Why Jeb Bush Couldn’t Win

For five painful days last year, Jeb Bush struggled to answer the obvious question facing anyone with his last name: Would he repeat his brother's fateful decision to invade Iraq?

When Fox News anchor Megyn Kelly asked the inevitable question, Bush said he backed up his brother. "I would have, and so would have Hillary Clinton, just to remind everybody," Bush said. As the media swarmed and donors fretted, the presidential candidate ham-handedly struggled to clean up his unforced error, ultimately declaring that knowing what he knows now he would have made a different decision than the 43rd president.

The events illustrated everything that was wrong about another Bush candidacy. The uncertainty. The role of his dynasty. The limits of money over personalities. His unfamiliarity with an unforgiving modern news cycle that rewards gaffes over well-thought policy. The fear of letting his famous family down.

That was in May. He never really recovered.

In the end, John Ellis Bush was not the candidate Republicans were looking for in 2016. He didn't even live up to the hype, years in the making, that this scion of one the most powerful families in Republican politics could be a stellar leader.

And, with a whimper, the former Florida Governor packed up his campaign Saturday night and went home to Miami. In typical Jeb Bush fashion, he would want to know what they could have done differently and where they went wrong. But first, he just wanted to exit a race for the GOP nomination that has defied precedent, civility and, at time, belief.

In a year when experience was a vulnerability rather than a resume line, Bush insisted on running a policy-centric campaign in a year that saw bluster overtake substance. "In this campaign, I have stood my ground, refusing to bend to the political winds," he said before leaving the stage, tears visible in his eyes. His insistence on running his campaign his way proved his undoing. While rivals mastered clipped sound-bites, he held forth on policy. When reporters tried to goad him into questions about politics, he defaulted to wonkdom. If a voter took the time to attend his town halls, he owed it to them to give a thoughtful answer.

"This way my guy," said Tiffany Pritchett, a veteran of George W. Bush's White House and Commerce Department. "I'm shocked Trump did as well as he did, respectfully." The Davidson, N.C., resident spent her week knocking on doors in South Carolina for Bush, and she found herself getting more and more emotional about the idea of Trump sitting in the same office as George W. Bush. "I just wonder," she said, "what happens now."