Leonard is now a member of the Clippers but started his career in San Antonio, where he played seven seasons with the team before demanding a trade. In July 2018, the Spurs traded Leonard to Toronto, along with Danny Green, for DeMar DeRozan, Jakob Poeltl, and a 2019 first-round pick.
At the time, the trade was poorly received from the Spurs' perspective. Nearly three and a half years later, how well has the trade aged? Let's reassess the Leonard trade now that we have more data.
The decision to move Leonard to Toronto was a strategic one for the Spurs. While there were rumors of pick-heavy offers from teams like Boston, they ultimately chose to try and remain competitive post-Leonard. Looking back, it was an understandable decision, even if I didn't agree with it at the time.
After all, the Spurs were only a season removed from a second straight 60-win season and LaMarcus Aldridge was coming off a career year. So it seems reasonable, looking back, that they would try pairing Aldridge with another established star in hopes of keeping the team relevant.
Still, DeRozan, despite his obvious talent, was a questionable fit at best and an obvious downgrade from Leonard. To the Spurs' credit, they got the Raptors to throw in a first-round pick and Poeltl (a former lottery pick) to help overcome the talent gap. I’d say that's a pretty good haul for a team who was forced to trade a superstar, though other teams in similar situations have since done better.
For instance, Oklahoma City received five first-round picks and Shai-Gilgeous Alexander for Paul George while the Lakers threw the kitchen sink at New Orleans to get Anthony Davis. Different circumstances, of course, but the common denominator was an unhappy superstar.
Circumstances Mattered in the Kawhi Leonard Trade
It's worth noting that Leonard didn't want to play in Toronto, instead preferring to play in Los Angeles. He also had only one guaranteed year remaining on his contract, and both factors likely limited San Antonio's ability to ask for much more from the Raptors.
On the other hand, the Spurs' inclusion of Danny Green instead of Pau Gasol, as was rumored, was a big mistake. That decision not only gave Toronto a top-five player in Leonard, but also one of the league's best 3-and-D players in Green.
Worse yet, the Spurs weren’t able to extract another asset for including Green while also being stuck with Gasol, whom they later waived and continued to pay. That aspect definitely looks bad in retrospect, especially with Green and Leonard being a crucial part of the Raptors\ 2018 championship.
Meanwhile, the Spurs were left with a roster that made little sense and struggled as a result, especially on defense. Had they simply kept him, DeRozan’s fit would’ve been a lot better playing alongside Derrick White, Green, Rudy Gay, and Aldridge in the starting lineup.
Had that been the case, San Antonio would’ve likely won more than 47 games, gotten a higher seed, and maybe even advanced in the playoffs. It would’ve also kept the Spurs from over-relying on Bryn Forbes, who became a starter in part because they traded Green.
The Impact of DeRozan's Time on the Spurs
While the Green decision was inexcusable, DeRozan would at least go on to average a terrific 21.6 points, 5.3 rebounds, and 6.2 assists over his three seasons with the Spurs. Unfortunately, the team missed the playoffs in consecutive seasons for the first time ever with him as their best player, making his tenure something of a disappointment.
Therefore, entering this past offseason, it appeared doubtful that DeRozan would return, which would've meant that the Spurs missed their chance to trade him for assets. Yet, San Antonio was able to pull a rabbit out of a hat by agreeing to a sign-and-trade with the Bulls for DeRozan.
By acquiring Thaddeus Young, a 2025 Bulls first, a Lakers 2022 second, and the Bulls' 2023 second, San Antonio avoided losing DeRozan for nothing. It also helped them recoup some of the value lost in the initial Leonard trade.
Furthermore, if they can flip Young for another second-round pick, the Spurs will have received a total of two firsts and three seconds as a result of the Leonard trade. One of those picks (2019 first from Toronto) has already panned out in a big way, turning into Keldon Johnson.
Johnson is just 22 and is currently averaging 14.7 points and 6.1 rebounds. Also, with continued work on his shot, it's not crazy to think that he could eventually develop into a 20-point per game scorer in the NBA. As for Poeltl, who was also a part of the Leonard trade, he's emerged as one of the NBA's top centers.
Just the fact that Johnson and Poeltl are both now starters is a win for the Spurs, not to mention that they both project to play a big role with the team going forward. This compared to the Raptors getting one season of Leonard, albeit a championship season, only for him to dump them for the Clippers.
Who won the Kawhi Leonard trade?
Overall, San Antonio got a good but not great haul for Leonard initially. However, by later flipping DeRozan, the star they received for Leonard, they drastically improved their return. Factor in Poeltl and Johnson both becoming starters for the Spurs, and each still continuing to improve, and the trade looks a heck of a lot better now than it originally did.
As far as grades go, the Raptors still receive an A+ despite both Green and Leonard peacing out after a season. After all, they traded a top 25 player for a top-five player, didn't have to take back a negative salary, and also got one of the league's best role players for the relatively low cost of a good prospect and a late first.
They then won a championship based on that trade. As for the Spurs, I feel that a B is both fair and also impressive considering that they were painted into a corner by Leonard. Additionally, that grade could improve if they're able to move Young for a second, get another steal with the Bulls 2025 first, and/or select a rotation player with one of the two remaining seconds.
It's not crazy to think that at least two of those things could happen, which could bump them up a full letter grade. That could eventually make the trade a virtual tie, but the edge would still go to the Raptors unless Poeltl and Johnson help the Spurs win a championship.
Ultimately, losing Leonard still hurts, but the Spurs managed to make the best out of a bad situation and the trade could still pay big dividends going forward. Therefore San Antonio trading Leonard to the Raptors was actually the right call.