In June 2018, reports surfaced claiming that Leonard had requested a trade from the Spurs and that he did so after months of tension between his camp and the Spurs stemming from a disagreement over his injury rehabilitation program.
A month later, on July 18, Leonard and teammate Danny Green were traded to the Toronto Raptors in exchange for DeMar DeRozan, Jakob Pöltl and a protected 2019 first-round draft pick.
It was a risky move for the Raptors and their president, Masai Ujiri, given the concerns over Leonard's health and the possibility of him leaving as a free agent at the end of the season.
In his debut for the Raptors in their season opener on October 17, Leonard had 24 points and 12 rebounds in a 116–104 win over the Cleveland Cavaliers.
Two days later, he had 31 points and 10 rebounds in a 113–101 win over the Boston Celtics.

Leonard was named Eastern Conference Player of the Week for games played November 26 – December 2.
On January 1, he scored a career-high 45 points in a 122–116 win over the Utah Jazz.
On January 31 against the Milwaukee Bucks, Leonard's career-high streak of scoring at least 20 points in 22 consecutive games ended when he had 16 points in a 105–92 loss.

In Game 1 of the Eastern Conference semifinals against the Philadelphia 76ers, Leonard had a playoff career-high 45 points, on 16-of-23 (69.6%) shooting, to lead the Raptors in a 108–95 victory.
He became just the second player in Raptors history to eclipse 40 points in a playoff game, joining Vince Carter (50 points, 2001).
In the deciding Game 7, Leonard hit a shot from the corner at the buzzer that bounced off the rim four times before falling to give the Raptors a 92–90 victory over the 76ers to advance to the Eastern Conference Finals.
He finished the game with 41 points on 16-of-39 shooting.
This was the first Game 7 buzzer beater in NBA history and caused the normally calm Leonard to let out a victorious scream as he was swarmed by his teammates.
Leonard said of the shot afterward: 
It was great.
That's something I've never experienced before, Game 7, game-winning shot.
It was a blessing to be able to get to that point and make that shot and feel that moment.
It's something I can look back on in my career.

The Raptors continued their 2019 NBA Playoffs march against the top-seeded Milwaukee Bucks.
In Game 3 of the Eastern Conference Finals, Leonard scored 36 points, including eight in the second overtime, to help the Raptors beat Milwaukee 118–112 to cut the Bucks' series lead to 2–1.
In Game 5, he helped the Raptors take a 3–2 lead with 35 points on five 3-pointers to go with seven rebounds and nine assists in a 105–99 win.
In Game 6, he had 27 points and 17 rebounds to lead the Raptors into the NBA Finals for the first time with a 100–94 victory.
Leonard put an exclamation point on the conference victory with a huge dunk on Giannis Antetokounmpo that was set up by a Kyle Lowry steal.

Leonard led the Raptors into the 2019 Finals on the back of what was being described as an all-time great NBA playoff performance.
In Game 2, Leonard had 34 points and 14 rebounds in a 109–104 loss to Golden State.
Leonard helped the Raptors take a 3–1 series lead with 36 points and 12 rebounds in a 105–92 Game 4 win on the road in Oakland.
In Game 6, he scored 22 points in a 114–110 win to help lift the Raptors to a 4–2 series victory in claiming his second NBA championship.
He was subsequently named NBA Finals MVP for the second time, becoming just the third Finals MVP to have won the award with two teams, joining LeBron James and Kareem Abdul-Jabbar.
He is also the first person to win Finals MVP with a team from each conference.
Leonard scored 732 points during the 2019 playoffs; this was the third-best scoring total for a single NBA postseason in league history, behind only LeBron James (748, 2018) and Michael Jordan (759, 1992).
In June 2018, reports surfaced claiming that Leonard had requested a trade from the Spurs and that he did so after months of tension between his camp and the Spurs stemming from a disagreement over his injury rehabilitation program. A month later, on July 18, Leonard and teammate Danny Green were traded to the Toronto Raptors in exchange for DeMar DeRozan, Jakob Pöltl and a protected 2019 first-round draft pick. It was a risky move for the Raptors and their president, Masai Ujiri, given the concerns over Leonard's health and the possibility of him leaving as a free agent at the end of the season. In his debut for the Raptors in their season opener on October 17, Leonard had 24 points and 12 rebounds in a 116–104 win over the Cleveland Cavaliers. Two days later, he had 31 points and 10 rebounds in a 113–101 win over the Boston Celtics.
Leonard was named Eastern Conference Player of the Week for games played November 26 – December 2. On January 1, he scored a career-high 45 points in a 122–116 win over the Utah Jazz. On January 31 against the Milwaukee Bucks, Leonard's career-high streak of scoring at least 20 points in 22 consecutive games ended when he had 16 points in a 105–92 loss.
In Game 1 of the Eastern Conference semifinals against the Philadelphia 76ers, Leonard had a playoff career-high 45 points, on 16-of-23 (69.6%) shooting, to lead the Raptors in a 108–95 victory. He became just the second player in Raptors history to eclipse 40 points in a playoff game, joining Vince Carter (50 points, 2001). In the deciding Game 7, Leonard hit a shot from the corner at the buzzer that bounced off the rim four times before falling to give the Raptors a 92–90 victory over the 76ers to advance to the Eastern Conference Finals. He finished the game with 41 points on 16-of-39 shooting. This was the first Game 7 buzzer beater in NBA history and caused the normally calm Leonard to let out a victorious scream as he was swarmed by his teammates. Leonard said of the shot afterward: 
It was great. That's something I've never experienced before, Game 7, game-winning shot. It was a blessing to be able to get to that point and make that shot and feel that moment. It's something I can look back on in my career.
The Raptors continued their 2019 NBA Playoffs march against the top-seeded Milwaukee Bucks. In Game 3 of the Eastern Conference Finals, Leonard scored 36 points, including eight in the second overtime, to help the Raptors beat Milwaukee 118–112 to cut the Bucks' series lead to 2–1. In Game 5, he helped the Raptors take a 3–2 lead with 35 points on five 3-pointers to go with seven rebounds and nine assists in a 105–99 win. In Game 6, he had 27 points and 17 rebounds to lead the Raptors into the NBA Finals for the first time with a 100–94 victory. Leonard put an exclamation point on the conference victory with a huge dunk on Giannis Antetokounmpo that was set up by a Kyle Lowry steal.
Leonard led the Raptors into the 2019 Finals on the back of what was being described as an all-time great NBA playoff performance. In Game 2, Leonard had 34 points and 14 rebounds in a 109–104 loss to Golden State. Leonard helped the Raptors take a 3–1 series lead with 36 points and 12 rebounds in a 105–92 Game 4 win on the road in Oakland. In Game 6, he scored 22 points in a 114–110 win to help lift the Raptors to a 4–2 series victory in claiming his second NBA championship. He was subsequently named NBA Finals MVP for the second time, becoming just the third Finals MVP to have won the award with two teams, joining LeBron James and Kareem Abdul-Jabbar. He is also the first person to win Finals MVP with a team from each conference. Leonard scored 732 points during the 2019 playoffs; this was the third-best scoring total for a single NBA postseason in league history, behind only LeBron James (748, 2018) and Michael Jordan (759, 1992).
Kawhi Leonard