When posting about Jeb Bush, the first question is, ‘Does anyone even care?’ But, still…
IMHO Jeb had two fatal problems, and they were closely intertwined. The first and most obvious was, on key issues like Amnesty and Common Core, he was simply way to the left of the mainstream Republican voter. Jeb’s wealth and family connections insulate him from the consequences of mass immigration and bad public schools; he really doesn’t have skin-in-the-game on those issues and can’t relate to those who do.
The second is his inauthenticity. Jeb tried to run as a conservative and nobody bought it. Jeb has always been a Big Gov moderate like his dad and his brother. People who are insulated from the negative consequences of progressive, big government policies tend to favor them. Jeb Bush has always been a creature of the political establishment — that part of the GOP that has more in common with their Democrat counterparts than with the people who vote Republican. These are the guys who are always happy to compromise (i.e. capitulate) in the interest of “bipartisanship” and “showing the American people we can work together.” He even gave Hillary a medal, for Set’s sake.
If Jeb had run as the Big Government moderate he really is, in his heart of hearts, he would at least have consolidated the Establishment Moderate vote behind him. But by trying to pass as conservative, he only succeeds in alienating both wings. All of the really expensive video mailers in the world won’t help an inauthentic politician who is out of touch with his voters.
It takes the complicity of the entire national media to pull that off.