Growing up in Vegas I've always heard stories from multiple people (quite a few people actually) of how he was such a prick. Whether it's stories of him yelling at little kids at the local park for getting in his way or stories of him picking random fights with people at parties just for the hell of it or him just being a cocky self entitled dude, he has never been made out to seem like someone who wasn't a prick from people I've talked to.
It's good to see after all these years though that he has humbled himself quite a bit and now seems like a quite a stand up dude, and as others have said he's pretty damn sincere. Definitely wasn't expecting this at all.
From the D3 story to the Jamie Thomas stories, tons of good stories so far. Still haven't finished it all yet, a little over half way through, but so far this is my favorite episode in a while.