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Kawhi Leonard is heading back to Toronto, completing a remarkable full-circle journey nearly eight years after he first arrived in Canada. The Toronto Raptors officially completed a trade for Leonard on September 14, 2026, reuniting the franchise with the player who delivered its only NBA championship in 2019.
From San Antonio to Toronto
Leonard’s story with the Raptors began on July 18, 2018. Toronto acquired him and guard Danny Green from the San Antonio Spurs in exchange for DeMar DeRozan, Jakob Poeltl, and a protected first-round draft pick. The move was bold and immediately drew attention across the league.
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Leonard made his public debut with the team at Raptors media day on September 24, 2018. His now-famous “I’m a fun guy” comment went viral almost instantly. It became one of the most memorable moments of his time in Toronto, even before the season began.
He scored 24 points in his Raptors debut on October 17, 2018, as Toronto beat the Cleveland Cavaliers 116-104. Later that season, on November 29, 2018, he returned to San Antonio for the first time since requesting a trade. The Spurs won that game 125-107.
A Championship Season
Leonard’s defining moment came on May 12, 2019. He hit a buzzer-beating shot over Philadelphia’s Joel Embiid in Game 7, lifting Toronto to a 92-90 victory and the franchise’s first Eastern Conference Finals appearance. The shot became one of the most iconic in NBA playoff history.
Toronto then went on to face the Golden State Warriors in the NBA Finals. On June 13, 2019, Leonard scored 22 points as the Raptors won Game 6 by a score of 114-110, claiming the franchise’s first NBA title. Leonard earned NBA Finals MVP honors for his performance throughout the run.
Four days later, more than two million people lined the streets of downtown Toronto for the championship parade. Leonard greeted the crowd with his now-legendary phrase, “What it do, baby?” It was another unforgettable moment from a single extraordinary season.
Departure and Years with the Clippers
Despite the championship, Leonard left Toronto after just one season. On July 6, 2019, he signed as a free agent with the Los Angeles Clippers. The Clippers formally introduced him on July 10, 2019, marking his return to his home state of California.
His seven years with Los Angeles were defined largely by injury. In July 2021, he underwent surgery to repair a torn ACL suffered during the Clippers’ playoff run. The injury caused him to miss the entire 2021-22 season. However, Leonard bounced back in the 2025-26 season, averaging a career-high 27.9 points across 65 games.
Meanwhile, off-court controversy surfaced in September 2025. The NBA opened an investigation following allegations, first reported by journalist Pablo Torre, that Leonard had signed a US$28-million endorsement deal with Aspiration, an environmental financial technology company. The deal allegedly required no work beyond his continued presence with the Clippers. The league examined the arrangement as a potential salary-cap circumvention issue.
Return to Toronto Finalized
On June 30, 2026, the Clippers agreed to trade Leonard back to the Raptors. The deal included Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, a 2027 first-round pick swap, and two second-round picks.
The trade hit a significant obstacle on July 9, 2026. The NBA told the Raptors they would assume the risk of any outcome from the ongoing Clippers investigation. Toronto put the deal on hold as a result.
The situation resolved on September 2, 2026. The NBA declined to suspend Leonard or void his contract following the conclusion of its salary-cap circumvention investigation. That decision cleared the path for the trade to move forward. Toronto and Los Angeles then made the deal official on September 14, 2026, formally bringing Kawhi Leonard back to the city where he made history.
