Chapter 3: The Nightmare | Crooked Media
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July 16, 2018
The Wilderness
Chapter 3: The Nightmare

In This Episode

Why did Democrats lose the 2016 election? The candidates, campaigns, and conditions that led to America’s worst person becoming president.


The Wilderness is a documentary from Crooked Media and Two-Up about the history and future of the Democratic Party. Pod Save America’s Jon Favreau tells the story of a party finding its way out of the political wilderness through conversations with strategists, historians, policy experts, organizers, and voters. In fifteen chapters, the series explores issues like inequality, race, immigration, sexism, foreign policy, media strategy, and how Democrats can build a winning majority that lasts.




[sponsor note]


[clip of Chief Justice John Roberts] Please raise your right hand and repeat after me, I, Donald John Trump, do solemnly swear.


[clip of President Trump] I, Donald, John Trump, do solemnly swear.


[clip of Chief Justice John Roberts] That I will faithfully execute


[clip of President Trump] That I will faithfully execute


[clip of Chief Justice John Roberts] The office of president of the United States


[clip of President Trump] The office of president of the United States


[clip of Chief Justice John Roberts] And will, to the best of my ability


[clip of President Trump] And will to the best of my ability


[clip of Chief Justice John Roberts] Preserve, protect and defend


[clip of President Trump] Preserve, protect and defend


[clip of Chief Justice John Roberts] The Constitution of the United States


[clip of President Trump] The Constitution of the United States


[clip of Chief Justice John Roberts] So help me God


[clip of President Trump] So help me God. [echoes] So help me God. So help me God. So help me God . . .


Dan Pfeiffer: We lost the most winnable open presidential race in modern American history. It was so winnable. Donald Trump’s a fucking clown. I use the Patriots example for you, but if the Patriots lost to the Cleveland Browns because of one bad call at the end, like you say: oh if that call went differently, the Patriots would have won. But the question you have to ask yourself is why were the Patriots one bad call away from the Cleveland Browns? And I think that’s a question we have to ask ourselves.


Jon Favreau: Sorry, we have to talk about 2016 again. I know it’s not great, but don’t worry, we’re not going to re-litigate every little dumb argument from the most miserable election of our lives, we’re only going to re-litigate some of them. We know by now that Trump had help from Russia, and Jim Comey’s letter, and a media that couldn’t tear itself away from the Trump show even when it was just an empty podium. But no matter how much or little this all made a difference, Democrats still need to figure out why we were one bad call away, and more importantly, what we can do to make sure that we don’t find ourselves in that position again. So we’re going to talk about the candidates we chose, the campaigns that they built, and how they all navigated the cultural and economic tides of the 2016 election. Ready, good. Let’s dove into this dumpster fire one more time. I’m Jon Favreau. Welcome to The Wilderness.


[clip of President Obama] You know, nothing truly prepares you for the demands of the Oval Office. Until you’ve sat at that desk, you don’t know what it’s like to manage a global crisis or send young people to war. But Hillary has been in the room. She’s been part of those decisions. She knows what’s at stake in the decisions our government makes, and no matter how daunting the odds, no matter how much people try to knock her down, she never, ever quits. That is the Hillary I know, that’s the Hillary I’ve come to admire, and that’s why I can say with confidence there has never been a man or a woman more qualified than Hillary Clinton to serve as President of the United States of America. [cheers]


Jon Favreau: If you had told me in 2008 that eight years later, I’d be helping President Obama write a speech endorsing Hillary Clinton as his successor. I’d have said that you were out of your goddamned mind. I wasn’t Hillary’s biggest fan back then. The primary between her and Obama was brutal. Sometimes it got even nastier and more personal than the one in 2016. But after a few years of being around Secretary Clinton and cabinet meetings and on foreign trips, I really came around. I thought she was brilliant. I thought she was caring and genuine and worked harder than anyone else in the administration. I liked that she was such a team player. I liked that she wasn’t going to try to distance herself from Obama or run as a more centrist version of the president. I just liked her. I could see her as president. She’s always had that quality.


[voice clip] So we arrived at Wellesley and we found, as all of us found that there was a gap between expectation and realities. And the challenge now is to practice politics as the art of making what appears to be impossible possible.


[voice clip] Does it concern you that maybe other people feel that you don’t fit the image that we have created for the governor’s wife in Arkansas?


[clip of Hillary Clinton] In a way, it’s kind of a tribute to the state that someone who may or may not fit an image is accepted on her own terms.


[clip of Hillary Clinton] I suppose I could have stayed home and baked cookies and had teas, but what I decided to do was to fulfill my profession, which I entered before my husband was in public life.


[clip of Katie Couric] Do think the American people are ready for a first lady who is that involved at a policy-making level in the White House?


[clip of Hillary Clinton] Well, I hope so, because I think what I represent is generational change. It’s not just about me. I think that every American is entitled to guaranteed health insurance, not just because it is the right thing to do for the individual, but because it is the smart thing for our country to do, to make sure everybody is insured.


[voice clip] Do you folks out here think that she has remodeled the role of first lady? And maybe she has.


[clips of Hillary Clinton] Let it be that human rights are women’s rights, and women’s rights are human rights, once and for all  . . . I am honored today to announce my candidacy for the United States Senate from New York . . . I will work my heart out for you for the next six years . . . somebody in that White House told the EPA, don’t tell the people of New York the truth . . . that I will well and faithfully . . . we have in the leadership of President Obama, someone who wants us to reach out to the world, to do so without illusions, understanding that the difficulty . . . I am running for president of the United States.


[news clip] Breaking news tonight . . . Hillary Clinton will become the first woman nominated by a major political party for the presidency of the United States.


Jake Sullivan: Hi, my name is Jake Sullivan, and I was the senior policy advisor on Hillary Clinton’s 2016 campaign for president. I did not meet Hillary Clinton until I interviewed with her for a job on the 2008 campaign, the primary campaign. I met her in early 2007 in her Senate office and honestly, my first impression of her was that she was a very normal human being, in a bizarre way, because I’d obviously seen her on TV for the preceding 15 years. And when you sit down with her, she’s somebody who looks you in the eye, she asks you questions, she actually listens to the answers, which is fairly unusual for people of her stature. She actually still to this day, cuts articles out of newspapers, literally, and creates a folder that she’ll then carry around in her bag and every now and again, we’d be traveling in some foreign country as Secretary of State or in the years that followed, she’d pull it out and say: here’s some things I read that are interesting that I’ve been thinking about. And that’s what’s so unusual about her, because she’s been built into a certain kind of caricature. But in person, she’s so down to earth. She is at her best when she is occupying a position where she can actually roll up her sleeves and put policy into action.


[clip of Hillary Clinton] So it’s true. I sweat the details of policy, whether we’re talking about the exact level of lead in the drinking water in Flint, Michigan, the number of mental health facilities in Iowa, or the cost of your prescription drugs. Because it’s not just a detail, if it’s your kid, if it’s your family . . .


Jake Sullivan: I think she ultimately decided to run because at the end of the day, Hillary Clinton believes that if you get a chance to serve in a senior role in government, you can do some unbelievable things for people. And that, more than anything, is what motivated her as first lady and a senator and a secretary of state. I think she looked at the presidency and thought, there’s no job in the world where I could do more good for more people than this.


Jen Palmieri: Had not worked for Hillary directly, but I had worked for her husband, knew her relatively well. I knew the Clinton world well.


Jon Favreau: Jen Palmieri was Hillary Clinton’s communications director, and before that was Obama’s White House communications director.


Jen Palmieri: My very first day on the job in March of 2015, Hillary basically vomited up what had been like to be her for the last 25 years, and her interactions with the press and the public, and how they reacted to her. It was pretty remarkable. She said she didn’t have any answers and: I’m skeptical that the press is ever going to react to me in a different way, but you should never censor yourself, you should always be frank with me about what you think I need to do, what you think I should do, I’m going to say no a lot, but don’t ever censor what you think is the best advice. I knew it was going to be a hard campaign. I didn’t think it would be fun necessarily, but it seemed like, OK, I should do this.


Jon Favreau: In hindsight, it seems odd that everyone in the party establishment just lined up behind Hillary so early, but at the time it made perfect sense.


Michelle Goldberg: I’m Michelle Goldberg. I’m an Op-Ed columnist at The New York Times. People forget, but when she started her campaign for president, she was the most respected woman in America, right? Her approval ratings were around 66%. There was no woman with higher approval ratings. And so in retrospect, you can say: well, why did we ever think that Hillary Clinton with all of her baggage, was a viable candidate? That’s why.


Brian Beutler: Harry Reid was very anti-primaries, and Barack Obama was very anti-primaries.


Jon Favreau: Brian Beutler, editor in chief of


Brian Beutler: If a primary could be avoided, it should be avoided. So there was like this institutional reluctance to letting every qualified Democrat flood the primary zone. At the time, it seemed justified.


Jon Favreau: Obama always said that his long primary campaign against Hillary Clinton made him a better candidate in the general election. That’s true. But it was also 16 months of pure misery for everyone involved. One reason primaries can be particularly nasty is that you have a bunch of candidates from the same party who all have similar positions on the issues. So they end up fighting about differences in their voting records, or leadership styles, or personal qualities, which can get pretty nasty. That was mostly the case with Obama and Hillary, and there was still lingering resentment among a small segment of Clinton supporters by the time we get to the general election. I think a lot of party leaders wanted to avoid that in 2016. And so if you wanted to run against Hillary, you needed to have real policy and political differences, and you needed to not give a shit what the party establishment thought about you. Lo and behold, Senator Bernie Sanders checked both of those boxes.


Faiz Shakir: People don’t appreciate how difficult it is to step out of line from what the party structure wants.


Jon Favreau: This is Faiz Shakir, who’s the ACLU National Political Director. Before that, he was a senior adviser to Senator Harry Reid, a job he left to become an adviser to Bernie Sanders’s presidential campaign.


Faiz Shakir: At a time when you’re coming post Obama, when a lot of people are feeling like: pretty good job, feeling a little bit of taste in my mouth of wishing that it had been more. Right? You’re feeling a little bit of like: man, probably left something on the table. And at the same time we see the reasons those things were left on the table is corporate control, corruption over our system, you know. And then here comes Hillary offering essentially: I’m just going to do the same thing. So here comes Bernie: take them on full throated.


[clip of Senator Bernie Sanders] Today with your support and the support of millions of people throughout our country, we begin a political revolution to transform our country economically, politically, socially and environmentally.


Dan Pfeiffer: Bernie Sanders, 70-year old socialist from Vermont.


Jon Favreau: Dan Pfeiffer, co-host of Pad Save America and former senior adviser to Barack Obama. Also for the record, Bernie is 77 years old.


Dan Pfeiffer: It was not surprising to me that for Democrats there would be an anti-establishment vehicle. There is always been someone in open races who filled that void, right? Howard Dean in 2004, Bill Bradley in 2000, and Jerry Brown, among others.


Dan Pfeiffer: Barack Obama in 2008.


Dan Pfeiffer: Barack Obama in 2008, right? And, so someone is always fill that void. He was running a campaign to get his message out, like he wasn’t even trying to win. And so it did not surprise me that Sanders was going to show strength, but I thought once the rubber hit the road, he would fade pretty fast.


Heather McGhee: I remember talking to one of her policy advisers—


Jon Favreau: This is Heather McGhee, a policy expert who’s advised on Democratic campaigns.


Heather McGhee: —and this adviser asked me a very smart question, which is: what would you say about the candidate if it weren’t to me? And I responded and said, my biggest concern is that we are in an anti-establishment moment and I just don’t know how Secretary Clinton can be an anti-establishment candidate. I just don’t know how she can muster the sense of outrage at what’s going on right now, when she’s a continuation of what’s going on right now.


[clip of Senator Bernie Sanders] When the greed and recklessness and illegal behavior of Wall Street brought this country into the worst economic downturn since the Great Depression of the 30s, the obvious response to that is that you got a bunch of fraudulent operators and that they have got to be broken up. Now, Secretary Clinton was busy giving speeches to Goldman Sachs for $225,000 a speech.


[clip of Hillary Clinton] I stood up against the behaviors of the banks when I was a senator. I called them out on their mortgage behavior.


Dan Wagner: He certainly figured something out. He certainly spoke to the anxieties of people directly and in principal.


Jon Favreau: Dan Wagner is a data scientist who worked on Barack Obama’s 2012 campaign.


Dan Wagner: He says, I recognize the crises in your communities, and he kind of directs people towards an addressable villain and he speaks to it authentically.


[clip of Senator Bernie Sanders] There is something profoundly wrong when one family, the Walton family of Walmart, owns more wealth than the bottom 130 million Americans.


Becky Bond: We always said the biggest asset that we had on the campaign was Bernie’s message, and the second most important asset we had was Bernie as a messenger.


Jon Favreau: Becky Bond, a senior adviser on the Bernie Sanders campaign.


Becky Bond: So many people saw the Bernie movement as being idealistic, but I think for the people that really got involved, they saw it as the only practical solution. Our problems are so radical, we’re going to need radical solutions in order to solve them.


Jon Favreau: Needless to say, the Democratic primaries starting in Iowa in February of 2016, pretty much went exactly as nobody expected.


[news clip] Now classifying Iowa’s Democratic presidential caucuses as too close to call.


[clip of Senator Bernie Sanders] Tonight while the results are still not known, it looks like we are in a virtual tie.


[news clip] Hillary Clinton riding high today after narrowly edging out Bernie Sanders by fractions of a percent in the Iowa caucuses.


[clip of Senator Bernie Sanders] The people of New Hampshire have sent a profound message to the political establishment, to the economic establishment and, by the way, to the media establishment. We won because of your energy. Thank you all.


[clip of Hillary Clinton] Thank you, Nevada. Thank you so much.


[news clip] CBS News projects. Hillary Clinton has defeated Bernie Sanders in today’s Democratic caucuses.


[news clip] Bernie Sanders says he is not going anywhere. He is defiant tonight. He says he’s taking this all the way past the convention to the very end. And he’s got the money right now to go pretty far.


[news clip] He does. But Jon Karl, pretty big delegate lead for Hillary Clinton.


[news clip] It’s a delegate tsunami for Hillary Clinton tonight.


[news clip] We have breaking news tonight.


[news clip] Hillary Clinton has clinched the majority of delegate support she will need for the Democratic nomination.


Jon Favreau: The primary went all the way until June, and it opened a rift in the Democratic Party. Bernie supporters believe that Hillary Clinton was too tied to the Democratic establishment, too tied to Wall Street, too tied to the past. Hillary supporters believe that Bernie was hurting the party’s chances to win in November by attacking Clinton after it was clear she won the nomination. It was hard to tell how much of this Hillary-Bernie divide was real, and how much was overhyped by the media, and the candidate’s most vocal supporters. The divide was definitely on display during the first couple of days of the Democratic convention in July, especially after Russia and WikiLeaks released thousands of stolen DNC emails that embarrassed everyone involved.


[news clip] Good evening from Philadelphia tonight, where the Democratic National Convention hasn’t even started and we already have our first major controversy. The chair of the DNC, Congresswoman Debbie Wasserman Schultz, has announced her resignation.


Jon Favreau: Fortunately, by the end of the convention, things were going pretty well.


[clip of President Obama] And tonight, I ask you to do for Hillary Clinton, what you did for me. I ask you to carry her the same way you carried me.


[clip of President Bill Clinton] She is still the best darn change-maker I have ever known.


[clip of Michelle Obama] We need to pour every last ounce of our passion and our strength and our love for this country into electing Hillary Clinton as president of the United States of America.


Jon Favreau: This is Brian Beutler again:


Brian Beutler: Democrats, despite a lot of internal tensions and a lot of like infighting at the convention itself, put on this presentation. It’s like you could feel the people in the room realizing that, OK, we can get over this primary and we can, like, move into the general election. And I tweeted, Hillary Clinton going to win, or something like that, realizing that what we’re offering is so much better than what we just saw. Right?


Jon Favreau: What we just saw was the Republican National Convention, a three-day shit show centered around the theme that everything in America was awful and only one man could fix it.


[clip of Jon Voight] Hello, I’m Jon Voight. I want to share with you the story of my friend Donald Trump.


[voice clip] Yes, that’s right, lock her up. You know why we’re saying that? Because if I did a tenth, a tenth of what she did, I would be in jail today.


[voice clip] [unclear] Donald Trump. All lives matter!


[voice clip] One America.


[voice clip] In Iran and Russia and Cuba. And here at home for risking America’s secrets to keep her own and lying to cover it all up.


[voice clip] Imagine a young mother at home with her baby when a violent predator kicks the door in, and he’s a three-time loser who was released from prison early because some politician wanted to show their compassion.


[voice clip] Islamic extremist terrorism.


[chanting] We want Trump.


[clip of Donald Trump] I am your voice.




Jon Favreau: Coming up after the break, more of The Wilderness presented by honey.


[ad break]


Jon Favreau: Donald Trump. It’s hard to say where this all started, but like most things pertaining to that man, it was probably on Twitter.


[news clip] A year later, Trump tweeted: An extremely credible source has called my office and told me that Barack Obama’s birth certificate is a fraud.


Jon Favreau: Trump’s political life started with him parroting the same bullshit conspiracy theories and racist garbage that you’d hear on talk radio and see on Fox News. And his presidential campaign was basically the same thing. Trump was a talk-radio caller who decided to run for the most powerful job in the world.


Lynn Vavrek: Trump just seems really different.


Jon Favreau: Lynn Vavrek, professor of political science and communication at UCLA and contributor to The New York Times Upshot.


Lynn Vavrek: He’ll just say anything. Spin, spin, whatever. Doesn’t have to be true. Just say it like you believe it, and say it over and over again.


[clip of Donald Trump] I know more about ISIS than the generals do, believe me.


[clip of Donald Trump] Number one selling tie anywhere in the world.


[voice clip] Number one selling tie anywhere in the world.


Lynn Vavrek: But he’s also a TV character. So a lot of Americans know him as Donald Trump from the boardroom. You know, why do so many people feel like they understand him as a businessman? Because he was on TV doing it!


[clip of Donald Trump] New York City. It’s the benchmark for success, believe me. I know . . . Trump Ice: the purest, best tasting water you can imagine.


Lynn Vavrek: So when he changes his mind day to day and just repeats things and says things, maybe they’re true, maybe they’re not. Doesn’t matter. People think back to the Donald Trump, who was on The Apprentice.


[clip of Donald Trump] I mean, you’re so stupid. What you did was just stupid.


Lynn Vavrek: Where he behaved the same way, but at the end of that particular episode, he was always right.


[clip of Donald Trump] Kevin, you’re fired . . .  Sandy you’re fired. You all have problems. Life is full of problems. You’re fired.


Adam Serwer: The other thing is, part of the appeal to Trump was that he gave incredibly simple answers to really complicated problems.


Jon Favreau: This is Adam Serwer, Deputy Politics Editor at The Atlantic.


Adam Serwer: And that’s not something that a lot of politicians do well. Trump would just say: this is the problem, there are some bad people, I’m going to hurt the bad people and make it better; there’s just a bunch of corrupt people who are preventing us from solving this problem and once the corrupt people are gone, because I’ll get rid of them, I’m just going to make everything better.


Lynn Vavrek: Also, Trump, really, he lit up these racial attitudes. He didn’t create them. Everybody knows they exist. They’ve existed. He just, he lit them up in a way that, you know, we really haven’t seen in a long, long time.


[clip of President Trump] They’re bringing drugs. They’re bringing crime. They’re rapists. And some, I assume, are good people . . . What do you have to lose? You’re living in poverty. Your schools are no good. You have no jobs. What the hell do you have to lose?


Lynn Vavrek: Everybody knows this is a way that they could get more white voters, if they poured some gasoline on race, but nobody would do it. Here comes Donald Trump and he just goes where no other of the 16 candidates who ran for the Republican nomination in 2016 would go. Are you going to let shame stop you from winning a presidential election?


[clip of President Trump] This judges of Mexican heritage. I’m building a wall.


[clip of Anderson Cooper] So no Mexican judge could ever be involved in a case that involves you.


[clip of President Trump] Well, he’s a member of a society where, you know, very pro Mexico. And that’s fine. It’s all fine.


[clip of Anderson Cooper] That’s something you’re calling into question.


[clip of President Trump] Ah, look at my African-American over here. Look at him. Are you the greatest?


Jon Favreau: A good portion of the Republican base saw Trump as a successful businessman who would blow up Washington, fix politics and fight for them—them meaning white people. And against all the other stiff, overly scripted, blow-dried Republican candidates, it worked.


[voice clip] —ordinary tableau, Donald Trump, a businessman and reality star with no political experience, now the Republican nominee for president of the United States of America. Streamers and balloons . . .


Jon Favreau: So now we’re ready to relive our worst nightmare: the general election matchup between Hillary Clinton and Donald Trump. We don’t need to cover all the details. We all remember that Trump said some truly awful and unforgivable shit just about every day.


[clip of Donald Trump] You’re going to hear it once: all lives matter. . . You mention food stamps and that guy who’s seriously overweight went crazy . . . They say, I have the most loyal people where I could stand in the middle of Fifth Avenue and shoot somebody and I wouldn’t lose any voters . . . I think Islam hates us.


[clip of Hillary Clinton] But what we want to do is to replenish the social security trust fund.


[clip of Donald Trump] Such a nasty woman.


[clip of Donald Trump] I moved on her like a bitch. I couldn’t get there, and she was married. And all of a sudden I see her she’s now got the big phony tits . . . and when you’re a star, they let you do it. You can do anything.


[clip of Billy Bush] Whatever you want.


[clip of Donald Trump] Grab them by the pussy. You can do anything.


Jon Favreau: And lest we forget Hillary Clinton spent most of the campaign under investigation by the FBI, which is not ideal.


[clip of Senator Bernie Sanders] The American people are sick and tired of hearing about your damn emails.


[clip of Hillary Clinton] Thank you. Me too. Me too.


[voice clip] I’m here to give you an update on the FBI’s investigation of Secretary Clinton’s use of a personal email system during her time as Secretary of State. They were extremely careless. We are expressing to Justice our view that no charges are appropriate in this case.


Jon Favreau: More on that later. Point is whether you think it’s fair or not, every piece of polling and data show that these were two of the most unpopular candidates to ever run for president.


David Binder: It was very, very difficult to make a real good guess as to what was going to happen by watching the focus groups.


Jon Favreau: This is David Binder, who conducted focus groups for Democratic campaigns, including Barack Obama’s and Hillary Clinton’s.


David Binder: Primarily because those people that we were looking at—which tended to be undecided swing voters who sometimes vote for Democrats, some, sometimes vote for Republicans—they really disliked both candidates to a degree that we had not seen before in the previous campaigns or previous research. And one of the techniques that we use in focus groups occasionally is you use projective techniques to get people out of their normal thinking. One of the exercises we do is ask people to think of a candidate in terms of an animal. Like what animal represents Hillary Clinton best? What animal represents Donald Trump best? In the ’16 campaign, we had people that said the contest between Hillary Clinton and Donald Trump was essentially a contest between a snake and a baboon. I can’t tell you how many times in our focus group somebody brought up the idea that there’s a list of people who had ended up dead or missing because they, at some point in their lives, had crossed the Clintons.


Jon Favreau: I heard that.


David Binder: This is not, that was not one time. That was, I would say, every other focus group, at least one person brought that up again and again.


Jon Favreau: Had you ever heard anything like that in any other races with any candidates, that kind of—.


David Binder: No, I mean, the conspiracy stuff generally is getting worse and worse, I think just lately, just because more people are buying conspiracy theories. But it’s definitely, it definitely wasn’t—what I saw in the Clinton-Trump race with regard to conspiracies was unprecedented. And I don’t hear anyone talking conspiracies about Trump. They just thought he was an idiot. But with Hillary, there was this concern that she was nefarious. It’s not just isolated incidents. A lot of people have brother-in-laws that are sending them these emails that make it sound like Hillary and Bill Clinton have a mafia ring that are killing people.


Jon Favreau: We should talk about this. The Clintons have been dealing with scandals since the moment we first heard about the Clintons: from Whitewater and Bill’s affairs, to Benghazi and Hillary’s email server. Some of these scandals were real, but many, like the list of people they supposedly killed, were decidedly bullshit. But talk radio and Fox and the Internet have pushed Clinton scandals forever. And they got plenty of coverage from mainstream outlets in 2016, especially the email story. In fact, a Columbia Journalism Review study found that in just six days, The New York Times ran as many cover stories about Hillary Clinton’s emails as they did about all the policy issues combined in the 69 days leading up to the election. When you throw in the fact that the Russians and WikiLeaks hacked and published the inboxes of Hillary’s campaign chairman and DNC staffers, you start to realize just how much extra shit she had to wade through on the way to November. You also begin to realize why Hillary has spent so much of her career being more cautious and guarded than the typical politician.


David Binder: I think the biggest thing we learned in ’16 is a sense of authenticity was the most important factor in causing some people to choose the candidate they did. Donald Trump talked to them like somebody at the bar would talk to them. So they felt like: I don’t really like what’s coming out of his mouth, but whatever is coming out of his mouth, it sounds real, it sounds genuine. And they didn’t feel that way about Hillary Clinton. Hillary was structured. She was scripted. She was polished. She had some veneer over her. And everything that she said was focus group tested, which kind of made me feel like an idiot.


Jen Palmieri: I had this sickening thought in October of 2016 when we’re like sitting on the tarmac in Florida.


Jon Favreau: Jen Palmieri.


Jen Palmieri: And I thought we have made Hillary a female facsimile of the qualities we look for in a male president. Like that’s what we have done. And it felt like a gut punch. Like, right, well, of course, people think she is inauthentic. Of course, people, they don’t think they really get who she is because they put this very ill-fitting suit, if you will, and, like, forced it on her. And it’s like a fundamental flaw in the design. You have to go all the way back to beginning to fix.


Rebecca Traister: There’s an emphasis placed on authenticity. And this is completely related to the experience that Hillary Clinton had, because as a woman running for a job that has always been a man’s job, she was being told to fit into the mold of leadership that existed.


Jon Favreau: Rebecca Traister.


Rebecca Traister:  I’m a journalist. I write about politics, media, entertainment, social movements, from a feminist perspective. As we know about her 2008 campaign, Mark Penn, her campaign adviser, told her basically to cross-dress. You know, we don’t, “the country is not ready for a first mama, but it is ready for our first papa, who is a woman” was what he said in a memo to her. And so the boxy pantsuits and the voice modulation and, you know, all of these things she was told from the beginning: lose your name, lose your coke-bottle glasses, cut your hair, do all these things to conform to this very narrow idea of what authoritative leadership might look like in a woman. And that’s basically to sort of make it look slightly off-brand male. And then she was—I think, you know, for very good reason—criticized for not coming across authentically, not as herself, for being robotic, for being canned. All these messages were sent to her that were like: don’t be the person that you naturally are, be a different kind of person to persuade us that you could be a politician and a leader. But then it was: but now you’re this kind of person and I think you’re faking it.


Jon Favreau: In hindsight, there are plenty of reasons to worry about Hillary Clinton’s chances in 2016. She had a long, drawn-out primary where a good chunk of voters decided that she didn’t represent enough of a change from Obama’s two terms, especially on issues of economic inequality. She had an opponent in Trump who fueled and then exploited the racial backlash to Obama’s presidency in the most explicit and shameless way possible. She had 35 years of very public baggage, and she had to deal with the sexism and misogyny that comes along with being the first female presidential candidate. On top of all that, Jim Comey decided to send a letter to Congress less than two weeks before the election, suggesting that the FBI investigation into Hillary’s emails may not be over—a misconception he only corrected two days before most voters stood in line to cast their ballots. So that wasn’t helpful. And yet, believe it or not, in spite of all that bullshit, when the polls opened on November 8th, 2016, Hillary Clinton was still the favorite to win. Here’s Dan Pfeiffer:


Dan Pfeiffer: I thought Hillary, barring some change in the economy or some other exogenous events like spiking gas prices, or war, if it was another financial crisis, that she would win because Democrats had a rock-solid Electoral College advantage, and the country was getting bluer by the second. Like fully recognizing that Hillary Clinton has some challenges as a candidate, but—and it wasn’t, you know, it’s funny because it wasn’t even really a question.


Jon Favreau: Rebecca Traister.


Rebecca Traister: I think back on the night before the 2016 election and there was a rally in Philadelphia and the Obamas were there and Hillary was there. Bill was, too. And it was the really remarkable rally.


[clip of Hillary Clinton] Hello, Philadelphia.


Rebecca Traister: There were so many people there, it was so quiet, but in a good way.


[clip of Hillary Clinton] I am so grateful to be—


Rebecca Traister: And I remember thinking, it was such a symbolic thing, obviously, they’d gone to Independence Hall: the Black first family and the woman that everybody thought the next day, or everybody, I think on that stage actually did think, was going to be elected president the next day. They’d gone to this place where the founding documents that had cut all those people out of our political leadership had been written. And I thought it was really brave because it was such an open rebuke to the kind of fetishized approach to our founding fathers and the country’s founding that we’re so used to in politics. It was such a direct critique of who had been excluded from the American compact up until that point.


[clip of Michelle Obama] Brothers and sisters who are all infinitely worthy, all an important part of this great American story.


Rebecca Traister: Whatever the mistakes that were made—and of course, there are a million—I will always be so impressed by the fact that part of that campaign was also built on genuine hope for our ability to change that.


[clip of Michelle Obama] This country has always been great. A country where a girl like me from the south side of Chicago, whose great great grandfather was a slave, can go to some of the finest universities on Earth.


[clip of Hillary Clinton] We love this country. We love what it stands for—not that we are blind to its flaws, its problems, its challenges—but I believe with all my heart that America’s best days are still ahead of us if we reach for them together.


Jake Sullivan: So Election Day—


Jon Favreau: Jake Sullivan, policy adviser to Hillary Clinton.


Jake Sullivan: I was at the Peninsula Hotel with Hillary and her speechwriters, Bill Clinton, some of her other senior staff, and pretty early on, as the results from Florida started coming in, it became clear to me that this night might not go our way. Had a pit in my stomach and thought, you know, that was eight o’clock or not long after eight o’clock, this this is not looking good.


David Plouffe: I was with my wife on election, I was with my kids.


Jon Favreau: David Plouffe, Obama’s former campaign manager and White House senior adviser.


David Plouffe: We had a bunch of friends over, some in politics, some not. So those of us who’d worked in politics were down on my computer in my basement and looking at Florida numbers. And it began to get really concerning. Places where she was supposed to get 42 or 44 for she was getting 32 or 33.


[news clip] Some of the numbers we’re seeing coming in from Florida right now—.


[news clip] It’s 40% already of the vote in and it’s all early voting here.


[news clip] Now we have it as too close to call. But Clinton, with a 49-48 lead there. What are you seeing—.


[news clip] 91% in. I think Trump’s leading by about 60,000 votes. I don’t know if there’s enough vote left for Clinton to win.


David Plouffe: When I began to look at some of the counties in Ohio, I mean, these were catastrophic changes.


[news clip] 2700 votes there in Ohio. Still a lot of vote out there, but 37% percent reporting—


[news clip] Top Clinton campaign officials, and they say they’re not panicking even if they don’t hold Florida or Ohio. The states that they are focused on right now include Michigan, Colorado, Virginia and Pennsylvania. Lester we—.


[news clip] A new projection in the state of Ohio, NBC News projects when the votes are counted, Ohio will go to Donald Trump. Donald Trump will win Ohio.


David Plouffe: If you’d shown me those numbers in Pennsylvania a week before the election, I would have thought it was fake news. I wouldn’t have thought it was possible.


[news clip] There’s our, we’ve updated our electoral scorecard.


[news clip] What is going on? We are going to make this decision now. The Fox News decision desk has called Pennsylvania for Donald Trump. This means that Donald Trump will be the 45 president of the United States, winning the most unreal, surreal election we have ever seen.


Amanda Litman: At around midnight, 12:30, I think—time is a flat circle—but somewhere around then we knew we were going to lose.


Jon Favreau: Amanda Litman, email director for Hillary Clinton, was at the Javits Center the night of the election.


Amanda Litman: People were crying. People were sobbing. Podesta went out and spoke to the convention hall.


[clip of John Podesta] They’re still counting votes and every vote should count.


Amanda Litman: We close our computers, we start walking out, we’re probably the last people in Javitz. At this point I think they turned the Wi-Fi off. And we see a tweet from Maggie Haberman that Hillary had called to concede, and couldn’t get a hold of anyone else on the staff to figure out what to do, and started pulling everything back, and hot-spotting our phones and figuring out what—we didn’t have a plan. We didn’t have a plan.


[voice clip] The President-Elect of the United States of America, Donald Trump.


Amanda Litman: I remember walking through Times Square that night from Javitz to find a cab and seeing all the people in their Make America Great Hats and being terrified, just terrified.


[clip of Van Jones] People have talked about a miracle. I’m hearing about a nightmare. It’s hard to be a parent tonight for a lot of us. You tell your kids, don’t be a bully. You tell your kids, don’t be a bigot. You tell your kids do your homework and be prepared. And then you have this outcome and you have people putting children to bed tonight. And they they’re afraid of breakfast.


Amanda Litman: And then taking a cab home from Times Square and all the way out to my apartment in Brooklyn with one of my friends, and we both broke down in the cab, sobbing. I had to pull over the cab to throw up because I was like: I can’t keep this inside anymore. And then the next morning, we had to figure out what to do for her speech. God, it was bad.


Jon Favreau: I’m a worrier by nature. In 2008, my friends on the Obama campaign used to make fun of me for freaking out about every single poll, even if it was from a shit pollster. Same thing in 2012. David Plouffe would say: don’t be a bed-wetter. And so in 2016, I tried not to be a bed-wetter. In fact, I told everyone else not to be bed-wetters. Trust in the data, I said, look at the fundamentals. But on election night, as I saw those first results from Florida trickle in, I started having these flashbacks to a few different times during the campaign where I had these moments of panic. I thought about Bernie winning all those primaries right before the convention. I thought about how the polls were all tied-up in September when she should have been way ahead of him. I remembered how I felt sick when I first got the news alert about Comey’s letter, and how I had a full freak-out when I heard the polls in Michigan and Wisconsin were tightening the weekend before the election. And then I started wondering how I ever could have fooled myself into thinking that this thing was in the bag. But I didn’t have that much time to reflect because I was also in the middle of a live stream. Tommy Vietor, John Lovett and I were on set at The Wringer, the media company that produced our old podcast Keepin’ It 1600. And we were all speechless. We tried to be professional. We tried to hide the shock and misery on our faces and just keep calmly analyzing the results for whoever was watching us. But after a while, we just couldn’t do it. And so we finally cut the feed and drove home, and I just remember standing outside my house talking to my wife on the phone, because she’d been in Florida all weekend knocking on doors, and she was crying and she kept asking me: how did this happen? What does this mean? What are we going to do? And I didn’t have answers for her. You know what happens from there. We’re still living it, every day. But the purpose of everything you’ve heard so far, the entire podcast up to this point, has been to give you some context for that question we asked at the very beginning. How do we fix what’s wrong with the Democratic Party? I’ve heard more than a few people say: don’t nominate Hillary Clinton next time. OK, sure. As we just heard, Hillary had specific baggage and faced a unique set of circumstances. But Hillary’s loss doesn’t explain the last decade of Democratic losses in Congress or state houses. And Hillary’s campaign wrestled with a series of challenges that all Democrats will have to wrestle with in future elections, challenges that will spend the rest of the series talking about. Challenges like: the voters and how they see the Democratic brand.


[speaker 1] It’s hard to be a big tent party, and it’s hard to balance those interests and make people see, like, listen, you got to get X number of seats to control this body in the state and sometimes you have to make compromises. This isn’t always Mr. Smith goes to Washington.


Jon Favreau: The backlash to the racial progress of the last decade.


[speaker 2] Trump won majorities of white voters in every income bracket. So that says that it’s about more than just poor people in West Virginia who don’t have coal mining jobs anymore.


Jon Favreau: The debate over immigration.


[speaker 3] The big mistake Democrats are making on immigration is that you don’t develop your immigration policy indigenously, based on your own dynamics, but reactively.


Jon Favreau: The growing inequality that comes from globalization and technology.


[speaker 4] I think we’re living through a historic change. After the Industrial Revolution came the progressive era. That was a very big and bold answer to the challenges that that industrial revolution created. Where is the progressive answer?


Jon Favreau: The hawkish views of the Washington foreign policy establishment.


[speaker 5] A lot of Democrats feel like they, they need to just sound tough. And tough is a version of what the Republican message is with some of the rough edges sanded down.


Jon Favreau: The media.


[speaker 6] Well, so, yes, the media like would rather cover a car crash than a, you know, a safe and efficient commute. Right? Why did the media do the 2016 election the way they did?


Jon Favreau: The Democratic Party establishment and the way we organize?


[speaker 7] You had no state party infrastructure whatsoever as Secretary Clinton is entering in this historic race to elect the first woman as our president. And she inherited a party that had been completely decimated.


Jon Favreau: The bench of candidates we’ve recruited.


[speaker 8] The number of new people who are running for office, the number of women who are running for office: those are the kind of candidates that have the ideas and the vision that I think will fundamentally bring us into the future of our politics.


Jon Favreau: The obstacles faced by women who run for office.


[speaker 9] This country has a real problem getting enthusiastic about women’s movements, right? We’re not a country that swells with pride when we think about, like making progress for women.


Jon Favreau: And finally, the message we deliver about who we are and what we stand for.


[speaker 10] I don’t know what the best messaging is about, sort of the big “we”, but we better figure it out and Democrats better engage there oe we’re going to tear this country apart.


Jon Favreau: Look, none of this is easy. This isn’t supposed to be a how to guide or a strategy memo. It’s a documentary based on a series of interviews I conducted over the last year with nearly 100 people who study, criticize, work with, believe in, and lead the Democratic Party. Each of the next 12 episodes will deal with a different challenge facing the party, each with a history as old as this country, questions we’ve been wrestling with since our founding. Now, I want to leave you with one last exchange I had with Rebecca Traister on why this is all worth the fight.


Jon Favreau: I remember when we were sitting down to work on the second inaugural. You know, Obama as usual, came up with the whole idea, he was like: you know, we should start with the first line of the declaration, because my belief is that the, you could write the entire history of the United States and the entire story of America is us, is each generation trying to make that first line of the declaration real, because it wasn’t when it was written but the promise was always in the founding, and the idea is that each each generation tries to do it. You know, those were back in the hopeful days. Before Trump.


Rebecca Traister: But it’s because and this is the thing, this is, this is the bigger story—is that he was right to have that hope. I mean, I do sometimes think that he believes we were closer to it than we were, obviously.


Jon Favreau: Right. Right.


Rebecca Traister: But he was right to have that hope because it is possible. It is possible. But the fact that it’s possible is precisely what has provoked the punishing pushback that we’re living through right now. It’s the fact that it’s within our grasp to make another huge set of steps toward inclusion and equality and toward the promises, the unfulfilled promises of our founding. It’s because we’re on the brink of getting to that next place, that we are being hit so hard. That’s exactly what we’re in the midst of right now, and it’s not because it’s impossible to get to that next step. It’s because it’s really possible.


Jon Favreau: The Wilderness is written and directed by me, Jon Favreau of Crooked Media. It’s produced by Zach Akers and Skip Bronkie of Two Up, and Ruth Lichtman. Tanya Somanader of Crooked Media is our co-producer. Andrea B. Scott is our editor and David Fox is our assistant editor. Our archival producer is Rebecca Kent, and our archival researcher is Gianna Jefferson. Music by Marty Fowler. Sound design and mixing by Joel Robbie. Tracy Lien is our lead interviewee researcher. Additional writing from Zach Akers and Andrea B. Scott. John Maynard and Dan Kelly were a recording engineers. Fact checking by Anna Altman. Promo segment editing from Allison Grasso. Agency services from Ben Davis at WME. Legal services from Dean Bahat at Ziffren Brittenham and Chad Russo at Ramo Law. Clearance Counsel is Kathryn Alimohammedi from Donaldson + Califf. Thanks for listening.