Back in 2019, when Kawhi Leonard was fresh off leading the Toronto Raptors to their first-ever NBA championship, his camp was apparently asking for a lot more than just a max contract. According to Bruce Arthur of The Star, Leonard’s uncle, Dennis Robertson, even asked for an ownership stake in the NHL’s Toronto Maple Leafs during free agency talks.
“Sources in Toronto say, in one meeting, Uncle Dennis asked for an ownership stake in the Toronto Maple Leafs, because that way he wasn’t asking for a piece of the Raptors. It was politely explained to him that both teams were owned by the same company, and that the request was impossible.”
Kawhi Leonard Departure From Toronto
Leonard ultimately left Toronto in the summer of 2019 after delivering the franchise its long-awaited championship. He signed a three-year, $103 million deal with the Los Angeles Clippers, and the team quickly paired him with Paul George in a blockbuster trade with OKC.
But according to The Athletic, Robertson wasn’t just asking the Raptors for unusual perks. He reportedly approached other teams with “improper benefit” requests during Kawhi’s free agency meetings—including the Lakers—before Leonard committed to the Clippers.
The “Aspiration” Controversy
Things didn’t stop there. On the Pablo Torre Finds Out podcast, several former employees of a now-bankrupt environmental company called Aspiration alleged that Leonard received a massive $48 million “no-show job” that was really just a way to funnel him money outside the NBA’s salary cap.
Aspiration had deep ties to the Clippers and owner Steve Ballmer, who himself invested $50 million into the company. Ballmer, however, denied having anything to do with Leonard’s deal.
He told ESPN that the company simply asked him to introduce them to Leonard in late 2021—months after the Clippers had already locked Kawhi into a four-year, $173 million extension. Around the same time, the Clippers also announced a huge $300 million partnership with Aspiration.
A Complicated Legacy
Kawhi Leonard remains one of the greatest players of his generation, but these stories show just how wild things got behind the scenes after his 2019 title run with Toronto. From ownership stake requests to shady sponsorship deals, the off-court drama around his free agency is nearly as unforgettable as his Game 7 buzzer-beater against the Sixers.
