Kawhi Leonard’s uncle asked Raptors about ‘no-show’ endorsement jobs in 2019, per report

The dominant story in the NBA is the investigation into whether Clippers owner Steve Ballmer circumvented the salary cap by funding a “no-show” endorsement deal for Kawhi Leonard through one of the Clippers’ sponsors, Aspiration. 

The league has opened an investigation into the matter, which was first detailed on “Pablo Torre Finds Out,” and Steve Ballmer recently sat down with ESPN to deny any alleged impropriety, insisting he was a victim of a scam by Aspiration. All of it is incredibly murky and it’s not clear if the NBA will be able to tie anything firmly to Ballmer or Leonard that could lead to a serious punishment for either the player or team. 

On Tuesday, a new report from Bruce Arthur of the Toronto Star indicated that, if the league expands its investigation to discussions with teams that pursued Leonard in free agency in 2019, they’ll find that Leonard’s apparent “no-show” deal with Aspiration isn’t quite as shocking as it initially seems. Arthur spoke with a number of sources with the Raptors who were part of free agent negotiations with Leonard that involved his uncle and manager Dennis Robertson, and his demands allegedly went well beyond what teams can offer, including an ownership stake in the Toronto Maple Leafs.  

Robertson asked for ownership stakes in outside companies: not just the Leafs, which he seemed to believe was separate, but with other companies with whom MLSE had a relationship. And two, the Raptors were told they needed to match at least $10 million per year in extra sponsorship income. Teams are allowed to introduce players to team sponsors; teams cannot negotiate deals, and MLSE was aware of that fact.

But it didn’t end there. As one source put it, when told about all the corporate sponsors in Toronto who would be happy to have Leonard as a pitchman, his camp said, “We don’t want to do anything.” Raptors representatives said any sponsor would want to shoot ads or arrange appearances; Robertson reiterated Leonard didn’t want to do anything for the money.

MLSE rejected those proposals and Leonard eventually signed with the Clippers after they met enough of his demands, including trading for Paul George. 

Aspiration’s deal with Leonard could end up as the biggest cap circumvention scandal in NBA history. Players signing with teams for a discount always raises eyebrows, but what makes this situation so fascinating is how apparently brazen it all is. 

Leonard’s LLC set up for payments — KL2 Aspire LLC — is simply his initials, number and a shortened version of Aspiration’s name. The $28 million agreement and the subsequent $20 million stock deal align extremely closely with Ballmer’s $50 million investment in Aspiration, and for it all to come out after Robertson apparently made these demands to other teams in free agency could provide enough circumstantial evidence for the league to hand down a punishment even without a true smoking gun. 

If the league expands its investigation to include any correspondence between Robertson and other teams, as well as interviewing those who were part of those negotiations (as Arthur did here), and finds evidence these were actual demands, that could help put the complete picture together. 

We’ll eventually find if the league’s investigation ends up piecing all of this together to come to a firm conclusion, but each report about the Leonard saga adds to the drama and intrigue about how exactly Leonard ended up in Los Angeles.