Timeline: Kawhi Leonard’s road to, from and back to Toronto
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TORONTO – Kawhi Leonard is returning to Toronto seven years after leading the Raptors to the franchise’s only NBA championship. Here’s a look at 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.
Sept. 24, 2018 — Leonard is introduced at Raptors media day, where his awkward “I’m a fun guy” comment becomes a viral moment.
Oct. 17, 2018 — Leonard scores 24 points in his Raptors debut, a 116-104 victory over the Cleveland Cavaliers.
Nov. 29, 2018 — Leonard returns to San Antonio for the first time since requesting a trade. The Spurs defeat the Raptors 125-107.
May 12, 2019 — Leonard hits a buzzer-beating shot over Philadelphia’s Joel Embiid to lift Toronto to a 92-90 Game 7 victory and its first Eastern Conference final appearance.
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 is named NBA Finals MVP.
June 17, 2019 — More than two million people attend the Raptors’ championship parade in downtown Toronto. Leonard’s “What it do, baby?” greeting to the crowd becomes another memorable moment from his lone 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 formally introduce Leonard after his return to his home state of California.
uly 2021 — Leonard undergoes surgery to repair a torn ACL 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 beyond remaining with the Clippers.
2019-26 — Leonard battles injuries throughout his seven years with the Los Angeles Clippers but averages 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 2027 first-round pick swap and two second-round picks.
July 9, 2026 — The Raptors put the trade on hold after the NBA said the team would assume the risk of any outcome from the league’s ongoing investigation into the Los Angeles Clippers.
Sept. 2, 2026 — The NBA declined to suspend Leonard or void his contract after its salary-cap circumvention investigation into the Clippers, clearing the way for his trade to Toronto.
Sept. 14, 2026 — The Raptors and Clippers make the deal official.
This report by The Canadian Press was first published Sept. 14, 2026.