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TORONTO – Kawhi Leonard returns to Toronto seven years after leading the Raptors to the franchise’s only NBA championship. Here are the key dates from Leonard’s first stint with the Raptors to his return to Toronto:
July 18, 2018 — The Toronto Raptors acquire Kawhi Leonard and Danny Green from the San Antonio Spurs in exchange for DeMar DeRozan, Jakob Poeltl and a protected first-round draft pick.
September 24, 2018 — Leonard is introduced at Raptors media day, where his awkward “I’m a people pleaser” comment becomes a viral moment.
October 17, 2018 — Leonard scores 24 points in his Raptors debut, a 116-104 win over the Cleveland Cavaliers.
November 29, 2018 — Leonard returns to San Antonio for the first time since requesting a trade. The Spurs beat the Raptors 125-107.
May 12, 2019 — Leonard hits a thunderous shot over Philadelphia’s Joel Embiid to lift Toronto to a 92-90 victory in Game 7 and its first Eastern Conference finals appearance.
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June 13, 2019 — Leonard scores 22 points as the Raptors defeat the Golden State Warriors 114–110 in Game 6, winning the franchise’s first NBA title. He was named MVP of the NBA Finals.
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June 17, 2019 — More than two million people attend the Raptors’ championship parade in downtown Toronto. Leonard, “What does it do, darling?” his greeting to the crowd was another memorable moment from his only season with the franchise.
July 6, 2019 — Leonard leaves Toronto after one season, signing as a free agent with the Los Angeles Clippers.
July 10, 2019 — The Clippers officially introduce Leonard after his return to his home state of California.
start 2021 — Leonard underwent surgery to repair a torn ACL he suffered during the Clippers’ playoff run, causing him to miss the entire 2021-22 season.
September 2025 — The NBA opens an investigation following allegations first reported by journalist Pablo Torre that Leonard signed a US$28 million “no-show” endorsement deal with Aspiration, an environmental financial technology company, that required no work other than remaining with the Clippers.
2019-26 — Leonard battled injuries during his seven years with the Los Angeles Clippers but averaged a career-high 27.9 points in 65 games in the 2025-26 season.
June 30, 2026 — The Clippers agree to trade Leonard to the Raptors for Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, a swap of 2027 first-round picks, and two second-round picks.
July 9, 2026 — The Raptors postpone the trade after the NBA says the team will assume the risk of any outcome from the league’s ongoing investigation into the Los Angeles Clippers.
September 2, 2026 — The NBA refuses to suspend Leonard or void his contract following a salary cap circumvention investigation against the Clippers, paving the way for his trade to Toronto.
September 14, 2026 — The Raptors and Clippers make the deal official.
This report by The Canadian Press was first published Sept. 14, 2026.
© 2026 Canadian Press
