Timeline: Kawhi Leonard’s road to, from and back to Toronto

Kawhi Leonard, a Toronto native, returned to his hometown NBA team after seven years away, leading the Raptors to their first NBA championship in 2019. Here's a timeline of Leonard's journey with the Raptors:

On July 18, 2018, the Raptors acquired Leonard from the San Antonio Spurs along with Danny Green, in exchange for DeMar DeRozan, Jakob Poeltl, and a protected first-round draft pick. Leonard immediately made an impact, scoring 24 points in his debut game against the Cleveland Cavaliers on October 17, 2018.

However, Leonard's time with Toronto was short-lived. He returned to San Antonio for the first time in November 2018, where the Spurs defeated the Raptors.

Leonard's breakout season came the following year, when he helped the Raptors win the NBA Finals against the Golden State Warriors, clinching the franchise's first championship. Leonard was named the NBA Finals MVP after scoring 22 points in Game 6 against the Warriors.

In July 2019, Leonard left Toronto to join the Los Angeles Clippers as a free agent. However, his stint with the Clippers was marred by injury and controversy. In July 2021, Leonard underwent surgery to repair a torn ACL, which forced him to miss the entire 2021-22 season.

Despite these challenges, Leonard continued to perform at a high level for the Clippers. In the 2025-26 season, he averaged a career-high 27.9 points per game in 65 games.

In June 2026, the Clippers agreed to trade Leonard to the Raptors in exchange for several draft picks and assets. The trade was put on hold temporarily due to an ongoing NBA investigation into the Clippers' potential salary-cap violations. However, after the investigation concluded without any penalties being levied against the Clippers, the trade was finalized on September 14, 2026. Leonard is set to begin his second stint with the Raptors in Toronto.