Chapter 1

“Or I Wouldn’t Have Run”

Hillary clinton had a new rendezvous with destiny on her mind. Her motorcade sped toward Roosevelt Island on the morning of June 13, 2015. In a little more than an hour, she would officially kick off what she hoped would be a trailblazing, glass-ceiling-shattering campaign for the presidency. For most of the previous forty-eight hours, she had been trying to give a feel of historic importance to her first major address. It just wasn’t there yet.

She picked up the phone and called her chief speechwriter, Dan Schwerin. After two days of trading drafts with Hillary, after waiting through the delay of a power outage at her Chappaqua, New York, home, the bearded thirty-two-year-old with a signature chestnut pompadour was just about to board the tram connecting Manhattan to the East River island. He had stayed up all night, pulling together tweaks to the 3:30 a.m. version of the speech, and he looked hungover. Now, battling exhaustion and the sweltering heat, Schwerin pulled out his laptop one more time and sat down on the platform so that Hillary could dictate her final edits.

The key passage of the speech was an explanation of why she was running for president: “to make our economy work for you and for every American.” In the middle of that run—about how she would do it and who she would fight for—Hillary wanted to connect herself and her campaign to Franklin Roosevelt, the president who defined the aspirations of the Democratic Party and much of the nation for generations.

“Here on Roosevelt Island,” she said to Schwerin, “I believe we have a continuing rendezvous with destiny.”

He tapped the echo of FDR’s 1936 Democratic convention speech into his computer at 11 a.m. and took the next cable car to the island. Few would notice the last-minute change. The cluttered speech had become a testament to the aimlessness and passive-aggressive infighting that plagued the early stages of Hillary’s campaign. Hillary had tried to put together a team this time that would feature far less internal drama than her failed 2008 bid. Back then, big personalities had clashed openly, aired dirty laundry and strategy details in the press, and sometimes pursued their own goals at the expense of hers. In the intervening years, she’d assigned a lot of the blame for her loss to the warring inside her campaign. But that was hardly the only ailment from 2008 that she hoped to remedy. She hadn’t sold a vision for the country. She’d run away from being a woman instead of leaning into the unique aspect of her political story. To manage her campaign, she’d tapped a friend rather than the top pro. She’d let her husband run wild on the trail. And she had failed to take advantage of the latest technology to build a movement of grassroots supporters and donors.

From a strategic standpoint, she’d dumped millions of dollars into Iowa, the first-in-the-nation caucus, even though that only elevated the importance of her devastating third-place finish there. She’d gone on the attack against a better-liked rival whose platform more closely mirrored the values of the party’s base, creating a boomerang effect on her personal standing. Perhaps worst of all, she’d obsessed over winning the popular vote in big states rather than targeting the all-important delegates and superdelegates whose votes at the Democratic convention determined the party’s nominee.

But the idea burned into her mind as much as anything else was that she had lost because she’d hired people who put their own interests above getting her elected. The absence of palace intrigue on her opponent’s side—the “no drama Obama” campaign—was the kind of purpose-driven loyalty she pined for.

Over the next seven years, Hillary would rebuild her political organization while working at the State Department and the Clinton Foundation, punish those who had been disloyal to her, and prepare herself to mount a second bid for the most powerful job on the planet. When she conceded to Obama in 2008, she’d thanked voters for putting “18 million cracks” in the glass ceiling of the presidency. By the time she finished the 2016 campaign, she believed, that glass ceiling would lay shattered beneath her feet. And yet what Hillary couldn’t quite see is that no matter how she recast the supporting roles in this production, or emphasized different parts of the script, the main character hadn’t changed.

Huddled around a white table in the conference room of the Clintons’ midtown Manhattan personal office in the early spring of 2015, months before she would go to Roosevelt Island to deliver her first major address, the first hires of Hillary’s worst-kept-secret campaign outlined a plan to fly her to Iowa. They had pegged the Hawkeye State, where caucus-goers had doomed her first bid for the Oval Office, as the best spot for her kickoff speech. But Hillary didn’t like what she was hearing. She didn’t want to go big, at least not yet. And she didn’t want the first major address of what could be a history-making campaign to be set against a minimalistic backdrop like some farmer’s back porch.

To the chagrin of campaign manager Robby Mook, who would have to build a billion-dollar apparatus, Hillary had been dragging her feet about making things official. She understood that her team needed to start raising funds, hire more staff, and begin recruiting volunteers. But she also knew she had to be fully prepared for this battle. And she just wasn’t ready.

Mook, clean-cut with close-cropped brown hair and lively hazel eyes, was antsy. At one point, there was even discussion of his starring in a campaign-launching video announcing the formation of an “exploratory” committee. But Hillary was wary of repeating some of the major mistakes of her 2008 bid. She had rushed into her announcement that year to compete with Obama, and she had made it all about her: “I’m in it to win,” she’d said in her campaign-opening video. This time, she wanted to show she was listening to voters—talking with them one-on-one or in small groups and in informal settings (all with the knowledge that everything she did would be dutifully reported by a press corps hungry for nuggets from the trail).

“We’ve come so far under President Obama, but we have so many problems,” she told her advisers. “I want to make sure I’m the right person.” Given that everyone in the room had ostensibly been hired to run her campaign, and that some of them had been in on earlier discussions about the timing and logistics of her launch, no one believed she was really so ambivalent. But, sitting by a bank of three windows, twenty-seven floors above the bustle of Seventh Avenue, Hillary rendered a clear verdict on the Iowa kickoff plan: “No.”

She would go to Iowa in April, she said, but not to deliver a launch speech—and not in a private jet. She would drive, in a van, and try to find people along the way who weren’t expecting to run into her. After a quarter of a century locked inside the political bubble of the New York–to–Washington stretch of the Acela corridor, Hillary was eager to find out what people thought about the state of the country—and about her. She didn’t want to officially kick off the campaign until she’d had a chance to repeat what she’d done when she first ran for a New York Senate seat: gather information from voters. “She wanted to do that before giving a big speech and having a big event and saying ‘I have all this figured out,’ ” said one aide. “We didn’t have it all figured out.” Her big opening address would come at a location with more historic consequence, but for now, a “soft” launch could go forward—an upbeat video followed by the road trip.

The time would come for her to speak into the winds of history, but, as much as she knew Iowa wasn’t the place, she also knew that her moment hadn’t yet come. She’d been off the political battlefield for seven years. As secretary of state, she’d worked to win concessions in diplomatic back rooms across the world, but she didn’t have to worry about securing millions of votes. Barack Obama had been elected president and the Tea Party had risen in the time since she’d last been on the campaign trail as a candidate. The nation’s political bearings had shifted. And, if her 2014 book tour had taught her anything, it was that she was rusty as hell. Talking to voters, she hoped, would help her sharpen her political skills and develop her vision for the country’s future.

Obama had been relentlessly superb at telling voters why he was running for president and giving them a window into how he would govern. He was confident, cocky even, about his vision. Hillary, a modest, midwestern Methodist with a love of minutiae, was unshakably focused on the trees rather than the forest. This campaign would test the A student’s ability to adapt—to subordinate her nature to her need to win.

In preparing to campaign again, she studied Obama’s February 2007 launch speech in Springfield, the one he delivered on the steps of the Old State Capitol—the one that connected him with fellow Illinois state legislator Abraham Lincoln, who had freed the slaves in an act that set the first stone on Obama’s improbable path to the presidency. “She kept harkening back to Obama in Springfield,” said one of Hillary’s top advisers. “She had gone back to read that speech and how important it was for people as a marker of what he would do in the presidency. She viewed it as an important kind of road map for her governing principles and her actual plans to be president.”

In her mind, the first landmark address of what she hoped and believed would be a historic campaign couldn’t be about the politics of the moment, about tipping a few Iowa caucus-goers in her direction. It had to be about how she could reshape the nation from the Oval Office. For Hillary, a wonk in the best and worst senses of the word, that meant devising her policy agenda before she ever stepped to the podium. Most politicians understand that voters are looking for big, bold principles—easy-to-grasp concepts—and that the details can be filled in to fit them. For Hillary, policy is vision, and she would try to build a platform, program by program, into a blueprint for the country.

This prospect was actually a relief. It was more comfortable for her to sit in four-hour meetings at the conference table with her policy chief—the reedy, whip-smart Jake Sullivan—than to define herself by a small set of guiding principles and shape her policy ideas to fit them.

Hillary adored the thirty-eight-year-old Sullivan, enough to joke publicly about her confidence that he would someday be president of the United States. He had served Hillary as deputy chief of staff at State, a position from which he gradually vacuumed up all or parts of the jobs of several senior colleagues. Hillary appreciated both his competence and his ambition. His instincts on policy and politics matched hers. So she turned to him to run what she thought was the most important part of the campaign: the substance. That’s what bonded Hillary to her young protégé—they geeked out over policy—and it’s what she wanted at the heart of her first address to the voting public.

“This is her deeply held thing: elections should be about policy,” said one senior Hillary adviser. “There’s a textbook quality to her articulation of things.” That would make every step of narrative building its own form of excruciating drudgery. But it would soon seem like a minor nuisance for a campaign that was miserable even before it started.

In early March, just as she was planning to reintroduce herself to a nation that felt it knew her all too well with a video announcement of her campaign, the New York Times reported that Hillary had used an e‑mail address tied to a personal server at her family home in Chappaqua, to conduct official State Department business. The e‑mail story would bedevil her straight through Election Day, robbing her of the ability to create a positive narrative for her candidacy and, as one top adviser put it, returning to her like a cold sore. “You never know when it’s going to pop up,” this adviser said. “You think you’re over it and then [it pops]up again.”

At the time, it was impossible to know how long the e‑mail story would last and just how badly it would damage the campaign.

“Did you have any idea of the depth of this story?” campaign chairman John Podesta asked Mook when it broke.

“Nope,” Mook replied. “We brought up the existence of emails in research this summer but were told that everything was taken care of.”

“That’s reassuring,” Podesta shot back. “Yikes.”

“Yeah,” Mook responded. “This is going to be an interesting campaign. I’m in this zen place now where I’m focusing on the website and telling myself this is all background noise!”

For those who couldn’t bury their heads, praying for divine intervention was an attractive alternative. “I’m lighting candles in church all the time,” pollster John Anzalone told Mook.

When the e‑mail story first hit, Hillary’s aides were still trying to get a feel for one another. The crisis acted as a catalyst for infighting. Publicly, she was running a no-drama campaign. But behind the scenes, Hillary’s brain trust broke into tribes:

•The Mook Mafia, led by Mook; Marlon Marshall, his top lieutenant; Elan Kriegel, the data analytics chief; and Oren Shur, the paid media director

•The State Crew, led on the inside by Huma Abedin, the vice chairwoman; Jake Sullivan; Nick Merrill, the traveling press secretary; and Dan Schwerin, the chief speechwriter; with longtime Clinton advisers Cheryl Mills and Philippe Reines invisibly guiding Hillary behind the scenes

•The Consultants, led by Joel Benenson, the chief strategist; Jim Margolis, the ad-maker; and Mandy Grunwald, the longtime Clinton message maven

•The Communications Shop, led by Jennifer Palmieri, the communications director; Kristina Schake, her deputy; and Christina Reynolds, the research director, who had worked with Palmieri on the John Edwards campaign

At the start, Podesta was seen as a high-level troubleshooter. Short, wiry, and in his midsixties, the marathon-running former top aide to Presidents Bill Clinton and Barack Obama had deep ties to every power center in the Democratic Party. He was supposed to play an adult-in-the-room role on the campaign, coordinating with Bill’s office, the White House, Democratic interest groups, and major donors. In theory, Podesta would provide air cover in Clintonworld, lessening the burden on Mook and allowing the campaign manager to focus on executing.