Who Is Kawhi Leonard’s Advisor Uncle Dennis? Everything to Know About Dennis Robertson

Back in 2019, the Lakers appeared to be ahead until the Raptors made a comeback, but it was the Clippers who ultimately emerged victorious. It was the free agency saga of Kawhi Leonard that dominated the headlines for weeks. But it’s 2025, and once again that deal is under scrutiny thanks to new reports from Pablo Torre. The journalist alleged that Clippers owner Steve Ballmer made payments to secure the services of the 2x NBA champion by circumventing the salary cap. However, these were not the only names responsible, and ‘Uncle Dennis’ was another part of this puzzle.

Who is ‘Uncle Dennis’, Dennis Robertson?

Uncle Dennis’ name with any Kawhi Leonard’s contract or negotiation is not new. Dennis Robertson is the brother of Leonard’s mother, Kim Robertson, and has played a vital role in the life of the 6x All-Star since the superstar’s father’s death. Professionally, Robertson has 3 decades plus experience in banking and marketing, and he serves (or served) as president of the Elite Athlete Division at Protocol International. Whether it be the exit from Spurs or goodbye from the Raptors, Uncle Dennis dominated the headlines.

Former NBA player Bruce Bowen was not shy about calling out Leonard’s advisor. “I think he’s getting bad advice,” Bowen said. “I think what you’re starting to see now is an individual given a certain amount of advice, and it’s not the right advice.” But these words did not change the relationship between the 2x Finals MVP and his uncle. In fact, Robertson played a pivotal role in guiding Leonard through his free agency, including his high-profile move from the Raptors to the Clippers.

Why was Uncle Dennis investigated by the NBA in 2019?

The move to Southern California wasn’t straightforward. Robertson was at the center of an NBA investigation focusing on whether he asked teams for impermissible benefits during Leonard’s free-agent process. While the Clippers ended up signing Kawhi on a three-year, $103 million deal, reports emerged of demands that violated the CBA rules. But the league claimed it had no evidence that the Clippers granted illegal benefits to Leonard during his free agency. The team, Leonard, and Robertson did not face punishment as a result of the investigation.

At the time, a source told Sam Amick of The Athletic that NBA commissioner Adam Silver considered the issue “a cardinal sin of the NBA.” That’s why the league, however, threatened it could reopen its investigation into the situation if new evidence were presented. Which Pablo Torre did in his exposé recently and found multiple evidence tying Leonard to an “allegedly fraudulent” tree-planting firm, Aspiration. The journalist further alleged a $28 million payment to KL2 Aspire LLC, owned by Leonard. Shocking news in the NBA, and even the Clippers reacted in their statement, clearing the air if there is any truth to those claims.

NBA Investigation and Conclusion

Robertson, according to The Athletic, was asking for an ownership stake, a private plane available at any time, a house, and “a guaranteed amount of off-court endorsement money that they could expect if Leonard played for their team.” A strict violation of Article XIII of the CBA serves as the league’s strict anti-circumvention rule. It bars teams from compensating players outside their contracts.

Adam Silver at the time said, “We are looking at the behavior from the summer. We have and we continue to look at it. First and foremost, we want to change the way business is done going forward.”But the league had no proof, and that’s why no ban/punishment to the Clippers, Kawhi, and his uncle Dennis.

Kawhi Leonard publicly stated he had “no knowledge” of these alleged demands. Over the years, Robertson earned the tag of ‘difficult’ even when his nephew was playing for the Spurs. One can say that nature has helped the Clippers star earn $325,772,011 through his NBA earnings. His high-profile presence during pivotal free agency discussions, even without public visibility, underscores his role as Leonard’s primary career strategist.