I've long had the impression that Maher is a reluctant leftist. He'll toe the line enough to be accepted by his side and despised by ours, but too often he'll point out something that's (to us) obviously fucked up about the Left. I don't think he does it to play both sides, because he doesn't do it enough to gain any fans over here, just weaken his position over there. Each time he does it, it's to his own detriment.

My working hypothesis is that he's a normal, sane liberal comedian who for whatever reason (compromising honey-pot stuff?) found himself positioned as a mouthpiece for the Progressives, and can't see a way out without them annihilating him.

If he wasn't a public figure (read: "wasn't deeply compromised/controlled"), I honestly think he'd have wound up as one of us former Obama voters who said fuck this and joined Trump's side long ago.