First I'd be very concerned about his defense. Why has his teams always been in the lottery? Now the Pistons are in the playoffs and the Bucks are in the lottery which isn't entirely a coincidence. We'd have to change the entire offense with Monroe in it. Yeah he gets easy buckets, but how many sets have to be run for him to get the ball instead of pick and roll's for our guards? Dame and CJ wouldn't be scoring 20 ppg. Post players aren't as valuable in the modern NBA. Looks at Boogie, Brook Lopez, those teams struggle. The modern NBA is dominated by pick and roll with 3 point shooting. We could use a third offensive creator with screens or pick and roles. We need bigs who defend. Worrying about mathing up with Golden State when we aren't a HCA team is silly. Even so I don't see how Monroe running all over the court trying to defend Draymond Green is a matchup advantage for him.
It's not that Monroe doesn't have some value; its that he's on a max contract, will be due a huge raise a year from now, and his team will want an asset in return. If for some reason Milwaukee dumps him for nothing sure do it. But he's not an all-star level talent thats worth giving up multiple assets for.