When Kawhi Leonard joined the Los Angeles Clippers in 2019, it was supposed to mark the start of a new era. Steve Ballmer had poured billions into turning the once-ridiculed franchise into a powerhouse, and Leonard’s arrival alongside Paul George was hailed as a franchise-defining moment.
But six years later, the results tell a different story. The Clippers have won only three playoff series since Leonard arrived, and now, frustration has been bubbling inside the organization for two very specific reasons.
The first source of tension is Leonard’s injuries and lack of availability. According to Baxter Holmes of ESPN, some within the Clippers had grown “fatigued” by Leonard’s constant health issues, which have limited him to just 42 percent of the team’s games since 2019.
The numbers are staggering: Leonard has missed a whopping 191 games in the past five seasons, the third most in the NBA during that span. That’s more than two full seasons lost to injuries, and it has repeatedly derailed the Clippers’ postseason hopes.
The concern boiled over during the 2023-24 season, when Leonard was eligible for a massive four-year, $220 million extension. Instead of handing him the max, the Clippers prioritized salary cap flexibility, knowing that Leonard’s reliability was a major question mark. That decision wasn’t only about money.
The team understood that any other franchise considering Leonard would demand a full medical evaluation, meaning the Clippers held leverage over his future.
Simply put, the organization knows exactly “what’s under the hood,” as one staffer put it, and they’ve grown weary of building around a superstar who cannot consistently stay on the floor.
The second reason is the secrecy and off-court drama surrounding Leonard, which has dragged the team into repeated legal and financial headaches. From the moment Leonard signed in Los Angeles, the Clippers bent over backwards to accommodate demands from his camp including special living arrangements, skipped media duties, and a wall of secrecy around his health.
That secrecy has created internal rifts between staffers and strained the culture of the organization. Worse, it has also landed the team in repeated controversy. Since 2019, the Clippers have been fined multiple times and investigated on at least three separate occasions by the NBA over issues tied to Leonard.
The latest and most damaging involves Aspiration, a now-bankrupt financial company tied to Clippers governor Steve Ballmer. Leonard received $28 million in sponsorship money from Aspiration, including a delayed $1.75 million payment that coincided with a $1.99 million investment from Clippers co-owner Dennis Wong.
The NBA has launched a formal investigation into whether this deal amounted to salary cap circumvention, and insiders say this time the scrutiny cuts directly into Ballmer’s credibility.
Taken together, Leonard’s health problems and the baggage around his camp have left the Clippers in a difficult position. On one hand, teammates still admire Leonard’s focus, discipline, and relentless effort when he plays.
In fact, he agreed to a three-year, $153 million deal in January 2024 after showing flashes of his old dominance. But on the other hand, the team has grown tired of living in constant fear of upsetting him, only to be rewarded with more missed playoff runs and another round of controversy.
Now 34 and under contract for two more seasons, Leonard remains the face of the Clippers, but insiders say the organization has quietly shifted its focus.
The franchise knows it cannot keep building around him forever. Injuries and secrecy have defined the Kawhi Leonard era in Los Angeles, and for many within the Clippers, that reality has become exhausting.
