,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts\/222028\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/media\/222029"}],"wp:attachment":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/media?parent=222028"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/categories?post=222028"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/tags?post=222028"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}