The Biggest Question Cleveland Cavaliers Still Haven't Answered This Offseason

The Cavaliers are getting ready for the 2026-27 season, but as the offseason progresses, there is something they need to address.

Nov 2, 2025; Cleveland, Ohio, USA; Cleveland Cavaliers guard Jaylon Tyson (20) celebrates with Cleveland Cavaliers guard Donovan Mitchell (45) during the first half against the Atlanta Hawks at Rocket Arena. Mandatory Credit: Ken Blaze-Imagn Images | IMAGN IMAGES via Reuters Connect

The 2026-27 NBA season is getting closer, and teams are making moves. The Philadelphia 76ers have added significant pieces, and after finishing seventh in the East, they are shooting for the top spot.

While some teams have been active, the Cleveland Cavaliers are an exception. They signed Mario Hezonja, and he will play in the NBA for the first time since the 2019-20 season. Outside of that signing, the Cavs have made very few moves.

Cleveland is considering multiple free agents, but nothing is set in stone. Both players could help the team in a specific area, but negotiations are at a standstill.

Cleveland's Free Agent Targets Remain Unsigned

Jonathan Kuminga and Peyton Watson are the Cavs' targets, and they could be the wing the team is searching for. Cleveland needs help in that area, and while their games are different, acquiring one of them would give the Cavaliers a legitimate wing.

That position remains the biggest question for the Cavs, and the answer depends on what happens with these free agents. If Cleveland adds one of them, the team will have its starting wing.

In his time with the Atlanta Hawks, Kuminga played 16 games. He came off the bench in most of them, and before that, he was a reserve for the Golden State Warriors. If he comes to Cleveland, he could become a starter and play alongside Evan Mobley and Jarrett Allen in the frontcourt. Or, Kenny Atkinson could keep him in a reserve role, and have someone else in the starting lineup. Either way, the 23-year-old wing can contribute.

Watson moved to the starting lineup last season, as he started in 40 of his 54 games. The year before that, he played 68 games, and he started in 18. The young forward had a respectable 2025-26 season, and he can build off of that momentum in 2026-27. The Cavaliers will give him a chance to do so.

In the event the Cavs miss out on both players, they have someone who could step into the role. Jaylon Tyson had a breakout sophomore season, and he was a starter for 42 games. So, he would be comfortable in the role. The Cavaliers could also turn to Max Strus, but he may remain a reserve and give them a boost off the bench.

The starting lineup could look different this season, and the difference will be the small forward position. One has to wonder who will have that role and whether the Cavs will make a move to address that area.

For now, it looks like Tyson will be the starter, but once Kuminga and Watson make their decisions, the Cavs will have a clearer vision, and they can prepare accordingly.