Eli Stokols is a national politics reporter.

Jeb Bush, the Republican establishment’s last, best hope, began his 2016 campaign rationally enough, with a painstakingly collated operational blueprint his team called, with NFL swagger, “The Playbook.”

On page after page kept safe in a binder, the playbook laid out a strategy for a race his advisers were certain would be played on Bush’s terms — an updated, if familiar version of previous Bush family campaigns where cash, organization and a Republican electorate ultimately committed to an electable center-right candidate would prevail.


The playbook, hatched by Sally Bradshaw, Mike Murphy and a handful of other Bush confidants in dozens of meetings during the first half of 2015 and described to POLITICO by some of Bush’s closest and most influential supporters, appealed to the Bush family penchant for shock-and-awe strategy. The campaign would commence with six months of fundraising for the Right to Rise super PAC and enough muscle to push aside Mitt Romney. There would be a massive, broad-based organizational effort to plant roots in March states at a time when other campaigns were mired in Iowa and New Hampshire. The plan outlined Bush’s positive, future-focused message with an emphasis on his decade-old record of accomplishment as Florida governor.

And it included several pages about Bush’s case to prosecute against top rivals — dire political threats such as Wisconsin’s Scott Walker.

The plan roundly underestimated threats: Bradshaw, his closest adviser and longtime defender, for example, told at least one campaign aide that Marco Rubio wouldn’t challenge Bush. Besides, Bradshaw and other top advisers believed, it would be next to impossible for someone with so little experience to beat him. “They thought there was going to be much more reverence and respect for the fact that Jeb Bush, a Bush, was getting into the race,” said one Florida-based supporter, an alumnus of Bush’s gubernatorial campaigns and former staffer. “When they got Romney to step aside, they figured everyone else would too.”

Most critically, the playbook, people who have read it tell POLITICO, contained nothing about Donald Trump, who would spend the next excruciating year turning Bush into his personal patrician piñata.

“The rules all changed this year. It was all about taking on the establishment,” said a Republican operative close to the Bush family. “When you’re the son and brother of former presidents, the grandson of a U.S. senator, how do you run in a year like this? It is just a year of personality, not message. All of a sudden, there was no path for him. They just kept falling back on his record as governor, which is all he has — and no one gives a shit.”

Bush suspended his campaign Saturday night after a fourth-place finish in the South Carolina primary.

Interviews with more than two dozen Bush insiders, donors and staff members illuminate the plight of an earnest and smart candidate who was tragicomically mismatched to the electorate of his own party and an unforgiving, mean media environment that broadcast his flaws. The entire premise of Bush’s candidacy, these insiders tell POLITICO, was an epic misread of a GOP base hostile to any establishment candidate, especially one with his baggage-weighted last name.

And Bush, known for toughness and hard-work ethic in Tallahassee, just couldn’t project the kind of Reagan-on-’roids strength demanded by Trump.

“They were just captive to it,” one Washington-based Bush donor said. “And they didn’t adjust very nimbly.”

***

By August, just six weeks after officially launching his campaign, the only thing Bush’s staff could agree on was the problem: Donald J. Trump.

They’d paid no attention to the New York celebrity’s launch in June, just a day after their own. In early August, well after Trump began to dominate news coverage of the race, they still believed he was a blessing in disguise who would deprive Bush’s lesser-known rivals of the media oxygen needed to break through. But as Labor Day neared, Bush found himself on the defensive, peppered daily with questions from reporters asking him to react to Trump’s hard-line positions and seemingly outrageous statements on immigration.

But almost immediately, Trump baited Bush into a fight, staking out a position to the far right of the Floridian by calling for an end to automatic citizenship to any baby born in America. He ridiculed Bush’s earlier comment that immigrants who come to the United States illegally do it as an “act of love” for family, and called him unelectable.

Bush fired back, poorly. He went on conservative radio and used the derogatory term “anchor babies” when making the case that he would be a tough enforcer of immigration laws — opening the floodgates of criticism.

The following week, inside a Mexican restaurant in McAllen, Texas, just a few miles from the U.S.-Mexico border, Bush compounded the problem he was trying to clean up when he explained rather didactically that he was referring to Asians, not Mexicans, whom he argued were more guilty of taking advantage of the country’s birthright citizenship provision.

Inside his Miami headquarters, Bush’s senior staffers were coming to the collective realization that the race was veering out of their control.

But that’s where the consensus ended.

David Kochel, the early-state strategist initially hired to serve as campaign manager, and senior adviser Trent Wisecup, a protégé of Murphy’s, suggested that Bush challenge Trump to a one-hour, live televised debate on birthright citizenship, perhaps on “The O’Reilly Factor.” The Fox News host, they argued, supports birthright citizenship, and his show would offer a high-profile platform for Bush to demonstrate his policy knowledge and articulate his more unifying message, bringing the contrast between himself and Trump into sharper relief.

But Bradshaw, the most senior figure in the operation, and campaign manager Danny Diaz couldn’t be convinced it was a risk worth taking, according to high-level campaign staff.



By early August, Bush's team all agreed their main problem was Donald Trump, who had begun baiting Bush into fights almost immediately after his campaign launched. Above, the three candidates at the New Hampshire debate in early February. | AP



Days later, on Aug. 25, Trump was on stage at a rally in Dubuque, Iowa, when he offered an impression of Bush and characterized him as “low energy,” a critique he’d come up with after the first debate a few weeks earlier.

Bush’s team was stunned, first by the insult and then that it stuck. Kochel and Wisecup raced to respond and saw their already planned event that very same day — on the anniversary of Hurricane Katrina — as the perfect opportunity for Bush to respond forcefully and directly to Trump. They envisioned Bush in Pensacola, Florida, speaking straight to Trump: “You think I’m low energy, why don’t you come down here and talk to these people about how I took charge in a crisis.”

But once again, Bradshaw and Diaz couldn’t be convinced. Trump, they decided, wasn’t in Bush’s “lane” and so the campaign need not worry about responding to him. They went ahead with the event as planned, rolling out a two-minute video telling the story of Bush’s leadership during several hurricanes in 2004 and 2005. The following day, the headlines mainly served to remind readers of another Bush with a less-heralded record on Katrina—George W. “One Bush gets praise for his handling of hurricanes” was The Washington Post’s version.

They got defined as ‘low energy’ by a guy who took an escalator to his own announcement.”

“The Jeb people knew that literally every day when he was governor, he’d walk the steps of the Capitol at a jog pace,” one longtime Bush bundler and confidant said recently. “The building was 30 stories high. You’d hide because you wouldn’t want him to catch you and make you walk the stairs. He’d email you at 5:30 a.m. This was not at all a low-energy guy. It wasn’t true, but it stuck.”

“They got defined as ‘low energy’ by a guy who took an escalator to his own announcement.”

***

Those pivotal days in late August were one of the most critical inflection points for Bush’s troubled presidential campaign—the moments when Bradshaw, Kochel and Diaz might have reconsidered the assumptions made months earlier and redirected their candidate. They didn’t, because that redirection wasn’t part of the playbook.

“You cannot run a political campaign and not have the ability to adapt, to pivot,” one longtime Bush donor who has supported all five of the family’s presidential campaigns. “To sit there and say ‘We have a book’ just shows the immaturity.”

Bradshaw, who remained based in Tallahassee throughout the campaign, not the Miami headquarters, is exceedingly close to Bush. She has run all of his gubernatorial campaigns and served as his chief of staff. She acts as his strategist, his confidante and his muscle, defending him from critics and acting as a wall between Bush and almost everyone else. But some donors worried that she and other Bush loyalists wouldn’t be able to see his flaws as a candidate.

Early on, Murphy warned some incoming top aides about the loyalists. “If Jeb walks into a room and asks for a coconut,” Murphy told them, “the loyalists would drop everything to make sure Jeb got a coconut.”

When Bradshaw held her first meeting with about 40 of the campaign’s most connected donors in Washington, D.C., last spring, laying out the playbook, explaining the structure of the operation and confidently asserting the high likelihood of Bush becoming the GOP nominee, she left the sleek law-firm conference room without assuaging some donors’ doubts about the plan — specifically, the decision to focus the first half of 2015 almost exclusively on raising unlimited amounts of cash for the super PAC and the structure of the campaign itself — or her willingness to speak tough truths to Bush himself.

“She told this story about how Jeb upset the young kid tasked with collecting and distributing the [news] clips because he said he didn’t want anyone reading the clips, he wanted them focused,” a top Bush bundler who attended the meeting recalled. “And she said she told the kid, ‘Don’t worry, just take Jeb off the list and keep doing them.’ She’s in a room with 40 of us basically saying that she’s hiding things from the principal. We were like, ‘Why are you telling us this?’”

Bradshaw brushed off donors’ concerns that focusing so much on filling the super PAC’s coffers might leave the campaign cash-poor. At the time, so much money was rolling in, that situation was hard to imagine. Bush’s finance team, led by Heather Larrison and Jack Oliver, was confident it would have the money it needed and instructed Kochel, then serving as the unofficial campaign manager, to build out a massive campaign with ballot-access teams working every state and senior staffers earning more than $200,000 annual salaries. Early on in the campaign, for example, Bush hired scores of policy aides — a reflection, perhaps, of his own wonkiness. Yet it was a luxury: Most of the campaigns hired only a small number of policy aides.

Once Diaz was named campaign manager in June, he went on a cost-cutting spree — implementing painful across-the-board cuts that affected staffers at nearly every corner of the campaign. Even junior staffers making mid-five figures found their salaries reduced. By late fall, the campaign was no longer leasing a second office space on the sixth floor of its Miami headquarters, with so many staffers having been either laid off or relocated to Iowa and New Hampshire.

“[Sally] would be the one who could be direct with Jeb about his flaws — but she doesn’t see the flaws,” said a GOP operative who has worked with Bradshaw. “She doesn’t understand how other people don’t see it, and anyone who is critical of Jeb is dead to her.”

Bradshaw especially was obsessed with Rubio, whose audacity in simply entering the race and challenging his friend and former mentor was, to many Bush loyalists, unforgivable. Once the GOP debates began in August, sparking new interest in the golden-tongued Rubio, Bush’s team agreed it was time to engage with a challenger who, in its view, posed a greater obstacle to Bush consolidating support from mainstream Republicans.

In October, Bush began laying the groundwork to prosecute his case against Rubio, dinging the first-term senator for his poor attendance record and missed votes in the Senate. Heading into the third GOP debate in Boulder, Colorado, on Oct. 28, Bush and his entire team were on the same page — and brimming with confidence. They hinted at what was coming, planting stories and calling reporters on debate day to ensure that the attack on Rubio was the dominant storyline.

They’d rehearsed the attack on Rubio dozens of time during debate prep, but when it came time to execute on stage, Bush “just whiffed,” one senior staffer lamented later. “That stuff he said about being one of Marco’s constituents and being disappointed, that wasn’t anything we’d practiced,” the staffer continued. “He’s Jeb Bush. No one is going to empathize with him as someone who needs his senator to work on his behalf.” When Rubio hit back, dismissing Bush’s attack by citing the fact that “we’re now running for the same position,” Bush failed to respond.

“Sometimes you just fuck up,” the Bush staffer said.

It wasn’t until that debacle that Bush’s advisers decided to address the candidate’s poor performances themselves, hiring Jon Kraushar, who generally works with television anchors, as a public speaking coach.

***

Looking back now after his early exit from a nomination battle he vowed to be in “for the long haul,” his slow, awkward stumble from August through October encapsulates everything that caused the operation viewed as “Jeb!, Inc.” to fail. Bush was on the wrong side of the most galvanizing issues for Republican primary voters; he himself was a rusty and maladroit campaigner and his campaign was riven by internal disagreements and a crippling fear that left it paralyzed and unable to react to Trump.

The problem, many donors say they believe, is that there wasn’t anyone on the team who both recognized his shortcomings and was willing to point them out to the principal himself.

“He did not put an adult as the chairman of the campaign and a lot of the mistakes flow from that,” said one longtime Bush donor. “Reagan put Bill Casey in that position. 41 put Jim Baker. 43 had Don Evans. You always had someone above the campaign manager who could tell people and the candidate what needed to happen, who could see the big picture. By putting Sally, who loves you, in charge, you don’t get the fair perspective, the right perspective.”

But the blame is not Bradshaw’s alone. The entire premise of Bush’s candidacy now looks like a misread of an electorate that wasn’t amenable to establishment candidates—and a misunderstanding of a modern media environment ill-suited to a policy wonk who speaks in paragraphs, not punchy sound bites. He couldn’t sell experience to an electorate that wanted emotion. He couldn’t escape his last name. His millions couldn’t buy popular support.

Given how the race has gone, the real mystery of Jeb Bush’s campaign isn’t why he failed — but why anyone ever thought he would succeed.

Glenn Thrush and Alex Isenstadt contributed to this report.