Yes, he was the son and brother of a president and member of a family featured in American history for multiple reasons. And yes, he was a two-time Florida governor with such a hearty donor network, collectively built by the various Bushes who have sought public office, that early on his advisers thought the size of his campaign war chest would scare other Republicans out of the race. But as a result, Bush and his campaign staff were so sure that Jeb Bush, presidential candidate, would suffer only from what are basically one-percenter political problems that they even went with "Jeb!" — just "Jeb!" — on his campaign materials.
But it wasn't long before far more fundamental problems with the Jeb! machine — everything from the candidate's posture and demeanor on the campaign trail and the debate stage to answering uncomfortable but valid questions from reporters and, oh, appealing to voters — came to occupy some of the campaign's time and resources.
Bush pulled out of the presidential race Saturday night after a distant fourth-place finish in the South Carolina Republican primary, garnering just under 8 percent of the vote. In memory of the big campaign that couldn't, The Fix has compiled this timeline.
- In mid-June when Jeb Bush officially announced that he was running for the White House, he had already been discussed, written about and generally described as the clear Republican front-runner for weeks. Bush launched a six-month exploratory effort to contemplate a White House run and raise campaign cash without the restrictions federal law puts on declared candidates. With all that obvious advantage baked in from the start, it wasn't surprising that Bush opted to announce his campaign at a community college, Miami-Dade Community college, the largest in the United States and a school with one of the nation's most significant Latino student bodies, to be exact. Jeb Bush, candidate for president and third of his surname to pursue the Oval Office, was a man of the people. While he was there, Bush made sure to mention that he was his own man who had found and navigated his own path. And before the announcement, Bush shook up his campaign staff in what the Washington Post reporter closely following him described as an admission that Bush's six-month-long campaign exploratory phase hadn't produced desired results.
- By July, Bush had begun to demonstrate some of his unique strengths and weaknesses as a candidate. A fluent Spanish speaker, Bush set about giving interviews and sharing his policy positions on a variety of issues — including immigration — in both Spanish and English. Bush's Spanish and his more moderate positions on issues such as immigration had many Republican operatives convinced that the Bush campaign could secure much more of the Latino vote than the Romney campaign had in 2012 or the McCain operation did in 2008. For Republicans, fixing or at least making progress in the direction of building a voter base that looks like the entire country is a critical feature of the party's long-term strategy. Bush, it seemed, might be a linchpin. But that same month, Bush stumbled when he suggested that America's economic woes could be fixed if Americans would simply work more. The campaign insisted that Bush's statements were not a suggestion that American workers aren't putting in enough time on their jobs, but rather a statement about a shortage of full-time jobs for those who want one. Neither claim fully stands up to a fact check. But that's what Bush prescribed.
- The following month, Bush ran into a type of trouble that most political observers and voters likely expected him to be fully prepared to manage. When asked about his brother's decision to invade Iraq and the subsequent fallout, Bush defended the widely unpopular decision, then backtracked and called it a big mistake. There was some more back and forth and some more embarrassing sessions where Bush seemed genuinely torn between a desire not to do his own brother dirty and demonstrate the kind of decision-making that Americans want in a president. It was an understandably tough spot for any candidate. But with Bush's run seemingly long-planned, and a kind of trial run of this question and Bush's bumbling answers already out of the way in June, lots of people expected more. And with his campaign resources so vast, the difficulty perhaps should not have been so very obvious in public. By the end of that month, Politico reported that some of the Bush campaign's fundraisers were leaving the operation. One bit of good news for the Bush campaign came when the Planned Parenthood video controversy prompted other candidates to try to demonstrate long-term opposition to the organization. Bush told Americans he had cut off funding for the organization when he was governor of Florida. And that was true.
- September, October and then November were supposed to mark retooling time for the Bush campaign. By September, Bush had already delivered a few debate performances that were not widely praised or generated split-screen Trump/Bush mash-ups. Donald Trump had even refused to apologize for a slight directed at Bush's wife after a direct request from Bush. Optically, that was bad. Very bad. But Bush was demonstrating an ability to speak in a sharper, more direct fashion — in Spanish. And in October, CNN said that Trump had basically done Bush the favor of needling him out of some kind of slump. Politico said Bush was in the midst of an identity crisis, while CNN chimed in with it's own theory: an existential crisis. All the while, Bush was on the campaign trail and spending what his campaign later said was such significant time preparing for debates that he was just beginning to really focus on voters. In addition, during an October debate, Bush once again found himself under attack by Trump via his brother's presidential record. And once again, Bush defended his brother. This time, Bush spoke out against Trump claims that 9/11 was George W. Bush's failing.
- In early November came a formal and very public-facing campaign overall, including the introduction of a widely ridiculed campaign slogan — "Jeb Can Fix it." Let's just say there was not a lot of buy-in. Oh, and the campaign did not buy the actual "Jeb can fix it" domain name. Predictably, Internet antics ensued. Bush's long-sagging polling numbers reached what some considered a real crisis point when a much-respected Quinnipiac University poll found only 4 percent of Republican voters nationwide were backing Bush. Bush's massive campaign coffers hadn't scared off rivals, nor, it seemed, had it helped him win many votes. And Bush told a group of New Hampshire school kids that knowing that he had disappointed his dad has been known to send him into a "deep, spiraling depression." Just imagine the questions moms and dads in New Hampshire got that night.
- By December, Bush had turned in at least two debate performances widely regarded as solid. They were not winners, but sturdy, reasonably energetic and confident. They were what most reporters described as likely to help the candidate build some voter support. The New Yorker magazine said Bush had transformed himself into a willing "Trump fighter." But by this point, Trump had been living at or near the top of most polls for months.
- In January, exceedingly optimistic predictions about Bush's supposed long-game, his chances for winning Iowa and his newfound or at least newly displayed toughness were cropping up in newspapers and magazines. Murmurs were starting that Bush, of the "I am my own man" campaign, was reready to ask for help and deploy every member of the Bush team he could to salvage his flagging campaign. And near the end, that's precisely what he did.
- At the start of February, Bush announced another new hire, a national campaign adviser who played a key role in George W. Bush's 2000 and 2004 campaigns in Ohio. But he also turned in a speech before a New Hampshire audience focused on what he would do to protect the country as president that generated such a silent response that Bush uttered those now infamous words: "Please clap."
- On Saturday, Bush's utter investment — campaign resources and staff, ground effort, as many Bushes as were fit to travel — failed to pay off. Bush's defeat in South Carolina was likely especially difficult because the state had played such a strong role in the presidential bids of both his father and brother. And South Carolina, on paper, looked to the Bush campaign like the kind of place where a traditional, establishment Republican could, perhaps should, do well. Bush did not and called an end to his campaign.