Don't know enough about Middleton to comment, so just a question for
supporters of this idea.
What about Middleton other than his size is a reason to do this trade?
Good page for looking at when players are eligible for trades: http://www.hoopsrumors.com/2015/11/special-trade-eligibility-dates.html
Middleton not until January 15th, Gallinari not until February...
Middleton is a 40% 3pt shooter that has excellent shooting stroke/mechanics, and is a good 3 and D player with the versatility to guard 1-4 positions. I always said if he bulked up, he could be like a better shooting, with lesser defense, version of Draymond Green.
While his impact defensively isn't as resolute or resounding, Middleton offers plenty of useful attributes. Good attitude, hard worker, seems to have great locker room chemistry with all of his teammates, great passer for his position, (someone on the Bucks blog once posted Middleton had really high passing percentage, but none that resulted in an assist, I'll find it later!) and great ability to guard the 2 and 3 extremely well due to his length/wingspan.
I just suggested this trade, simply cause Middleton in my opinion should be a 3. He should only be a 2, if there isn't any room for him, because I just don't like making him a spot up or catch and shoot. Middleton can score in the low post, and can also hit fade away mid range jumpers.
I also always felt Middleton could score 16+ if he took more shots, considering he hasn't taken more shots than Avery Bradley, who has taken more shots in lower minutes. With Monroe, Parker, and Giannis, I always wondered if they had too much talent in the 3 spot. I don't like Parker at the 4, but if the Bucks want to run a faster offense, Monroe at the 5, and Parker at the 4 makes sense. Bradley could fit perfectly in their offense, plus it gives a guy that will hustle on defense, and set the tone by being a pest. Middleton doesn't have the same speed as Bradley, but uses his length extremely well to bother scorers on offense.
A back court of Smart, and Middleton could actually really work well. It allows Crowder to focus mainly on defending the Small forwards and just make the right play without having to score consistently.