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’s executive team believed Leonard’s deal, which was never announced publicly, held little value to the company. A former Aspiration C-Suite executive said that the deal “materialized essentially out of the ether.”
As part of the deal, Leonard also received $20 million in equity via Aspiration shares that came directly from Sanberg.
Emails between Aspiration executives obtained by The Athletic reflected confusion and frustration with the contract. One marketing executive emailed that the deal had “pretty big flags” while bemoaning that it only guaranteed Aspiration one eight-hour production day, adding that Leonard’s lack of social media presence would “significantly hamper” the company’s ability to extract value from the deal.
The contract was, however, much richer than Aspiration’s 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.
Leonard never publicly promoted the company.
39 comments
Kawhi making more than Iron man is where u draw the line. He better be banned from the NBA.
RDJ, DiCaprio, Drake, Cindy Crawford, and many more all combined made less than Kawhi. If you can’t see this was an attempt to circumvent the cap then you’re just delusional or stupid enough to think that A-List celebs combined have less reach than Kawhi Leonard lmfao
Meanwhile the ex-CEO is claiming this contract was normal. Fucking hilarious. Couldn’t even convince his own people this is normal. And now thinks he can convince the world. He’s going to convince Cuban though.
>“In the **months of discussion among our executives** before signing the sponsorship, I don’t remember conversations about the NBA salary cap,” Cherny said.
https://www.bostonsportsjournal.com/2025/09/04/exclusive-kawhi-leonard-endorsement-deal-that-triggered-nba-investigation-actually-worth-48-million
>But the Leonard deal was a curious one, a source within the company told Boston Sports Journal. According to our source, none of the high-powered executives were consulted about the massive, $28 million endorsement deal Leonard signed, and Cherny never presented the deal to Aspiration’s Board of Directors. BSJ has learned the deal was presented to the executive team as-is, with no opportunity for further analysis.
Someone’s lying here.
That makes sense though Kawhi is much more personable and famous than RDJ and Leo
Kawhi should be banned from the nba. He knew he and his uncles demands were illegal . So he and his uncle and anyone else involved in this saga. Deserves to have the book throw at them .
Leo and Robert need better agents 😂😂😂
DiCaprio and Downing Jr each have 100+ million social media followers and got paid $2 million each.
Kawhi has less than 1 million social media followers and got paid $28 million plus 20 million in stock
is this the part where the story becomes this is all because Sanberg is a kawhi super fan
>**After Sanberg introduced the idea, members of Aspiration’s executive team believed Leonard’s deal, which was never announced publicly, held little value to the company.**
>”Hey everybody I know money is tight right now but we are going to give $48m to a basketball player most people in the US have never heard of.”
>”Uhhh, okay, what will he do?”
>”Nothing! Also we’re not going to talk about this to anyone.”
Can’t imagine why this would be confusing
And Mark Cuban still thinks this was normal lol. 50 million for no work while Hollywood celebs fuck an Avenger only got like 5% of that lol.
Adam Silver is definitely lying awake at night thinking “this never would have happened if I hadn’t made Sterling sell the team”
Is there confirmation that Leo and RDJ were paid in cash, aside from the $2 million in equity? If this is all there is, they essentially received nothing.
Lmao did Kawhi somehow involuntarily bankrupted a company???
“The Ether,” located right behind “The Wall,” is Steve Ballmer’s private office
Kawhi doing ABSOLUTELY NOTHING is just soooooo funny. Like 1 RT or 1 tree could have been at least “see” but not a SINGLE thing for Asperation
Guys we can’t pay our bills and now we have to lay off 20% of our employees.
Also please stop asking why we have to keep paying Kawhi to do nothing for us, nothing to see here!
Watch Pablo’s first episode about this – they go through the contract
Meanwhile in the Clippers sub: “Why did the Lakers fans do this? The employees at Aspiration, Pablo Torre, everyone involved (other than Ballmer and Kawhi) must be Lakers fans, this is all Lakers fans doing”
Call a spade a spade man what are we doing with all these mental gymnastics? NBA needs to come down hard or they will lose all integrity and the Knicks and Lakers will sign all the top players and win the next 20 championships. Clippers max fine lose even more draft picks at least 3 1st rounds and kawhi void contract and suspended for 1 year also ban his pos uncle from anything NBA related
Balmer is going down for this
Don’t you people realize that Kawhi doing absolutely nothing leaves zero carbon footprint, whereas RDJ and Leo are going to be requesting private jets and stuff with big emissions? Cmon use your brains, Aspiration was just doing what it claimed to do and was helping the environment.
I still don’t think I’ve seen them combat the whole clause of “if Kawhi is no longer a clipper the contract is voided” What other logical reason could there be for this besides what’s being speculated?
Kawhi leonard making more than tony stark and jack wow.
Everyone knows what’s up. They should just come clean already. You aren’t fooling anyone Balmer!
I’d love to see kawhi have to talk in court
Still waiting for that smoking gun!
/s
To be fair, DiCaprio has never shot over 30% from three
Kawhi the offseason MVP because the hits just keep on coming
The narrative becomes clearer to me all the time. Aspiration leadership protected the nonsensical Kawhi no show endorsement deal internally because they trusted/hoped Ballmer would subsidize the company (Aspiration) indefinitely. It was a roll of the dice, but one well worth taking for management.
“But they conned me!”
The fact that this reporting is even necessary is crazy. Balmer and Cuban clearly think we’re idiots.
Ballmer is cooked.
So Leo and RDJ which did promote Aspiration got paid in worthess equity while Kawhi get 48 mil for secret endorsement?
Is this how endorsement deal work ?
Kawhi has the charisma of a sea urchin, not surprised the grunts at Aspiration were like wuh?
pablo reported this already
Sounds like A-list actors aren’t board men
Is it possible that these two scammer founders knew about the clippers situation and wanted to land a big investor like Ballmer and did this to appease him?
Just trying to look at this from all angles. I feel like getting ballmer on the cap table is a HUGE get.
Balmer gave them 50M and they paid out 48M so I believe this could have been framed as a revenue stream.