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Dennis Robertson’s Requests To Teams Went Beyond Norms

September 25, 2025 by Real GM

Dennis Robertson, uncle of Kawhi Leonard, has long been one of the NBA’s more notorious characters but the way he has conducted business has received an increase of attention amid allegations of cap circumvention committed by the Los Angeles Clippers.

When Robertson was representing Leonard during the 2019 free agency period, he asked the Toronto Raptors, Los Angeles Lakers and Los Angeles Clippers for a number of items that were against the NBA’s collective bargaining agreement.

“There’s no beginning and there’s no end to what he’d ask for,” an executive involved in the negotiations said. “…There’s a bizarre expectation, not entitlement, but like a willingness to ask for crazy things.”

While many representatives of players will make these types of requests from teams, the audacity of what Robertson asked for set him apart.

“There was no one governing him,” an agent said. “… He worked without any guardrails.”

The Lakers repeatedly told Robertson that his requests were against NBA rules. Jeanie Buss even told Robertson he should attempt to get other teams to agree to his terms in writing, which was meant to underscore the absurdity of his requests.

Some sources told The Athletic they were amused by Robertson’s boldness, while others expressed animosity.

“I was amused by it,” said one former team employee. “I appreciated the hustle of ‘He’s my nephew, he’s the leader of the team and we want everything.'”

Robertson isn’t a registered agent, but he has an extensive background in business.

“He’s a sophisticated guy and a smart guy and aggressive,” a former GM said of Robertson. “If he asked for stuff and he did things; I think it’s not as much of an outlier as he’s being positioned as being. If he were an insider and a traditional agent, everyone would say ‘Agents do this all the time.’ But the framework is what makes him different. And a lot of people don’t like it.”

One team source told The Athletic that it wasn’t so much Robertson’s asks that were the issue as much as he the fact that he didn’t stop making them.

“They never went against each other,” a league source who worked with Leonard said. “They’re one and the same in my mind. But Uncle Dennis doesn’t mind being the bad guy.”

Filed Under: Raptors

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