Juan tries to maintain the progressive con of always arguing the diametric opposite of Good, Right and Moral. Just as Alan Combs use to do on the old H&C show.
His portrayal of being right about his arguments shows up in his mannerisms from time to time because he knows that what he's arguing is wrong. He knows it. Many of these progressive fucks know it. "Never give up the con".
And Neil? He's a never Trumper. Fuck him.