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Hillary Clinton's Path To Election Day: Plans, Luck And Self-Inflicted Wounds

Hillary Clinton claims victory in the Democratic primary in the Brooklyn Navy Yard on June 7, 2016.
Drew Angerer
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Hillary Clinton claims victory in the Democratic primary in the Brooklyn Navy Yard on June 7, 2016.

When it comes to Hillary Clinton's historic run for the presidency, if she's ultimately able to shatter that highest, hardest glass ceiling it will be because a combination of good luck and better planning helped her overcome challenges, many of her own making.

Donald Trump's name is on the ballot, but Clinton's biggest opponent may well have been herself — as she was dogged by emails, questions over the Clinton Foundation and paid speeches.

Those controversies have kept the presidential contest between Clinton and Republican nominee Trump close at the end. But Hillary Clinton will reach Election Day with the real prospect of becoming the first female president in U.S. history.


She's been a candidate for 19 months. Clinton's official campaign launch was preceded by months of will-she-or-won't-she chatter, but there was lots of work behind the scenes and a "Ready For Hillary" superPAC working out in the open to prepare for Clinton to get in.

But who would she face?

Winning The Opponent Lottery

In April 2015, when Hillary Clinton officially entered the race for president, she was looking over her left shoulder. It was apparent in her very first remarks, at a community college in Iowa.

"I think it's fair to say that, as you look across the country, the deck is still stacked in favor of those who are already at the top," said Clinton. "And there's something wrong with that."


Clinton's team had an eye on Vice President Joe Biden, with his everyman appeal and ability to speak the language of white, working-class voters. But ultimately Biden, whose son died of brain cancer in the spring of 2015, opted not to get into the race.

Massachusetts Sen. Elizabeth Warren resisted progressive recruitment efforts and didn't get into the race either.

In the end, Clinton only faced one primary opponent who truly threatened her chance at the nomination: Bernie Sanders. He did far better than likely even he imagined was possible, going from oddity to rock star, with legions of adoring supporters. Sanders' movement grew over the summer of 2015 with an active online community boosting his name recognition.

The crowds at his speeches and rallies kept growing to the point that he was filling sports arenas. As one Democratic activist in Iowa put it to team Clinton, "Objects in mirror may be closer than they appear." And those large crowds gave Sanders' campaign more media attention and more credibility.

"You know, sometimes our campaign has been referred to as a fringe campaign. Well, if this is fringe, I would like to see mainstream," Sanders said to a packed auditorium at Drake University in Des Moines, Iowa, in June 2015.

Clinton barely won the Iowa caucuses and Sanders then trounced her in New Hampshire. That juiced his fundraising, allowing him to run television ads and compete throughout the primary season. But Sanders' weaknesses became apparent in the South Carolina primary. His core message of income inequality and the influence of money in politics didn't resonate with many African-American voters, who felt the racial inequality they experience wasn't addressed with a focus simply on economics. That showed as the primaries moved to southern states where black voters sometimes favored Clinton by 80-point margins, according to exit polls.

Sanders also famously let Clinton off the hook on her emails and didn't go after her on making paid speeches to big Wall Street banks, particularly Goldman Sachs, until late in the primary fight.

Bernie Sanders and Hillary Clinton take part in the first Democratic presidential debate on Oct. 13, 2015 in Las Vegas, Nev.
Joe Raedle
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Bernie Sanders and Hillary Clinton take part in the first Democratic presidential debate on Oct. 13, 2015 in Las Vegas, Nev.

Looking toward the general election and the growing Republican field in early 2015, Donald Trump wasn't even on the radar. Few believed he would run and even fewer believed he could mount a serious candidacy. He had toyed with a presidential campaign many times before without jumping in. There was little reason to believe this time would be different. On the night of the first Republican presidential debate, Clinton's team welcomed reporters into its Brooklyn headquarters as its rapid response team crafted tweets and senior aides offered spin during commercial breaks. "I think they're digging the hole deeper," Mook said to a small gaggle of reporters on the Clinton beat. But his attention quickly turned back to the TV. "Don't get between me and Donald," Mook said.

Their plan was to tie all the other Republicans to Trump's extreme statements, because they hardly imagined Trump would ultimately become the nominee.

For Clinton, there was a generational concern. In 2008, Barack Obama represented hope and change and his relative youth was part of the appeal. In a 2016 general election, Sens. Ted Cruz or Marco Rubio would be able draw the same contrast, painting the baby boomer Clinton as a relic of the past.

It was clear that was the general election challenge Clinton and her team were anticipating when she gave the big speech at her official campaign kickoff event on Roosevelt Island in New York. "Now there may some new voices in the presidential Republican choir, but they're all singing the same old song," Clinton told a crowd estimated at 5,000. "A song called, 'Yesterday.' You know the one. All our troubles look as though they're here to stay. And we need a place to hide away. They believe in yesterday. And you're lucky I didn't try singing that, I'll tell you."

According to hacked emails released by WikiLeaks, behind the scenes, senior advisers were especially concerned about Rubio, the Florida senator.

"I'm beginning to worry more about Rubio than the others," Joel Benenson, the campaign's pollster and chief strategist wrote in February 2015. "He has stronger right wing cred than Jeb and he's finding a way to the middle enough for now and he will be the most exciting choice to Republicans. Could pose a real threat with Latinos etc."

But in the end, Trump outlasted the entire Republican field, leaving Clinton to face an opponent with well-known shortcomings and an opposition research file bigger than Trump Tower. Hillary Clinton won the opponent lottery. Not just in the primary, when Warren and Biden stayed out, but in the general election as well. There were certainly risks in facing Trump: his ability to dominate news coverage, the difficulty in pinning him down on policy. Trump's taxes, business dealings, treatment of women and tendency to say and tweet things that hurt him with voters were a constant throughout the general election campaign. But many Republicans and even some Democrats believe, with a more disciplined opponent, Clinton would easily have been facing defeat on Election Day.

A Team Of (Former) Rivals

For the first time in at least 100 years, a sitting U.S. president has campaigned vigorously for his chosen successor. In the closing weeks of the campaign, President Barack Obama has been a regular fixture on the campaign trail for Hillary Clinton, pitching her to voters more effectively than she could pitch herself.

Hillary and Bill Clinton attend the 37th Harkin Steak Fry on Sept. 14, 2014, in Indianola, Iowa.
Steve Pope
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Hillary and Bill Clinton attend the 37th Harkin Steak Fry on Sept. 14, 2014, in Indianola, Iowa.

With an approval rating solidly above 50 percent and his natural ease on the stump, Obama essentially doubled Clinton's firepower in swing states. But he wasn't the only one.

First Lady Michelle Obama, Vice President Joe Biden, Massachusetts Sen. Elizabeth Warren and even Bernie Sanders campaigned hard for Clinton and her running mate, Tim Kaine.

Clinton won Sanders over by agreeing to modify her debt-free public college proposal to more closely track with Sanders' free college plan. He started slowly, but by the end of the race Sanders was traversing the country trying to convince his young supporters to go to the polls and not vote for a third-party candidate or Trump.

The ally Clinton always had making the case on her behalf was her husband, former President Bill Clinton.

By contrast, Trump's surrogate operation was thin. There were no former presidents or even former Republican presidential nominees, save Bob Dole, who appeared at the Republican National Convention. Mitt Romney actively opposed Trump and relatives said both former presidents Bush would likely vote for Clinton.

Clinton's 'Damn Emails' (And Wall Street Speeches)

From before Hillary Clinton even entered the race for president, her campaign faced headwinds of her own making. There was the private email server she used for official business while secretary of state and there were the lucrative speaking engagements during the time after she left the State Department and before her campaign officially began.

Hillary Clinton speaks to the media after keynoting a Women's Empowerment Event at the United Nations March 10, 2015 in New York City, just days after it was revealed she used a private email server while secretary of state.
Yana Paskova
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Hillary Clinton speaks to the media after keynoting a Women's Empowerment Event at the United Nations March 10, 2015 in New York City, just days after it was revealed she used a private email server while secretary of state.

When the news of Clinton's server broke, top officials in the campaign were seemingly blindsided. In hacked emails released by WikiLeaks, campaign chairman-in-waiting John Podesta emailed campaign manager-in-waiting Robby Mook asking if he knew the extent of the email issue in advance.

"Nope. We brought up the existence of emails in research this summer but were told that everything was taken care of," Mook wrote at the time.

Clinton's campaign has refused to verify the authenticity of emails released by WikiLeaks and has also avoided commenting on any of the content. Clinton's campaign says the release of emails hacked from Podesta's personal Gmail account is part of a Russian effort to interfere with the U.S. election.

In one chain, Podesta and Neera Tanden, a longtime Clinton ally, complain about the email story coming out so late in the game. "Why didn't they get this stuff out like 18 months ago? So crazy," she asked. In a later email, Tanden answered her own question: "They wanted to get away with it."

Bernie Sanders gave Clinton a gift when he took the email server off the table as an issue in the Democratic primary during the first debate.

"Let me say something that may not be great politics, but I think the secretary is right. And that is that the American people are sick and tired of hearing about your damn emails," said Sanders.

Clinton jumped in, "Thank you, thank you," she said. "Me, too!"

Right after that came the 11-hour hearing of the House Select Committee on Benghazi. Clinton maintained a calm, somber demeanor throughout and left with House Republicans revealing no new bombshells.

Hillary Clinton testifies before the House Select Committee on Benghazi on Oct. 22, 2015.
Chip Somodevilla
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Hillary Clinton testifies before the House Select Committee on Benghazi on Oct. 22, 2015.

That October was one of the best months of her campaign. But Clinton's email troubles were far from over.

Just as she was launching into the general election, only hours before Clinton was to campaign with President Obama for the first time, FBI Director James Comey held a press conference. On the face of it, his announcement was good news. The FBI had been investigating whether Clinton's use of a private email server violated the law, whether she and her aides had improperly handled classified material. He said no reasonable prosecutor would pursue the case and he was recommending against charging Clinton or her aides with a crime.

"Although we did not find clear evidence that Secretary Clinton or her colleagues intended to violate laws governing the handling of classified information, there is evidence that they were extremely careless in their handling of very sensitive, highly classified information," Comey said.

His statement raised more questions than it answered and brought the email saga back into focus for voters.

At the Republican National Convention in Cleveland, delegates began chanting "lock her up!" That chant became a regular feature of Trump rallies.

Ten days before Election Day, Comey brought the email issue back into the spotlight, announcing emails had been found in the course of another investigation focused on former congressman Anthony Weiner, the estranged husband of Clinton's closest aide, Huma Abedin. This meant the cloud of Clinton's email server would hang over her campaign from beginning to end, and likely well beyond if she wins.

Another lingering problem for Clinton's campaign came from the speeches she gave behind closed doors to Goldman Sachs and other Wall Street banks. Clinton made millions of dollars on the speaking circuit and the implication was that she was saying something behind closed doors with corporate executives that she wasn't telling voters.

By the end of the primary, Sanders regularly called on her to release the transcripts. And there were transcripts, compiled by the speaker's bureau that booked Clinton's appearances.

Clinton's campaign never released the transcripts. But a policy adviser did review them, sending around an email to senior staff highlighting the most potentially politically problematic excerpts.

We know this, because of the hacked emails released by WikiLeaks. In addition to posting the speech excerpts, WikiLeaks also released the full text of all three of Clinton's Goldman Sachs speeches. It turns out they weren't speeches at all, but rather extended on-stage question and answer sessions.

Had the transcripts leaked out during the primary, they might have been more damaging. But coming out in October, they barely registered.

Making A Plan — And Sticking To It

Hillary Clinton loves plans. Or at least she loves to talk about them.

"Maybe it is a bit of a woman's thing, because we make lists," Clinton began saying at rallies in the final weeks of her campaign. "We do, we make lists, and we try to write down what we're supposed to do and then cross them off as we go on in the day or the week. So I want you to think about our plans as our list. Our list for our country."

Clinton is a wonk at heart. Digging into the policy weeds is where she is most comfortable. She is far less comfortable with sweeping themes and inspiring speeches.

So, her campaign made a plan to just let Hillary do Hillary. They kept her events small and held numerous town hall-style events and roundtable conversations. Clinton did a lot of listening and the campaign released plans and policy papers on everything from autism to defeating ISIS.

The strategy was to be boring. And with that as a goal, Clinton's campaign was a success. Though there were certainly times when this baffled those watching from the outside.

And while Clinton was making relatively small promises to small audiences, her campaign was building an infrastructure to reach voters where they were and bring them to the polls.

The campaign started early with the slow, hard grind of person-to-person contact known in campaign lingo as organizing. The campaign was building communities, groups of people brought together by a common goal of electing Clinton, but motivated and inspired as much by their fellow volunteers as by the candidate. By the end, the campaign had half a million volunteers working to get her elected.

Organizing isn't flashy. Neither were Clinton's plans and speeches. But rather than fighting against her weaknesses as a campaigner, the campaign played to her strengths.

Getting Under Trump's 'Thin Skin'

Just as the first general election debate was ending, Hillary Clinton said something that set Donald Trump off.

"This is a man who has called women pigs, slobs and dogs," Clinton said, echoing an ad called "Mirrors" that her campaign had been running in swing states and on national cable leading up to the debate. Trump hit back, making it clear he had seen the ad and didn't much like it.

"Hundreds of millions of dollars on negative ads on me, many of which are absolutely untrue," Trump said. "They're untrue, and they're misrepresentations. And I will tell you this, Lester, it's not nice and I don't, I don't deserve that. But it's certainly not a nice thing that she's done. "

In that same exchange, Clinton mentioned the former Miss Universe Alicia Machado, who Trump had allegedly called "Miss Piggy" and "Miss Housekeeping," mocking her for her Latino heritage and for gaining weight.

Hillary Clinton leaves the stage after the first presidential debate at Hofstra University in Hempstead, N.Y., on Sept. 26, 2016.
Timothy A. Clary
AFP/Getty Images
Hillary Clinton leaves the stage after the first presidential debate at Hofstra University in Hempstead, N.Y., on Sept. 26, 2016.

The case of Alicia Machado is a perfect example of the Clinton campaign's meticulous planning. Before the first debate, the campaign had already sat down with her, shooting a video where she talked about Trump mocking her weight and her struggles with eating disorders. This was edited together with archival footage of Trump bringing reporters to the gym to watch her work out.

Within an hour of the debate, the campaign had released its video featuring Machado and the next day she was on a conference call with reporters.

The morning after the debate in a phone interview with Fox and Friends, unprompted by the anchors, Trump started talking about Machado. He defended himself by saying she really had gained weight. Clinton had snagged him.

"Not only that — her attitude. And we had a real problem with her," Trump added.

The whole week following the first debate was consumed by Trump and his surrogates arguing it wasn't OK for Machado to gain weight while Miss Universe. He couldn't get much further off message.

This all culminated with Trump going on a pre-dawn tweet storm attacking Machado and encouraging followers to "check out sex tape."

Clinton made a strategic choice once she knew Trump would be her opponent. She wouldn't run against him like any other Republican. She would portray him as an outlier, an existential threat and build a case that he was "temperamentally unfit" to be president of the United States. This made it more a race about values, personality and temperament than policy.

"Imagine him plunging us into a war because somebody got under his very thin skin," Clinton said in a national security speech at Kent State University in Ohio.

With carefully laid traps like the attack involving Machado or from the parents of a Muslim U.S. Army captain killed in Iraq, the Clinton campaign was able to get Trump to help make their point, one tweet or TV interview at a time.

If Hillary Clinton convinces enough Americans Donald Trump is simply unacceptable for the presidency, she will become America's first female president. But she would also face incredible challenges, including repairing her own reputation, battered by two years of campaigning and the email scandal that may never fully go away.

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Hillary Clinton speaks during the National Action Network's 25th Anniversary Convention on April 13, 2016, in New York City.
Justin Sullivan
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Hillary Clinton speaks during the National Action Network's 25th Anniversary Convention on April 13, 2016, in New York City.