Aug 11, 2026; Toronto, Ontario, Canada; Los Angeles Clippers forward Kawhi Leonard (center) and his partner Kishele Shipley enjoy a light moment with a fan as they watch Naomi Osaka (JPN) play Elena Rybakina (KAZ) during quarter final play at Sobeys Stadium. Mandatory Credit: Dan Hamilton-Imagn Images
Aug 11, 2026; Toronto, Ontario, Canada; Los Angeles Clippers forward Kawhi Leonard (center) and his partner Kishele Shipley enjoy a light moment with a fan as they watch Naomi Osaka (JPN) play Elena Rybakina (KAZ) during quarter final play at Sobeys Stadium. Mandatory Credit: Dan Hamilton-Imagn Images
NBA superstar Kawhi Leonard has a lot going on right now. After a successful 2025-26 season that saw him post a career-high of 27.9 points per game, he’s currently eligible to sign a two-year, $120+ million extension that would keep him among the NBA’s highest-paid players. He’s also fresh off his trade to the Raptors, the same team he led to the 2019 championship.
In the background of all this is the NBA’s looming cap-circumvention investigation, clouding his situation in even more uncertainty. But despite the drama and chaos surrounding his future, Kawhi is showing no signs of distress. In fact, he made a rare public appearance today during the National Bank Open in Toronto. Besides the location, fans were quick to notice Leonard’s company: his longtime girlfriend, Kishele Shipley.
Kawhi Leonard attending the National Bank Open in Toronto alongside his girlfriend, Kishele Shipley, and Toronto realtor Sam McDadi.
— Omer Osman (@OmerOsman200) August 11, 2026
Kawhi and Kishele met at San Diego State University, where they began dating. They’ve been together for over 16 years now and have two children. For the most part, the duo lives a private life, rarely giving the public a glimpse of their relationship. That’s what makes today’s appearance so surprising, especially in light of the current circumstances.
Stars are out in Toronto 💫
A front-row seat at #NBO26 for Kawhi Leonard 😏 pic.twitter.com/8meEoQBeih
— Sportsnet (@Sportsnet) August 12, 2026
As Kawhi settles down in Toronto, he’s still waiting for the NBA’s ruling on the cap-circumvention investigation, which could threaten his return to Canada. It all began almost a year ago, when Leonard’s no-show endorsement deal with Aspiration (a fraudulent tree-planting company) was first unearthed. He seemingly got paid millions by the company, which was bankrolled by Steve Ballmer before eventually going bankrupt.
As time has passed, more and more ties have emerged between Ballmer, Kawhi, and payouts made by Aspiration. Recently, it was even discovered that Leonard may have had another secret endorsement deal with the Clippers’ scoreboard maker, Daktronics.
The suspicious discoveries prompted the NBA to launch a full investigation, and the implications could be disastrous for Kawhi and the Clippers. If found guilty, the team could face potential fines or the loss of draft picks. Kawhi himself could be suspended or have his contract voided if he is found to have played an active role in the scheme. Nevertheless, he’s acting and moving like the trade is already done and that he will avoid any major penalties.
So, if Kawhi’s appearance at the National Bank Open today means anything, it’s that he’s relatively unbothered by the noise. Even though the trade hasn’t gone through yet, he’s fully convinced that he’ll be a Raptor, and he wants everyone to know it. What it says about the actual investigation is unclear, but the Clippers have expressed a similar level of confidence in their innocence.
Ultimately, it could be weeks before we know where Kawhi will play next season, but he hasn’t looked this happy in a long time. Now that he’s back in Toronto, the two-time champion has seemingly found peace, and he likely won’t be willing to give it up without a fight.