More than a year after his trade-deadline acquisition from the Miami Heat, the Justise Winslow era in Memphis marked two milestones during the weekend: His 10th* game in a Grizzlies uniform, and his first time to play the second half of a back-to-back set. The former established enough of a sample for a check-in, and the second suggested some progress after Winslow’s year-long absence due to multiple injuries.

*OK, yes, I know Winslow had played actually a dozen Grizzlies games leading up to Monday night’s meeting with the Boston Celtics. But after a year of inaction, it seems fitting to give Winslow an evaluation mulligan for those first two games back in which he shot a rusty, hide-your-eyes 4-for-24 from the floor. 

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Winslow looked more like himself in the third game for the Grizzlies, a Feb. 25 win over the Los Angeles Clippers in which he had a kind of delayed Memphis coming-out party, playing impact defense in a big win. 

But even if we consider that night a kind of real-Winslow debut, it now looks only half-representative of the player the Grizzlies have gotten so far. 

Winslow hasn’t had another moment as memorable as when he ripped a ball away from Clippers star Kawhi Leonard that night. But he essentially has been the kind of frontline defender the Grizzlies imagined in February 2020 when they leveraged veterans Jae Crowder and Andre Iguodala and a willingness to absorb short-term bad contracts (of departed Dion Waiters and soon-to-be-departed Gorgui Dieng) into a chance on the then-injured, then-23-year-old forward.

Since that night, the Grizzlies have had the NBA’s second-best defense, and injecting Winslow’s physical, versatile style into a rotation that also includes generally positive-impact multiple-position defenders Dillon Brooks, Kyle Anderson and De’Anthony Melton seems to have a lot to do with that. In these dozen games (Winslow sitting two of them), only Melton has a better overall “defensive rating” (team performance with a player on the floor), and with the rotation taking a small-ball turn that often has pushed Winslow to power forward, only center Jonas Valanciunas has been better on the defensive boards.

Offense has been a different story, for Winslow and the team, which has scuffled around the league’s floor for the past month. 

Winslow has something of a point-forward’s game, and while he hasn’t functioned as a lead ballhandler for the Grizzlies, even on bench units, he has been third on the team in offensive usage in this stretch. But not much good has come of it yet: He has been the worst all-around shooter in the team’s rotation, with nearly as many turnovers (15) as assists (17).

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Is Winslow a viable 3-point shooter or not? The answer in a Grizzlies uniform so far is a deafening “not.” That 4-for-24 overall shooting in the first two games, the ones we’re wiping off the record here? It’s still one make better than his 3-point shooting since (3-for-24).

Winslow came into the NBA a bad long-range shooter, but over the course of his second and third NBA seasons, for Miami, he shot 38% from 3-point range on nearly 400 attempts. That was an advance on which the Grizzlies hoped to build once he got healthy again.

Winslow has never been a significant scorer, and the Grizzlies didn’t necessarily expect that to change, but a 3-and-D wing with a little extra ballhandling oomph? That was the idea. It’s far too soon to call that notion a bust, but if at least league-average 3-point shooting never comes, does the Winslow idea still really work?

The Grizzlies have a team option on his contract for $13 million next season, and face what at the moment seems to be a difficult decision, with three primary paths:

1. Exercise the option and bring Winslow back on an expiring contract, extending the evaluation window and retaining a potential trade chip for next season. 

2. Decline the option and let Winslow walk, banking $13 million in likely cap space to use in free agency or for trade flexibility this summer. 

3. Decline the option and roll the dice on negotiating a new long-term contract, perhaps at a “buy low” number if Winslow remains healthy but continues to struggle offensively during this compressed season.

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Door No. 1 once seemed perhaps least likely. If Winslow couldn’t get healthy, a team might prefer to move on without him. If he got healthy and became everything the team wanted, they’d presumably want to lock him up long term. Now?

Well, the good news is that the Grizzlies don’t have to make that decision now. If Winslow will play back-to-backs, or at least not sit them all, the Grizzlies should be able to triple — maybe nearly quadruple — this current 10*-game sample, and we can revisit this question with more information at hand.

Final thoughts on the trade deadline

The NBA trade deadline is 2 p.m. on Thursday. I worked through some broad paths — no made-up trades, sorry — the Grizzlies might pursue in this space a couple of weeks ago. 

The general takeaway was that Dieng was obviously available, but that finding a workable deal might be difficult. Beyond that, much was possible but standing pat was most likely.

With the clock ticking, none of that has changed. Dieng is still very available, but the size of his contract ($17.3 million) makes a deal at least somewhat unlikely.

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What happens to Dieng if the Grizzlies can’t find a deal? Given that they are in a playoff race themselves, there’s a clear argument against buying out a useful player who isn’t obviously disgruntled. But the fact the Grizzlies have fully removed Dieng from the mix — he hasn’t appeared in a game in nearly a month, even sitting out empty-the-bench stretches at the end of blowouts — suggests an understanding.

The Grizzlies didn’t formally announce Dieng was done with the team, the way the Spurs recently did with veteran LaMarcus Aldridge, but the situation seems much the same. I’d be surprised to see Dieng still with the Grizzlies to end this season, even if he doesn’t get traded.

Will the Grizzlies do anything else? Tea leaves still suggest no, but recent struggles — or maybe just observer restlessness — make me wonder. There’s so much duplication on this roster: Are Grayson Allen and Desmond Bane going to be on this roster next season? Winslow and Brooks and Anderson? Do the Grizzlies need to have $9 million in cap space invested in a backup point guard like Tyus Jones? Does Valanciunas, a few years off the likely Ja Morant/Jaren Jackson Jr. timeline, have more trade-market value than many of us think?

All of this could be sorted out this summer, or even beyond. That’s most likely. But I wouldn’t be shocked to see the Grizzlies do some of their inevitable sorting a little early if opportunity strikes. We won’t have to wait much longer to find out.