The deal
Raptors get: Forward Kawhi Leonard and guard Danny Green
Spurs get: Guard DeMar DeRozan, center Jakob Poeltl and a protected 2019 first-round pick
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San Antonio Spurs: D

San Antonio must really like DeMar DeRozan.
In trying to understand the final permutation of this Spurs-Raptors deal, rumored since last week, San Antonio valuing DeRozan as the kind of star player other teams were unlikely to offer for Leonard in the final year of his contract is one of two possible explanations I see. Either the Spurs had become convinced that a trade had to be made before training camp because their relationship with Leonard had become irreparable and no other team was willing to offer a compelling package, or San Antonio values this package much differently than I do -- a disagreement that probably centers on DeRozan's value.
An optimist would point out that the Spurs just got back a player voted All-NBA second team last season, and to the third team the year before that. And, since San Antonio won 47 games last year getting virtually nothing from Leonard (who played just nine games), the logic goes, adding DeRozan to the returning core will make the Spurs a contender again.
There's some merit to that argument. DeRozan has been a highly productive offensive player during the regular season, carrying heavy offensive loads (up to 34 percent usage in 2016-17) while scoring with league-average efficiency the past three seasons. He also has become a capable distributor, which will help a San Antonio team that doesn't typically get much playmaking from point guards Dejounte Murray and Patty Mills. DeRozan handed out more assists per 100 team plays last season (6.8) than either Murray (5.9) or Mills (4.9).
Yet all the focus on DeRozan's penchant for midrange jumpers -- and don't worry, we'll get to that in a second -- tends to obscure his real weakness: dreadful defense. Over the past three seasons, DeRozan has rated no better than last season's minus-1.4 points per 100 possessions in defensive impact, per ESPN's real plus-minus (RPM). Toronto has consistently been at its best with DeRozan on the bench, when other lineups -- historically backcourt-mate Kyle Lowry and a second point guard, but last year all-bench units with Fred VanVleet and Delon Wright in the backcourt -- have performed much better defensively.
With this trade, the Spurs have lost their two best wing defenders (Leonard and Green) and replaced them with a below-average one. Murray was an elite defender at the point during his second season and Gregg Popovich's defensive scheme is sound, but having previously agreed to sign Marco Belinelli, San Antonio now has one of the league's worst collections of defenders at shooting guard and the forward spots. The best of the group, depending on rookie Lonnie Walker's ability to get up to speed, is probably either Dante Cunningham or Rudy Gay. That's trouble in a conference that has added LeBron James to the likes of Kevin Durant and James Harden in those spots.
The other issue with DeRozan's game is his tendency to struggle during the playoffs, when the regular trips to the free throw line on which he depends to score efficiently dry up. DeRozan's free throw rate has declined in the playoffs three of the past four years, typically by a large amount.
There's nothing unusual about a player getting fouled less often in the playoffs, but in DeRozan's case it highlights how inefficient his diet of mostly midrange shots is. While DeRozan's overall true shooting percentage (which incorporates free throws) has been around league average, his effective field goal percentage (measuring only his efficiency on shots from the field) is far worse than that mark.
Last season's .488 eFG was the best of DeRozan's career and still not close to the league average of .521. Making matters worse, DeRozan has been unable to match his regular-season shooting from the field, seeing his eFG drop substantially too (to .462 last season). Add it up and DeRozan hasn't rated better than league average offensively in the playoffs by Basketball-Reference.com's box plus-minus metric since 2014.
By adding DeRozan to LaMarcus Aldridge as their go-to scorers on offense, the Spurs are doubling down on their fondness for midrange attempts. Last season, Aldridge ranked first and DeRozan third in 2-point attempts outside the paint, per NBA Advanced Stats, and together their 1,057 attempts were more than five teams -- including, remarkably, DeRozan's Raptors -- attempted total. Though Belinelli's arrival will help, swapping Green for DeRozan (who shot just 31 percent on 3s, though his 1.1 per game were a career high) further constricts San Antonio's spacing. The Spurs can probably make it work during the regular season, but the playoffs will likely be a different matter.
Dealing for DeRozan will likely keep San Antonio in an increasingly crowded Western Conference playoff mix, but it also seems to put a ceiling on what the Spurs can accomplish the next couple of seasons with an Aldridge-DeRozan core. It's unlikely San Antonio will be one of the two best teams in the conference or a serious challenger to the Golden State Warriors in the West. That makes it all the worse that the Spurs got so little long-term value out of this trade.
A trade centered on Leonard and DeRozan could have made sense for San Antonio depending on the other players and picks involved. Remarkably, the Spurs got just a single draft pick and agreed to top-20 protection with a one-year window for the first-rounder to actually convey. Odds are the Raptors will pick in the bottom 10 of next year's first round, sending their first-round pick to San Antonio, but somehow the pick has both low upside (because of the protection) and high downside (because if Toronto somehow falls apart, the Spurs won't even get a first-rounder out of the deal).
Meanwhile, San Antonio was also unable to get much out of the Raptors' corps of young prospects, landing only Poeltl. The 22-year-old Austrian has been productive during his first two seasons and shown enough mobility that he might be able to keep up in a league that's increasingly unfriendly to 7-footers on defense. But the high level of replacement at center takes a big chunk out of Poeltl's impressive-looking performance on offense (including 66 percent shooting on 2s), rendering him more likely to be a quality backup than an above-average starter.
Maybe the Spurs were never interested in picks and young players; Popovich is 69, after all, and San Antonio's other contracts were ill-suited for the team to pivot toward rebuilding after Leonard's camp asked for a trade. Nonetheless, given the swagger with which the Spurs reportedly began negotiations with Leonard suitors, to not get a single top prospect or quality draft pick feels like a failure. San Antonio didn't even manage to clean up its cap sheet going forward by getting off one of the team's bad long-term contracts (Mills, who will make $13.3 million in 2020-21 when Aldridge and DeRozan can both become free agents, or Pau Gasol, further marginalized by Poeltl's arrival). So DeRozan had better prove worth it.
Toronto Raptors: A-

I don't think I like this trade for the Raptors quite as much as I dislike it for the Spurs. Leonard re-signing in Toronto seems like a long shot given what has been reported about his intentions to go to the Lakers when he's a free agent, which is very different from what we heard from Paul George when he was traded to Oklahoma City a year ago and ultimately re-signed. This deal works fine for the Raptors as a rental, but if Leonard is so unhappy that he'd prefer to continue rehabbing his inscrutable quadriceps injury rather than report to Toronto, that's a problem.
For the Raptors, giving up one of their nominal star players, a recent lottery pick and next year's first-round pick makes sense because they're in position to shake things up after getting swept each of the past two years. Perhaps LeBron heading West was all Toronto needed to perform better in the playoffs, but with the Boston Celtics and Philadelphia 76ers on the rise in the East, I agree with Masai Ujiri's willingness to take a bold risk to be able to get to the NBA Finals this season.
If Leonard is healthy and reasonably motivated, the Raptors should be considered the best team in the East and the favorites to reach the Finals. I've already laid out all the reasons DeRozan wasn't as big a factor in Toronto's regular-season success as his scoring average and accolades would suggest. Swapping him for Leonard is a huge upgrade, and the Raptors have somehow also managed to get another valuable two-way wing in Green.
It has been three years (and one Lasik surgery) since Green last shot better than 40 percent from 3-point range, so he should no longer be considered an elite 3-and-D wing. Nonetheless, Green has been a league-average 3-point shooter in that span and he's a versatile defender who's as comfortable checking smaller, quicker opponents as he is more physical ones.
Alongside a healthy Leonard and promising second-year forward OG Anunoby, Green is somehow Toronto's third-best wing player. That gives new Raptors coach Nick Nurse the flexibility to deploy lineups with all three players together that are ideally suited to defend the NBA's best teams.
If Leonard walks away after this season, Toronto is still in decent shape. The Raptors will likely pay the luxury tax this season, the first time they would do so since 2003-04 per Mark Deeks. However, Green is also in the final year of his contract, making Toronto's payroll more manageable going forward. The Raptors would have the ability to spend their non-tax midlevel next summer if both players leave, adding to a young core that is largely still intact.
Poeltl was a useful player for Toronto, but barring a Jonas Valanciunas trade his path to the starting lineup was blocked and Pascal Siakam may be able to play more minutes at center, possibly alongside Serge Ibaka in smaller lineups. The Raptors kept their best young players, Anunoby and point guard VanVleet (ineligible to be traded after recently re-signing), and will at worst lose a bottom-10 first-round pick in addition to Poeltl.
Given all that, I think this trade was well worth the risk for Toronto as long as Leonard is able and willing to don a Raptors uniform, even for only one season.