The Los Angeles Clippers have agreed to trade Kawhi Leonard to the Toronto Raptors, per ESPN. The deal would send Leonard back to Toronto, where he spent one season and led the Raptors to the 2019 championship -- something he was never able to accomplish during a disappointing seven-year tenure in Los Angeles.
In the end, Leonard's time with the Clippers will be remembered for his dramatic arrival, a parade of injuries, a lack of playoff success and a bizarre investigation. He missed the entire 2021-22 season with a torn ACL, played in 331 of a possible 554 regular-season games, won three playoff series and never appeared in a game beyond the second round. (The Clippers made the Western Conference Finals for the first time in franchise history in 2021 after Leonard tore his ACL in the second round.)
Though Leonard is no longer with the team, the Clippers remain under investigation by the league for allegedly circumventing the salary cap by using a no-show endorsement deal with Aspiration, a now-bankrupt sustainability company, to funnel money to Leonard. Both Leonard and Dennis Robertson -- Leonard's uncle and advisor -- have been interviewed as part of the league's investigation.
The Leonard era in Los Angeles won't be fully complete until the league closes its investigation, but the on-court aspect has now ended, so let's take a look back at the seven-time All-Star's time with the Clippers.
Kawhi Leonard trade grades: Clippers get 'A+' for franchise-altering pivot as Raptors take major risk Sam Quinn
A foreboding late-night arrival
In the summer of 2019, immediately after he led the Raptors to the first title in franchise history, Leonard was able to make a real case as the best player in the world. At the time, he was the most sought-after free agent during a star-studded summer that also saw Kevin Durant, Kyrie Irving and Jimmy Butler change teams.
While Durant and Irving quickly agreed to deals with the Brooklyn Nets, and Butler went to the Miami Heat in a sign-and-trade deal a few days later, Leonard bided his time. The Raptors and Los Angeles Lakers both thought they had a real chance to sign Leonard, but he eventually settled on the Clippers -- though not until after they had agreed to acquire Paul George in exchange for Shai Gilgeous-Alexander, Danilo Gallinari, five first-round picks (four unprotected) and two first-round pick swaps.
Late on July 5, 2019, (or extremely early on July 6, depending on your location), the deal(s) were finally done. They came in conjunction just hours after a 7.1-magnitude earthquake struck Ridgecrest, California. The most powerful earthquake to hit Southern California in nearly 20 years could be felt as far away as Las Vegas, where multiple NBA Summer League games were canceled.
"I'm just fired up to be here today. Pretty cool, pretty damn cool," an emphatic Clippers owner Steve Ballmer said, before screaming into the microphone a few weeks later at Leonard and George's introductory press conference. "... Being number two, being number four. We're only here for one reason. We want to win it all."
"We've got something special," Leonard said. "We can make history here, and we've got the right team to do it."
Injuries, injuries and more injuries
In his Clippers debut on Oct. 22, 2019, Leonard went off for 30 points, six rebounds and five assists in a win over LeBron James and the Lakers. Eight days later, he was absent 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 sat out again against the Milwaukee Bucks. Prior to that game, then-Clippers coach Doc Rivers said Leonard felt "great," and there was no reason for long-term concern. The league later fined the Clippers $50,000 due to Rivers making comments that were "inconsistent" with Leonard's health, but determined that Leonard did have a medical reason for sitting out of back-to-backs.
"Kawhi Leonard is not a healthy player under the league's resting policy, and, as such, is listed as managing a knee injury in the LA Clippers injury report," league spokesman Mike Bass said in a statement at the time. "The league office, in consultation with the NBA's director of sports medicine, 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."
Leonard was not fully healthy when he arrived in Los Angeles, and he would rarely be over his seven years with the franchise.
Leonard's games played in Los Angeles
SeasonRegular season Playoffs2019-20
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
--
Total331/554 (59.7%)35/50 (70%)Most notably, Leonard tore his ACL during Game 4 of the Clippers' second-round series with the Jazz in 2021. The injury knocked him out of the playoffs, sidelined him for the entire 2021-22 season, and contributed to him missing 19 of the team's first 25 games in the 2022-23 season. In Game 2 of the Clippers' first-round series with the Phoenix Suns in 2023, Leonard tore his right meniscus and had to undergo another surgery.
"I feel good and I'm ready to go," Leonard said ahead of the 2023-24 season. "I think last year came off of the ACL, so pretty much it's like a two-year process. Talking to guys [who suffered ACL injuries] and seeing when they do start feeling good or just trusting your knee, it's just something that you feel and I mean one day just turns around for you. So it wasn't really nothing too different."
True to his word, Leonard played 68 games in the 2023-24 season, his most in a Clippers uniform. However, his right knee flared up in the spring, and despite an injection, he missed the final eight games of the regular season and four of the Clippers' six games in the first round of the playoffs against the Dallas Mavericks.
Leonard, who was sent home from Team USA training camp and did not participate in the 2024 Olympics in Paris, underwent another procedure on his right knee ahead of the 2024-25 season and missed the first 34 games. He wound up playing just 37 games -- his second-fewest with the Clippers.
Though Leonard was largely healthy last season, and had arguably his best individual campaign -- 27.9 points, 6.4 rebounds, 3.6 assists and 1.9 steals on 50.5/38.7/89.2 shooting splits -- it wasn't enough for the team to make the playoffs. Midway through the season, the Clippers pivoted to a rebuild.
Clippers did not lift 'the Larry O'B'
The Clippers' franchise history dates back to 1970, when they debuted as the Buffalo Braves. They relocated to San Diego in 1978, before permanently moving to Los Angeles in 1984.
When Ballmer purchased the franchise in 2014, they had won four playoff series in 10 postseason appearances and had never advanced past the second round.
"We're going to be bold. Bold means taking chances," Ballmer said in 2014 after completing his historic purchase. "We're going to be optimistic. We're going to be 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 just one more series win. Leonard (and George) were going to finally take the Clippers to the promised land, Ballmer boasted.
"Kawhi said something when [the Raptors] won the championship this year about the Larry O'B. The only thing that matters is the Larry O'B." Ballmer said during Leonard's intro presser. "When I first got here, I think I called it the Lawrence O'Brien. From now on, it's all about the Larry O'B."
The Clippers made the playoffs in five of Leonard's seven seasons with the team and, in 2021, reached the Western Conference Finals for the first time in franchise history, but still have not lifted the Larry O'B. Leonard, who did not play in the 2021 West Finals due to his torn ACL, was fully healthy for just two of the Clippers' five playoff appearances: 2020 and 2025.
Clippers' playoff results during Leonard's time in L.A.
SeasonRegular season recordPlayoff seedPlayoff result2019-20
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
Leonard, to his credit, was generally incredible when he was on the floor in the playoffs. Over 35 playoff appearances, many of which came at far less than 100%, he averaged 27.7 points, 8.2 rebounds, 4.8 assists and two steals on 52.7/37.1/85.3 shooting splits. He scored at least 30 points in 15 of his 35 playoff games with the team.
At the same time, Leonard scored just 14 points on 6 of 22 shooting in their Game 7 loss to the Denver Nuggets in the second round of the 2020 playoffs in the bubble when they blew a 3-1 lead. And in their 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 33 points when he was on the floor.
Major aspirations come crashing down
In September 2025, ahead of Leonard's final season with the Clippers, investigative journalist Pablo Torre dropped a bombshell report alleging that the organization circumvented the salary cap by helping Leonard secure a $28 million no-show endorsement deal with Aspiration.
Aspiration, founded by Joe Sanberg and Andrei Cherny in 2013, was a sustainability company that pledged to provide "socially-conscious and sustainable banking services and investment products." They received a $60 million personal investment from Ballmer and were also a major sponsor for the Clippers. In September 2021, the Clippers signed a $300 million endorsement deal with Aspiration, making the company the "first founding partner" of the Intuit Dome, the Clippers' new arena, which opened in 2024.
Aspiration went bankrupt in 2025 and Sanberg was sentenced to 14 years in federal prison earlier this month.
Clippers' Kawhi Leonard and 'Uncle Dennis' interviewed by NBA investigators in Aspiration case, per report James Herbert
"We made an investment in the company," Ballmer told ESPN in September. "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."
Ballmer, Clippers executives, Leonard and Robertson have been interviewed as part of the league's investigation, which is being conducted by New York-based law firm Wachtell, Lipton, Rosen & Katz, and remains open.
NBA commissioner Adam Silver was most recently asked about the investigation earlier this month ahead of the 2026 NBA Finals. While he said the investigation is "far along," he would not provide a timeline for its expected completion.
"The investigation is being conducted by a law firm independent of the NBA," Silver said. "I mean, yes, 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.
"What essentially happens here is that the factual report, together with findings, will be made by this independent firm," Silver continued. "That's presented to me. It's then, ultimately, my role to determine what the appropriate discipline, if any, should be meted out based on their findings."
The possible punishments for the Clippers could include a fine, suspensions for team personnel and/or a loss of draft picks. Or, they may not be punished at all.
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