Patient Sheppard Assembles 5-Team Sign and Trade for Significant Upgrades to Wizards Roster – Bullets Forever

The series of moves that transmogrified John Wall into Russell Westbrook into Spencer Dinwiddie, Aaron Holiday, Kyle Kuzma, Montrezl Harrell and Kentavious Caldwell-Pope is why Tommy Sheppard ultimately got the job as the Wizards’ top basketball executive.

It’s fair to question some of his roster moves and talent evaluations, but engineering a five-team trade is a master class in patience, negotiation and relationship development. Ask anyone who knows Sheppard, and they’ll tell you those are his strengths. He knows everyone. He listens to everyone. Everyone likes and respects him. And when other executives deal with him, they may not get exactly what they want, but they can live with what they get.

The draft night trade of Westbrook for the three former Lakers is now expanded to include bringing in Dinwiddie, the starting point guard the Wizards desperately needed. As would be expected in a five-team deal, it’s complex. To recap: the net-net for Washington is Westbrook, Chandler Hutchison and some draft collateral (second round picks and a second round pick swap) for a starting PG, a backup PG, a starting SF or high-minute G/F, and another potential starter at either forward spot.

Now, let’s not get nuts about what this means for the Wizards next season. No one they’ve acquired is great, or likely to be. But, as I’ve written previously, the team need a starting SF, an upgrade in production at PF, size in the backcourt, a starting PG (after they dealt Westbrook), and production at center until Thomas Bryant returns from his ACL injury.

Sheppard and the front office deserve a ton of credit for checking all those items on the “to-do” list while also building in some tradable spare parts for later. While they’ve done well this offseason, it’s also fair to point out that the primary reason the middling players they’ve acquired are an upgrade is because the team was so lacking in key areas last season. But again, credit where it’s due — with limited player acquisition resources, the Wizards have upgraded the overall roster.

Here’s a quick look at the newcomers:

  • Spencer Dinwiddie, PG — At 6-5, Dinwiddie brings some size and toughness to the backcourt. His overall production has been basically average. His rating in my PPA metric (in PPA, 100 is average, higher is better, 45 is replacement level) over the past five seasons and 7,612 minutes is 101. His peak is 117 in 2017-18, which he followed with an 85 and a 109. He’s a solid scorer and playmaker but a subpar three-point shooter and a so-so defender. At $62 million over three seasons, he’s probably a modest overpay but it’s not egregious. If he stays healthy, he’s a good bet to provide the team solid PG play over the next three seasons.
  • Kentavious Caldwell-Pope, G/F — At 6-5, the Wizards reportedly envision KCP as the starting SF next season. He’s strong and tough and played well during the Lakers’ championship run in the bubble, and he’d be a massive upgrade from the replacement level detritus Washington deployed last season. Whether he starts or comes off the bench behind Corey Kispert, KCP is likely to get 33+ minutes per game at SF and SG. He’s well established as average — peak PPA was 110 in 2017-18, which was also the only season he rated above average. Last year: 95.
  • Kyle Kuzma, F — Could start at either forward spot or come off the bench. Could also be traded or pave the way for someone else to be move. He’s another middle-of-the-pack player. Last season, his PPA was 95, which was the best mark of his career so far.
  • Montrezl Harrell, C — Above-average regular season player who excels coming off the bench. He’s been played off the court the past couple playoffs, but the Wizards are in a position where making the postseason is far from guaranteed. If Bryant comes back healthy and effective, either of them could be traded.
  • Aaron Holiday, PG — As a backup PG for a few minutes per game, he should be fine. He was replacement level last season (and his rookie year) and was solidly below average in 2019-20. He’s a decent shooter and so-so playmaker who defends well despite being just 6-0.

Assuming the Wizards don’t make major roster moves before the season, their rotation will probably look something like this:

PG: Dinwiddie, Raul Neto, Holiday

SG: Beal, KCP

SF: KCP, Kuzma, Kispert, Avdija

PF: Hachimura, Bertans, Kuzma

C: Gafford, Harrell (until Bryant returns)

The forward spots look like something of a logjam, but it’s really not because all the players are different flavors of average. Although KCP or Kuzma would be okay starting at SF, I think the team could still benefit from trading 2-3 frontcourt guys for a starting wing…if one becomes available…and maybe another PG to take Holiday’s likely spot in the rotation.

Still, given Washington’s meager asset arsenal, Sheppard and company have done well to improve and flesh out last season’s skeletal roster and give the team flexibility for additional moves in the months ahead.