Timeline: Kawhi Leonard’s path back to Toronto

On July 18, 2018, the Toronto Raptors acquired Kawhi Leonard and Danny Green from the San Antonio Spurs, trading them for DeMar DeRozan, Jakob Poeltl, and a protected first-round draft pick. Leonard made his Raptors debut on October 17, 2018, scoring 24 points in a 116-104 victory against the Cleveland Cavaliers. His first season with the Raptors saw him win the NBA Championship, earning him the NBA Finals MVP title.

However, Leonard's time with the Raptors was not without controversy. In July 2019, he left Toronto, signing with the Los Angeles Clippers as a free agent. Leonard suffered a torn ACL while playing for the Clippers, forcing him to miss the entire 2021-22 season due to surgery.

In September 2025, the NBA began an investigation into Leonard after allegations surfaced that he had signed a $28-million "no-show" endorsement deal with Aspiration, a financial technology company. This deal required no work beyond remaining with the Clippers. Throughout his time with the Clippers, Leonard battled injuries but averaged a career-high 27.9 points in 65 games during the 2025-26 season.

The Clippers and Raptors agreed to trade Leonard on June 30, 2026, with the deal held up due to the NBA's ongoing investigation into the Clippers. The investigation, which centered around potential salary-cap violations, was resolved by the NBA on September 2, 2026, clearing the way for Leonard's return to Toronto. The trade was finalized on September 14, 2026, marking Leonard's return to the Raptors seven years after his first stint with the team.