No. 2: Caris LeVert
The dilemma with Caris LeVert is not a new one. He's a talented player who operates best on the ball. Given the reality that the Cavaliers have two players in Donovan Mitchell and Darius Garland who are better options to have the ball, LeVert's value to the Cavaliers is less than it would be to many NBA teams.
At the same time, LeVert hasn't refused to adjust but has worked on his defense and shooting to become a better fit for what Cleveland is asking of him. When one of the Cavs' two starting guards misses time, LeVert is an incredible insurance policy. The Cavaliers aren't going to be shopping LeVert as a team motivated to get rid of him.
LeVert makes $15.3 million this season and is therefore the best pathway for Cleveland to match salary in a trade for a more expensive player without breaking up their four-man core. That makes LeVert the likeliest player of any on this list to be a part of a trade this season, and such a deal could be executed anytime after December 15.
No. 1: Max Strus
The Cavaliers' top addition this summer was Max Strus, both in the amount of money handed out on his contract and the starting role he has stepped into for the team. Strus has been healthy and available for all 21 of the Cavs' games and his movement and gravity on offense have clearly had a positive effect.
There are certainly players in the league who bring a similar skillset to Strus as a movement shooter while bringing either improved accuracy or more size defensively, but the reality is that the Cavaliers don't have the scratch to pursue them. Strus was their target to upgrade in that area, and he has been a positive player worth the contract he was given. There's no viable path to him being traded once he becomes eligible in a week.
None of these players are particularly likely to be traded; when and if the Cavs do make a deal, incumbent players such as Isaac Okoro, Ricky Rubio and Dean Wade seem more likely to be sent out, or even perhaps Jarrett Allen in a more tectonic trade. Even so, it's helpful to have options, and the Cavaliers will soon be free to trade any player on their roster.