3 trades for Cavs to give Dylan Windler a second chance

The Cleveland Cavaliers have found a couple of young stars in the NBA Draft in recent years. Darius Garland is already an All-Star, Evan Mobley will soon be on, and Collin Sexton is both polarizing and still a success of an eighth-overall pick. While Jarrett Allen and Lauri Markkanen came via trade, the Cavs would not be where they are without nailing some draft picks.

On the other hand, they have also had some big draft whiffs. We wrote yesterday about how the Cavs would be in a very different place if they had drafted Tyrese Haliburton instead of Isaac Okoro in the 2020 draft, and the Houston Rockets are currently developing Kevin Porter Jr. after the Cavs organization gave up on him for primarily character reasons.

The Cleveland Cavaliers look like they might move on from Dylan Windler. If they do, these three trades could mean a second chance for Windler’s career.

The biggest draft mistake thus far, however, has been Dylan Windler. Over the past five years the Cavs have drafted seven players in the first round, and he is the only one who is not a rotation player. He has been ravaged by injuries, but even mostly healthy last season he couldn’t establish himself or crack the rotation. It seems very likely that his time in Cleveland is done.

If the Cavs and Sexton agree to a deal in the coming weeks, the organization will need to cut a player to get down to the maximum of 15 on the roster. A prime candidate would be Windler, but with four million guaranteed for next season the Cavs could look instead to trade him and open that space back up under the luxury tax.

Let’s look at three options for the Cavs as they explore a trade, and how each landing spot could be an opportunity for Dylan Windler to get a second chance. How can the Cavs open up a roster spot and put Windler in a new environment to take another crack at an NBA career?