Does Justise Winslow Have a Future in Portland?

The Portland Trail Blazers’ 2021-22 season has come to an end. The summer ahead will hold plenty of decisions for the club. They put 27 different players on the court during the regular season. Not all are still with the team, but enough are that there’s no way the Blazers could retain them all...if they even wanted to. A 27-55 record would argue against a high retention rate, but asterisks abound despite the dismal performance.

Into this question-filled swamp stride Dave Deckard and Dia Miller with their annual review of Portland’s roster. They talk about each player, then decide whether they would keep or yeet (toss) the player in the coming year. Performance, fit, age, salary, and team priorities/direction are all open for discussion.

Today we get to Justise Winslow. The Blazers acquired the 6’6 forward in a mid-season deal that sent Norman Powell and Robert Covington to the Los Angeles Clippers. Winslow averaged 10.7 points and 6.3 rebounds in 26.8 minutes per game over 11 appearances for the Blazers. He shot 40.5% from the field, 27.0% from the arc. He has a single year remaining on his contract. Is he worth keeping around next season?

Dave: Most of the guys we’ve talked about so far have been either starters or deep bench players. Here we have one of the few tweeners on the team: Justise Winslow. He’s making $4 million next season on the last year of his deal. We’ve already talked about trying to keep Drew Eubanks and Trendon Watford. Do you keep Winslow too?

Dia: Winslow comes in solid with defense. So in the past that would be a really quick keep. That’s always a place of struggle for the Blazers, and getting rid of defensive players in the past was always risky because we needed them so badly. I’m kind of at a place now with this season where so much is up in the air and the roster could change, so maybe the way to think about this is, “Is this a player that I want next to Damian Lillard?” While I want the ball in Dame’s hands as much as possible offensively, I like what Justise has to offer.

Dave: I’m more neutral. Granted, I liked some of what he showed this year in Portland. But I’ve liked Winslow’s potential before. He’s never been able to put it all together. I pledged this year that unless there was a strong reason to keep someone, I’d vote yeet. This team needs change.

But here we go. Portland’s situation is such that the common sense move and the smart move are not always the same. Real talk: they don’t really need Winslow. He’s not going to move the needle for them. He’s not shown he can provide solid mid-rotation play, which is what they need out of someone in his position. Also real talk: their bench is a shambles. They have few mid-range contracts to play with. They can’t generate cap space without losing major players. Under those conditions, it doesn’t make any sense to drop Winslow, even if they could. He costs $4 million. That contract can be used in trades. Otherwise he’ll give them something, and the difference between him and a veteran’s minimum contract wouldn’t matter anyway.

So yay! He’s athletic, brings defense, and will maybe provide a nice duel with Trendon Watford for minutes? Also he seems to enjoy playing in Portland so far.

Dia: I always love when these turn into keep! I like Justise. And I agree with your points. I think he’s worth keeping as a rotational player. Plus, you know, he’s fun to watch.

Dave: Yes, well, ideally the Blazers would have enough players on the roster to make watching him optional, with him playing mostly if he’s worth watching, but you know how that goes. Last question: Do you see any chance he finally breaks out and becomes a higher-rotation player here? He’s had shots with the Heat, Grizzlies, and Clippers. That said, he’s still only 26. Do you expect him to develop more?

Dia: I would say yes. I think who players are surrounded by (teammates specifically) can have a dramatic impact on development at any age. Especially for guys like Justise who aren’t necessarily stuck in their current ways. One of the things I’ve always appreciated about Damian Lillard on this team is his ability to help players grow into the best version of themselves. While this training and coaching staff is new, so we don’t know quite as much what their potential is, Portland seems to have a way of developing players. I think he will grow and become a better version of himself with this team,

Dave: For me, this whole vote is under protest. This has little to do with Mr. Winslow himself. He might be good; he might not. I’m just getting a little fatigued with the, “This isn’t the best move, but because of the current structure, it probably makes sense,” line of reasoning I’m having to take through most of these. It feels like an episode of Kitchen Nightmares where the restaurant owner whines, “But the creamed corn casserole is popular with my regulars.” If you only take the explanation that far, then keeping everything makes sense. But news flash: your restaurant is in trouble. It needs a new structure based on different assumptions. So do the Blazers.

I know they’ll keep Winslow and I’m fine with them doing so because of the reasons I just stated. In the spirit of, “But they should feel free to move him in a trade,” and because he’s probably not important to their long-term future, I’m still saying yeet.

Our story so far...

Anfernee Simons: Dave—Keep, Dia—Keep

Jusuf Nurkic: Dave—Keep, Dia—Keep

Ben McLemore: Dave—Yeet, Dia—Keep

CJ Elleby: Dave—Yeet, Dia—Yeet

Nassir Little: Dave—Keep, Dia—Keep

Trendon Watford: Dave—Keep, Dia—Keep

Drew Eubanks: Dave—Keep, Dia—Keep

Justise Winslow: Dave—Yeet, Dia—Keep