2. Isaac Okoro
Okoro is a restricted free agent this summer. The two sides couldn't agree on an extension before the 2023-24 season, and it will likely take $15-20 million per season to keep him. Do the Cavaliers want to lock him in with Evan Mobley and Donovan Mitchell getting fresh contracts? Okoro continues to improve, but Cleveland is unlikely to spend well beyond the second tax apron.
They could let him walk in free agency, but the Cavaliers have the power to match any offer. It certainly gives them leverage. Okoro has been a role player in his first four seasons and likely struggles to find an offer for more than the mid-level exception outside of Cleveland. That is an easy match for the Cavs, but things get complicated beyond that number.
The Cavaliers should try to find a sign-and-trade if Okoro wants to leave. It would cap them at the first tax apron, but it is Cleveland’s best path to getting something in return for the 23-year-old wing. Working out a deal will have challenges. The Cavs will be forced to embrace them to maximize their roster.
The most likely scenario is Isaac Okoro returns to Cleveland, but there are several dominos to fall before that date. The biggest would change everything for the Cavaliers and may force a total retool of their roster.