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2022-23 Cleveland Cavaliers season preview: Is this Dylan Windler’s last chance?

The idea of Dylan Windler has always been his most attractive NBA feature.

Milwaukee Bucks v Cleveland Cavaliers Photo by Jason Miller/Getty Images

Dylan Windler’s NBA career has and might always be one question: What if? He fit the bill of a Joe Ingles-like player for the Cleveland Cavaliers — a bigger forward that can provide high-level shooting, playmaking, rebounding and size. But, due to a myriad of injuries, the potential was never reached with Windler. This season could be his last hurrah with the Cavaliers, or in the NBA, if he doesn’t show he can be reliable.

Position: Shooting guard, Small forward

Age: 26

Height: 6-6

Weight: 196 lbs.

2021-22 stats: 50 GP, 9.2 MPG, 2.2 points , 1.8 rebounds, 0.7 assists with .378/.300/.833 shooting splits

The self-actualized idea of Windler could have been for the Cavaliers is always going to linger while he’s on the roster. Especially now that there’s such a glaring need at the small forward spot. If Windler was able to stay healthy and grow into his potential, then Cleveland could’ve been fairly solid at every position in their starting five.

But, if and if was a fifth, we’d all be drunk and the idea of Windler is no exception to this. The unfortunate reality of the situation is that team development is dynamic and runs tangentially to how players grow and develop. Sure, you can be hung up on the idea of what Windler could’ve been but he’s never going to be that. There’s still something there in Windler overall as a player but it’s likely not going to hit its apex with the Cavaliers.

There were moments last season when Windler showed faint glimmers of the player everyone hoped he could be. He’s only in his mid-twenties and there’s still some room for him to grow and develop.

But it might not be with Cleveland. Windler is in the final year of his rookie-scale contract, worth roughly $4 million. If anything, there could be a team that’s intrigued by the upside that still might be there in Windler. That could be a valuable negotiating chip for Cleveland during trade talks, especially after giving so many first-round selections to acquire Donovan Mitchell.

Or, more likely, his expiring salary would appeal to other teams. If Cleveland were to combine Windler’s deal with Cedi Osman’s semi-expiring contract worth a few shades above $7.4 million, along with a few second-rounders, you could possibly net an answer to your nagging small forward question. Jae Crowder clearly wants out with the Phoenix Suns. A cobbling of Osman and Windler matches the salary required to obtain him. The same can be said with San Antonio sending out Josh Richardson. Or the Orlando Magic and Terrance Ross. There are ways the Cavaliers could use Windler to broker a deal with an opposing organization. It all just really depends on whether or not the team on the other side of things is interested in acquiring him.

But, let’s say there isn’t an opposing front office willing to bite on Windler. If that were the case, the only realistic path to him cracking the rotation is in the event there are injuries or nights where load management takes priority.

There could still be something in there still with Windler, it’s just a matter of him finding it in time.