Clippers Stunned Former GM With Secret Deals Involving Kawhi Leonard

A former Clippers executive sheds light on long-rumored deals surrounding Kawhi Leonard, as new revelations raise fresh questions about the team's tactics and NBA compliance.

The Kawhi Leonard-Aspiration saga might’ve quieted down in headlines, but behind the scenes, it’s anything but over. Pablo Torre has continued to peel back the layers, and what he’s uncovered could have lasting implications for the Clippers - and potentially, the league.

Let’s rewind a bit. In January, Torre reported that the Clippers were allegedly using the financial services company Aspiration to funnel additional money to Leonard outside of his official NBA salary - a major salary cap no-no.

The report sent shockwaves through the league, prompting an NBA investigation and sparking a firestorm of speculation. But as the Clippers started winning and Leonard kept producing at an elite level, the noise faded.

On the court, things were clicking. Off the court?

It seemed the controversy had been shelved.

But now, Torre is back with new claims - and this time, he’s got a quote from someone who was inside the Clippers' front office during the early days of Leonard’s tenure.

Michael Winger, the Clippers’ former general manager, reportedly asked a pointed question during his time with the team: “How many side deals have we made with Kawhi?” According to Torre, that quote has been confirmed by multiple sources within the organization. If true, it suggests that Aspiration may have been just one piece of a much larger puzzle - a pattern of behavior rather than a one-off.

Torre's reporting also suggests the roots of this situation stretch back further than most assumed - all the way to 2017, when Leonard was still with the San Antonio Spurs. That’s when the Clippers reportedly began laying the groundwork to lure him to Los Angeles.

One key move? Hiring Randy Shelton, Leonard’s longtime trainer.

According to Torre, the Clippers told Shelton in 2017 that they’d bring him on board if Leonard eventually signed with the team. That’s a bold move - and one that raises eyebrows, especially considering who represented Shelton at the time: Leonard’s uncle, Dennis Robertson, better known in league circles as “Uncle Dennis.”

Fast forward to today, and Shelton is now suing the Clippers. Torre suggests that Shelton may have been part of a broader network of side arrangements designed to secure Leonard’s commitment to the franchise.

Of course, none of this is official - yet. The NBA’s investigation is still ongoing, and there’s no clear timeline for when (or if) the league will release its findings.

Until then, it’s all smoke without confirmed fire. But the details emerging from Torre’s reporting are painting a picture of a franchise that may have gone to extraordinary lengths to land - and keep - its superstar.

For now, the Clippers are focused on winning basketball games, and Leonard continues to perform at an MVP-caliber level. But the shadow of this investigation still looms. And if the league eventually determines that rules were broken, the consequences could be significant - not just for the Clippers, but for how teams across the NBA approach player recruitment and compensation going forward.