I think he had the confidence but no success. Then with a little confidence ie being himself, he said things that everyone was thinking...
He's in the enviable position that he can now be himself.. who in essence is one of us.
I think that we're in a time that is a lot like '92. And I think people are searching for that person who comes across with something different. Perot did it in '92. Trump is doing it in '16. Does he do better than Perot? That's yet to be seen.
Honestly, I think we more in a time like the late 60's. Not exactly, but similar. We have re-awakened a lot of the social movement issues of that time. But instead of female equality, it's now LBGT. We have a seen a rise in tensions in black communities much like we did in the late 60's and early 70's. They haven't tipped as severely like during that time, but have come close. We've gone from pro-war in the early 2000's to cautiously anti-war today. Not as bad as the 60-70's, but the support for war has severely waned. Recreational drug/pill use seems to be on the rise again. Young people again have began to be on edge.
I really believe that Trump's success at this stage is a bit of a surprise to him as well to many others.
For now, he's not beholden to the usual groups and money that candidates traditionally have to ally with to be in the game. Will someone from one of those groups 3rd party him if he becomes the standard bearer? I thinking primarily social conservatives who could find his social stands of the past repugnant or they support someone more vocally proactive.