I do like the idea of taking a chance on Dion Waiters. I do not think he is worth giving up on Sullinger though. His trade value should be lower than that given the continued problems Waiters has had in fulfilling his talent.
I am low on Tristan Thompson. Unskilled PF. An offensive liability. I do like his potential as a defender & rebounder but I see as a backup PF long term due to his offensive limitations. I think someone like Ed Davis can give you 90% of what Thompson does for a much lower cost. So my interest level in Thompson is extremely low. Only rate him at a 1-2 2nd round pick in terms of trade value.
I'd rather leave Thompson out of the deal altogether. Celtics have 2 superior PFs in Sully and Bass and maybe even a 3rd in Olynyk. See no reason to pursue him. I'd rather target Waiters by himself.
I do love the idea of trading Bradley for Waiters and I do think such a trade is feasible given the problems Cleveland have had with defensive quickness at SG position in the backcourt position + need for someone who can play off the ball and accept a smaller role on offense. Both are strengths of Bradley. Given Cleveland's push for a Championship, I could see them settling for the less talented Bradley in an effort to boost immediate title hopes.
I think Waiters would be a great fit alongside Marcus Smart. An aggressive higher usage offensive player who is a talented dribble drive player, quality secondary ball-handler and playmaker & a strong outside shooter. I think he is the type of aggressive SG that a low usage PG like Smart could work well with.