ReGrade the Trade: Raptors land superstar wing to lead them to a championship

Laying out the Kawhi Leonard trade

Understanding the background for the Raptors is crucial for evaluating the deal, but it is also necessary to grasp what was going on with the San Antonio Spurs and why they were open to trade a former Finals MVP firmly in the prime of his career.

The Spurs were still a formidable team in 2017, reaching the Western Conference Finals before star forward Kawhi Leonard suffered a significant ankle injury that kept him out for the rest of the playoffs. While rehabbing the ankle injury, Leonard was also dealing with a quad injury. That injury would not go away and led to Leonard missing the start of the next season and be in-and-out of the lineup all year.

The tension between Leonard and the Spurs only grew as it was Leonard's camp rather than the Spurs' medical team who called the shots on when he would be available for games. After appearing in a handful of games Leonard sat out the rest of the season. His relationship with head coach Gregg Popovich only deteriorated, and his teammates became increasingly public in their frustration with Leonard's apparent apathy toward returning to the court.

That set the stage for the offseason, when Leonard's camp made it known that he wanted a trade and ideally to the Los Angeles Lakers, who were hoping a trade for Leonard would convince LeBron James to sign in free agency. Leonard had one season remaining before he could reach free agency in 2019, giving him some amount of leverage in requesting a destination. The Spurs shopped Leonard around to multiple teams, including the Lakers and Boston Celtics, but a few weeks into the summer did not have a deal in place.

That's when the Toronto Raptors, on the fringes of the trade discussions to that point, swooped in and made their best offer. It was enough to convince the Spurs, who agreed to terms on a deal on July 18, 2018. Here is what the trade looked like:

The Spurs sent Leonard and valued 3-and-D wing Danny Green to the Raptors in exchange for two players and a future first-round pick. DeMar DeRozan was the centerpiece of the deal, an All-NBA wing who was in line to boost the Spurs' offense as the primary engine. Jakob Poeltl was an unpolished center who was far from the Raptors' best young prospect.

The first-round pick landed at 29 in the 2019 NBA Draft, a best-case scenario for the Raptors. The Spurs used the pick on Keldon Johnson, who has proven to be much better than the average 29th pick but was not a franchise difference-maker either. Poeltl netted the Spurs multiple draft picks back from the Raptors in a 2023 trade, while DeRozan played multiple solid seasons in San Antonio before the Spurs sent him to the Chicago Bulls for Thaddeus Young and a trio of draft picks. The Spurs later flipped Young to the - you guessed it - Raptors for draft considerations.

The Spurs moved on from an MVP candidate and got back solid but unspectacular players in return. Did the deal work out better for the Raptors?

It certainly did. Let's take a closer look from Toronto's point of view.