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Kawhi Leonard is set to return to the Toronto Raptors seven years after leading them to their only NBA championship. The article outlines key dates from his initial acquisition in July 2018 through to his trade back to Toronto on September 14, 2026. Notable events include his playoff performances with the Raptors, signing with the Los Angeles Clippers in 2019, and facing an investigation over a potential "no-show" endorsement deal in 2025 that did not impact his return to Toronto.
Written by the local model on 2026-09-15,
using this article's own text rather than the other coverage of the
same event (that is the story summary below).
Story summary
In July 2021, Kawhi Leonard underwent surgery to repair a torn ACL sustained during the playoffs with the Los Angeles Clippers, causing him to miss the entire 2021-22 season. On September 24, 2025, the NBA launched an investigation into allegations that Leonard had signed a $28 million "no-show" endorsement deal with environmental fintech company Aspiration while playing for the Clippers, requiring no work beyond remaining on the team. This timeline details significant moments from Leonard's first stint with the Toronto Raptors, including his trade to Toronto in July 2018 and leading them to their first NBA championship in June 2019.
Written for “Kawhi Leonard Return Timeline” on 2026-09-15,
grounded in this article and the 0 other(s) covering the same event.
Why this leaning score
This article does not take a side on a contested political
question, so it has no leaning score. That is an
answer rather than a gap: a match report or a rescue can be warmly
or critically written without being left or right, and scoring it
anyway is how approval of a subject gets recorded as a political
position.
No political leaning scored for article 9697 · logged 2026-09-15
TORONTO – Kawhi Leonard is returning to Toronto seven years after leading the Raptors to the franchise’s only NBA championship.
asserted
Leonard → return → championship
Here’s a look at key dates from Leonard’s first stint with the Raptors to his return to Toronto:
asserted
look → ’ → 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.
asserted
Raptors → acquire → DeRozan
Sept. 24, 2018 — Leonard is introduced at Raptors media day, where his awkward “I’m a fun guy” comment becomes a viral moment.
asserted
comment → introduce → day
Oct. 17, 2018 — Leonard scores 24 points in his Raptors debut, a 116-104 victory over the Cleveland Cavaliers.
asserted
Leonard → score → Cavaliers
Nov. 29, 2018 — Leonard returns to San Antonio for the first time since requesting a trade.
asserted
Leonard → return → trade
The Spurs defeat the Raptors 125-107.
asserted
Spurs → defeat → Raptors
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.
uncertain
Leonard → hit → victory
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.
asserted
Raptors → score → title
He is named NBA Finals MVP.
asserted
He → name → ?
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June 17, 2019 — More than two million people attend the Raptors’ championship parade in downtown Toronto.
asserted
people → get → Toronto
Leonard’s “What it do, baby?” greeting to the crowd becomes another memorable moment from his lone season with the franchise.
asserted
greeting → become → 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.
asserted
Clippers → leave → 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.
asserted
that → undergo → 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.
asserted
Leonard → battle → 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.
asserted
Clippers → agree → 2033
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.
asserted
team → put → 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.
asserted
deal → decline → Toronto
This report by The Canadian Press was first published Sept. 14, 2026.
asserted
report → publish → Press
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