Khris Middleton, Milwaukee Bucks
This season is either going to be a great year for the Milwaukee Bucks or it's going to be a disaster. I'm not sure there's any in-between for a team that went all-in on this build last offseason by acquiring Damian Lillard. Even though it didn't work out for Lillard and the Bucks last year, there's hope it can work in the opposite direction this season. But if it doesn't and if that becomes clear early on in the season, I wouldn't be surprised to see the team explore a potential in-season big move - one that could revolve around a potential trade of Khris Middleton.
If the Bucks aren't able to make their build work this season, you'd expect some big changes come next summer. But if Milwaukee isn't prepared to wait until next summer to make a big move, perhaps trading Middleton could be on the table for the team heading into this next trade season.
Who knows what Middleton's trade market would be but he's the most likely trade candidate of all the core players on the roster.