Cavs: We could see Dylan Windler, Cedi Osman both on floor for stretches

Cedi Osman and Dylan Windler could seemingly both get plenty of burn for the Cleveland Cavaliers next season.

Looking at next season for the Cleveland Cavaliers, while I don’t see him as a long-term starting 3 option, Cedi Osman will get a considerable minutes-share. It was a positive that Osman hit 38.3 percent of his three-point attempts in 2019-20, and looking onward, him proving to be a nice spot-up threat should aid Cleveland’s drivers when he’s out there.

That said, Osman is pretty limited in the on-ball sense at this point, and defensively, he has struggled mightily over the past two seasons against starting-caliber 3’s. With next season in mind, though, it would seem that Dylan Windler could very well be Osman’s primary backup at the 3 and/or could potentially take Osman’s starting spot at the 3.

Windler of course did not play at all in 2019-20 due to complications involving a stress reaction in his left leg, but is reportedly participating in Cleveland’s in-market minicamp/is set to participate in the team bubble workout portion of that. I’d imagine that we’ll see Windler mostly healthy next season, too.

And we could maybe see Windler take over Osman’s spot due to him seemingly being a much more capable shooter off movement, and having parking lot range. Windler, who hit 40.6 percent of his three-point attempts at Belmont in college over four years, is also a gifted finisher.

He is much more of an on-ball scoring threat than Osman and he could end up being lethal in the pull-up game, especially after dribble hand-offs, too.

Granted, I’d think we could definitely see the Cavaliers end up selecting a wing such as Auburn’s Isaac Okoro or Florida State’s Devin Vassell in the upcoming draft, sure.

That said, with Osman at least being an instinctive cutter himself and having nice secondary playmaking/passing feel, and solidifying himself as a quality spot-up threat, he’ll likely still get his chunk of minutes either way. Windler, who projects as such a versatile shooter and offensive weapon, I’d expect to, also, and a significant amount at the 2 could play out for him.

And whether or not Cleveland does end up drafting a wing to end up becoming their starting 3 at some point, I’d still think we could see Dylan Windler and Cedi Osman both on the floor together for stretches on occasion.

We could see Windler and Osman together in some stretches for the Cleveland Cavaliers.

I’d think that next season, Kevin Porter Jr. could get a fair amount of burn at the 1 in relief of Darius Garland, and while Collin Sexton will get his run on the floor sans Garland, and I’d think more next year, Windler and Osman could get run at the 2/3 at times together.

The key is for the Cleveland Cavaliers in some stretches, with both Windler and Osman being more than willing and able passers, they could mesh well with Garland sure some, but especially Sexton and KPJ at the formal 1.

Both of those players can really break down opposing defenses, and having Windler and Osman at the 2/3 could aid in terms of floor spacing, and could help out Andre Drummond and/or Larry Nance Jr. inside, along with Kevin Love in the mid-post.

In addition, with both being active cutters, Osman and Windler occasionally screening for each other off-ball could lead to some high great high percentage looks via deliveries from perhaps Porter/Nance.

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And though Windler seemingly has better touch, Osman can get some runners to go and has a solid up-and-under move that does generally bode well for him when he’s attacking after hard close-outs or after cuts.

Plus, with Windler’s shooting ability potentially making it tough on off-ball defenders, that could work well and maybe some open looks could pop open for Windler, conversely as a counter.

Now, on the defensive end, the Cavs would be wise to have the likes of Nance and likely Drummond to aid Windler/Osman in these potential stretches.

But with the two being floor spacers, smart cutters and having good passing feel, I could see them at the 2/3 for stretches working out pretty well for the Cleveland Cavaliers next season.

Maybe Dante Exum could occasionally get some burn at the 1 in these instances with them, too, albeit I’d expect more so to have Sexton or Porter as a primary on-ball player, with them being much more capable as scorers/being able to collapse defenses.

So again, even if the Cavs do go wing in the 2020 NBA Draft, I’d still expect to see the Cavs end up having a variety of natural wings in the fold next season, and we could seemingly see Windler and Osman both on the floor for stretches together, which could be a promising wrinkle for Cleveland in some matchups.

Now I wouldn’t expect that to be in every game, but it could help some throughout games from a ball movement/spacing standpoint and enable the likes of Sexton/Porter to penetration often.

We’ll have to see what shakes out involving the wings next season, and Nance I’d think should get some burn again at the 3 at times, just as The Athletic‘s Kelsey Russo (subscription required) believes. Ultimately, though, but if Windler can stay mostly healthy, I wouldn’t expect KPJ to play a ton at the 3 like he did last season, when he mostly appeared there.

Moreover, it’ll be intriguing to see what sort of approach Cavs head coach J.B. Bickerstaff takes with the wings next season, but I’d expect him to utilize a bunch of varying combinations.