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- [00:00]
Kara Swisher
Three people I would never be. I can't even write it with myself.
- [00:03]
Josh Dossey
I mean, a book of this scope on this turnaround is better with friends.
- [00:18]
Kara Swisher
Hi everyone from New York Magazine and the Vox Media Podcast Network, this is on with Kara Swisher. And I'm Kara Swisher. My guests today are Isaac Arnsdorf, Josh Dosse, and Tyler Pager, three political reporters and the authors of 2020 How Trump Retook the White House and the Democrats Lost America. It's easy to get swept up in the chaos of Trump 2.0 and forget how wild last year's presidential election was. But it's important to look back, analyze the presidential race with the benefit of hindsight, and draw out the key takeaways. And that's exactly what this book does. Isaac Arnsdorff is a senior White House reporter for the Washington Post. His reporting on the first Trump assassination attempt was essential to the Post's 2025 Pulitzer Prize for breaking news, and he's the author of Finish what We Started about the Maga movement. Post January 6th Josh Dossey is a political investigations and enterprise reporter for the Wall Street Journal. Josh was part of the Washington Post teams that won the Pulitzer prizes in 2022 for coverage of January 6th and in 2024 for coverage of the role the AR15 has played in American life or really death. And Tyler Pager is a White House correspondent for the New York Times. In 2022, he won the Gerald R. Ford Journalism Prize for Distinguished reporting on the Presidency. This conversation is very insightful, so stick around. Support for this show comes from ServiceNow, who are enabling people to do more fulfilling work, the work they actually want to do. You know what people don't want to do? Boring, busy work. But now with AI agents built into the ServiceNow platform, you can automate millions of repetitive tasks in every corner of your business, it, hr, customer service, and more. And that means your people can focus on the work that they want to do. That's putting AI agents to work for people. It's your turn. Get started@servicenow.com AI Agents.
- [02:25]
Tyler Pager
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- [03:03]
Kara Swisher
Support for this show comes from Pure leaf iced tea.
- [03:06]
Josh Dossey
When you find yourself in the afternoon.
- [03:08]
Kara Swisher
Slump, you need the right thing to make you bounce back. You need pure leaf iced tea.
- [03:13]
Josh Dossey
It's real brewed tea made in a.
- [03:15]
Kara Swisher
Variety of bold flavors with just the right amount of naturally occurring caffeine. You're left feeling refreshing and revitalized so you can be ready to take on what's next. The next time you need to hit the reset button, grab a pure leaf iced tea. Time for a tea break. Time for a pure leaf.
- [03:34]
Isaac Arnsdorf
It is on.
- [03:36]
Kara Swisher
Isaac, Josh and Tyler, thanks for coming on on.
- [03:38]
Josh Dossey
Thanks for having us, Kara. Good to be here.
- [03:40]
Isaac Arnsdorf
Thanks for having us.
- [03:41]
Kara Swisher
We're going to talk about your new book, 2024 and I want to set the table by getting your assessment of how powerful President Trump is right now. The Supreme Court limited nationwide injunctions, which are one of the few restraints on his authority, although it' complicated. Senator Thom Tillis and Representative Don Bacon both recently announced their retirement, thinning the already depleted ranks of Republican non bakers willing to stand up to him. And his signature so called big beautiful bill is working its way through Congress. It's deeply unpopular, though with the American public by every poll that you could look at. But by the time this episode airs, it may have passed. So talk about how strong is Trump right now. Why don't we start with you, Josh, and then Tyler and then Isaac.
- [04:21]
Isaac Arnsdorf
Yeah, I think he's extraordinarily powerful, particularly in the Republican Party. I mean, as you saw, anytime any Republican senator has moved to vote against him or signaled that he would vote against Till as one of his nominees, they could sort of stick the MAGA mob on them and these folks quickly leave office. I mean, Tom Tillis is not running again. Don Bacon, as you said, is not running again. A lot of these senators, you know, privately do not like this bill. They've expressed all sorts of misgivings about it, but publicly are still planning to vote for it. You sort of saw in our book, right, like Trump sort of understood how to pressure people in a way. He did it on the campaign trail. He's doing it now. He just sort of wears people down. He just goes over and over and over at them. And then he has this sort of cacophony of his base and his supporters in the background that make it painful if you don't go along with what he wishes. So for a large portion of the country, maybe he's not entirely powerful, but for the Republican Party, I think he's as powerful, if not more powerful than ever before.
- [05:23]
Kara Swisher
Okay, Tyler.
- [05:25]
Tyler Pager
Yeah. And I think just to add on to that, one of the things that differentiates this administrative, this term from the first term is that he and his aides have a better understanding of how to use the levers of government to get what they want. And I think he has figured out how to use the administrative state to achieve his goals in a way that he was unable to in the first term, in part because he was not surrounded by complete loyalists. And I think that's another thing that was a huge priority of his, and we've seen him be able to use that to his advantage is across the administration in even some positions that most people don't even think about, there are people that are just loyal to Donald Trump.
- [06:02]
Josh Dossey
Isaac, in terms of his legal, his functional power, he and his advisors have been very clear about the way that they view the mandate that the country gave him and the way that he has been going about governing as like a king or an emperor. I mean, that is how he is acting. Whether the other institutions of government and civil society are going along with that has been a little bit more mixed. I mean, I think that initial period of what people call the Great Capitulation has sort of passed and more pockets of resistance have started to emerge. And then, you know, politically the picture is also a little bit in flux. The unpopularity of his trade policies and the turn against him, the shift against him in public opinion on his signature issue of, of immigration. So I think that that story is. We're in the middle of it right now and we don't know which way it's going to go.
- [07:00]
Kara Swisher
Isaac was mentioning political liabilities. Give me each of you, Tyler and Josh 1. Tyler first.
- [07:06]
Tyler Pager
Yeah, I mean, I think Isaac noted this, but just to hit it harder, the immigration thing and his aggressive crackdown is a political liability. We've been writing about the tension between his zero tolerance policy for undocumented immigrants and agriculture and hospitality industries, saying if you follow through with this crack, we are going to not be able to produce the nation's food supply. And so I think we're already seeing there that Trump is being squeezed in some ways by two parts of his base.
- [07:36]
Kara Swisher
Josh.
- [07:36]
Isaac Arnsdorf
I mean, the core calculation on the campaign from Trump and his advisors were that the economy was why he would win. And every poll they did internally, they showed a double digit issue. They were winning on the economy over Harris and Biden almost, really until the end. And when folks like Trump and Stephen Miller and others would want to talk about immigration, his top pollster, Tony Fabrizio would say, just talk about the economy that's gonna win us this election. And Trump, historically, no matter what has gone right or wrong for him, he's polled extraordinarily well on the economy. And now those numbers have gone down a little bit. You see him haranguing Jerome Powell, the Fed chair, every day to lower rates. You see all sorts of threats he's making against companies. You better not raise your prices because of tariffs. I think the economy. And whether or not he could actually bring prices down at some point, that is going to be an issue if he doesn't show the kind of progress that people voted for him to show.
- [08:34]
Kara Swisher
Yeah.
- [08:35]
Josh Dossey
And we have to talk about national security also. I mean, the Iran strike did not have majority support. You know, once Trump made that decision, most Republicans fell in line behind him. But there was a lot of open fighting within the coalition about that intervention beforehand. And as we learn more about the effectiveness in the longer term and what's gonna happen in the region, that could change again. Right.
- [09:00]
Kara Swisher
Not obliteration, as we found out. So after Trump won last year, one of the leading narratives used to explain the victory was this post. Pandemic inflation led to losses for incumbents around the world. But you begin the book by painting a picture of a very vulnerable Trump at the start of his campaign. Was he beatable? And if so, why? Let's hear from each of you. Tyler, you first, then Josh, then Isaac.
- [09:23]
Tyler Pager
I think one of the scenes in the book that is most dramatic is Donald Trump's campaign launch at Mar A Lago. He couldn't even get members of Congress to stop. It was this sad event. The next day, the New York Post sort of chided him by saying, florida man makes an announcement. There was all this energy and enthusiasm, and this was coming after the midterms. And if you recall, the Republicans were supposed to do quite well in those midterm elections, and they did not. The big winner of that election for the Republicans was Ron DeSantis. He romped to victory in Florida. The New York Post puts him on the COVID saying defuture. And a lot of the energy was around sort of this idea that Trump was not the sort of kingmaker he was, because a lot of lawmakers wouldn't even show up to his announcement speech. I think one of the real turning points in this election, and as we catalog in the book, is the indictments of him. Immediately after the indictments, a lot of lawmakers came rushing to Trump's defense, and he was able to use that to argue that they were coming after him and his entire base of supporters. And so that sort of politic, the way he politicized those indictments, was hugely critical in him winning back a lot of support from the Republican Party.
- [10:37]
Kara Swisher
Josh?
- [10:38]
Isaac Arnsdorf
Yeah, I think that's right. I think after the indictments, you saw a lot of the other Republicans really struggle to galvanize on a message against him. In fact, most of them came out and defended Trump. And when I was talking to Trump for this book on the interview, he said even he was surprised at how quickly so many of his Republican critics came out and just immediately, you know, defended him and said, you know, we're. We're with Trump against illegal justice. I mean, part of the challenge, Kira, was that most of them were running campaigns saying they were sort of like Trump, kind of like Trump, but Trump is also great. And what we found is that for some of those core voters on the right, they could not find attacks that actually they would believe against Trump. DeSantis. Others commissioned all these focus groups, polling. They were trying to come up with a way to beat him. But there were other voters in the middle who, you know, we believe, based on our reporting, that over time, could have fallen away from him. But through a confluence of factors, some of the charges, some of the way the other candidates behaved, he sort of coalesced and consolidated all of that support. But it wasn't fait accompli. It didn't have to be that way.
- [11:47]
Kara Swisher
Didn't have to be that way. Isaac, do you think he would have been beatable if not for the indictment?
- [11:52]
Josh Dossey
Yeah, absolutely. Well, it's not just if not for the indictments, though, and the desantis people will go down insisting that at the point that he was going to get indicted four times and that was going to dominate the news coverage, there was nothing that they possibly could have done to stop him. And the reality is they waited too long. DeSantis missed his chance, that he didn't actually announce until after the first indictment. And that gave Trump this huge head start to start this comeback and to reassert his control over the party and regain all that support, such that that's what pushed all the other Republicans to come to his support. If you imagine the counterfactual, where DeSantis had really jumped in, right, had seized on that momentum he had coming out of the midterms, and Trump looked like old news then. By the time the indictments came around, it would have looked like kicking someone who was down, not forcing everyone to defend someone who was winning, right?
- [12:49]
Kara Swisher
So explain for people why DeSantis weighed in how Florida law constrained his ability to announce earlier.
- [12:54]
Josh Dossey
Well, they also will downplay the role of this. But the truth is, Florida had a law that you couldn't be the sitting governor and run for president at the same time. And so DeSantis, if he wanted to keep his day job, had to change that. And in order to change that, he really couldn't do it until the end of the session, because otherwise, all the legislators would lord it over him the whole time. Right. But they really won't just come out and admit that. And instead, the strategy that they came to accommodate this factual necessity was that they were going to do a state house strategy, that they were going to focus on the legislative session, have DeSantis keep his head down, and then that would form the springboard. His legislative accomplishments in Florida would form the springboard for him to launch the national campaign. And the reason that didn't work is because Trump just spent the entire time pummeling him. And. And he just had nothing to answer for. And so by the time he stuck his head up and he showed up and, you know, started talking about Florida, everyone was like, are you running for president or are you running for governor?
- [13:56]
Kara Swisher
Right, right. According to the book, no one outside Biden's inner circle seriously believed he would run. So, Josh, back when Trump thought they'd be facing a different Democratic challenger, who were the three potential rivals they feared most?
- [14:09]
Isaac Arnsdorf
Well, it depend did exactly who you ask in his circle, but there was a lot of fear of Shapiro in Pennsylvania, and I don't know that they had a ton of fear for anyone other than a Rust Belt candidate, because they believe those main three or four states were key to the election. But I think the Trump folks were not fearful of Kamala Harris.
- [14:30]
Kara Swisher
Yeah. So after Democrats outperformed expectations in 2022, Biden decided to run again, essentially by default. He never declined to run, so therefore he was running. So was. Was Biden beatable in this case in the Democratic primary?
- [14:44]
Tyler Pager
The bigger question is why didn't any Democrats step up and put pressure on Biden? They sort of all just fell in line. And in part, that was because the Biden team made it extremely difficult for anyone to mount a challenge. First, they took advantage of agita over the primary calendar and the order, which had Iowa, New Hampshire first. And there was a process in which they were changing that or considering changing it. And the Biden people basically just proposed their own order, putting South Carol first. So by pushing South Carolina to the front, it Made it very hard for anyone to really mount a challenge because that's the state that Biden was always going to do the best in. The other thing they did is they created this advisory board. And it sounds very niche, and not that it matters all that much, but they basically stocked it with anyone that could run for president. And what they said was this would be a board of prominent Democrats that could travel, surrogate, fundraise on behalf of the president. And they told some people about it, and some of them found out about it when the the was published in the press. And so it was sort of this trick to get everyone that might run against Biden to bring them inside the tent. And I think it's also, you know, if you look at someone like Dean Phillips, who tried to run, he's a backbencher member of Congress that most people didn't know. So it was hard for him to raise money or get a national profile, but the structural factors there really made it so that Biden was on a glide path to the nomination.
- [16:05]
Kara Swisher
Right.
- [16:06]
Tyler Pager
And the one thing, Cara, I just want to add quickly to that is that that voters kept saying, we do not want Biden to run again. Poll after poll showed the majority of Democrats thought he was too old. And even internal data that we got for this book, the DNC was measuring voter enthusiasm through different metrics. And one of the striking things they found was this digital community of volunteers and activists who wanted to support Democrats dwindled after Biden won. And as he geared up to run again, people were just not excited for him. And that was not a secret. And so the idea that people didn't know Biden was old or did not know that that was a challenge is just not true because everyone across the party knew it.
- [16:43]
Kara Swisher
Yeah, yeah. And you could see it. So the Biden theory of the case was that even though his approval ratings were very low, once voters realized they had a binary choice between him and Trump, they remembered how destructive Trump was. They would vote against Trump for Biden. But Trump actually got more popular as race went on. Isaac, how did Democrats misjudge the electorate so completely?
- [17:01]
Josh Dossey
So I, I think about that when I was talking to the Democrats, they were always talking about what was on the nightly news, you know, like so called regular people consuming and watching. And then the Trump campaign was much more focused on, you know, like they would say their reaction to the Harris Trump debate, which, you know, you would admit Trump didn't do that. Well, in was. Doesn't matter, because if you were watching that debate, you're a high information voter and we don't care about those people. Right. They were, they, they recognized that, you know, the midterm electorate, the more reliable voters were shifting Democratic, and they were going out to find new, low propensity voters who they thought looked like a Trump supporter. And, you know, that's hard. There was a lot of reason to be skeptical that they could pull that off, but they absolutely did. And they were focused on, you know, podcasts and, you know, we call it life in the YouTube comments. You know, you kind of think about it as like the scummy underworld of the Internet, but they turned it into real people. And, you know, the Democrats also just, you know, like with Biden's age, like with the economy, they just never came up with any answer. They, they recognized that they needed answers to these problems, to these political vulnerabilities, and they still never managed to articulate one and stick to it and drive that message. And that caught up with them.
- [18:20]
Kara Swisher
Yeah. So the point of going after low propensity voters. In March, Trump essentially kicked out Ronna McDaniel as chair of the Republican National Committee, and his campaign took over the rnc. Suzy Wiles, Trump's campaign manager, had her team. The data of 2016 and 2020 election found that Trump could win by just matching his totals with men from 2016, which went against conventional wisdom, which basically said Canada should appeal to persuadable voters, which were often reduced to white suburban women. Josh, two questions for you. First, how come no one realizes sooner? And two, what decisions flowed from Wiles analysis?
- [18:56]
Isaac Arnsdorf
So the analysis that we obtained in an internal memo that we write about in the book is that the biggest slippage From Trump from 2016, by the.
- [19:04]
Kara Swisher
Way, which I presume Sus Wells handed to you, but go ahead, go ahead. You don't have to tell me. I'm so sorry.
- [19:11]
Isaac Arnsdorf
She did not, actually. But we won't discuss where we did get up. But the internal memo says, and this was written back in February of 2024, that the biggest slippage of voters from 2016 to 2020, for Trump, the conventional wisdom was that folks were upset about COVID in 2020 and upset about the BLM handling of the protests in the street, but that his biggest slippage was actually white men and that they needed to do what they could to dredge up support against white men. We have a chapter in the book called It's a Man's World, but what we look at is how they kind of crafted their entire campaign strategy around trying to get more White men to vote. So they did sort of the manosphere of podcasts. They went on every sort of podcast they thought would appeal to white men. They scheduled events like around UFC and football games and all sorts of other masculine sort of seeming events to try and appeal to white men. They did advertising that was all meant to appeal to white men watching, you know, NFL on Sundays even. The whole campaign strategy was less about how do we get independent voters, suburban women, all sorts of others to come out and more about how do we get people to come out who only vote for Trump and may not come out at all, may just stay at home. Right. The white men who voted for him in 2016, you know, so. So it was a different play. And that's why I think you saw in some of these where he would say insensitive, incendiary things and the campaign wouldn't even do that much to walk them back or try to walk them back, because it was a play to get more white men to vote for him.
- [20:52]
Kara Swisher
Yeah. So Biden's campaign pushed for an unusually utter debate. And so in June 27, Biden had his disastrous performance. According to Jack Tepper and Alex Thompson's book, Original Thin, there were essentially two Joe Bidens, one who was sharp and one we saw on the debate stage. They claimed there was a cover up by Biden's inner circle to hide the second Biden from the party public. Talk about those allegations. Let's hear from each of you. Tyler, Isaac, and then Josh.
- [21:16]
Tyler Pager
Yeah, look, I think the story of Joe Biden's age is complicated and nuanced. And as I said earlier, I think one of the things that we really focus on in the book is how age was ever present in every single conversation. And in our book, we recount many examples of Joe Biden performing inadequately, him forgetting staffers, names, and, you know, know, people not being able to get access to him. You know, it's hard to exactly prescribe the word cover up to our reporting because I think it is a more nuanced and complicated story than that. I think, you know, one of the really remarkable scenes in our book is Biden goes out to the Air Force Academy and he trips over a sandbag and that video gets played over and over again on social media. And it is, look, old man Joe incapable of walking across the stage. Immediately upon returning to the White House, he walks in and runs into Jeffrey Katzenberg, who is the billionaire movie producer and co chair of the Biden campaign that helps with fundraising. And Biden says, I got sandbagged Jeffrey. And Jeffrey responds and says, I'm glad that happened. And his point is that we need to spend more time focused on dealing with the realities of an octogenarian.
- [22:31]
Kara Swisher
Katzenberg was glad the tripping happened early, before people were really paying attention.
- [22:34]
Tyler Pager
I think, too, that was his point, is that it happened early and more than a year before the election, and they could adjust for that.
- [22:41]
Kara Swisher
Right.
- [22:42]
Tyler Pager
And so they make a lot of accommodations to position Biden to perform his best. So that's some of the physical things we see. You know, this stairs on Air Force One, instead of taking the really big, long stairs that we've seen many presidents trip over, he does the shorter stairs. He wears sneakers more. He doesn't do the dinners at international summits. Katzenberg wanted Biden to be much more rigorous about his age and his health. One of the things that he kept telling Biden and his aides to do was to go to a doctor, an ent to work on his voice. He was worried about how raspy it sounded and how that further underscored concerns about Biden's age. And so I think the thing about Biden is that age was everything that they were thinking about because they wanted to present him in the best possible light, light for voters. And so obviously, that was more an intensive process with an octogenarian than another president. But it was interesting. I've had many conversations with Biden people, Biden allies, Biden critics, people that have worked for other administrations, and they say every president accommodations are made for because presidency is a demanding job and you want them to be their best. That being said, obviously, it was taken to a greater degree with Biden. And so there's. There's a lot in the book that sort of captures the complicated way Biden dealt with the age.
- [23:58]
Kara Swisher
Isaac, go ahead, Isaac, Then, Josh.
- [24:00]
Josh Dossey
I think the fallacy of the way that the Biden team was approaching this is basically their argument was when he's in the Oval Office, when he's in the Situation Room, he's really sharp. He can do the job, and he just doesn't speak as well, he doesn't debate as well, he doesn't campaign as well as he used to. The problem with that argument is that the number one job of the president is to communicate. And so he can't do the job if he can't communicate, if he can't make the case to. To the public for his leadership, his agenda, his accomplishment. That is the president's job. You know, this dichotomy that they were trying to establish between doing the job and speaking about the job is just the complete wrong way of thinking about it, Josh.
- [24:44]
Isaac Arnsdorf
I mean, one of my favorite scenes in the book is near the end of the book where Trump comes and meets with Biden in the Oval Office after Trump has won. And they have a pretty air. You die. Interesting conversation. For 90 minutes, Biden is going around the world and giving his opinions on different world leaders and Trump. They leave the Oval Office, and Trump says to Susie Wiles, like, where was that guy during the debate? He seemed like a totally different guy. And I think what our book sort of captures is that there were lots of days where Biden was sharp and could have long meetings like that and held it together. And then there were other moments where he would forget senators names or trail off in meetings or obviously the debate performance. And, you know, it was sort of uneven.
- [25:27]
Tyler Pager
I think one sort of amazing anecdote in the book is at the very end when I got Joe Biden's cell phone number and called him. Yeah, so for months I'd been trying to interview Joe Biden for this book. We had an interview that Josh did with Donald Trump, and we thought it was very important to get Biden's take on the election. I spoke to many of his aides, made the pitch, and they just said he wasn't available. Their excuse was that he was writing a memoir and so his participation in our book would conflict with his memo. I tried to make the case that that's absolutely not true. But anyways, eventually I got Joe Biden's cell phone number directly. And one evening I called him. He. I didn't leave a message. He didn't pick up. And a little bit while later, he called me. So I answered it. The President's on the phone and I tell him what I'm doing. He says he's about to have dinner. It's around 7pm but I should call back tomorrow. So it's like, great. Joe Biden's gonna do an interview for the book. Immediately, I get a lot of texts and messages from Biden's aides. I didn't answer them. They made clear they didn' speaking, but he said he wanted to talk. So the next morning, I call him back. He answers. This time, he's standing on the Amtrak train platform. So he's about to board the train to go from Wilmington to Washington, and I ask him if he has any regrets, what he thinks about Trump. And then he hangs up to board the train, but sort of suggests that he might be open to continuing the conversation. Immediately I get a flood of calls and texts from Biden's aides who are freaking out that I got his phone number. I, you know, tried to call him later, went straight to voicemail listeners. His voicemail is just him saying his first name, Joe. And then I tried one more time the next day, still just got Joe. The next day I call and it is replaced by a Verizon wireless message that the number had been changed and could no longer be reached. So that is my brief sorger in trying to get an interview with Joe.
- [27:12]
Kara Swisher
Biden for the last. This is why they lost. What are you talking about? This is why they lost, boss. So funny. That is so funny. And you never talk to him. Never.
- [27:19]
Tyler Pager
I mean, I got those that brief time when he was about to board the train in Wilmington.
- [27:24]
Kara Swisher
That's not an interview, though.
- [27:25]
Tyler Pager
Yeah, that's not an interview.
- [27:26]
Isaac Arnsdorf
And I can say for the record that Trump's cell phone number has not been changed.
- [27:29]
Kara Swisher
I know he'll pick up anything.
- [27:31]
Isaac Arnsdorf
Trump's cell number, he'll answer. He'll answer the phone in the White House and say, hello, Hello.
- [27:35]
Kara Swisher
Yeah, he'll talk to the pizza place. We'll be back in a minute. Foreign.
- [27:47]
Tyler Pager
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- [28:25]
Kara Swisher
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- [29:01]
Josh Dossey
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Tyler Pager
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Josh Dossey
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Tyler Pager
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- [29:31]
Kara Swisher
So after the debate, Biden pushed back against the idea that he was polling poorly or that biology is undefeated. And your book makes it seem like Biden's inner circle insulated him against that reality too much. And even though there was plenty of publicly available polling showing his support was cratering. Tyler, how is it possible that Biden didn't see or believe the polls the rest of the country was seeing? He surely had to have seen this.
- [29:54]
Tyler Pager
Yeah, he was definitely confronted with it. I think one of the striking scenes in our book is he does this George Stephanopoulos interview. And George says to him, Mr. President, the polls show this. And he says, that's not what I'm seeing. And so the way to understand that moment is twofold. One, the pollsters, Biden's own pollsters watching that interview, freaked out. And they were like, what is he saying? George is reading accurate polling, and that is closer to our understanding of the race. So pollsters were worried about their reputation that Biden was going out there saying. Saying that the polls were inaccurate. So that's one part of it. And those pollsters never actually met with Joe Biden for the entirety of the campaign. They never had since he launched. They never had a meeting with the president, which is sort of unheard of. The other thing, another, I think, really revelatory scene in the book is when Nancy Pelosi meets with Joe Biden and she confronts him about the polls too, and says she's really concerned about the polling and not only Biden losing, but it impacting Congress to.
- [30:51]
Isaac Arnsdorf
To.
- [30:52]
Tyler Pager
And Biden gets his aide Mike Donlin on the phone to go back and forth with Nancy Pelosi about how they disagree about what the polls show. And I think that is one of the things to understand about Mike Donlon. Mike Donlin has long held a contrarian view of polling. He does not take much stock in it. He often has a different view than the conventional wisdom. And so Mike Donlan and Steve Ruschetti together really focused on polling that largely bolstered their view that Biden could win and he could stay in the race.
- [31:21]
Kara Swisher
They also did less polling than usual, right?
- [31:24]
Tyler Pager
Absolutely. He did a lot less polling. And I think that's evidenced by the fact that the pollsters, who are respected pollsters that work with top Democrats, Molly Murphy, Jeff Pollock, Jeff Garon, never met with the president to discuss the polling the one time they were supposed to Meet with him. As we recount in the book, they had the meeting scheduled for 2pm it was pushed to 4pm then it was pushed again, pushed again, and it never happened.
- [31:43]
Isaac Arnsdorf
You just mentioned Donnell. And I thought one thing worth noting was how much they tried to restrict access to Biden around polling and other information. I mean, one of the scenes in the book is after the debate goes so poorly, DNC staffers, campaign staffers are having donors hang up on them. They can't raise any money. Everyone's telling them he's gotta go, and they can't talk to Biden. A lot of the staff, senior staff, wanna talk to Biden about what's going on. And Donilon and Machete, you know, are not setting up meetings. And instead, Adrian Elrod, one of his staffers, call Joe and gives Joe Scarborough a presentation or tells him how bad the data is, and maybe it's time for Biden to go, because they thought it was the only way they could get to the president. I mean, the folks who were right around Biden just really took access to him and just kept so many people from having any ability to give him information.
- [32:35]
Josh Dossey
But to be clear, that's the staff, the advisors, hiding the world from Biden. Biden. Right. It's not hiding Biden from the world. Right. That's something else. This is like classic advisors covering for themselves and trying to protect their own hide.
- [32:53]
Kara Swisher
Yeah, yeah. By the way, people don't know Steve Rachetti, a very lovely man, was his campaign chair, but they were all insistent that he wasn't old. I was in conversations with, and I'm not even a political reporter, I was like, he seems old to me. I don't know.
- [33:06]
Tyler Pager
All right.
- [33:06]
Kara Swisher
On July 13, the gunman tried to kill President Trump in Butler, Pennsylvania. Isaac, in the book, you report for the time that Iran tried to capture Secretary Mike Pompeo in France. People in the campaign, including Trump, have thought Iran might have been behind these assassination attempts. Talk about how it affected Trump psychologically and how the effects played out in the campaign. Even though it was a horrible tragedy, it was also helpful for Trump, including the way he reacted and the visuals around it.
- [33:34]
Josh Dossey
Well, and he was musing in the interview with Josh. You know, I wonder if it could have been different if that hadn't happened.
- [33:40]
Kara Swisher
I doubt he was saying, thanks, Iran.
- [33:41]
Josh Dossey
Well, and we have to be super clear, like, there are two things that are true. Like, the threats from Iran were very real. Our reporting is that the US Officials briefed the Trump campaign that Iran had active kill teams in the US during the campaign, they came very close to killing Mike Pompeo on a trip to Europe, as we report in the book. And there were also Iranian operatives who were indicted trying to kill former National Security Adviser John Bolton. And there was another scheme that was stopped in Brooklyn. So these are very real threats from Iran targeting Trump and a lot of precautions and safety measures, security measures that were taken around that. There were also these two assassination attempts that investigators have not identified any link to Iran or any other foreign actors. They also also were not, when they briefed Trump about them, they were not able to definitively rule that out. Right. They couldn't prove the negative. So, you know, the Trump campaign, looking at those two separate but related things, both being true and feeling that stress and that danger day to day, you know, there was some blending that went on. And in that September, October period of the campaign, it really affected the daily operations of the campaigns, their ability, you know, where they could go, how they could get there. There. There were some events that had to be reorganized at the last minute because of security. There's a great scene in the book where they went to a remote place in Wisconsin that had a small Runway so they couldn't take the big plane. So there wasn't enough room for the full Secret Service detail on Trump's plane. So the Secret Service had to take a separate plane. But the Secret Service plane was slower than the campaign charter. And so they had to wait for the Secret Service plane to get where it was going. And Trump's just like sitting on the tarmac going crazy cuz they're running behind.
- [35:36]
Kara Swisher
So after the attempt in Butler, Elon Musk endorsed Trump and Jeff Bezos and Mark Zacharya moving towards Trump, saying he looked cool, I guess. Josh, how meaningful was the tech money, including around $280 million from Musk to Trump's eventual victory? Obviously in that outburst, I'd say outburst one, he's just having the new one recently. How important was it? I know Musk thinks that's the case.
- [36:00]
Isaac Arnsdorf
Well, the financial infusion from Musk was huge. I mean, not only was Musk giving more than $250 million to the campaign and financing sort of this aggressive effort, he was also trying to convince other billionaires and other tech guys to get on board. He became a crucial emissary for Trump. And I think there was also part of it, Kira, with that after J6 and sort of the insurrection at the Capitol and all of the different things that happened and by these guys getting back on board with Trump, it sort of became less verboten to be with him. Right? You saw sort of cultural figures, tech figures, all of these folks coming back on board. There wasn't sort of as much resistance from others, Right. And I think Trump immediately saw them as incredibly important figures. I mean, he only had so many seats on the day at his inauguration, right. And what did he do? He gave a lot of them to these tech figures he knew helped win the election. When I visited him at Mar a Lago in January, I'm sitting out on the couches in the lobby and he comes over to me, he's running like 45 minutes late. He's like, I'm sorry, I'm running late. And he whispers in my ear, he's like, mark Zuckerberg's in there. And I'm like, what? And he's like, oh, Zuckerberg's in there. And they were mediating a lawsuit that day where he was getting money from Zuckerberg and he loved having Zuckerberg in there. He was telling everyone at the club, like, go look at Mark Zuckerberg. And then in the middle of my interview with him, Elon Musk walks in the room and starts giving him advice on various things he should be doing. So Trump quickly understood how powerful these guys were in some ways and surrounded himself with them and touted them publicly. He wanted the world to know.
- [37:41]
Kara Swisher
But what about their actual help? I understand he used them as props. That was. And he did it masterfully, I have to say, at the inaugural. But would he have won without Musk's money, as Musk asserted in Tantrum Number One?
- [37:53]
Isaac Arnsdorf
I mean, it's hard to know, right, if he would have or not. I mean, I certainly think Musk filled a very key void in some of these states and financed all sorts of get out the vote efforts, all sorts of door knocking efforts, advertising efforts. I mean, you might argue in another world, the Trump folks could have found money themselves and done it without Musk, But I don't know if they would have or not. I mean, at the time, I remember reporting in real time how grateful Trump's advisors, Susie Wiles and others were for what Musk was doing. Cuz he was filling a key gap for them in these states that really needed to work.
- [38:30]
Kara Swisher
All right, let's get to the Harris campaign then. On July 21, Biden withdrew from the race and endorsed Vice President Harris, effectually making her the nominee. But former President Barack Obama and Speaker Emerata Nancy Pelosi thought a public process to choose a nominee would be better. Tyler, why do they and the rest of the Democratic passion have so little influence on Biden to get him to do that? There was a very short amount of time, too, obviously. But why. Why did that not come to pass?
- [38:55]
Tyler Pager
Pass, Yeah. I think there's two things playing at once here. One is that Biden felt, and Jim Clyburn basically told him as much, that it would be a huge hit to his legacy if he did not endorse Kamala Harris. Biden and Harris genuinely had a good relationship. Biden liked her, and also it was the first decision he made as picking her as his running mate. And so I think he was convinced that if he did not anoint her as his successor, it would mean that he regretted his decision and looked poorly on his legacy and his. His record.
- [39:27]
Kara Swisher
The other thing is Obama did it, but go ahead.
- [39:29]
Tyler Pager
Yeah, yeah. And yeah, he did. And I think the other thing to note is Obama and Pelosi's relationship with Biden had particularly soured. I mean, Obama and Biden's relationship has been the source of fascination for more than a decade at this point, and there is some genuine warmth there. But when it comes to politics, there is a huge, huge schism between the two of them. Obama has long not thought that highly of Joe Biden's political skills. It's exactly right, Kara. Why he did not endorse or support him moving forward ahead of the 2016 election. And so Obama's political advice to Biden was particularly unwelcome. And Pelosi, too. I mean, there just wasn't the sort of influence that anyone had over Joe Biden. And that's part of why he ran again in the first place. And that's part of the reason why it took him so long to drop out. There were just not people, people close to Joe Biden that would, you know, say it straight to him or even external voices that could really access him.
- [40:21]
Kara Swisher
Yeah. Now, Trump ended up making significant gains with Latinos, black men, and low propensity voters. They're also to be a vital part of the Democratic coalition. Isaac, what. What did Trump do to win them over, and what could Harris have done to keep them in the fold? Obviously, Biden being there wouldn't have helped what happened there, because there's somewhere they should have been so strong.
- [40:43]
Josh Dossey
Yeah, well, I mean, the man strategy that Josh was talking about earlier wasn't just about white men. It was very successful with Latino men and to a lesser but meaningful extent, with black men. And that was finding the Republicans were interested in Finding these kind of other valences of identity that they could communicate with these voters, like sort of Latino men kind of behaving as voters, more like white men. Um, and the Trump campaign talked about reestablishing Trump as a cultural icon, you know, kind of reintroducing him or for younger voters, introducing him for the first time as the kind of celebrity figure who he was for most of his career before he was the very divisive politician. With Harris, they really struggled to. To fight that with, like there was this asymmetry, you know, podcasts with kind of left leaning audiences. So you would sort of think of the left wing analog to the manosphere. So they were podcasts with audiences that would tend to be. Look like Democrats, but not overtly political. And they kept telling Harris no, that they wouldn't have her on. So the Democrats just found that they didn't have the kinds of platforms to reach those voters to message in this new media landscape the way that the Republicans were successful at doing.
- [42:07]
Kara Swisher
Yeah, the Kelsey brothers said no. The Kelsey. Josh, why do you think that is? What was from your perspective? She didn't do her first interview until over a month after Biden dropped out. And I think people didn't understand the anger towards Biden. You wrote about that in the book. And she didn't separate herself. Josh first. Why? He kind of pressured her not to, which you write in the book. But why the cautious approach?
- [42:32]
Isaac Arnsdorf
Yeah, Biden called Harris and said, you know, that she should not separate herself. I think the cautious approach was that she didn't exactly know how to do it that way. It seemed genuine and authentic that she did not know what issue she should do it on. I mean, she had a lot of staff around her asking for some separation, particularly on Gaza and Israel, some on immigration, on places where Biden's numbers were just an albatross. Right. They were just so incredibly behind Trump. They wanted some. Some distance and she just did not want to give distance. There was a memo that we have in the book where the Harris campaign hires sort of a moderate Republican to try and help them get right voters and center right voters who don't like Trump. And she outlines in these long memos for Janelle Malley Dillon, here are all the places we could create some distance from Biden because we desperately need it, and she doesn't do it. And there's a great scene in the book where she's on set with the View and backstage, you know, they practice his answer about if she gets a Biden question and then instead of giving the answer that they so meticulously practiced. She says, I can't think of a single place where, you know, I would do anything different. And Rob Flaherty, her deputy campaign manager backstage, puts his head in his hands and is like, oh my God. Right? You know, that was a horrible answer. And then they try to get the host to even ask the question again.
- [43:58]
Kara Swisher
Why did she heed that self serving advice? To avoid Chris, as in probably the single biggest mistake she made, presumably.
- [44:04]
Tyler Pager
Yeah. So one of her communications advisors, Stephanie Cutter, went to the host during the commercial break and tried to get them to give her another chance to answer that question. I think we've spent a lot of time re reporting out that exact day and trying to figure out what happened. Kara, as you say, it was probably the most. One of the most destructive things she did during the campaign in which she largely did not have major mistakes in public. And what they say is that she just got tripped up by the phrasing of the question is what they say.
- [44:33]
Kara Swisher
She didn't want to do it.
- [44:34]
Tyler Pager
It was a very delicate issue for her. Not a great excuse, but she basically answered the question literally. And instead of hearing the question and then giving the answer, that they had practice. But I think just to build on this idea of why it was so hard for her, One of the challenges was the way that they framed her as a vice president was in the room for all the big decisions, the last person to leave and intimately involved in everything. Now, that wasn't true, but that was the narrative that they were out there saying. And so it then makes it harder to be like, actually I disagreed with X, Y and Z policy because then she opens herself up to, okay, so why did you go along with it? Why didn't you say, speak up. Can we get people in the room saying she actually did disagree. And the other thing, the one issue where it was very clear she disagreed with Joe Biden was Israel, Gaza. And she was under some pressure from the national security space to not publicly break with him. One of the things that obviously a big tension point was having a speaker of Palestinian descent at the convention. They ultimately did not do that as Gaza protests going out inside and outside the convention. And one of the things was national security officials were saying this could make it harder for the president to negotiate with Hamas to get the release of the hostages. And whether or not that's true, we don't know. But that was one of the arguments that Harris's team was hearing, is that if she created distance with the president, it could impede negotiations and diplomatic efforts in Israel and Gaza.
- [45:56]
Josh Dossey
Something that I think really comes through in the Harris section of the book is just like, like her and her advisors were so inside their own head to the point of just paralysis.
- [46:05]
Kara Swisher
Yeah, it's exhausting.
- [46:06]
Josh Dossey
How are we going to deal with the view thing? How are we going to deal with a trans ad? How are we going to deal with the McDonald's attack? And there are all these parts in.
- [46:14]
Tyler Pager
Joe Rogan defining Trump and there are.
- [46:16]
Josh Dossey
All these examples in the book where they're just spinning their wheels on this on and on, and they just end up doing nothing. I mean, maybe the best example of that is in her debate prep. They literally, they're like, well, what's her answer gonna be about the economy? And they keep saying, like, well, let's come back to that one. And they never got to anywhere.
- [46:33]
Isaac Arnsdorf
They had insane amounts of paralysis on how to handle the transgender attacks and the cultural issues from Trump. They did all sorts of polling, they tested all sorts of answers. They worked through various things. She could say if she was asked about it, she might say, what did these people think about it? And then at the end of the day, she ended up doing none of it. She just did nothing. I mean, they did weeks and weeks and weeks of polling and prep for nothing.
- [46:56]
Kara Swisher
Right. We'll be back in a minute.
- [47:05]
Tyler Pager
Hey, it's Ryan Reynolds here from Mint Mobile.
- [47:07]
Josh Dossey
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- [47:14]
Tyler Pager
So I thought it would be fun if we made $15 bills, but it.
- [47:19]
Josh Dossey
Turns out that's very illegal. So there goes my big idea for the commercial.
- [47:24]
Tyler Pager
Give it a try@mintmobile.com Switch upfront payment.
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Kara Swisher
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- [47:34]
Tyler Pager
See mintmobile.com this episode is brought to.
- [47:38]
Josh Dossey
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- [48:03]
Kara Swisher
Don't miss blinds.com's 4th of July mega sale. Happening now. Save up to 50% plus get a free professional measure. Blinds.com invented a better way to shop for window treatments with upfront pricing. No showroom markups and no salespeople in your home. Choose from classic shutters to outdoor shades and more. All backed by our 100% satisfaction guarantee. Don't miss blinds.com's 4th of July mega sale. Save up to 50% plus get a free measure. Rules and restrictions may apply. The title of the book is 2024. This is the last question. How Trump retook the White House and the Democrats lost America. So did Trump win in 2024? Did the Democrats Democrats lose? And each of you, what's the key takeaway from your reporting as we look towards 2026 and 2028? Let's start with Josh, then Tyler, then Isaac.
- [48:54]
Isaac Arnsdorf
Yeah, I think it was a bit of both. But I think Trump made a series of shrewd choices as we sort of highlight in the book to win the election. I mean he for example, on abortion, right, Instead of going for a national 15 week ban like some of his advisors wanted him to, he realized I was not going to play well and did not go to those inst. Ended up as much as he questioned the election was stolen in 2020 and said all of these false scenes about the election. He taped ads promoting early voting. His advisors, they believe that was a huge difference in the election. He often, even though he would go on these stem winder tangents at rallies, followed the script way more than he did in the past. He cultivated donors. He spent hours and hours and hours making phone calls for money that he would never do in the past. I mean he was a more disciplined candidate. And I know some of your listener probably laugh at me for saying that, but he just was like I think govern him for this long. He ran a more disciplined race I think on the Democratic side. Now let Tyler talk about this more. But there were all of these red flags for the Democratic Party. What voters wanted, what they said they wanted, the enthusiasm, the donor frustrations that sort of went unheeded. And then as the election went on, it was clear that Trump was winning on a lot of fronts in September, October and there wasn't much done to sort of recalibrate the race. Now one might argue, was there anything they could have done at that point? I don't know the answer, but I think what the book shows is a series of compelling choices on the Democratic side where they miss these warning signs of which way this was heading. They were losing the electorate. The candidates, both Biden and Harris had lots of problems with different voter demographics and there just wasn't enough done about it to keep them in the gang all right, Tut.
- [50:39]
Tyler Pager
Yeah. To focus in on how the Democrats lost. I think they did not listen to what their voters wanted. They shoved their nominee down the voter's throat and said, we don't care that you think he's too old. We don't care that you don't want this. We are giving you this. I think also with that, the Biden AIDS did not present Biden with the truth always. And I think one of the compelling anecdotes in our book that hasn't been reported is that right before October 7, when Hamas attacked Israel, there was a window that September where some of Biden's closest aides were preparing to approach him and say, look, this is going to be really, really hard. Think about your responsibilities as a president, as a father, and are you the best person to do this? You know, we'll support you. We'll help you do this, but really think critically about this. The filing deadlines are coming up. He had already announced he's running, but they were really going to have a tough con or what they thought was a tough conversation. Now, people often say that and don't follow through, and obviously here they didn't. October 7th happened, and it sort of fell by the wayside. But Democrats ignored what their voters were telling them for months and months and months. And then again when they did Kamala Harris, the party came behind her, but she, too, was never the most popular Democratic figure. I mean, I covered her campaign in 2019, then it flamed out very quickly. She didn't even make it to the Iowa caucuses, and she launched with these huge rally in California. And so I think Democrats just ignored what voters said, and they just never came up with a message about why they were running and what they were going to do. They were focused on what they had done, not that what they were going to do, going to do. Elections are often about the future, not about the past.
- [52:18]
Kara Swisher
Right, Isaac?
- [52:20]
Josh Dossey
So the, the downside for the Republicans of how Trump won by expanding the electorate with low propensity voters who were drawn to his personal appeal is that's very dependent on his personal appeal. And people who don't historically vote that much and whether that's going to prove to be durable. You know, again, it was. There was good reason to be skeptical that they would pull it off in 2024, and they did. So it could happen.
- [52:44]
Kara Swisher
Well, they need a new character is what you're saying.
- [52:46]
Josh Dossey
There's good reason to be skeptical that you can build an enduring political majority coalition on people who are just excited about one guy and don't routinely vote. As for the Democrats, the Democrats who outperformed Harris in 2024 were consistently more moderate, more Republican, like on the key issues. And what Trump did did was actually position the Republicans on the popular side of the key issues, even abortion, which if you would have said that in 2022, would have sounded insane. But he did. And so that's the challenge that the Democrats have, is finding an issue where they have the popular position and that voters are going to identify them with that. And I really haven't seen any Democrats articulate yet what that possibly could be. But, you know, a situation where you're just kind of Republican light, that's not.
- [53:43]
Kara Swisher
Gonna buy the real thing.
- [53:44]
Josh Dossey
Right?
- [53:45]
Kara Swisher
All right. Thank you so much. Again, the book is 2024. Are you writing 2028 already? We all laugh.
- [53:52]
Isaac Arnsdorf
We should probably finish your chef fist first.
- [53:55]
Kara Swisher
Anyway, thank you guys so much.
- [53:57]
Josh Dossey
Thank you, Kara.
- [53:58]
Tyler Pager
Thank you.
- [54:00]
Kara Swisher
On With Kara Swisher is produced by Christian Castor Wisell, Kateri Yoakum, Megan Melissa, Bernie, Allison Rogers, and Caitlin Lynch. Nishat Kurwa is Vox Media's executive producer of podcasts. Special thanks to Brad Sylvester and Eric Litke. Aaliyah Jackson engineered this episode and our theme music is by Trackademics. Go Wherever you listen to podcasts, search for on with Kara Swisher and hit follow. And don't forget to follow us on Instagram, TikTok and YouTube at on with Kara Swisher. Thanks for listening to on with with Kris Swisher from New York Magazine, the Vox Media Podcast network, and us. We'll be back on Thursday with more.