3 trades for Cavs to give Dylan Windler a second chance

3 Dylan Windler trades for Cavs: Orlando Magic

In this trade scenario, the Cavaliers find another rebuilding team with a lack of small forwards to move Dylan Winder to. The Magic have bolstered their backcourt and their bigs lately, but could use some depth on the wing behind Franz Wagner. Dylan Windler could have a chance to catch on and join the core they are bringing.

In this deal the Cavs move two players for one, opening up that roster spot they need to re-sign Collin Sexton and getting a solid veteran wing in Gary Harris in return. Osman has value on a fair contract, and the Magic could keep him or more likely flip him to another team looking for wing depth.

The Cavs take on a slight bit of salary here, which may be a non-starter for them, but they would do so to add a solid contributor who has playoff experience. Harris could start at the 2 or be the bench wing complement to Collin Sexton, and he is no stranger to a small role as an off-ball player after his years running with Nikola Jokic. His non-guaranteed deal for 2023-24 is also useful to a team that may use cap space next summer, or may want to use it the one after that.

The Magic might be hoping to get more back for Harris, but if they don’t get a better offer then this gives them a young player to take a chance on, a veteran wing to flip, and a reasonable second-round pick. It’s in the realm of possibility that this is enough to get such a deal done.