Good on you for spending time checking him out. Definitely full of himself but I really enjoy his absolute irreverence for being offended.
I also enjoy that and have long felt the key to not feeling crushed when a bigot, sexist, right winger, left winger, athiest..whatever... attacks you verbally, is to ****ing fire back. get under THEIR skin. Being complete dick and trying to get under peoples skin can fun, and he believes it is necessary (and that it needs to be ramped up by 10000%) to get over this oversensitive PCism era we are in. I see the beauty in that at a high level, but what are the lines? I think he believes there are none as long as there is no physical violence. Yet I'm guessing that his male fans and fellow "its all fair game" trollers would not high five a guy that muttered "You fat ****ing ****" to their wife or kids in public. Common sense says that is just being an asshole, not trolling, but how many of his followers see a difference? Also..is it all fair game on the internet and in writing, but then we go back to social norms when conversing in person?
He's also a bit of a hypocrite in that he believes he can say anything at all while trolling, but then whines when two lesbians troll the Indiana pizza guy by taking photos of them eating his pizza at their wedding. I saw several other instances where he talked about how "ugly and hateful" somebody was because they said something hurtful towards him. Nah dude, if you are going to dish it out and say that that is the center pillar of your party, not only do you have to take the trolls that come back at you, you have to cheer them on. Otherwise your whole schtick is exposed as bs.
He's also 100% partisan to his party, which can make him similar in ways to the most extreme Republican and Dem talking mouth pieces. It will be interesting going forward to see if he ever disagrees with Trump on anything.
I both like and respect him for his intelligence, but I also want to smack the shit out of him.