In the summer of 2019, fresh off delivering the Toronto Raptors their first-ever NBA championship, Kawhi Leonard held the basketball world in suspense. But behind closed doors, the free agency negotiations weren’t just about basketball, they veered into territory that left Raptors executives stunned and speechless.
According to sources cited by Toronto Star columnist Bruce Arthur, during one of the Raptors’ meetings with Leonard’s camp, his uncle and advisor Dennis Robertson, known to fans as “Uncle Dennis”, made an eyebrow-raising request: an ownership stake in the Toronto Maple Leafs.
Yes, the NHL team.
The logic? Since Robertson couldn’t legally ask for a piece of the Raptors due to NBA rules prohibiting players or their associates from receiving ownership stakes, he allegedly tried to sidestep the restriction by targeting the Leafs instead. The Maple Leafs, after all, are part of a different league.
But there was one glaring problem: both the Raptors and Maple Leafs are owned by the same parent company, Maple Leaf Sports & Entertainment (MLSE). The Raptors’ brass reportedly responded with polite disbelief, explaining that the request was not only unconventional, it was impossible.
This wasn’t the only bold move from Uncle Dennis during Kawhi’s free agency tour. Reports suggest he made similar demands to other teams, including private planes, guaranteed endorsement deals, and even real estate perks. While none of these were granted, they painted a picture of a negotiation style that pushed boundaries, and perhaps bent a few rules.
The NBA investigated the Raptors’ negotiations at the time but found no concrete violations. Still, the league issued a warning to all teams about maintaining compliance with free agency regulations going forward.
The Maple Leafs request has resurfaced in light of recent allegations that Leonard may have received improper benefits from the Clippers via a no-show endorsement deal with a now-defunct environmental company. With the NBA launching a new investigation, the 2019 Raptors saga suddenly feels less like a quirky anecdote and more like a piece of a larger puzzle.
Kawhi ultimately chose the Clippers, leaving Toronto with memories of a championship and a negotiation story that will live in sports lore. The idea that an NBA free agency meeting could include a pitch for NHL ownership is absurd, audacious, and somehow, perfectly on brand for the enigmatic Leonard camp.
