I dont see how we could get both of those players and not be giving a top pick in the draft to do it. This trade would definitely fill 2 big needs on our team. I would imagine if they are asking for late picks this year, it would be in addition to a top pick in 17 or 18 which I am less inclined to consider unless I have a commitment from someone named Durant that Green is going to be his color for the next decade.
I would do 16, 23 and a good/top player and pieces on our roster for Middleton and Monroe without hesitation. Monroe's plus minus is not horrible last year on a horrible team(don't look at his last 6 games though- -15) and even his FT percentage is acceptable and not Rondo like anymore. Play Monroe 35 a game and we are looking at 10-12 rebounds and 17 plus points. It is hard to blame Monroe for the Bucks woes last year though..that lies with the coach. Middleton would be our end of game shooter along side with IT and I believe it would free up IT a lot more and save him from double teams.
Back to reality though, I just don't see this trade happening. On a scale of 1-100 on likely of happening it might be close to a 0 without a top pick thrown into the mix.