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NBA trade grades: Who wins the DeMar DeRozan deal between the Chicago Bulls and San Antonio Spurs?

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After adding Lonzo Ball in a sign-and-trade agreement Monday, the opening day of NBA free agency, the Chicago Bulls are back on the hunt. Tuesday, they reached agreement on a three-year, $85 million deal with DeMar DeRozan and a sign-and-trade with the San Antonio Spurs sending Al-Farouq Aminu, Thaddeus Young and draft picks in exchange for DeRozan.

Will adding the four-time All-Star help the Bulls end a four-season playoff drought? And where are the Spurs headed after an unexpected first 24 hours of free agency?


The deal

Bulls get: DeMar DeRozan

Spurs get: Thaddeus Young, Al-Farouq Aminu, a future first-round pick, two future second-round picks


Chicago Bulls: D-

In a vacuum, it's debatable whether DeRozan or Young was the more valuable player to their team last season. My wins above replacement player (WARP) rating estimated DeRozan as worth 7.1 wins based on his production as compared to 4.2 for Young, but other value metrics that don't place as much emphasis on positional value favored Young. He was one win better than DeRozan according to the estimated wins model from Dunks & Threes and nearly three wins better based on FiveThirtyEight's RAPTOR metric.

It's a little less debatable whether Young is as valuable on his current contract ($14.2 million for this season before expiring) as DeRozan is at more than $28 million per year over the next three, which takes him through age 34.

It's no longer so debatable whether DeRozan at $28.3 million per year is more valuable than Young, a protected first-round pick and two second-round picks.

And it's not debatable at all whether this trade makes sense in the specific context of the Bulls' current position. DeRozan is ill-fitting with Chicago's current core.

Let's consider first how DeRozan fits on offense, where he proved most valuable in San Antonio operating as a point forward. DeRozan displayed strong playmaking last season, averaging a career-high 6.9 assists per 36 minutes while handling the ball 37% of the time the Spurs spent on offense, according to analysis of Second Spectrum tracking data.

It's unlikely DeRozan will get to play on the ball that much with the Bulls. Incumbent All-Star Zach LaVine led Chicago by handling the ball 36% of the time he was on the court, while newcomer Ball led the Pelicans with 33% time of possession. Add it up and that's 106% time of possession for the Bulls' three perimeter players.

To some extent, each will handle it more when at least one of the others is on the bench. But something's got to give in the starting lineup, which will likely push DeRozan more to an off-ball role that highlights his limited shooting range. After almost completely abandoning the 3-pointer during his first two seasons in San Antonio, DeRozan attempted 1.2 per game last season -- more than his combined average in 2018-19 and 2019-20. Still, DeRozan hit just 26% of those attempts, down from his 28% career mark. He simply doesn't threaten defenses at all as a spot-up shooter.

If Chicago head coach Billy Donovan gets creative, using DeRozan functionally as the big man in lineups with Nikola Vucevic and Patrick Williams as the other two frontcourt players could work. Both Vucevic and Williams have the ability to space the floor around pick-and-rolls with DeRozan as the screener. Switching a LaVine-DeRozan pick-and-roll would likely give one of those two players an advantage to attack one-on-one. Still, DeRozan's fit on offense is unorthodox at best.

That's before we get to the defensive end. For all the focus on DeRozan's non-shooting, his teams have typically scored more efficiently with him on the court, sometimes dramatically so. The problem is DeRozan's teams defend far, far worse when he plays. Per Cleaning the Glass analysis, they've allowed more points per 100 possessions in each of the past six seasons and only in 2018-19 was the difference smaller than five points per 100 possessions.

In DeRozan and LaVine, the Bulls are now pairing on the wing two of the 68 players -- some of them no longer in the league -- with a luck-adjusted impact of more than -1 point per 100 possessions on their team's defense according to the three-year RAPM model on NBAshotcharts.com. Ball is an above-average defender for his position and Patrick Williams is on his way there, but it's unlikely Chicago can build a competitive defense around that duo given Vucevic's limited rim protection as a center.

The other bit of context here is that the Bulls already gave up their 2021 first-round pick and are out a protected one starting in 2023 from the Vucevic trade. If that pick conveys in 2023 and this one conveys in 2025 -- a best-case scenario in many ways, given the protections -- Chicago will be left with just two first-round picks through 2026.

I might feel better about the Bulls' prospects for 2021-22 if they can add capable backups in the frontcourt to replace Aminu and Young. Adding Ball, DeRozan and Alex Caruso leaves Chicago approximately $15 million from the tax line with seven roster spots to fill. That's enough for them to pay one player about $11 million if the rest are minimums. Finding a way to use that flexibility will require a sign-and-trade deal.

The best path for the Bulls would probably be a double sign-and-trade involving Caruso and Daniel Theis, who agreed to a four-year, $36 million deal with the Houston Rockets on Monday. The Rockets taking Theis into a trade exception would allow them to preserve their non-taxpayer midlevel exception for other purposes and the Bulls to do the same, while giving the Lakers a trade exception for a portion of Caruso's salary.

If Caruso came via sign-and-trade, Chicago could then use the midlevel to help fill out the frontcourt. Alternatively, the Bulls could try to add a player by sending Lauri Markkanen to another team in a sign-and-trade.


San Antonio Spurs: B+

At the price the Bulls paid, retaining DeRozan would have made little sense for the Spurs, who should be building around a core of young talent including Keldon Johnson, Dejounte Murray, Jakob Poeltl and Derrick White. Getting a first-round pick for taking on one year of Aminu's salary is a strong outcome for San Antonio, which might be able to add more draft compensation by flipping Young to a contender at the deadline.

The question for the Spurs is whether the way they used their remaining cap space was sensible. San Antonio went big for Doug McDermott, agreeing to a three-year, $42 million deal with the unrestricted free agent on Monday. At 29, McDermott doesn't fit the Spurs' timeline either, and his defensive shortcomings figure to be exacerbated as he hits his 30s.

San Antonio also signed Zach Collins to a three-year, $22 million deal. It remains to be seen whether some of that money is protected for the Spurs in case Collins continues to deal with injuries after missing 62 games in 2019-20 following surgery to repair a shoulder labrum tear and all of the 2020-21 campaign due to recurring stress fractures in his ankle that have required three surgeries in the past year.

I'm surprised the price was so high, but at least there's a theory to signing Collins. He showed potential as a mobile defender who could space the floor prior to his injuries. If Collins gets healthy, there's a chance San Antonio snagged a bargain, although all the rehab has also prevented Collins from working to develop his game.