Cleveland Cavaliers Roster Outlook: Wings

The transaction window of the summer has unofficially opened in the NBA. The NBA Draft has come and gone, trades have been consummated, and free agency is set to arrive on Friday evening.

The Cavaliers have holes on the roster to fill, whether through trades or free agency signings. This week, we’ll dive into what could be available on a position-by-position basis. Today, we’ll take a look at the wing spots.

What’s in Place

Late last week the Cavaliers decided to pick up the $1.9MM team option on Lamar Stevens’ contract for this season, locking him into the roster. Stevens has certainly been a nice developmental story after being undrafted out of Penn State. Last season for the Cavs his role fluctuated quite a bit. There were times when he was in the starting lineup while the Cavs were fully healthy, and other times when he was collecting DNP-CDs. Overall, he’s a nice player to have at his $1.9MM salary as a spark off the bench.

The other player the Cavs have under contract, at least for today, is Cedi Osman. Osman is entering the final year of his four-year, $31.1MM contract extension that kicked in during the 2020-21 season. The deal is one that has declined over the past few seasons, and this year’s $6.7MM is non-guaranteed until tomorrow, June 29.

Whether or not the Cavaliers fully guarantee Osman’s contract, there’s a chance he’s not on the team next season as a potential trade piece that could be moved. There are nights when he’s capable of scoring 20 points, and other nights where it’s clear Cavaliers head coach J.B. Bickerstaff doesn’t trust him. Finding a more consistent player in that role is something that certainly could benefit the team, even if it means parting ways with the longest tenured player on the Cavs.

Potentially Departing Free Agents

The Cavs being short on wings means that not only are the players set to return at this spot part of a short list, but the players that are reaching free agency are too. The first name on the list is little used and often injured Dylan Windler. Windler can be a restricted free agent, but as of this writing the Cavs have not extended a qualifying offer to him. The team has until June 29 to do so. Windler played in just three games this season and has played in only 84 in his career due to various injuries, mostly of the lower body variety. The qualifying offer for Windler would be $5.9MM for this season, and it’s difficult to see the Cavs wanting to spend that type of money on a player that doesn’t play very often.

The other wing the Cavs could be losing in free agency is Danny Green. He was signed by the Cavs after reaching a buyout with the Houston Rockets in February (following his trade there from Memphis). Green played eight regular season games with the Cavs and four of their playoff games. There certainly could be interest in bringing him back. He played last season as a 35-year-old that was less than a year removed from a torn ACL suffered in the 2022 playoffs. More time for his body to get right could lead to a bigger role with the Cavs this season.

What Else is Out There: Free Agency

This is the area where the Cavs should be the most active in attempting to acquire help this summer. The Cavs won’t be in on the big name free agents at this spot – don’t expect Khris Middleton to land in Cleveland – but it’s entirely possible they use their full mid-level exception on a player that can help out at the small forward spot. Players like Donte DiVincenzo, Max Strus, and Yuta Watanabe, are all unrestricted and make some sense for the Cavaliers. We’ll dive deeper into which players the Cavs should be after on Friday, but that’s a short list of names that could help the Cavs.

What Else is Out There: Trades

The Cavs can very rarely be accused of not being aggressive in the trade market. That accusation can really only be made for this past trade deadline. This summer, the aggression should turn back up. Maybe the Cavs can’t find themselves dealing for a star on the wing like Paul George, but they should be involved in most conversations for complimentary wing players. A team like the Nets, that features a surplus of wings, should make for a good trade partner. Finding a way to acquire someone like Royce O’Neale would be a really strong move this offseason for the Cavs.