Even more than six years out from his last game played for the Toronto Raptors, Kawhi Leonard’s departure from the team still manages to make headlines.

Over the last week, details have emerged about an alleged secret contract between Leonard and Aspiration Inc., a company that had reportedly received a US$50 million investment from Los Angeles Clippers owner Steve Ballmer.

Aspiration co-founder Joe Sanberg was arrested on fraud charges in March, with the company listed as a tree-planting firm and classified as a “sustainability non-profit.”

In its bankruptcy filings, podcaster Pablo Torre uncovered that Leonard had been listed to take home US$7 million per year over four years from Aspiration for what was classified as a “no-show job”: Leonard would have had very little in actual duties to collect the money other than to remain employed by the Clippers.

Boston Sports Journal’s John Karalis added a previously unreported $20 million investment also being paid to Leonard, later corroborated by Torre and other sources.

On the surface, the story appears to be a case of salary cap circumvention, with the payments beginning at the same time Leonard started his second contract extension with the Clippers in 2021, two years after joining them as a free agent.

The Clippers and Ballmer have publicly refuted the story, stating that Leonard’s deal with Aspiration was separate from Ballmer’s and not a form of cap circumvention.

But it appears to have an interesting Toronto wrinkle.

According to Toronto Star’s Bruce Arthur, the Raptors’ ownership brass in MLSE was “being asked to arrange no-show jobs” for Leonard in the 2019 free agency period by his representative and uncle, Dennis Robertson.

Arthur had previously also reported that Leonard’s camp had pushed for a stake in the Toronto Maple Leafs, also owned by MLSE. Leonard ultimately left Toronto after just one season, weeks after winning the 2019 title and NBA Finals MVP.

“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,” Arthur wrote in an article published Tuesday. “MLSE rejected both proposals.”

The NBA is actively investigating the claims.

Lead photo by

Sergio Estrada-Imagn Images