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Is the Kawhi Leonard Trade a Triumph for the Spurs?

Even knowing he is on the way out, San Antonio was able to land an All-NBA-level player in return

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After a nearly yearlong saga, Kawhi Leonard has finally found his new home: Toronto. Yeah, so no one saw this one coming. The Raptors are shipping DeMar DeRozan, Jakob Poeltl, and a few other assets for Leonard and Danny Green. Does that make this deal a huge win for San Antonio? Bill Simmons, Kevin O’Connor, and Shea Serrano talked it out on the latest episode of The Bill Simmons Podcast.

Bill Simmons: Tell me this take is wrong—the Spurs just traded the fifth- or sixth-best player in the league, who didn’t play last year, for somebody who played crunch time in the All-Star Game in February, who was eighth in the MVP balloting, who is in his prime, who is somewhere between the 10th- and 13th-best player in the league. And they got Jakob Poeltl, and they got a protected first-round pick. I feel like this was a huge win for the Spurs. Plus, [DeMar] DeRozan is under contract for three years. Is this the best they could do?

Kevin O’Connor: Yeah, I think based on the fact that they didn’t want a picks-based package, certainly. You can disagree with that. I would’ve rather had a future-focused type of deal if I’m the Spurs, but based on what they desired, this is a win for them. Because you imagine DeRozan under Gregg Popovich—with their system, maybe his play is elevated to another level. Because, look, DeRozan, he’s in his [late] 20s right now, but there’s still room for him to grow [like] he has each of the last four seasons. ... There’s still room for him to get better. It’s a great deal for the Spurs, considering the circumstances, in a no-win situation.

Simmons: Yeah, I feel like he is somebody that every summer works hard to add something to his game or improve something in his game. He’s not going to decline. At the very least, he’ll be a 23-five-and-five guy like he’s been the last couple years. He’s somebody who can play in crunch time. Shea, I know it’s a bleak day for you.

Shea Serrano: It’s not.

Simmons: I just want to point out, you have two All-NBA guys on your team. Two current, reigning, All-NBA guys. Only 15 guys make the All-NBA team; it’s a 30-team league, and you have two of them. I feel like this is a triumphant day for San Antonio.

Serrano: This is a very good day for San Antonio for two different reasons. No. 1: the one you’re talking about. We’ve already, 10 minutes after the news came out, talked ourselves into DeMar DeRozan. We’ve got Chip Engelland. Chip Engelland will teach [DeRozan] to shoot the 3. He taught Tony [Parker] to shoot the 3. He taught Kawhi—we’re fine. We’re good there.

Simmons: And in LaMarcus Aldridge and DeMar DeRozan, two of the most dynamic personalities in the league. Oh, wait, not at all. But it kind of fits in with the Spurs.

O’Connor: It does. And Shea mentioned Chip Engelland being able to help DeRozan as a shooter—DeRozan started off last year shooting the ball really well, then he fell off. But the one thing that he continued doing well last season was playmaking. He improved drastically as a passer. Before, he’d just pull up from midrange. Last season, he started to look for cutters, or he kicked it out to 3-point shooters. DeRozan became a better player last season, turning 28 years old. Maybe now in San Antonio, maybe the next step is, as Shea said, improving that 3-point shot under the guidance of Chip Engelland.

Simmons: I thought it was really unfair how it played out for [DeRozan], from a where-his-place-in-the-league-is standpoint last season. Through February, he was an MVP candidate. I actually ended up voting [Victor] Oladipo over him for second-team All-NBA. But it was close, and Oladipo was somebody who was the best player on a team that went toe-to-toe with Cleveland. But the sweep against Cleveland [in the Eastern Conference semifinals] really kind of flipped people on him, and all of a sudden, with the last two weeks, when there rumors that Toronto was involved, nobody was like, “Wow, they’re trading DeRozan?” The attitude was more like “Eh, Toronto, time to blow it up.” They fired Dwane Casey, and they basically, late last night, traded their best player.

But I actually think he’s a little undervalued now because, you know, we see it in Boston with Al Horford. People pick apart the stars, but there really aren’t a lot of stars. DeRozan, let’s say he’s the 12th-best guy in the league. This is the entire league. There are 30 teams. I would much rather have that than Zhaire Smith, or [keeping] my fingers crossed for the Miami pick. I also don’t feel like that’s the Spurs way. Pop has two years left. Do you think that was part of it, Shea? Pop’s like, “I’m not going down as a rebuilding thing. I want to compete”?

Serrano: Yeah, absolutely. Everybody knew Pop was leaving. I mean he’s supposed to be gone in 2020 or something like that. Let’s load it up and let’s fire two last shots and see what happens, for sure. You know what I’m excited about? The big knock on DeRozan, and I’m guilty of this, too, is we just talk about how the Raptors fall apart in the playoffs. I’m excited to see what happens when he’s in a spot where they’re known for not doing that. Because everything changes when you’ve got that reputation behind you now.

O’Connor: Yeah, it’s a 47-win team adding one of the best scorers in the league.

Simmons: Yeah. [Over the] last three years: 24.5 points a game, 46 percent field goal percentage, 84 percent on free throws. He’s actually a good closer. I call them the coolers—at the end of the games, guys who can come in when you’re up three with a minute left and you just need somebody to get fouled and go to the line. In the last three years, [DeRozan has averaged] eight free throws a game attempted. I love guys that get to the line. So, KOC, him and Aldridge together—he’s never really had a pick-and-pop guy like this. What do you see with the spacing with those two? And like, if I’m defending that and everybody else is cleared out on the other side, what does that look like?

O’Connor: It’ll be interesting. ... [San Antonio was] one of the most midrange-heavy teams last season. They were kind of the one team zagging where everybody else was zigging to shoot more 3s. I wonder if they stick with that now that you have another kind of midrange player like DeRozan. Or maybe you’re stretching those guys out and trying to push their games to the 3-point line. I think San Antonio is always going to be a motion-based offense, and that’s why DeRozan’s evolution last year is so exciting—elevating his plays as a passer, and he improved early on as a shooter. ...

[And Aldridge] is another guy who’s kind of underrated here. He was an All-NBA guy last year, a borderline MVP candidate. The way he carried San Antonio into the playoffs without Kawhi Leonard, he was remarkable last season. It was one of the best seasons of his career. I’m excited for the San Antonio Spurs, to see how some of their younger guys develop alongside two stabilizers in DeRozan and Aldridge.