Kawhi Leonard's 'Uncle Dennis' Asked The Raptors For A Stake In The Toronto Maple Leafs In 2019 Free Agency

Kawhi Leonard and his camp have a history of making illegal requests, but the extent of their demands is only just now coming to the surface. Back in 2019, during his free agent meetings with the Raptors, he allegedly asked for a stake in the Toronto Maple Leafs of the NHL before being denied.

"During negotiations, Leonard remained engaged with [Raptors] for a great deal of the process," wrote the Toronto Star. "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."

The Raptors and Leafs are both owned by "Maple Leaf Sports & Entertainment," making the request impossible. These conversations sparked an investigation by the NBA, only for them to find nothing incriminating at the time.

"The league investigated and didn’t find anything concrete, but issued a warning on free agency rules going forward," the Star reported.

Of course, that was just one of the many outlandish requests made by Kawhi and his camp that summer. Kawhi was turned down by Jeanie Buss and the Lakers for making similar demands, including guaranteed endorsement deals, a partial ownership share, private plane access, and a house.

Even after Raptors ownership scrambled to secure up to $15 million in endorsements, Leonard still turned them down in favor of the Clippers, who are now being investigated for cap circumvention. With the NBA now investigating the scandal, it could use these prior incidents to establish a history of trying to break the CBA.

It all connects to Kawhi's uncle, Dennis Robertson, who also serves as one of his primary business representatives. He played a role in Kawhi's ugly divorce from the Spurs, claiming that a "lack of trust" with the organization led to an irreparable rift that led to his trade request. Robertson was the one who arranged for Kawhi to seek outside opinions after his quad injury that season, which kept him from action for nearly an entire year.

In 2019, it was Robertson who spoke on Kawhi's behalf and tried to force teams into granting unprecedented, illegal, and sometimes impossible requests. The fact that he tried to get a stake in the Maple Leafs only furthers the idea that he was willing to break any and every rule to get Kawhi the best deal he possibly could.

Now, in the ongoing "Aspiration" scandal, there's a mountain of circumstantial evidence that Robertson may have helped orchestrate a scheme to get Leonard an extra $28 million in the form of a "no-show" sponsorship deal from a company bankrolled by Steve Ballmer.

Whether driven by greed, ambition, or ego, it's clear that "Uncle Dennis" has been pulling the strings for Kawhi's career, and he seemingly didn't care how outlandish his requests were during ongoing negotiations. Only time will tell the nature of his involvement and what other things may be happening behind the scenes, but every new detail only adds another layer of mystery and shock to this growing conspiracy.