Hillary Clinton talks her big mistakes and coming to terms with failure

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Anna Fielding
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Chappaqua is a small town, an hour outside Manhattan on the Harlem line train from Grand Central Station. The houses are mostly smartly painted clapboard, blues and creams and greys, set in clearings among the trees. The next town along the railway line is called Pleasantville. It’s calm and quaint and wealthy without being flashy. You feel that nothing bad could happen to you here. It would be the perfect place to recover from a crushing blow. Which is just what one of the town’s most famous residents has been doing for the past year. She is Hillary Clinton and Chappaqua’s other most famous resident is her husband, Bill.

The Clintons have owned a home here since 1999. Last year, in the run-up to the election, they also bought the house next door, thinking it would be useful for the extra people required to surround an incoming president. Instead, Hillary has spent much of 2017 redecorating the new house, hanging a vintage Suffragette banner above the fireplace and writing her book in the dining room, confessing that sometimes she just wanted to “scream into a pillow”. Still, Chappaqua is friendly, a good place to be. People smile at me, a stranger. I’m here to meet Hillary.



Here’s the thing about Hillary Clinton. She’s often slated for being an ambitious woman. There’s an idea that her extreme competence and drive make her somewhat robotic. Firstly, this isn’t true in person: she smiles with her eyes, looks at people properly and gets genuinely agitated where any sane person would.

But secondly, Hillary represents something for a certain type of woman. You know who I mean. It’s us. The achievers, the triers, the exam passers. We’re on your commute with a hardback book and a change of shoes. We’re your boss and your intern. We’re the birthday card buyers and the appraisal writers and we’re forever stuck on an impossible see-saw, trying to find the mid-point between pleasing people and being a bitch who gets sh*t done. If you see anything of yourself in Hillary Clinton’s efforts and resilience, know that Hillary Clinton recognises you too.

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“I come across it all the time,” she says.

“It really makes me happy, because I don’t want young women to be discouraged by the resurgence of nastiness. If you put your head up on Twitter or YouTube and say something, you’re going to engender this nasty response. I want to give confidence and be, maybe, an example of resilience in the face of loss. Because we all have losses and disappointments.”

And we keep on going.


Meet and greet

We’re sitting in a cellar room in Crabtree’s Kittle House, a country hotel in Chappaqua. It’s a favourite haunt of the Clintons. Hillary threw a baby shower for her daughter Chelsea here and it’s home to the annual Christmas party she and Bill throw for their secret service personnel and their families. Usually this room is used for dining and wine tasting but today two secret service wait outside the door. Before she enters, I hear her approach, heels clicking on the flagstones of the corridor, chatting to her assistant. Then, suddenly, she is there. The woman who was very nearly the world’s most powerful. “Oh, this won’t do,” she says looking at the faraway chair earmarked for her. She pulls out the one next to me. “Hi, how are you? I’m Hillary.”

Pioneering spirit

Hillary. Hillary Rodham Clinton. Dressed in the same style she was for much of her presidential campaign: black trousers and a structured, collared top in blue silk. Unusually for a famous person, she looks exactly like… Hillary Clinton. Before speaking to me she was doing an on-camera interview for CNN, so her make-up is immaculate and her otherwise sensible haircut has been teased and shined for extra glamour. The CNN were in reception earlier. In a room full of wealthy or famous people, you can always spot the journalists: we’re the only ones who have done our own hair.

We have all developed a visual shorthand for recognising famous people: if orange skin and a strange white-yellow pompadour equal Donald Trump, then brightly coloured tailoring and smartly layered blonde hair are all we need to conjure up Hillary. But, obviously, she’s more than just symbols. Hillary Clinton is now 69, one year older than my own mother. Chelsea Clinton and I are about the same age. For most of our conversation, Hillary moves between on-message answers, political opinion and justifiable pissedoffness. But occasionally there are flashes of something else. 




“No, no! You’re doing great!” she encourages, when I check to see how much time we have left.

You can see why her assistant says he feels so happy to work with her. You can feel how it might be to be one of her mentees. Perhaps, just a sliver, of how it might be to be Chelsea. She lights up when talking about younger women. She wants us all to do really well.

Hillary has done things very few women – very few people – get to do. Secretary of State for the United States. First female Senator for New York. First Lady of the United States. Co-founder of Arkansas Advocates for Children and Families. Alumna of Yale Law School and the prestigious all-female Wellesley College.

She’s a person who does not fail often. When a professor at Harvard Law School said, “We don’t need any more women at Harvard,” she kept on going and chose to study at Yale instead.

When, in the early Eighties in Arkansas, people would fill the public gallery of the courthouse for the novelty of seeing “the lady lawyer”, Hillary kept on going. In 1998, when Bill Clinton was accused of having an affair with White House intern Monica Lewinsky, Hillary kept on going.

But after delivering her concession speech on 9 November last year, Hillary Clinton left the New Yorker Hotel in midtown Manhattan feeling “completely and totally depleted”. “All I wanted to do,” she says in her new book “was get inside, change into comfy clothes, and maybe not ever answer the phone ever again.”

But here we are, a year later, and Hillary Clinton is, somehow, still going. Her new book, What Happened, is her memoir of 2016, but also her attempt to analyse why a qualified candidate lost out to a showman.

“I’m very distressed about what he means to our country and the world,” she tells me. “He started by attacking our closest allies: Great Britain, others in Europe, the Nato Alliance, the United Nations. It is a continuation of his reality TV show persona and I think it has confused and distressed people around the world. I think part of the role of the American presidency is to provide stability, consistent with values of democracy and human rights, both of which he seems to disregard.”

young Clinton

Reality bites

Hillary Clinton’s electoral battle with Donald Trump was perhaps the biggest story of last year. On 8 November, the world waited by their TV screens to watch the result. It was a choice between the United States of America having their first female president, or voting in a man who boasted about sexual harassment, dismissed climate change and tacitly encouraged violence against minority groups, journalists and political rivals. West Virginia, South Carolina and Alabama went to Trump; Connecticut, Delaware and Washington DC to Clinton.

Trump’s supporters had a different view. His rival was part of the decadent liberal elite, the walking embodiment of a political establishment who hadn’t delivered the change promised by Barack Obama’s presidency. What could ‘Crooked Hillary’, to use Trump’s nickname, do for the no-longer-working man, they asked. 

Ohio, Florida, North Carolina. All Trump. What was going on? People started to pray Clinton would rally. Wisconsin for Trump.

Finally, at 2.35am EST (7.35am in the UK), Hillary Clinton conceded defeat. Donald Trump would be the 45th president of America. The world looked on in shock.

“I have a great sense of responsibility, for not winning, for letting people down,” she says. “Even more so when you consider who my opponent was. If I had run against someone whom I disagreed with politically, but believed was up to the job, of course I would have been disappointed. But being in a position where I ended up losing to someone who I don’t think is qualified or temperamentally ready to be president was a very deep personal regret.”

‘Ready’ is an interesting choice of word, because it implies that the person might grow into the role at some point.

“Well, you can always hope.” She smiles, just briefly. “There hasn’t been much evidence of it.”



Family retreat

Scattered Books is a small family-run bookshop in Chappaqua. The outside is painted blue and they have a display of the picture book version of It Takes A Village, a child-friendly reimagining of the book Hillary wrote in 1996 when she was First Lady, demonstrating that an inclusive society benefits everyone. While I was browsing, a woman with a small child came in to pick up a copy she’d had put aside.

The town seems to care about Hillary. For Thanksgiving 2016, two weeks after her defeat, a group of neighbourhood children made pictures covered in hearts, rainbows and American flags and stuck them up near her home. “It was one of many kind gestures,” she writes in What Happened, “not just from friends and loved ones but also from complete strangers, that made that first month more bearable.”

She started hiking. She and Bill would lace up their boots and hit the trails in the woods around their house. Margot Gerster was out in the woods near Chappaqua, the day after the election. She heard rustling, and there were the Clintons. Gerster’s selfie with Hillary kickstarted a ‘HRC in the Wild’ meme, used by supporters and well-wishers to catalogue informal sightings of the former presidential candidate.

Hillary also went to the theatre. The New York Times showed her backstage at the Broadway revival of Sunset Boulevard talking to its star Glenn Close. She was also spotted having dinner with Kate McKinnon, who has played Hillary in Saturday Night Live’s recent political skits. Kate’s take on Hillary wasn’t too harsh: the comedian portrayed the politician as, yes, someone who wanted so badly to be president, but also who just wanted to fix things. There were even gags about the cliché of her being much warmer in person. (And can I join those ranks? She is much warmer in person.)


So, what did happen? There was the endless coverage of Hillary’s emails (“a dumb mistake and a dumber scandal,” she tells me). She’d sent messages from a private email server while acting as secretary of state, rather than using the servers maintained by the government. The case was closed without criminal charges in July 2016. Then, 11 days before the election, FBI head James Comey reopened the investigation (Hillary refers to him as Jim). He later said the idea the FBI may have influenced the result made him “mildly nauseous”.

Then there’s the suggestion that Russia deliberately interfered with the election. Trump has been open in his praise for Russian president Vladimir Putin, whereas Hillary pronounces Putin’s name with a disdainful stress on it.

But Hillary believes the world should have paid more attention to events in Britain. “I think Brexit was a bigger alarm than we understood here in the United States,” she says. “I think the skilful, deliberate lying by the Brexit campaign, which was not adequately addressed and refuted with an alternative, provided a big opening.”

A wave of fear and prejudice rushed through that opening. The Brexit campaign, says Hillary, was similar to the Trump campaign. There was “blaming, scapegoating, prejudice, paranoia and outright lying” in both.

Extreme measures

We’re now all familiar with Donald Trump’s ability to whip up rage in his supporters and direct it at particular targets. But last year, it was a new style in politics. “I think what was different was Trump’s appeal to a form of prejudicial populism. It’s one thing to say, ‘We need tougher rules on banks,’ it’s something else to say Mexicans are rapists and criminals.

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“I don’t think I did a good enough job in connecting with the anger that was out there, not to fuel it, but to do a better job of both recognising it and identifying with it so that people would then listen to me.”

There was also another strand of populism to contend with. For years it was thought that elections were won by picking up undecided centrist voters who could have gone either way. But the centre isn’t where it’s at any more. Here, we’ve seen Jeremy Corbyn become a stronger political force by injecting a fresh shot of socialism into the Labour Party. On the left in America was Bernie Sanders, senator for Vermont and Hillary’s challenger for the Democratic party’s presidential nomination.


Ultimately Sanders lost but he was a strong contender. He appealed to young voters. He attracted huge crowds. He promised to end college tuition fees, break up big financial institutions and extend free healthcare to all.

Ever the good girl, Hillary concentrated on carefully costed policies. But the world wanted to hear big ideas – from Sanders, from Trump – no matter their feasibility. Hillary’s pragmatic carefulness was out of fashion. The focus was on charismatic men with concise soundbites.

“You know, I obviously wish that what I was saying had been heard, but the press coverage made it very difficult. The entire 2016 campaign year, there were only 32 minutes in the whole year where television covered policies.”

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Hillary clearly still feels this keenly. “I was saying all these things and spending time getting them right and talking about how they’d be paid for. But nobody heard it and that was a big disappointment.” And she still partially blames herself. “I should have figured out some way to get through.”

Her frustration is even more understandable when you realise that some of her plans were quietly radical. She had been working on a policy to deliver a universal basic income, to ensure every citizen would be given a fixed amount of money on a regular basis. It’s a popular idea in left-wing circles but it’s downright surprising in American politics. Although Hillary sat up with Bill and tried to make the numbers work, she couldn’t. So, rather than promise something she couldn’t deliver, she dropped the big idea.

“If I could have come out with something that I thought was truthful and could withstand scrutiny, I would have done it,” she says. “I’m certainly aware of the power of those big ideas. But I personally think you have to be held to a higher standard.”

Popularity contest

In Chappaqua, Hillary is part of the community, talking to dog owners and walking in local parades. What Happened talks of yoga and chardonnay, as well as her feelings of failure and anger. It’s a softer, more open image than she’s projected before. Is that honesty an attempt to reposition Hillary Rodham Clinton?

“I don’t have any idea. Honestly. That’s for others to decide.”

Warmer? More human? Fan of hot sauce? 


“But you know, that’s been known. I have been the target of a concerted campaign for 25 years, by the right, by their allies, to accuse me of everything and to try to plant an image of me in the minds of people and particularly voters. Whenever I’ve had a job I get high ratings, people think I do a good job. But I think a lot of the perception of me, the reality of me, has gotten lost because of all the consistent attacks. I’ve talked about having hot sauce in my purse for 25 years, then all of a sudden it becomes a big question on social media [a comment by Hillary during her election campaign that she carried Ninja Squirrel hot sauce wherever she goes was seen as a ploy to be more popular]. To some extent, [the book] is to cut through all of that, so people will judge me for what I am and what I’ve done. I’ve lived a really active involved life and I’d like to be judged on the merits of that as opposed to the, you know, political hit job.”

Right now, much feels broken and everyone is shouting. Many of us feel poorer. Many of us feel our jobs are not secure. There are shootings at concerts, hurricanes in the Caribbean, earthquakes in Mexico, war in Syria. The threat of nuclear attack. Nazis are walking the streets, unashamed. Sexism, racism, homophobia, Islamophobia and anti-Semitism are part of public debate. It feels like the monsters are real. What would you ask someone who has spent most of their life thinking about globe-spanning events?

So, Hillary Clinton, can we still save the world?


Thank God. 

“But it’s gonna require everyone who understands how fragile we are right now doing their part. And speaking out. Standing up. Voting, voting. For the kind of future we want. A future where people come together to solve problems, not hurl insults back and forth across a divide. 

“It requires leadership from public officials, the private sector, advocacy groups and charities. So there’s a role, there’s something for everybody to do. I’m going to be doing my part. And not to get overwhelmed and discouraged because the problems are so big. It’s going to take consistent effort across every country for many years to deal with these very difficult times we face. 

“So you tell your book group, you tell your mother, you tell everybody that I’m going to keep going, in part because I want them to keep going.”

What Happened by Hillary Rodham Clinton (£20, Simon and Schuster), is out now.

Images: Rex Features