A very simple explanation for Jeb Bush's bombing in the primary season and failure to resonate with primary voters is the 14 year freshness rule. This is the hypothesis but might as well be a rule, proven through the last 10 or so presidents, that once a candidate wins a statewide governorship or senator position, they have a 14 year window to run for president. Jeb is running head long into this problem since he was elected governor of Florida in 1998.
Why 14 years? Part of this is time in front of the nation to make big mistakes, and part of this is preventing the party from leaving you behind. Clinton and Bush both face these problems today. Hillary gets attacked from the left nonstop today, and even was attacked by Obama on the left in 2008... seven years ago. Isn't Jeb just Romney redux? Jeb is not quite Mitt Romney despite being the Establshment's choice because at least Mitt had that Don Draper attractive, alpha businessman appeal. He was a winner. There is another weird thing about Jeb, and it is exemplified by other summer stories. Jeb Bush is Rachel Dolezal.
Rachel Dolezal and Shaun King were both white kids with white parents. They both exhibited oddities as teens of identifying with cool black cultural things. Both went to black colleges and earned scholarships intended for black recipients. Both married a member of their cultural object of affection and had at least one kid. They took their obsession and cultural identification with the "other" to its logical conclusion by pretending they were now part of the other tribe and took up the fight for the "other". Both became leaders of different political advocacy groups of their now assumed tribe.
Jeb Bush was raised in Texas. He was surrounded by Texas, Tejano and even Mexican culture due to his father's many deals with Latin Americans as founder of Zapata Oil. Jeb then went to college at the University of Texas to major in Latin American Affairs. He spent time in South American nations. He buddied up with connected Mexicans. He married into the culture and had kids. Spanish is the language of his home. He worked and made good money in another heavily Latin area, Miami. He even filled out a voter registration card and checked the Hispanic box. Jeb now places illegal immigrant, legal immigrant and potential Mexican immigrant interests above the interests of Americans.
Jeb has became part of his cultural object of affection. Jeb has taken up the interests of the "other" he now identifies with. Jeb is transHispanic. This is part of Jeb's problem. As identity politics take a new turn a man as craven as Jeb is to please the "other" is not going to resonate or generate connection with his voting bloc that is overwhelmingly not the "other". As white acting as Obama is and as removed from black culture he was his entire life, he needed Michelle as his "bleard" so that enough blacks could be tricked into thinking he was one of them. Jeb Bush, the preferred candidate of the GOP establishment, is just another Rachel Dolezal.