Steve Ballmer Allegedly Repeats Old Mistake as Kawhi Leonard Deal Allegations Puts Clippers in Serious Jeopardy

When mistakes repeat, people start calling them intentional. Or perhaps they were never mistakes at all. History now casts a sharp light on the Los Angeles Clippers, where 2015 and 2019 carry striking similarities under Steve Ballmer’s rule. The timelines overlap, and the whispers echo louder. And the scrutiny over his franchise? It’s growing again.

The DeAndre Jordan free agency saga in 2015 delivered pure drama as the 27-year-old first committed to the Dallas Mavericks before stunningly returning to the Clippers. Yet the real violation emerged elsewhere. According to the league, the issue stemmed from the Clippers’ July 2 presentation. During those negotiations, team officials improperly raised a potential third-party endorsement opportunity.

Now, the NBA later ruled that the endorsement pitch did not influence Jordan’s decision, since he chose the Mavericks immediately after the July 2 meeting. Furthermore, a source confirmed that the center never pursued business with the company tied to the presentation. Thus, the controversy circled intent rather than any executed agreement.

This resulted in blisters in Steve Ballmer’s pocket. NBC Sports reported back in 2015, “The NBA announced today that it has fined the Los Angeles Clippers $250,000 for violating NBA rules prohibiting teams from offering players unauthorized business or investment opportunities.” 

The Clippers reportedly offered DeAndre Jordan a $200,000 annual Lexus endorsement, which drew NBA disapproval. While teams may highlight market advantages or even hint at city-based sponsors, directly arranging specific deals crosses a clear boundary. In this instance, the league uncovered a directly facilitated Lexus offer, pushing the violation into undeniable territory. And yes, the NBA has strict punishments for the same.

Well, Article XIII of the CBA stands as the NBA’s strongest anti-circumvention safeguard. It blocks teams from compensating players beyond their contracts, whether through hidden deals, alternate jobs, or inflated sponsorships. It further bans inducements, investments, and business opportunities for players, agents, or family members. By doing so, it closes every possible channel for secretly bypassing the salary cap’s financial limits.

The same Article XIII empowers the league to identify violations through direct or circumstantial evidence, even by reviewing tax records. Penalties carry weight, including fines up to $6 million, draft pick forfeiture, suspensions of executives, and voiding contracts. The NBPA can suspend agents for a minimum of one year. Appeals face the deferential, arbitrary, and capricious standard.

History appears to circle back for Steve Ballmer and the Los Angeles Clippers. The spotlight once fell on DeAndre Jordan, but the plot has now shifted. It is Kawhi Leonard, the franchise’s prized star, standing at the center of fresh allegations that echo the past with even greater intensity.

Kawhi Leonard’s deal allegations open controversies for Steve Ballmer & Co

In 2019, Kawhi Leonard left the Toronto Raptors fresh off a championship and joined Steve Ballmer’s Los Angeles Clippers in a move that immediately stirred suspicion. Now the controversy has reignited, as journalist Pablo Torre alleges the Clippers exploited a loophole. He claims Leonard received $28 million for a fabricated role with Aspiration, a tree planting company tied to Ballmer, which later collapsed into bankruptcy, still owing $7 million.

Torre said he uncovered a paper trail linking Leonard through KL2 Aspire LLC, a company he owns. Yet despite the massive investment, Leonard never promoted Aspiration while other celebrities visibly endorsed it. Torre cited testimony from an employee who called it a “no-show job.” The employee recalled that someone told them the $28 million marketing deal existed solely to circumvent the salary cap and ordered them never to question it.

Meanwhile, the Los Angeles Clippers have responded to Pablo Torre’s claims. And well, they deny any wrongdoing. “Neither Mr. Ballmer nor the Clippers circumvented the salary cap or engaged in any misconduct related to Aspiration,” the organization wrote. “Any contrary assertion is provably false.”

Scandals have long shadows, and the Clippers seem to walk right back into them. From DeAndre Jordan’s Lexus entanglement to Kawhi Leonard’s alleged $28 million no-show deal, the echoes are unmistakable. The league has the rulebook, the fines, and the power. Yet the bigger question lingers—what comes next for the franchise?