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How Donald Trump won: The insiders tell their story

January 20, 2018

An oral history of 2016

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By the spring of this year, it was clear that Americans were heading into one of the ugliest, most consequential and often bizarre presidential campaigns in memory. Donald Trump would become the improbable Republican nominee, and Democrat Hillary Clinton the first woman to head a major-party ticket. Their clash challenged Americans to confront divisions over race, gender, ideology and our very national identity. This is how the race unfolded, as retold by the people who lived it. This oral history is based on four dozen on-the-record interviews with campaign advisers and other key players, conducted during the final two weeks.

May 3, 2016

Trump wins the Indiana primary and Sen. Ted Cruz (Tex.) quits the race, making Trump the effective GOP nominee. The Trump campaign begins to size up Clinton and seeks to broaden his appeal.


Paul Manafort
Former campaign Chairman for Donald Trump and convention manager

Trump views Hillary Clinton as the personification of what’s rotten in Washington. He really does make the connection between the rigged system, as he calls it, the corruption of Washington, the gridlock of Washington and the all-talk, no-action approach that Washington takes…. His point was that the opponent was more than just Hillary. She was the symbol.

Kellyanne Conway
Donald J. Trump for President campaign manager

There was maybe a 14-day period where she lost eight to nine contests, I believe, to Bernie Sanders. And I studied that and I thought, she’s going to have a real problem here because she’s somebody who’s always caught unaware. She was caught unaware by Barack Obama in 2008. She seemed to be caught unaware of Bernie Sanders’s surge…. And we could catch her unaware again.

Sean Spicer
Republican National Committee chief strategist

The narrative was already baked in. That was the beauty of her. In most campaigns, you’re trying to define a candidate. She was defined as someone that people don’t like and don’t trust, and all we had to do was reinforce the existing narrative.

David Bossie
Donald J. Trump for President deputy campaign manager

I always thought about prosecuting the case against Hillary Clinton very directly. The “Crooked Hillary,” the “drain the swamp,” those types of things which have become a little bit of slogans of the campaign are things that Republican conservatives for the last 20 years have really said, and maybe using different words, but they had never been able to get them to stick.

Kellyanne Conway
Donald J. Trump for President campaign manager

I just never have seen her as somebody who takes risks. And Donald Trump does take risks. And although his gets covered as being reckless, people like a risk taker. And Barack Obama is a risk taker. Bill Clinton is a risk taker.

Newt Gingrich
Former House speaker, former Republican presidential candidate, and Donald Trump adviser and surrogate

Trump has lots of weaknesses but he has a fearlessness borne out of authenticity. And that of course forces him occasionally to do things the rest of us can’t figure out because he thinks that’s what authenticity commands.

Carl Paladino
Donald J. Trump for President New York co-chairman and former Republican gubernatorial candidate in New York

This is not your normal election. This is a political revolution … They see this as the answer to something that’s been festering for years and years and years. They know something’s wrong. They know their government has not been straight with them. They now the middle class has been left behind. They also know, why do we have all these billionaires and why as a working man am I so poor?

Donald Trump, with daughter Ivanka Trump, left, and wife Melania Trump, addresses the media at Trump Tower following primary election results on May 3 in New York. (Ricky Carioti/The Washington Post)

Newt Gingrich
Former House speaker, former Republican presidential candidate, and Donald Trump adviser and surrogate

Trump is a remarkable entrepreneurial personality. The entrepreneurial personalities find it very hard to operate in corporate environments. Look at Steve Jobs…. And also, he had no habit of having to be disciplined and having to be aware of the fact that both his opponents and the news media would be watching every word and every gesture and will be digging through his past at levels that would be inevitably embarrassing.

Paul Manafort
Former campaign Chairman for Donald Trump and convention manager

He was comfortable with the success he had had in the rally approach and he didn’t see a need to change. My pitch to him was that we had to expand beyond the base he had in the primaries and we had to bring in establishment types, and the way to do that would be through presentation. Formulating speeches on policy that he would give off a teleprompter.

Phil Ruffin
Las Vegas business mogul and Donald Trump friend

You can give him all the advice you want, but he goes with his own instincts.

When it becomes clear that Trump will be the nominee, the fissures within the GOP grow deeper and the campaign struggles to unify party leaders


Ron Kaufman
Member of the Republican National Committee, former adviser to Mitt Romney and the Bush family, and Donald Trump supporter

I was caught in the middle between a lot of good friends who were in the Stop Trump movement, including people very close to me, and my belief that he won fair and square. It’s not about those folks who feel that way; it’s about the millions and millions of people who voted for Trump. The party had to get behind him.

Sean Spicer
Republican National Committee chief strategist

The sooner that we all got on the same page, the higher likelihood we would have of winning…. Trump was obviously very skeptical of the party and the RNC, so making sure that he and his team fully understood the capabilities that we had was crucial.

Charlie Sykes
Conservative radio talk show host on WTMJ in Wisconsin and Donald Trump opponent

I knew that [Republican National Committee Chairman] Reince [Priebus] was under no illusions about what Trump represented and what Trump’s nomination would mean…. That was the beginning of the collapsing of that distinction and Reince Priebus going all in for Donald Trump. Reince was not until that day a Trump Republican. I was disappointed.

Katie Packer
Founder of Our Principles PAC, an anti-Trump super PAC, and deputy manager of Mitt Romney’s 2012 presidential campaign

What do you do when the party that you’ve committed your whole adult life to goes in a direction like this? Do you acquiesce and bend the knee? Or do you say, “No, I can’t do it”?

Paul Manafort
Former campaign Chairman for Donald Trump and convention manager

He saw the value of [House Speaker Paul] Ryan being on the outside of where Trump wanted the campaign to go. He viewed Ryan to be part of what’s wrong with Washington, too…. I felt that while change was the main theme of the election, and he agreed with that, I felt that the face needed to be Hillary Clinton…. Because I knew, having looked at the data, that if we could keep the focus on Clinton, we win.

Russ Schriefer
Republican strategist and senior adviser on Mitt Romney’s 2012 presidential campaign

I thought that he would have a very difficult time putting together the coalition that he would need to be president and that we were going to be in for a very long six months between Indiana and Election Day.

At the same time, the Clinton campaign, still battling Sen. Bernie Sanders (Vt.) in the Democratic race, starts trying to figure out how to take on Trump.

Donald Trump addresses his supporters during a rally in Indianapolis in April. (Ricky Carioti/The Washington Post)

Mandy Grunwald
Hillary for America senior adviser

We know that there is a change versus more of the same dynamic that we don’t want to be in, but we do want to define the choice as the kind of country we’re going to be.

Robby Mook
Hillary for America campaign manager

I definitely remember we had a lot of angst around, like, how do we handle Trump? Like, how do you get your arms around this situation? The media runs wild with him. They just set the camera in front of him live and let it roll for as long as he speaks.

Jennifer Palmieri
Hillary for America communications director

Our big concern, of course, was that he would then morph into somebody else. I had heard things about him, such as he reacts with audiences in front of him … So the concern, well, if he gets in front of a general-election audience, is he going to moderate?

Teddy Goff
Hillary for America chief digital strategist

I always thought that he was the ideal Republican nominee…. The nomination of Trump was going to make this a battle about racism, misogyny, homophobia and dealing with immigrants. That’s not even getting into the core stability of our opponent.

Jennifer Palmieri
Hillary for America communications director

The most useful research was talking to people who know him…. John [Podesta] talked to a lot of people. [Christina] Reynolds talked to a lot of people. Jake [Sullivan] talked to a lot of people. I talked to a lot of people. I personally found the most useful Tony Schwartz, the guy who wrote “The Art of the Deal.” … I asked him, “Can he reinvent who he is? Can he morph into somebody else?” He asked me, “For how long?” And I said, “Six months.” … He says, “Six days, maybe. But six months, there’s just no way.”

Christina Reynolds
Hillary for America deputy communications director

What we found a lot of was sort of what makes him tick, what gets under his skin, what he is most sensitive about. He’s sensitive about his wealth…. He’s sensitive about his intelligence. You hear it a lot: “I went to Wharton. I went to the best schools.”

John Podesta
Hillary for America campaign chairman

There’s no question, I think, that [Trump] represents change. But the question is: What kind of change? And I think we put a lot into the argument that the country would succeed by rejecting that set of values which are based on division, on bigotry, on things he had said along the way, on his sort of history of abusing people.

Jake Sullivan
Hillary for America senior policy adviser

We began to look to see what is the shape or scope of his policy agenda. It was pretty shapeless and scopeless other than sort of his big bombastic statements. What was clear was if you try to have a traditional debate with him on a particular issue – whether it be tax policy, or infrastructure, or working families’ issues, or even in national security – you can have it. But you’d be missing the fundamental point of what was really happening here.

Robby Mook
Hillary for America campaign manager

We were always paranoid about leaving the economic argument off to the side…. Even to this day we struggle with: How much do we talk about his crazy tax plan that gives people tax-free schemes versus just saying like, “This man will have the nuclear codes and we could all be vaporized?”

Huma Abedin, Hillary Clinton’s campaign vice chairman, and Robby Mook, Clinton’s campaign manager, at a rally in Portsmouth, N.H. in July. (Melina Mara/The Washington Post)

Brian Fallon
Hillary for America national press secretary

We weren’t going to be able to predict whatever maelstrom we would encounter on a day-to-day basis. But if we had some principles that we were following and adhering to a North Star … we wouldn’t be making it up as we went along.

Mandy Grunwald
Hillary for America senior adviser

Joel [Benenson] and [Jim] Margolis and I met in Margolis’s office in April to have our first planning meeting about the convention…. What we had seen in the research – the notion that he was unfit to be president, however you put that – was the most important conclusion…. The two biggest parts of that had to do with his temperament and what that would mean for our national security…. The second was his divisiveness and the hateful things he had said about virtually every group in this country…. Both those things were well outside the norms for a Republican candidate…. The third category was economics.

Teddy Goff
Hillary for America chief digital strategist

I recall a senior staff retreat where that frame was presented to the state leadership who were on the phone. There was this silent, momentary reaction. He put the phone on mute and said they’re not buying it…. That was the moment when we realized bad on economy, bad on foreign policy, too divisive was not sufficient because it was a broader case. The guy is nuts.

Joel Benenson
Hillary for America senior strategist

His notion that he is a great businessman is total [expletive] because he is really a flop over and over again. But you could not convince people of that because they know he is wealthy. He is flying around in a plane with his name on it.

Jennifer Palmieri
Hillary for America communications director

So we decided there were arguments that we needed to pursue because they would be meaningful for voters. Then there were arguments that we should pursue that voters would never care about but would provoke him. That is the lane on questions about, is he really that successful or is his dad the one that got him started?

Guy Cecil
Chief strategist of Priorities USA, a pro-Clinton super PAC

We did video tests where we showed voters 40 different clips of Trump speaking – not ads, but just clips of him insulting a disabled reporter, a clip of him insulting Rosie O’Donnell…. Regardless of how we tested it – a full-out test, a clip test, online, regular survey, in-person focus group – the two things that consistently stuck out were the issue around his divisiveness and the issue around him being a danger to national security…. Mocking the disabled reporter was by far the top-testing clip. And, by the way, that stayed true through the whole campaign.

June 2, 2016

In mid-May, Clinton starts to lay out the case against Trump, calling him “unfit” in an interview. Two weeks later, in San Diego, she delivers a long, blistering attack on Trump as unfit to be commander in chief.

Hillary Clinton delivers a national security speech in San Diego in June, attacking Trump as unfit to be president. (Melina Mara/The Washington Post)

From → World Watch

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