John was alright 20 years ago, but he went through a lot of changes since then. I first met him when he came up to me in a store and started chatting with me and my girlfriend at the time while his wife was talking to a sales clerk. He was a decent guy back then. A couple of my old friends are in his music videos and I could have been as well, but it seemed too weird to actually get involved in that.
He seemed to take a hard left turn after he realized his fame was growing wider, but also growing a little thin since he struggled to make music with "serious messages" instead of music people actually enjoyed. So he jumped on the angry liberal bandwagon to keep the momentum going in his career. Hard to say what might have been, but at the time it was probably a calculated business decision and not an artistic one. I'm surprised he has been around this long and is still doing gigs, so maybe it was the right move for him.
I dont know, if he would have kept churning out "feel good" music he would have made LOTS of $, look how much Michael Jackson made, he was set and after those next couple of garbage albums it was like he died.