The Leonard-Clippers Saga Concludes: A Return to Toronto Amidst Lingering NBA Inquiry

Kawhi Leonard’s seven-year tenure with the Los Angeles Clippers has concluded with his trade back to the Toronto Raptors, a move that marks the end of an ambitious but ultimately unfulfilled era for the Clippers. Leonard, who famously led the Raptors to their first NBA championship in 2019, was unable to replicate that success in Los Angeles, departing amidst a backdrop of persistent injury concerns, limited playoff advancement, and an ongoing league investigation into alleged salary cap circumvention.

Leonard’s time in Los Angeles, spanning from his high-profile free-agent signing in 2019 to his recent departure, was characterized by dramatic expectations, a "load management" controversy that sparked league-wide discussion, and a series of significant injuries that hampered his availability. Over his seven seasons with the Clippers, he participated in only 331 of a possible 554 regular-season games, equating to approximately 59.7% availability. In the postseason, where his reputation as a "playoff performer" was built, he played in 35 of 50 possible games (70%). Despite his individual brilliance, the Clippers advanced past the second round only once, reaching the Western Conference Finals in 2021—a series he largely missed due to injury.

The conclusion of Leonard’s on-court chapter with the Clippers precedes the resolution of a significant off-court matter: an ongoing NBA investigation into the franchise for allegedly circumventing the league’s salary cap. The probe centers on a purported "no-show" endorsement deal with Aspiration, a now-bankrupt sustainability company, allegedly used to funnel money to Leonard. Both Leonard and his uncle and advisor, Dennis Robertson, have reportedly been interviewed as part of the league’s inquiry. The investigation’s findings and any potential disciplinary actions are still pending, casting a shadow over the full legacy of the Leonard era.

A Foreboding Late-Night Arrival

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The journey began in the summer of 2019, immediately following Leonard’s MVP-caliber performance that secured the Toronto Raptors’ historic championship. As arguably the most coveted free agent in a star-studded class that included Kevin Durant, Kyrie Irving, and Jimmy Butler, Leonard’s decision was the subject of intense speculation. While Durant and Irving quickly opted for the Brooklyn Nets and Butler joined the Miami Heat, Leonard prolonged his decision, creating a high-stakes bidding war between the Raptors and the Los Angeles Lakers.

Ultimately, Leonard chose the Clippers, but his decision was contingent on the franchise first acquiring another All-Star talent. This led to the Clippers executing a blockbuster trade for Paul George, sending a substantial package to the Oklahoma City Thunder that included Shai Gilgeous-Alexander, Danilo Gallinari, five first-round picks (four unprotected), and two first-round pick swaps. This unprecedented haul of assets underscored the Clippers’ determination to build an immediate championship contender around Leonard.

The dual announcements—Leonard’s signing and George’s acquisition—were made late on July 5, 2019, or in the early hours of July 6, coinciding with a 7.1-magnitude earthquake that struck Ridgecrest, California. The seismic event, the most powerful to hit Southern California in nearly two decades, was felt across the region and led to the cancellation of several NBA Summer League games in Las Vegas. For many, the unusual timing added a layer of dramatic, almost foreboding, symbolism to the Clippers’ audacious move.

At their introductory press conference weeks later, Clippers owner Steve Ballmer exuded infectious optimism. "I’m just fired up to be here today. Pretty cool, pretty damn cool," Ballmer declared, emphasizing the team’s singular goal: "We want to win it all." Leonard echoed this sentiment, stating, "We’ve got something special. We can make history here, and we’ve got the right team to do it." The expectations were sky-high, fueled by the arrival of two perennial All-Stars and the promise of a new era for a franchise historically overshadowed by its crosstown rival.

A Litany of Injuries and "Load Management"

Leonard’s Clippers debut on October 22, 2019, offered a glimpse of his potential, as he delivered 30 points, six rebounds, and five assists in a commanding victory over LeBron James and the Lakers. However, this early promise was quickly tempered. Just eight days later, he was sidelined for the team’s fifth game of the season, a loss to the Utah Jazz, due to "load management" for his left knee.

A week later, Leonard again sat out against the Milwaukee Bucks. Then-Clippers coach Doc Rivers initially stated that Leonard felt "great," prompting the league to fine the Clippers $50,000 for comments deemed "inconsistent" with Leonard’s actual health status. Nevertheless, the NBA ultimately concluded that Leonard did have a legitimate medical reason for avoiding back-to-back games. League spokesman Mike Bass confirmed, "Kawhi Leonard is not a healthy player under the league’s resting policy, and, as such, is listed as managing a knee injury… The league office… is comfortable with the team medical staff’s determination that Leonard is not sufficiently healthy to play in back-to-back games at this time." This incident marked the beginning of a pattern where Leonard’s health became a central narrative point throughout his Clippers tenure.

Indeed, Leonard was rarely fully healthy during his seven seasons in Los Angeles, with a series of significant injuries severely impacting his availability and the team’s continuity.

Season	Regular Season Games Played	Playoff Games Played
2019-20	57/72	13/13
2020-21	52/72	11/19
2021-22	0/82	—
2022-23	52/82	2/5
2023-24	68/82	2/6
2024-25	37/82	7/7
2025-26	65/82	—
Total	331/554 (59.7%)	35/50 (70%)

Most notably, Leonard suffered a torn ACL during Game 4 of the Clippers’ second-round series against the Utah Jazz in 2021. This severe injury not only ended his playoff run that year but also sidelined him for the entirety of the 2021-22 season. His recovery extended into the 2022-23 season, where he missed 19 of the team’s first 25 games. In Game 2 of the Clippers’ first-round series against the Phoenix Suns in 2023, Leonard sustained another significant injury, tearing his right meniscus, which required further surgery.

Despite these setbacks, Leonard expressed optimism about his health ahead of the 2023-24 season, stating, "I feel good and I’m ready to go. I think last year came off of the ACL, so pretty much it’s like a two-year process… one day just turns around for you." True to his word, he played 68 games that season, his most in a Clippers uniform. However, his right knee issues resurfaced in the spring, leading to an injection and causing him to miss the final eight regular-season games and four of the Clippers’ six playoff games against the Dallas Mavericks.

Further compounding his injury woes, Leonard was sent home from Team USA training camp and did not participate in the 2024 Olympics in Paris. He underwent yet another procedure on his right knee before the 2024-25 season, resulting in him missing the first 34 games and ultimately playing only 37 games—his second-fewest with the Clippers. While he recorded arguably his best individual campaign in the 2024-25 season, averaging 27.9 points, 6.4 rebounds, 3.6 assists, and 1.9 steals on efficient 50.5/38.7/89.2 shooting splits, his absence at crucial junctures prevented the team from making the playoffs. This mid-season failure prompted the Clippers to pivot towards a rebuild, setting the stage for his eventual departure.

Clippers Did Not Lift ‘the Larry O’B’

The Los Angeles Clippers franchise, with roots dating back to the Buffalo Braves in 1970, has a long history of playoff futility. Prior to Steve Ballmer’s historic purchase of the team in 2014, the franchise had won only four playoff series in ten postseason appearances and had never advanced beyond the second round. Ballmer’s acquisition was heralded as a new beginning, with the owner boldly proclaiming, "We’re going to be bold… optimistic… hardcore. Nothing gets in our way — boom! The hardcore Clippers. That’s us. I’ll boldly say the Clippers will win many, many more Larrys in the next 26 years than they did in the last 26."

By the time Leonard arrived in 2019, the Clippers had added four more postseason appearances but only one more series win. Leonard and George were explicitly brought in to finally deliver the coveted "Larry O’B" – the Larry O’Brien Championship Trophy. Ballmer, referencing Leonard’s championship experience, emphasized this goal during the introductory press conference: "The only thing that matters is the Larry O’B."

During Leonard’s seven seasons, the Clippers made the playoffs in five instances. In 2021, they achieved a franchise milestone, reaching the Western Conference Finals for the first time. However, this historic achievement was bittersweet, as Leonard was sidelined due to his torn ACL, preventing him from participating in the series. The team ultimately fell short, and the "Larry O’B" remained elusive. Leonard was fully healthy for only two of the Clippers’ five playoff appearances during his tenure: 2020 and 2025.

Season	Regular Season Record	Playoff Seed	Playoff Result
2019-20	49-23	No. 2	Lost in second round
2020-21	47-25	No. 4	Lost in WCF
2021-22	42-40	N/A	N/A
2022-23	44-38	No. 5	Lost in first round
2023-24	51-31	No. 4	Lost in first round
2024-25	50-32	No. 5	Lost in first round
2025-26	42-40	N/A	N/A

Individually, Leonard often delivered exceptional playoff performances when on the court. Across 35 playoff games with the Clippers, many played at less than 100% health, he averaged 27.7 points, 8.2 rebounds, 4.8 assists, and two steals, with impressive shooting splits of 52.7% from the field, 37.1% from three-point range, and 85.3% from the free-throw line. He scored at least 30 points in 15 of these 35 contests, demonstrating his individual capacity to dominate.

However, critical moments also saw him falter. In the decisive Game 7 loss to the Denver Nuggets in the second round of the 2020 playoffs, a series where the Clippers famously squandered a 3-1 lead, Leonard managed just 14 points on 6-of-22 shooting. Similarly, in the Game 7 loss to the Nuggets in the first round of the 2025 playoffs, he shot 6-of-13, and the Clippers were outscored by a significant 33 points during his time on the floor. These performances highlight the gap between individual brilliance and ultimate team success, a defining characteristic of his Clippers era.

Major Aspirations Come Crashing Down: The Aspiration Investigation

Adding a complex and potentially damaging dimension to Leonard’s Clippers saga is the ongoing NBA investigation. In September 2025, prior to what became Leonard’s final season with the team, investigative journalist Pablo Torre published a report alleging that the Clippers organization engaged in salary cap circumvention. The report claimed the team facilitated a $28 million "no-show" endorsement deal with Aspiration, a sustainability company, to funnel money to Leonard.

Aspiration, co-founded by Joe Sanberg and Andrei Cherny in 2013, aimed to provide "socially-conscious and sustainable banking services and investment products." The company had significant ties to the Clippers, including a $60 million personal investment from Ballmer and a major sponsorship role. In September 2021, Aspiration signed a $300 million endorsement deal with the Clippers, becoming the "first founding partner" of the Intuit Dome, the team’s new arena that opened in 2024.

However, Aspiration filed for bankruptcy in 2025, and Joe Sanberg, one of its founders, was subsequently sentenced to 14 years in federal prison earlier this month for unrelated charges. Ballmer, addressing his investment in Aspiration, told ESPN in September 2025, "We made an investment in the company. All fine. I had no control over this company. This is important under the salary cap rules. I owned less than three percent of the company. There were investors who put in a lot more money than I did. I had no board seat. I had no control. Heck, it was a fraudulent company. It’s possible nobody had control."

The NBA’s investigation, being conducted by the independent New York-based law firm Wachtell, Lipton, Rosen & Katz, remains open. Ballmer, various Clippers executives, Leonard, and Robertson have all been interviewed as part of the extensive inquiry. NBA Commissioner Adam Silver, most recently questioned about the investigation ahead of the 2026 NBA Finals, indicated the probe was "far along" but declined to provide a timeline for its completion.

"The investigation is being conducted by a law firm independent of the NBA," Silver stated. "Ultimately we are paying their bills, but they are doing the work independent of the league office. My instruction to them is we can’t be investigating forever, and at some point, we have to wrap it up, but at the same time, I think the most important thing is we get it right." He further explained that a factual report with findings would be presented to him, after which it would be his role to determine appropriate discipline, if any. Potential punishments for the Clippers could range from significant fines and suspensions for team personnel to the forfeiture of draft picks, or the league could conclude no violations occurred. The resolution of this investigation will provide a final, albeit off-court, chapter to Kawhi Leonard’s complex and memorable tenure with the Los Angeles Clippers.

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