Back in 2019, when the Toronto Raptors were desperately trying to keep their championship hero, Kawhi Leonard’s camp threw them a curveball nobody saw coming. We’re talking about demands that went way beyond the usual superstar wishlist—like wanting a slice of the Toronto Maple Leafs hockey franchise.
When Basketball Players Want Hockey Teams
According to The Toronto Star’s bombshell report, Leonard’s uncle and business manager Dennis Robertson wasn’t messing around during those high-stakes negotiations. He pushed hard for Leonard to get actual ownership shares in the Maple Leafs—yes, the hockey team that shares ownership with the Raptors under Maple Leaf Sports & Entertainment (MLSE).
But wait, there’s more. Robertson didn’t stop at hockey ownership. He wanted pieces of other MLSE-connected companies too, while also demanding the Raptors lock in a guaranteed $10 million per year in sponsorship money for his nephew.
The Anti-Endorsement Endorsement Strategy
Here’s where things get really interesting. While most NBA stars are happy to smile for cameras and show up at sponsor events, Leonard’s people apparently wanted none of that traditional stuff. Sources familiar with the talks say Robertson made it crystal clear they “did not want to do anything” when it came to actual sponsorship work.
When the Raptors explained that endorsement deals typically involve, you know, actually endorsing things through appearances and promotional activities, Robertson’s response remained firm: not interested.
The Clippers Investigation That Changes Everything
Fast-forward to today, and these Toronto revelations take on new significance. The NBA is currently investigating whether Clippers owner Steve Ballmer bent salary cap rules by setting up what investigators are calling a “no-show” endorsement deal between Leonard and Aspiration, an eco-focused company that sponsors the Clippers.
Journalist Pablo Torre broke this story wide open on his podcast, revealing that Leonard signed a four-year, $28 million deal with Aspiration in 2021—one that supposedly required zero promotional work from the two-time Finals MVP.
Double-Dipping on the Side
The plot thickens even more. Reports from the Boston Sports Journal suggest Leonard might have scored a second, separate arrangement with Aspiration—what insiders describe as a “side deal” worth another $20 million in company stock, coming straight from Aspiration co-founder Joe Sanberg’s personal stash.
Sanberg’s recent guilty plea to wire fraud charges—he admitted to scamming investors and lenders out of more than $248 million—has only intensified the spotlight on these financial connections.
The Legal Heavy Hitters Step In
The NBA isn’t taking this lightly. They’ve brought in Wachtell, Lipton, Rosen & Katz—one of those white-shoe law firms that charges by the nanosecond—to dig into Leonard’s endorsement arrangements and whether the Clippers crossed any lines.
Steve Ballmer, for his part, continues to deny any wrongdoing in connection with these deals.
Leonard’s Toronto negotiations and his subsequent endorsement controversies paint a fascinating picture of how modern NBA superstars—and their representatives—are reshaping the business side of basketball, pushing boundaries on everything from ownership stakes to sponsorship obligations.
