The Chicago Bulls' POV
If the Bulls entertain trading Caruso, it's hard to see the Bucks' offer being the best one for them.
Chicago is in a weird spot where they're too good to tank but not good enough to make a playoff run. And, without a real chance to improve the roster, they'll probably do good in collecting assets if they blow it up. So, since Caruso is the kind of player teams really want in a winning environment, it makes no sense to have him on a team that's actively struggling year after year.
By trading him to the Bucks, the Bulls would get Portis, who could become a trade asset in the future, Beauchamp, a young player they could try to develop, and one first-round pick, which they could use to get another young prospect. Assuming they also move on Zach LaVine in this scenario, they would finally become a lottery team and could rebuild after a few years stuck in the middle ground.
The thing is, if Chicago really goes for the rebuild, Caruso is going to be a very coveted player, and the Bucks won't be the only team offering a trade package. So, is this a winning offer? Likely not.
Beauchamp has shown some potential, but he's far from being a guaranteed solid player. The 23rd pick in a supposedly bad draft probably doesn't move the needle, and Portis doesn't really fit on a rebuilding team.
Another first-round pick could make things interesting, as the Bulls could possibly talk themselves into thinking Milwaukee will be a bad team down the line, making that pick extremely valuable. Yet, that is not the proposal here.
This trade could make sense for Chicago in a vacuum, but they wouldn't be getting the true value a player like Caruso could command on the trade market.
Grade for Bulls: D