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The Los Angeles Lakers came close to adding Kawhi Leonard in 2019. Six years later, one league executive believes missing out may have saved them from years of headaches.

“The Lakers wanted Kawhi badly,” the executive told Lakers Daily. “Boy, they dodged a massive bullet by not landing him. You think Rich [Paul] and LeBron are hard to deal with? Uncle Dennis (Dennis Robertson) is even worse. He thinks Kawhi is the second coming of Jesus.”

Instead of joining forces with LeBron James, Leonard signed with the Clippers and teamed up with Paul George. Now, Leonard and his team are under NBA investigation over allegations of circumventing salary cap rules through a $28 million endorsement deal tied to a now-bankrupt company partly funded by Clippers owner Steve Ballmer.

From Lakers Target to Clippers Star

Back in 2019, The Athletic reported that Robertson, Leonard’s uncle and top business advisor, made a series of unusual demands in free agency, including partial team ownership, a private jet and guaranteed off-court endorsement income. The Lakers pursued Leonard hard but ultimately lost out as he chose the Clippers, backed by Ballmer, the wealthiest owner in the league.

While the Lakers built their roster around James and Anthony Davis, whom the Lakers traded for after missing out on Leonard later that summer, Leonard’s Clippers tenure has been marked by long stretches of injury and limited availability.

“The guy barely plays, doesn’t market the team he’s on and now he’s in the news for the wrong reasons for the second time since signing with the Clippers,” the executive said. “This has been a huge headache for Ballmer and Co.”

The Current Probe

The latest controversy centers on a reported “no-show” sponsorship deal with Aspiration, an environmental startup that filed for bankruptcy after its co-founder pleaded guilty to defrauding investors. A whistleblower on the “Pablo Torre Finds Out” podcast alleged Leonard was paid millions through the arrangement in a way that skirted the salary cap.

“We also have a marketing deal with Kawhi Leonard, like a $28 million organic marketing sponsorship deal,” the former employee said. “And if I had any questions about it, don’t ask, because it was to ‘circumvent the salary cap. LOL.’”

The Clippers have denied wrongdoing, stating the team severed ties with Aspiration in 2023 after the company defaulted on obligations. “Neither Mr. Ballmer nor the Clippers circumvented the salary cap or engaged in any misconduct related to Aspiration,” the organization said in a statement sent to Torre’s podcast.

Possible Fallout

The NBA has opened an investigation into the deal, which could carry steep penalties if violations are confirmed. According to The Athletic, punishments could include fines, loss of draft picks, suspension of executives, and even voiding Leonard’s contract. Leonard himself could face a fine of up to $350,000 and be forced to return money tied to the deal unless he proves he was unaware of the violation.

The league has handed down stiff discipline in the past for cap circumvention, most notably when the Minnesota Timberwolves were stripped of five first-round picks in 2000 over an illegal arrangement with forward Joe Smith.

A Different Path for the Lakers

For the Lakers, the near miss in 2019 has aged differently. James and Davis delivered a championship in 2020, while Leonard’s Clippers have yet to make the NBA Finals and now find themselves entangled in another controversy

As one executive put it: “The Lakers dodged a massive bullet by not getting Kawhi.”