Nailed it.
Believe it or not, Bayless once was legit sports writer and called it like it was -- you know, "just another guy". As the years went on, he became more and more opinionated and realized that the more bizarre, outlandish his opinions were, the more attention he would gather, the more (im)famous he would become and the more money he would make.
It's amazing to see the amount of people who get worked up over his takes. The guy has it mastered. Take a nationally publicized figure (ala Tebow, the Cowboys, etc), side with the unpopular minority, and say it all with a straight face. As DDR alluded to, trolling at it's finest.
So yea, Skip has basically become sports' version of Stephen Colbert, and now look at where it's gotten him. Good for him.