For Jeb Bush's campaign, August was a cruel month. Donald Trump's attacks on the former Florida governor as a "low-energy" politician were beginning to stick, and the two were bickering over immigration. The issue before the Bush team was what to do about it.
Some advisers argued for an aggressive response, even to the point of challenging Trump to some kind of one-on-one confrontation. Others resisted, believing Trump's candidacy was unsustainable, while some cautioned against getting into a pigpen with a pig, as one adviser recalled. Others described it as trying to wrestle with a stump.
Those summer days crystallized the plight of a campaign that had begun with enormous expectations and extraordinary resources, as the scion of one of America's dynastic political families sought to follow his father and brother to the presidency.
At what would become a crucial moment, Bush's team had no clear strategy for a rival who was beginning to hijack the Republican Party that the Bush family had helped to build, other than to stay the course set months earlier of telling Bush's story to voters.
"There was no consensus," senior strategist David Kochel said of the discussions about how to combat the threat of Trump's candidacy. Other campaigns were wrestling with the same problems, but as the frontrunner in the polls at the time, Bush would suffer more than the others.
On Saturday night, the candidacy that had begun with such promise ended quietly after a disappointingly weak fourth-place finish in South Carolina.
Ever the gracious realist, Bush announced in his concession speech that he would end his campaign as Trump continued to soar as the GOP frontrunner. "I have stood my ground, refusing to bend to the political winds," he said.
Whether Jeb Bush ever had a chance to win the Republican nomination in a campaign year that proved so ill fitting for a rusty politician who preferred policy papers to political combat is a question that will be debated long after the 2016 race has ended.
"Donald Trump channeled the worst fears, frustrations and anxiety of voters, but he also magnified those same feelings," Sally Bradshaw, Bush's chief strategist and confidant, said on Sunday in an email. "It would be difficult for any solutions-oriented conservative to tackle Trump in this environment, much less one who was seen as having been so much a part of the establishment. He was never going to be an angry guy-and voters wanted angry."
The result is one of the most startling failures in the modern history of American politics: the fall of the House of Bush. It is a human story about the struggles of one of the most successful former governors in America in his bid to become president, like his father and brother, set against the backdrop of one of the strangest political cycles the country has seen in years.
Beyond underestimating the anger in the electorate, three other problems led to Bush's downfall. First, the candidate and his team misjudged the degree of Bush fatigue among Republicans.
Aides said an internal poll conducted last fall showed discouraging news: roughly two-thirds of voters had issues with Bush's family ties.
Second, Bush and his team miscalculated the role and power of money and traditional television commercials in the 2016 race. During the first six months of 2015, Bush raised more than $100 million, most of it stockpiled in a super PAC called Right to Rise USA, a strategy that seemed right at the time but came at the cost of not dealing with other pressing needs.
"We didn't use that time to introduce him as a unique brand," said Vin Weber, an outside adviser. "We used it to raise money. I don't want to say they made an obvious and clear mistake, but in retrospect it was a mistake."
The aggressive fundraising came to be known as "shock and awe," an echo of the initial bombing of Iraq by U.S.-led forces before the 2003 invasion. In the campaign context, it could be read as code to other potential candidates to get out of the way. But the prodigious fundraising of Bush's broad network scared off no one. As the Bush campaign would learn, every credible candidate today has a few billionaire friends who can enrich a super PAC. In the end, all that money came to symbolize frustration rather than power.
Third, Bush ran a campaign that, whether deliberate or not, was rooted in the past, managed by loyalists who admired Bush and enjoyed his confidence, but who, like the candidate, found themselves in unfamiliar political terrain.
His advisers were persuaded from the start that the more voters learned about what Bush had done as governor of Florida from 1999 to 2007, they would flock to him as their presidential candidate. Bush stubbornly held to that approach — even as evidence mounted that it was out of step with voters.
Doug Gross, a prominent Iowa Republican, recalled meeting with Bush in July 2014 in Kennebunkport, Maine, to talk about the impending campaign. "He definitely wanted to run, he's always had it in him and knew this was his last chance," Gross said. "He was trying to figure out how to do it his own way. I was struck by his obstinate avoidance of any political discussion. … He wanted to do it his way or no way."
Skirmish, then turning away
In contrast to the doldrums of August 2015, July seemed a glorious time for the Bush team. Early that month, Team Jeb gathered in Kennebunkport to celebrate that the campaign and two allied political committees had together raised nearly an unprecedented $120 million. The numbers were made public as nearly 300 major Bush fundraisers assembled to mingle with the Bush family and campaign advisers.
Guests were transported in black-and-red trolleys to Walker's Point, the Bush family compound. The group gathered for a photo with former president George H.W. Bush and Barbara Bush.
That evening, Jeb Bush touted the team's record fundraising as guests dined on lobster rolls and hamburgers at a luxury resort tucked among a forest of birch groves and balsam fir. "It was incredibly memorable to be there with several generations," said Jay Zeidman, a Houston-based investor who helped raise money from young professionals.
The next day, the donors got briefings from senior Bush aides including Bradshaw, campaign manager Danny Diaz and finance director Heather Larrison. They laid out how the campaign planned to take on contenders such as Sen. Ted Cruz of Texas, Sen. Marco Rubio of Florida and New Jersey Gov. Chris Christie. Throughout, there was little mention of Donald Trump.
None of the top aides thought he would last the summer, said one person who was in attendance and who spoke to the Washington Post on condition of anonymity.
At that moment, however, Trump was already in the process of undermining Bush's candidacy. If Bush had ever gone up against someone like Trump, it didn't show. Trump was a new and different kind of rival, one given to personal insults rather than policy debates, who monopolized media coverage and got away with provocative statements that would have sunk normal politicians.
After marching in two July 4 parades on a rainy Saturday in New Hampshire, reporters asked Bush about Trump's claim that Mexico was allowing immigrants to illegally cross into the United States. It was one of the hundreds of times he would face such questions.
Bush said "absolutely" he was offended by Trump's rhetoric. "We're going to win when we're hopeful and optimistic and big and broad rather than 'grrrrrr,' " he said — literally, growling — "just angry all the time."
That very night, Trump attacked Bush as soft on immigration and took aim as well at Bush's wife, Columba, who was born in Mexico and entered the country legally — retweeting and deleting a disparaging comment about her.
Nothing, however, cut as close to the bone as Trump's claim that Bush was too "low energy" to serve as president.
The accusation was laughable — until it began to stick. Trump's charge was in fact a proxy for a different and more difficult argument to combat, that Bush was neither strong nor edgy enough for a party seething with anger at the grass roots.
"Nobody tapped into it, for all the polling, all the focus groups," said Theresa Kostrzewa, a North Carolina lobbyist who raised money for the campaign. "The biggest thing they did was miss was just how angry the American electorate was and that Trump would be their Captain Ahab."
Bush's advisers would contest that claim. They could see the anger, they said. The issue was what to do about it. "Donors, political operatives and big thinkers from around the country urged us to ignore Trump for months," Bradshaw said. "There was no one in the news media or the operative class at the time who felt Trump would ultimately be a serious contender for the nomination."
At the same time, others feared that engaging Trump was almost beneath Bush and would thrust the candidate into a never-ending game of charge-countercharge.
Over at Right to Rise, Bush's super PAC, chief strategist Mike Murphy sent a clear signal: Trump is not our fight right now.
"If other campaigns wish that we're going to uncork money on Donald Trump, they'll be disappointed," the strategist told the Washington Post in late August. "Trump is, frankly, other people's problem."
At that moment, the Bush team's analysis showed that no Trump voters were likely to shift their support to Bush. Attacking Trump, an adviser to the super PAC said, would only have benefited other candidates. Bush's campaign needed to consolidate his position as the establishment candidate while hoping that Trump and Cruz would sort out the competition among the anti-establishment candidates.
Bradshaw also dismissed complaints from some donors that she cut the candidate off from advice. Noting that Bush long has been active on email, Bradshaw responded in a message by saying: "Donors constantly gave conflicting advice — attack Trump, don't attack Trump; smile more; smile less — you look like you are smirking. I didn't tell people they were wrong — not my style — I did a lot of listening, and I'm sure there were things we could have done better — but withholding info from the governor simply did not happen in our campaign."
For much of the autumn, Bush's engagement with Trump was on-again, off-again — skirmish, then turning away. Not until late last year did he truly start a concerted and sustained series of attacks. Aides said Bush was particularly affected by the terrorist attacks in Paris and San Bernardino, Calif., and felt, as one adviser put it, it was time to stand up to the bully. The adviser spoke to the Washington Post on the condition of anonymity.
"Jeb was the only candidate with the political courage at the time and frankly throughout the last six months to take on Trump directly for doing something that the governor felt was very harmful to the party and to the country," Bradshaw wrote. "There was no hesitation at that point given his comments about women, about Hispanics, his lack of knowledge on issues of national security and on and on."
A flat-footed image
Bush's failure to come to terms with one of the downsides of his family name came to a head over a four-day period in May, when he stumbled over the decision by his brother, former President George W. Bush, to go to war in Iraq.
Changing his answer on a daily basis, Bush came across as a flat-footed campaigner clearly uncomfortable articulating his views on the most critical moment of his brother's presidency. But it highlighted as well the double-edged nature of being a candidate named Bush.
In a January Washington Post-ABC News poll, nearly six in 10 Americans held an unfavorable view of Jeb Bush. He was the only Republican with a negative favorability rating: 44 percent said they had a favorable impression of the former governor while 50 percent rated him negatively. His rankings grew worse as the campaign progressed.
A fundamental weakness, supporters said, was the lack of a coherent rationale for Bush's candidacy and the failure to make inroads with activists on the right.
Bush offered ideas, but in a campaign dominated by Trump, they were ignored or lost to most voters.
One of the biggest tactical advantages Bush appeared to have early on – a richly endowed super PAC — was not the invincible weapon his team thought it would be. It cut off his access to a key adviser, Murphy, whom he installed at the group's helm.
It also meant that during the first six months of last year, nearly all of the coverage about Bush focused on how he was socking away millions into the super PAC, all while maintaining that he had not decided whether to run. In an election brimming with anger toward the wealthy elite, Bush seemed almost flippant about his pursuit of big dollars.
Murphy was convinced that much of what was taking place was noise and that when the voters began to check in, the super PAC's financial might would be overpowering.
First, the committee would use it to lay out Bush's biography. Then, as necessary, the group would turn its arsenal on his rivals. "Our job is just to amplify his story and what he's saying and we banked enough cash that nobody's turning our speaker off," Murphy told Bloomberg Politics in October.
Back at campaign headquarters, the team hewed to that timetable and sensibility. Once the Bush record was burned into voters' minds, attitudes would shift, Bradshaw said at the time.
By the end of January, Right to Rise had raced through at least $95.7 million out of the $118.6 million it had collected, according to Federal Election Commission filings. Almost $87 million went into a barrage of television ads, online videos, slick mailers and voter phone calls-to no avail.
Mel Sembler, a St. Petersburg developer and a former Bush ambassador who helped raise money for the super PAC and served on its governance board, said he believes the group's strategy was sound.
"We had confidence in Mike, and I think we did the best we could in deploying of resources," Sembler said. "That's not where the problem is. … The timing was not right for Jeb. Our candidate was just not connecting with the electorate."
Retaining his good humor
The final months were difficult for Bush. After a particularly weak performance during a debate in Boulder, Colo., in October in which Rubio appeared to get the better of him, there were suggestions that he might quit the campaign right then.
Reporters who made inquiries about the possibility were brushed off. In the middle of it all, Bush spotted a reporter who was a regular on the trail with him. "Hey — I didn't drop out, did I?" he shouted. "You know, that kind of stuff really gets my juices going. I'm going to win this thing, and when I do — you're going to give me a big hug."
Through it all, Bush attempted to keep both good humor and determination in the face of the inevitable.
"I was stunned by how well he handled the last month of this campaign when the writing was on the wall," said Tim Miller, Bush's communications director. "It is hard to go out there every day and put on a fake smiley face. He was in really high spirits and didn't lash out at people in private throughout the last two months."
The final indignity in a campaign that had suffered through many came three days before Saturday's primary, when South Carolina Gov. Nikki Haley endorsed Rubio rather than a man she described as a friend and mentor.
When it ended on Saturday night, Bush told saddened supporters: "We put forward details, innovative, conservative plans to address the mounting challenges that we face. Because despite what you might have heard, ideas matter, policy matters."
His final remarks as a presidential candidate were a reflection of the campaign he had constructed from the start, one he had built to his unique specifications, which nonetheless proved to be a mismatch for a political environment that had caught him by surprise — and for which he paid a hefty price.