Pod Save America and Crooked Media founding member Jon Lovett isn’t just a podcasting legend or Barack Obama’s speechwriting secret weapon. He’s a quick study of our political discourse and a cultural vanguard. Now he’s spilling the tea on everything from the “vandalism” Trump is unleashing on American institutions, the Hollywood heavy-hitter who had a hand in THAT Trump joke at the White House Correspondents’ Dinner and what it was really like working with Hillary Clinton. Lovett also offers some hard truths Democrats need to face if they hold any hope of getting back into power. Plus: his hot take on the Epstein scandal and whether it could deliver a knock-out blow to Trump’s support with the MAGA faithful.
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Note: This is a rough transcript. Please excuse any typos.
Jon Lovett: This is not policymaking, this is vandalism, and that’s part of what makes it so upsetting. It’s not that they have some set of overarching goals, they are cavalier and glib about institutions they benefit from, that provide data they benefit from, that helps us understand the economy, understand our world. But in decadence, in cruelty, in wanting to own the libs, they are doing vandalism.
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Nicolle Wallace: Hi, everyone. I will admit to being a little nervous about this week’s guest, because where I am a podcasting rookie, this is the podcasting trailblazer. Jon Lovett is here. It’s “The Best People” podcast, and it is made to tap into people who have the best insights about the moment in which we live, the moment in which we’re all trying to survive our politics, and something we talk about a lot, how culture can help our politics out of this death spiral it seems to be in. So this is “The Best People,” and this is Jon Lovett. Thank you so much for being here.
Jon Lovett: Thanks for having me. I think trailblazer, the trail had been blazed. There were ruts in the ground. We were in the right place at the wrong time, but you understand.
Nicolle Wallace: Well, I think that when I look at where all of the energy and the heat is, I mean, there’s like a volume business of stories every day about the death of legacy media. And you guys were way out in front of where, not just the heat, but where the trust was going in the media, with Crooked Media and with “Pod Save America,” and with all of your individual projects.
Jon Lovett: Well, I feel really proud. So we started “Pod Save America.” We realized we wanted to do it right after Trump had won in 2016. We launched in 2017. We called it a media company, but really it was a blog post on medium and a podcast feed that we started from scratch. Like, that was our media company.
And we were fortunate that it was at a moment where people were checking out podcasts. It was a moment where people were looking for political analysis that treated people like they had agency, that they weren’t just observers, and at a time where people really were getting, I think, a little bit sick of the view from nowhere self-seriousness. And so, we wanted to be an alternative to that.
And what we’ve realized over the years of doing it is like what keeps people coming back? And it has to be that; A, they know they can trust that we’re telling people how we feel. We don’t always get it right and we do have our biases, but we’re trying to be honest and help people sort through it. And to really deliver on a value proposition that we will figure out using smart people, not just from us, but, like, what are the ways you can actually have an impact? And also, by the way, what’s a lot of noise and a lot of attention that isn’t really worth your time?
Nicolle Wallace: And I think the irreverence isn’t just toward the people that come on. You know, they know they have to be prepared for sort of a no bullshit, no ground rule interview, but it’s the irreverence for the media itself. And I feel like a lot of people have followed you guys down that path, but I think you’re some of the first and most vocal critics of, I think people call it bothsidesism in the first term.
Jon Lovett: Yeah.
Nicolle Wallace: I don’t even know what they’re calling it now, because it seems like the media landscape is now also disparate. I feel like there’s not as much mainstream media criticism because people just are going to folks like yourselves, or they’re going to Substack.
Jon Lovett: Yeah. Well, look, after Trump wins the second time, people that work at Crooked, people, friends, family, they were all like, well, what do we do? Right? Once again —
Nicolle Wallace: Yeah.
Jon Lovett: — everybody back to one. And you know, there’s an old saying that Americans love a tragedy with a happy ending. And there was a sense of like we understood the story of taking on Trump when it’s this surprise cataclysm caught everybody off guard, not everybody, but I mean, collectively, there was a sense that this isn’t what was supposed to happen, that this was some kind of accident. And together, we were going to prove what America really was. We’re going to fight back. We’re going to win in the midterms, which we did. We’re going to take back the White House, which we did. And we were going to resolve this question, like the question of —
Nicolle Wallace: Right.
Jon Lovett: — what is America, and what does it do when confronted with someone as heinous as Donald Trump? And when Donald Trump wins again, you know, it’s not a linear path, where we are not just going backwards but that Trump is even more radical than he was before. And then you think, well, okay, like, what do we do now? And how do we understand where we’re at now?
And I do think you’re right that a lot of like media criticism has sort of fallen by the wayside, in part, because there’s a sense that that critique is of an institution that itself has been decimated by economic forces, by political forces. And you can’t really define yourself against the mainstream media because you realize now, oh, what’s left of the mainstream media, everybody outside of it, we are together in this last ditch effort to take on what is like someone in opposition to all of us.
Nicolle Wallace: Yeah. Like, this idea that so many people, half the country, half the voting public chose this is a totally different thing, and it feels like this shock that’s only beginning to set in.
Jon Lovett: Yeah. You know, look, it’s true to all presidencies, right? Like, there’s some sense in which in the first term, the White House kind of runs over the person —
Nicolle Wallace: Yeah.
Jon Lovett: — because they’re in this impossible job. You know, you’re in charge of Social Security payments, nuclear missiles. Like, it’s a ridiculous portfolio.
Nicolle Wallace: Yeah. It’s a ridiculous job.
Jon Lovett: Ridiculous job. You’re head of state. You’re welcoming the Boy Scouts. You’re meeting about Iranian nuclear programs. Like, it’s ridiculous.
Nicolle Wallace: Right.
Jon Lovett: And so there is a way in which no matter the confidence or the performance of confidence that anybody coming into that job will have, like anyone in a new job, it takes you a bit of time to learn the ropes and where like the White House runs you rather than you running the White House. And then they figure it out, and in the second term, I think presidents become more themselves for good and for ill. The White House doesn’t change who these people are, they become more themselves.
Nicolle Wallace: Right.
Jon Lovett: Trump, that’s true of him, right? We are seeing more of what he is, right? And he had an advantage, which is four years outside. He’s not disciplined in doing a long-term, but there were others around him doing Project 25 —
Nicolle Wallace: Right.
Jon Lovett: — and thinking about what happened in the first term that stood in the way of their most aggressive long-term goals, right? Not just what Trump would want to do around immigration and trade, which are the kind of animating things for him genuinely, but what the think tank types for whom Trump was an empty vessel, what they could actually do this time if they had power and there weren’t the establishment types that lent Trump credibility in the first term, standing in their way. And that’s what we’re seeing.
Nicolle Wallace: I mean, we were White House staffers, which is sort of ridiculous too. I mean, George W. Bush, I remember there were a lot of weekends when we were called in after 9/11 and lots of days we were somewhere and you were suddenly in, and you always had to go home and, like, change because he just came from his father, such reverence for the Oval Office. You’re like, this guy paved the Rose Garden in the first three months and I don’t think I’ve done a story about it yet. Like, the decimating of the rituals and history of the office are almost baked in. Do you ever think about that stuff and about how special it was to your boss?
Jon Lovett: Well, what’s funny is we got shit because I remember there’s a picture of me and I think it must be John, I think David Axelrod. We’re in the Oval for a speech prep. I might’ve been around a correspondent dinner, I don’t remember exactly why, but it was a Saturday or Sunday, and so we were in jeans. And we were in the Oval Office in jeans, and some W people were displeased about this.
Nicolle Wallace: Well, that’s ridiculous because we would have loved to have worn jeans. It was such a drag. It was such a drag.
Jon Lovett: At least 20% of the reason I wanted to leave politics was to stop wearing a suit. I would bike into the Old Executive Office Building and it’s D.C., and so I would basically bike in the morning, go into my office and close the door, and basically try to not change it to my suit until I had to leave the room again. I was not meant for professional life.
Like, John Favreau, who started Crooked with me and Tommy Vietor, and we do “Pod Save America” together, he was my boss. And man, I was unmanageable. And I look back on it now and I remember the time feeling like, I’m doing something wrong, and what was wrong is, like, I’m an animal. Like, I am not meant to be in an office setting. I’m a wildebeest.
So, yes, they’re paving the Rose Garden. He’s putting up giant flagpoles. He’s threatening to put in a 90,000 square foot ballroom, which is not a ballroom size. That’s a Walmart size. To me, like, there’s too much happening to care about it, and I think it’s actually like kind of small and ultimately silly example of what Trump is doing more broadly, which is vandalism. They are vandals. That’s what they’re doing to our country.
There’s something that Bryan Schott said in the run up to the passage of the big bill, and it really stuck with me. When the head of HHS, who is a crank, and is only there because Donald Trump was trying to win a crank vote in the election, and because it lent him some kind of credibility because he’s a Kennedy and a Democrat, and has purchased in this sort of vaguely conspiratorial, do-your-own research podcast media environment. He’s not the head of HHS. He’s canceling 22 mRNA projects that hold incredible promise, because of his crank beliefs, a false premise based on bullshit. That’s vandalism, right? Like, we can undo that if we retake power, but it’s destruction for its own sake.
Decimating institutions that are stodgy and slow and bureaucracies that, of course, need reform, but nonetheless provide a vital function that they don’t care about. NPR reports that they are going to spend time and energy burning up a satellite in the sky, a satellite that provides data on water and plant growth that helps farmers and ranchers and policymakers, because they don’t like the fact that it’s a carbon observatory because they don’t believe in climate change.
This is not policymaking, this is vandalism, and that’s part of what makes it so upsetting. It’s not that they have some set of overarching goals, they are cavalier and glib about institutions they benefit from, that provide data they benefit from, that helps us understand the economy, understand our world. But in decadence, in cruelty, in wanting to own the libs, they are doing vandalism.
Nicolle Wallace: I mean, I think you can also add they’re burning contraceptives that were part of what was distributed through USAID. They’re burning food aid. They’re bankrupting peanut farms. I mean, the destruction is almost the point, right? I mean, the DOGE cuts were destruction for destruction. And in the end, it turns out they didn’t save much of anything.
Jon Lovett: No. It had no real net positive benefits. Whatever modest savings they could ostensibly point to is obliterated by the spending and the deficits created by their omnibus bill. It’s so careless, right? Like, it’s careless. They don’t care. And so that to me is just so dispiriting, the whole thing.
Nicolle Wallace: A lot of ex-Republicans can make the case of why only the Democratic Party still believes we should live in democracy with more fervor and sort of true believer-ness than Democrats who feel dispirited. What is that piece of the DNA of being a Democrat that can’t capitalize on the heinousness and the lack of sort of a mandate for everything Donald Trump is doing?
Jon Lovett: So it’s a big question. I think it’s the question that we have to be sorting through now. I actually also think that how we answer it, the debates that happen in the upcoming primaries will be not just a way we figure out where we want to go, but the debate itself will be instructive to people watching it, about what the Democratic Party stands for, how do we figure out what we stand for.
But there’s a lot, I think, that went wrong and I don’t want to belabor the Joe Biden point. But even if the defense was that Joe Biden was up for the job, I didn’t appreciate how much we paid for having the bully pulpit basically open and unmanaged, because he was a poor communicator and getting worse all the time. But it’s not just Joe Biden. The American people were saying through this election, beyond it, that, yes, Joe Biden is too old. They worry he’s not up for the job. But they have deeper questions about what the Democratic Party stands for. They just don’t know.
Now, some of that is, there is an easy narrative, which is something like we know Democrats are against Trump, but what are they for? What are they for? People said that about Hillary. They said it about Kamala. They say about all kinds of Democrats. Well, if you give a bunch of policy addresses and then a reporter asks you while you’re passing him on your way out, what do you think about Donald Trump? That’s the news. The news is about Trump. And so, Trump sucks up a lot of oxygen that’s difficult to contend with.
But we just talked about Trump being able to put someone like RFK Jr. at HHS. Imagine the anger if Kamala Harris had said she was going to make Mike Pence head of HHS, a pro-life, Christian right member in good standing. It’s inconceivable. There’s something that Trump has shown Republicans that has given him a lot of goodwill and space to operate.
There’s an episode of “Madman” I always think about. There are these two guys competing for a job and this hard-working, ambitious but, you know, a vicious guy is like, why does he get everything? I don’t get anything. I work so hard. He’s so easy. He doesn’t seem to care. He gets everything. And he said, for you, the clients feel as though their needs are met. But for him, he makes the clients feel as though they have no needs.
Nicolle Wallace: Yeah.
Jon Lovett: And that’s what Trump does, right? He makes the base feel as though they have no needs. He doesn’t need to prove anything to them.
Nicolle Wallace: Yeah.
Jon Lovett: Ron DeSantis, Marco Rubio, JD Vance, they got to prove something to the base, that they can meet the base’s needs. But Trump makes them feel like their needs aren’t met and that gives him space to operate. Why? Because people know that when Donald Trump talks about immigrants in a vicious and aggressive way, that he means it. They know what he stands for on trade.
Now, he’s a liar and a bullshit artist, and made all kinds of promises he’ll never keep. He is a politician through and through. But the places where he has an authentic connection based around policy, agenda, voice, style, beliefs, that gives him room and trust, and Democrats just don’t have that. Like, Bernie Sanders has it. AOC has it. Mamdani has it, right? Barack Obama had it. Bill Clinton had it, right? It’s not always from an ideological point of view. But how do you build that connection, that authentic connection, that people understand what you stand for, understand your value, so that in the messiness of actual governing, you have some space and you don’t lose people because they don’t feel like they know you or understand where you’re going.
Nicolle Wallace: I mean, the thing about all four of them is they never had to shore up their sort of strong leader acumen, right? Like, if you were strong and you believe the things that I believe or you understood my life. Even if Obama seemed smarter than everybody, he was strong and he was going to do the things he said he was going to do, what is it that keeps Democrats wrapped up in the beauty contest phase and from just jumping over the cliff with one of these people who have it?
Jon Lovett: I don’t really totally even know what that would look like in practice. Like, we’re now going to head towards a midterm. I hope we’re going to recruit the best possible candidates that will have a range of views, depending on the district. And then we’re going to head into a big fractious Democratic primary, that a lot of people are probably going to jump into. There will be ideological divides. There will be tone and style divides.
Nicolle Wallace: Yeah.
Jon Lovett: You know, they’ll be points that we’ll be talking about abundance, and Medicare for All, and AI. I don’t know. That to me is like the cauldron where a lot of this will be sorted out.
Nicolle Wallace: Do you have a feeling from the folks that have come through your podcasts, who will fare better than others?
Jon Lovett: I really don’t. And I feel like this is sort of like who is it? Who’s it going to be? Who’s it going to be? Who’s the right person? And to me, it’s like they’ll be made in this moment. My one feeling about it, which by the way also could be wrong, I don’t know. You know, I’m trying a new thing which is called humility just for today, just to see how it feels, try it on.
But whoever ends up being the person to be the standard-bearer in 2028, they’re not going to show up on a white horse in 2027. Like, how do we know who’s the right person to take on Trump, and MAGA, and this radical version of the Republican Party? Well, it’s the person who’s going to be doing it now and having an impact, and is going to be out there fighting every day, not because of some like deeper kind of, whatever, political calculus, but just because the right person to take on the right today is someone who feels it in their bones —
Nicolle Wallace: Yeah.
Jon Lovett: — and isn’t going to sit back and wait for their moment.
Nicolle Wallace: Yes.
Jon Lovett: Donald Trump is relentless.
Nicolle Wallace: Yeah.
Jon Lovett: He is somebody that is out there every single day. The right people to take on this version of the Republican Party need to be relentless too —
Nicolle Wallace: Right. Yeah.
Jon Lovett: — and not just because they want to win or they have a political goal, but because they see something that Donald Trump does and they’re fucking pissed.
Nicolle Wallace: Yeah. I mean, Pete Buttigieg seems to be living this moment. Some of the really, really smart, strong governors seem to be sitting out this moment.
Jon Lovett: I have a little bit of sympathy for some of the governors because being a governor is a real job, and their practical realities where there are many that are negotiating deals with Republicans, that drawing the evil eye from Trump cost them. I think Gretchen Whitmer has been trying to figure that out.
Nicolle Wallace: Yeah.
Jon Lovett: I think sometimes it’s worked. Often, it has looked embarrassing, to be honest.
Nicolle Wallace: Yeah.
Jon Lovett: Then you see somebody like Gavin who’s trying to be out there. But at the same time, you know, he’s trying to figure out how to be anti-Trump while showing that he can talk to everybody. Is that working? I don’t know. Ro Khanna is out there a lot. Pritzker has now been trying to make the most of this moment with the Texas Democrats eating deep-dish in a basement somewhere. So, you know, like, people are trying stuff out. I think that’s good.
Nicolle Wallace: What is your sense of where Trump really is, in terms of political strength, and do you think it matters?
Jon Lovett: So in the first term, the two moments Donald Trump was at his least popular, his lowest ebb, they were around the Insurrection. But the second is around the effort to repeal Obamacare. When people are confronted with the actual agenda and the actual impact of the policies, they don’t like it.
Donald Trump, he campaigns like a populist, but he governs like an old-school Paul Ryan Republican. That’s what this big omnibus bill does. In many ways, his lack of discipline, his careening had protected him in the first term because it prevented them from achieving the policy aims that would have caused the most damage and led to the most political cost. He doesn’t face that this time.
Yeah, like, people were upset about cost. That’s ultimately why a lot of people were willing to give Trump a chance. Not only are they not seeing prices go down, they’re seeing him focus on immigration, in ways that go beyond what people expected. Look, was Donald Trump talking about mass deportations? Yes. There were signs at the convention saying mass deportations. But Donald Trump says what he needs to say to all kinds of audiences —
Nicolle Wallace: Right.
Jon Lovett: — and a lot of people heard that he was going to go after criminals. Tariffs are going to cause cost to go up. This big bill they passed is going to cause cost for lower-income people to go up. So, you know, not only are that people see him not focusing on what he said he would, he’s not solving the problem. He’s making it worse.
Of course, his political fortunes are falling. What does that mean? I don’t know. He remains popular among the people, Republicans. It means he remains a threat to any Republican who would lose in a primary if he endorsed the opponent, and that’s where a lot of the power is right now because Democrats don’t control anything.
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Nicolle Wallace: We’re going to take a quick break right here. When we come back, more with “Pod Save America’s” Jon Lovett. We’ll be back in a moment.
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Nicolle Wallace: What do you think the Epstein story means to him actually at a political level?
Jon Lovett: You know, right now, they’re trying to see if they can let attention shift and sort of see if it moves on. Maybe it’ll work for them. Like, Mike Johnson sends the House home rather than have a vote on the Massie, Ro Khanna bill. It’s clearly done damage. There’s a lot of people that took them seriously when they said they were going to get to the bottom of this I don’t think those people are all going to move on. I think some of them will. I think some of them are in the tank, but some of them aren’t.
And I just think you start putting it on this list of broken promises among not the diehards for Trump, not the resistance libs and the people that would never support Trump in a million years, but this sort of squishy middle that wanted cost to come down, heard he was going to cover IVF, thought he was going to get to bottom of some of these conspiracy theories, maybe like RFK Jr. because they have questions about vaccines, whatever it is that animates kind of politically heterodox, weird view holding populace of this perfect country of ours. And I think you lose people in that, right?
Nicolle Wallace: Yeah.
Jon Lovett: This movement lose people, and the trust is broken. And then all of a sudden, you have an opening. What do you do with that?
Nicolle Wallace: Actually, I first covered the Epstein story the day that Elon Musk tweeted Trump is in the Epstein files.
Jon Lovett: Yeah.
Nicolle Wallace: I was on the air and I was like —
Jon Lovett: How do you know it?
Nicolle Wallace: — what is that? Because we knew DOGE saw everything, but I was like, did they see that too? But I hadn’t covered it since it was an actual crime carried out against girls and was a sex trafficking story. I’d never really covered it as a conspiracy theory. I mean, obviously, it’s not a hoax. There were girls that were sex-trafficked and traumatized, and some of them have taken their own lives. I mean, are you clear on the facts of it, or do you think there are facts to be learned?
Jon Lovett: I think there’s still facts to be learned. Like you, I think I didn’t pay enough attention to it. That’s how I feel about it. I just didn’t pay enough attention to it. I thought it was heinous. Of course, it seemed like there were very rich and powerful people connected to it. But I always thought of it more as, yeah, these terrible things seem to have happened. He got away with it for a long time. But, no, obviously, it had been sort of turned into like there’s a global ring of pedophilic Hollywood —
Nicolle Wallace: Pedophiles.
Jon Lovett: — elites and deep state people. I just didn’t think about it as anything —
Nicolle Wallace: Yeah.
Jon Lovett: — other than a horrible story that the right had taken and run with. And then you dig into it, and I did do this, like, I dug into it. And you read about the failure to prosecute back in Florida in, I guess, 2008. You find out that the family of a girl who had been abused by Epstein, goes to the police. They find a bunch of other girls that were sexually abused. The Palm Beach Police have this.
And then somehow this guy gets a ridiculous agreement that allows him to return to a place of respectability somehow, even though he’s a registered sex offender. The deal forswears doing any kind of further investigation. And basically, this is a decade, where he’s allowed to continue donating, having fancy dinners, having celebrities and rich people and famous people in his home. He’s free to commit further abuses.
And it’s not until the Miami Herald does this investigation, that it reignites the case. And all of a sudden, people realized that this deal was ridiculous, that he was a serial predator, that these are some of the most notorious sex traffickers in American history. And then the DOJ reactivates on the case and he’s arrested. Maxwell is arrested and it seems like we’re going to get the truth, and then he’s dead.
Still to this day, the most likely reality is that Epstein dies because of incompetence, and broken systems, and embarrassing failures at the prison. That’s still the most likely circumstance. But I understand why people don’t believe that. I understand why people would think something else was going on.
And you know, the one thing that often happens with conspiracy theories, which is institutions, whether the media or the government, they declare something debunked, right? And really what they mean is we’ve looked into it and we have we have not found evidence of what you claim. But they haven’t proven it wrong. And for people that know every detail because they’re conspiracy-minded and see a kernel of truth in this, they say look at that, they’re claiming that this has been debunked, but there’s still a question I have that they haven’t answered. And in this case, that is absolutely true. That is absolutely true that there are questions that are not answered.
That is 100% right. He was a serial predator. He was connected to a bunch of famous people. A bunch of girls were really hurt. The government did do him favors. It is disgusting, and they are right about that. And then the government, whether maliciously or not, allows this person to die while in custody. It is an incredible failure that, of course, leads people with questions. And then they say they’re going to expose it, and they promise —
Nicolle Wallace: Yeah.
Jon Lovett: — all these people that whatever kind of brokenness leads them down this path are not wrong —
Nicolle Wallace: Yeah.
Jon Lovett: — about this. And they say they’re going to prove, they’re going to show everything, they’re going to reveal everything. But then it turns out his name is in the file, and then all of a sudden, it all has to go away. And then whatever truth there was about the conspiracy theory beforehand, they fucking make it true. They make it true. There is now a conspiracy between the Department of Justice and the White House to conceal information about what is in the Epstein evidence. That is absolutely true right now.
Nicolle Wallace: What I think is interesting is the coalition of people who believe what you just said. So the coalition includes the victims. They believe something is being hidden. They would like transparency. The MAGA base, Joe Rogan, for all his flaws, has drawn a line in the sand, since you’re being treated like a baby. Why can’t they figure this one out?
Jon Lovett: Or why is this pain more worth it than whatever the truth might be? Because he dispatches, first, his personal attorney till right before he joins the Justice Department, dispatches him to interview this person. They transfer her to a cushy place. It stinks. It just stinks.
Nicolle Wallace: Yeah.
Jon Lovett: And this is to your point about the media, because there are fewer places for reporters to get at Trump. Now, there are all these MAGA people kind of throwing out questions too. And Marjorie Taylor Greene’s boyfriend is there too. Like, what is the explanation?
Nicolle Wallace: Yeah.
Jon Lovett: What is the justification for this transfer? She’s a violent offender. Sexual abuse is a violent crime. Sex trafficking is a violent crime. I think because she’s a woman and because people have a certain image in their mind of what this is, that she is a violent offender. There were jokes in the open about Harvey Weinstein long before the story was fully exposed. Bill Cosby joked about what would ultimately be seen as sort of connected to his terrible crimes over many years in his stand-up. People joked about Epstein. Trump joked about Epstein, you know, likes younger women, whatever the exact quote, as I’m getting it wrong.
There was just a collective dismissal of these kinds of crimes, lack of attention on them, and it continues now because everyone is like, what’s in the files? What’s in the files?
Nicolle Wallace: Yeah.
Jon Lovett: There are victims, women who are telling you what happened. They are real and they exist. The truth is not always in a dark corner, right? The truth isn’t always hidden, and Trump takes advantage of that, right? He likes that the contours of investigations, and the dark and real truths must be uncovered. And so, he goes on television, just tells us that he’s going to do crypto. He just goes on television and tells us they’re going to do these real estate deals.
He just goes on television and confesses to doing what had been uncovered by an investigative journalist 10, 15 years ago, would be seen as a scandal that could bring down a presidency. But they do it out in the open. And so, here, too, it’s like the answer to the Epstein story may not be a secret. It’s the story these women have been trying to tell for over a decade.
Nicolle Wallace: It’s so true. I mean, in the first term, you’d sort of live with bated breath for the Washington Post to break something, or the Times to break something, some revelation from an investigation or from a whistleblower. They’re doing it all out in the open.
Jon Lovett: Right.
Nicolle Wallace: You know, I think we have to admit it’s working, right? His numbers don’t go up and down. How do you push back? I mean, how do you take all of what we know to be wrong and have it answerable and what we still have left of our political institutions?
Jon Lovett: So I think this is where I think independent media does come in. A lot of ways people used to get news, the local paper that would have national news. So those are gone. Like, a lot of stuff is gone.
The other thing too is a lot of people train themselves, whether it was Twitter, or Facebook, or Instagram, to kind of use their feeds to just get a sense of things. And when people started doing that, news was all over. And then slowly but surely, news fell out. And so, people still use those things to get a sense of things. They’re not seeking out the news, but they’re just getting less of it.
They’re just having less contact with news, and it doesn’t happen by accident or happenstance like it used to. And so, you have mainstream outlets with less reach. You have a whole right-wing ecosystem that backs Trump and also seeks out the silliest lefty professor or worst comment by a member of Congress, makes that who the Democratic Party is, all having a huge impact.
And we really need to build an alternative and that will require building a pro-democracy media ecosystem that runs from the Nicole Wallace’s, and Liz Cheney’s, and Tim Miller’s, and Sarah Longwell’s and anti-Trump, pro-democracy center-right figures, all the way to the Mamdani supporters of the left, that that treats everybody here as part of one big team, and that galvanizes people and makes them feel as though they are the means of reaching others who are outside of it.
We have to inform each other. And this kind of independent media ecosystem is going to be the ways by which you kind of get people what they need to know so that they can share it with the people in their life. And it’s a much harder job than everybody watching the nightly news, but that I think is the job. That’s what we’re trying to build at Crooked. That’s like, you know, here we are eight, nine years later, and that continues to be what “Pod Save America” is trying to build, alongside a lot of others that are kind of part of the fight.
Nicolle Wallace: Are you optimistic that that can be built and can work and can hold that coalition together in time to be successful in the midterms and the next presidential?
Jon Lovett: The joke is our goal is to build this either before or after it’s too late. And things will get better or things will get worse. There’s no point at which they will get so bad, that we will stop fighting. And there’s no point at which they will get so good, that we can declare any kind of permanent —
Nicolle Wallace: Then we stop fighting. Yeah.
Jon Lovett: — victory. Of course.
Nicolle Wallace: Yeah.
Jon Lovett: You know, I remember before this election, especially because I believe this right through the end, that Kamala was fighting from behind. We talked about this here. We talked about with the audience. Like, Trump may win, and it is as bad as we’re saying. It is as dangerous as we’re saying. But if he wins, that doesn’t mean we’re done. It doesn’t mean it’s over. You just keep fighting.
Like, I don’t know how bad it gets. I don’t know how hard it is to climb all the way back. How do you rebuild trust after decades of it being eradicated? How do you reestablish? Forget democratic values, social values around forbearance and integrity and mutual regard. Like, how do you rebuild what has been lost, that allowed someone like Trump to get into power in the first place? Nobody knows. It’s hard. It’s hard.
But you wake up every day, you see what’s happening. You try to help people understand what matters and what doesn’t, and know that what makes it sustainable is the fact that there are millions upon millions upon millions of people who feel the same way. And the more you can make that big group of pro-democracy Americans, whether super engaged with politics or not, whether they’ve been open to Trump in the past or not, whether they voted for Trump or not, the more you can make them all feel like they’re part of one big movement, the more powerful that gets, the weaker Trump gets, and the more success we’ll have.
Nicolle Wallace: I mean, something that ties your listeners to you guys is that it’s not eat your spinach. Here are my 11 charts. We’re going to do white papers about, you know, the history of Social Security. I mean, it’s also really appealing. Like, how do you ride the culture?
Jon Lovett: This is something we’ve sort of struggle with, because something people will say to us all the time is like, where’s pod save the climate? Where’s pod save the climate? We care about climate. You’re not covering climate. We talk about climate and try to cover it. But there’s this idea, like, oh, we just need to cover the things that matter and it will reach people. And I think sometimes on the left, there’s a lot of people building beautiful perfect cathedrals of information —
Nicolle Wallace: Yes.
Jon Lovett: — and they’re empty on the inside. They’re just empty.
Nicolle Wallace: Or they’re locked, or you don’t know how to get in.
Jon Lovett: Right.
Nicolle Wallace: I see them too and I’m like, we should have them on. But then you can’t figure out how to get in the cathedral. Is it air-conditioned? What is it about?
Jon Lovett: Never air-conditioned. It’s never air-conditioned. The heat rises, that’s why you got all the feelings.
Nicolle Wallace: Yeah, a few things cold.
Jon Lovett: But in this war for attention, with the media so stratified, with so much noise, with news competing with every streaming show and everything on social media, like making sure you’re offering, you’re delivering a value proposition which is not just we will help you understand what’s happening, but like you’ll be glad you spent the hour. It’ll be worth your time both because of the information it’s provided, but also because you’ll like the hang.
Nicolle Wallace: Yeah.
Jon Lovett: Like, that is not a good thing to have. It’s a must thing to have. You must have it.
Nicolle Wallace: It’s a barrier.
Jon Lovett: Yeah. And so, do we think this conversation was educational around an issue? That’s a more objective question, right? Like, were there facts in here? Was it accurate? Was it a good debate? Were the lines of the debate clear, whatever? Was it entertaining? Would somebody who didn’t know about this and check it out, want to stick around for a second episode?
Like, that’s a much more subjective question, and so it’s easy to forget it or treat it as an afterthought. But, like, no, when you’re competing with Donald Trump who is very entertaining and captivating, when you’re competing with the right which has built like, I’m sorry you watch like the first 15 minutes of Jesse Watters and there’s a lot of bullshit in there. There’s a lot of misinformation in there. But he gives his audience what they want. He gives them something entertaining.
Like, we have to provide an alternative to that, that brings more people in. And like the right wants a left. That’s embittered and divided and sour, and with a bunch of barriers to entry and codes that you need to unlock and know, and words if you use, you’ll be yelled at. They want us like that. They do. They want a sour and —
Nicolle Wallace: Yeah.
Jon Lovett: — cynical and dispirited. And so we have to be welcoming and entertaining and joyful. We will not build a party that can win, unless we are having parties people would want to attend.
Nicolle Wallace: Yeah.
Jon Lovett: And that is central, central.
(Music Playing)
Nicolle Wallace: We will be right back with more of my conversation with Jon Lovett. And in case you missed it, be sure to check out my recent conversation with New York Times bestselling novelist Daniel Silva. It’s available when you subscribe to MSNBC Premium on Apple Podcast.
(Announcements)
Nicolle Wallace: What is sort of your baby story of how you ended up in this moment, and in politics, in the Obama White House?
Jon Lovett: So in college, I was always drawn to politics, to comedy and writing, and to math actually. I was a math person and I ended up focusing on math in college. I remember, like, I would go to the gatherings of all the math majors and was just so out of my depth. I could do the funniest math presentation. But, my god, these kids could do Rubik’s cubes behind their back. Like, I was never going to hack it.
Nicolle Wallace: That’s so crazy.
Jon Lovett: I was never going to hack it. I couldn’t. I liked math and I was good at math compared to maybe, you know, people that weren’t math majors at Williams College, but I couldn’t compete. And so, I worked on it for a while, but decided I wanted to try something else.
And I was writing jokes and doing these open mics, while also trying to find a foothold in politics. I ended up volunteering for the Kerry campaign in 2004. That leads to a job as a very junior person in a Senate office on Capitol Hill. But somebody heard that, hey, we heard that there’s some junior kid that used to write jokes or do stand-up. Hillary Clinton has to do a roast of Barbara Walters. Can he write jokes? And so I ended up writing a bunch of jokes.
Actually, I got on the phone and they were some people that worked for Hillary, some great speechwriters, and Al Franken at that time, he was just, I think, doing Air America Radio, and it was like a dream to be on the phone with Al Franken. I remember I made him laugh and I don’t remember what the joke was.
Nicolle Wallace: It’s amazing.
Jon Lovett: But, for me, making Al Franken laugh was like such a big deal. And because he was somebody who wrote those great books, but he had also started Air America Radio —
Nicolle Wallace: Yeah.
Jon Lovett: — which was meant to be an answer to right-wing talk. And I bought a radio so that I could listen to it on the day it launched.
Nicolle Wallace: That’s amazing.
Jon Lovett: So I was a follower of like the hope for progressive media for a long time. Anyway, that leads to a junior speech writing job for Hillary Clinton and I really learned on the fly. I started for Hillary when I was 23 years old. And when I thought about that job in hindsight, when I was 28, 29, 30, I was like, oh, man, there are a lot of things you could have done better. And now, I look back on it, I was like, god, you were a child. Of course, you were overwhelmed, screwing up.
Nicolle Wallace: And was she good to write for? I’ve heard from other speechwriters, she was good to write for.
Jon Lovett: So it’s interesting because I’ve been a speechwriter for Barack Obama and Hillary Clinton who couldn’t be more different in terms of how they approach speeches, because Barack Obama approaches them much more as a story and as a piece of narrative. But Hillary Clinton and I appreciate this, she really approached them from policy. Like, for her, they were about how you really make policy clear and simple. And I learned a lot from her about that and how to do that.
And then one other thing I learned from Hillary Clinton which I have atrociously failed to carry through my life is how much for her, being a good person to work with, is about systems. It’s a small thing, but she would call everybody on their birthday. She had a great team around her that kept track of stuff, so that she would remember things. You know, there are always stories about she would bring flowers down to the people in the White House Military Office.
She built a system around her to have a discipline of kindness and thoughtfulness, and that flows from her as a person. And so, like, as a boss, like, she’s not the most available. She’d been in the public eye for 30 years. But you see that there’s such a apparatus around her, for taking care of people, and that, to me, spoke to something deeper about who she was as a person. And so, I learned a lot in those years. But I really was, like, over my head.
And then the primary ends, I was in the Senate office. I worked on the campaign, her ‘06 Senate and then her presidential. And then Barack Obama is hiring one more speechwriter, and I meet with John and the other speechwriters, and they actually did a blind test. They had everybody submit the same speech. A bunch of speechwriters and writers and journalists all had to submit the same energy and —
Nicolle Wallace: What was it?
Jon Lovett: It was an energy and environment speech to take place in Iowa, and I loved writing about energy and environment. I think because it’s technical, I loved it.
Nicolle Wallace: Yeah.
Jon Lovett: And Hillary Clinton was really passionate about it. Bill Clinton was really passionate about it. And so, there were these moments where I was like doing notes with Hillary, and then Bill Clinton would give notes on Hillary’s speeches about the climate and energy.
Nicolle Wallace: That’s amazing. Yeah.
Jon Lovett: So I just learned a lot and I felt quite adept in it. But I also am an undisciplined person, and so I ended up blowing through my three days to work on it, and I wrote it on a Megabus between D.C. and New York. But they pulled it as one of the ones they liked and that led me to getting the job at the White House for Obama. And I worked for Obama for the first three years of the first term, doing all kinds of speeches, the serious speeches about the economy and about energy and the environment, but also the Correspondence Center speeches which were my favorite to work on. Yeah.
Nicolle Wallace: Was President Obama good to write those speeches for?
Jon Lovett: Yes. He had such incredible timing.
Nicolle Wallace: Yes.
Jon Lovett: And we really like over the years —
Nicolle Wallace: Did you write the Trump joke?
(Begin Audio Clip)
Barack Obama: Donald Trump is here tonight. (Applause) Now, I know that he’s taken some flack lately. But no one is happier, no one is prouder to put this birth certificate matter to rest than Donald. And that’s because he can finally get back to focusing on the issues that matter like did we fake the moon landing? (Laughter)
So just recently in an episode of Celebrity Apprentice, at the steakhouse, the men’s cooking team did not impress the judges from Omaha Steaks. And there was a lot of blame to go around. But you, Mr. Trump, recognized that the real problem was a lack of leadership. And so, ultimately, you didn’t blame Lil’ Jon or Meatloaf. (Laughter) You fired Gary Busey. And these are the kind of decisions that would keep me up at night. (Laughter and Applause)
(End Audio Clip)
Jon Lovett: So there was a bunch of Trump jokes. So the year before, maybe two years prior, I think it was a year before, I had been working on the Correspondence Center, the weekend of the correspondence dinner. And we were waiting to get in to see President Obama, and Judd Apatow happened to be getting a White House tour. And he said, “Oh, well, I would love to help with jokes.” And I panicked. I’m not good at social moments. And it was like, would President Obama want to have Judd Apatow? Of course. But I can’t add somebody to a meeting right before the meeting. I don’t know. Like, what’s the right thing to do? I don’t know. I’m sure I just froze and went dead.
And then he told the story, he said, this is his term, “cock-blocked him from meeting the President,” which I didn’t mean to do. I really didn’t. Like, I just didn’t know what to do.
Nicolle Wallace: Well, normal White Houses, I will defend you here. You don’t just bring someone into a meeting. And I’m sure it happens all the time with Trump. But in a normal White House, you have to ask somebody, at least the president.
Jon Lovett: And I appreciate that, but I’m just trying to convey to you I’m so overwhelmed by the idea of even figuring out who to ask, how to ask. I froze up. And so, the next year, I said, oh, look, we would love your help. I’m sorry, I didn’t know what I was doing. Of course, you’re Judd Apatow. You’re incredible. You’re a great writer. Of course, help us. We need as much help as we can get.
And so, I got on the phone with him and he had this idea for this riff about the Apprentice and how hard it is versus being president. And that was the way we kind of got at some of that. And that became the run of jokes about Trump at the Correspondence Center. But a lot of people submit a lot of great jokes. And we had figured out that President Obama would have to go really hard at himself because the harder you are on yourself, the more space you would have to make fun of others.
And there was this balance that we would also strike in the rest of it, which is David Axelrod, who is Barack Obama’s senior advisor for a long time, great writer himself, former journalist. He’s a very funny guy, great sense of humor. He’s very avuncular. You know Ax and he’s a very avuncular guy. And so, he’d write these sort of sweet, befuddled, kind of dad style, uncle jokes. And my platonic ideal of a joke is Barack Obama throwing the podium over and just going, fuck you, fuck you, fuck you. Like, I don’t even need a joke. I can be mean.
And Jon Favreau was really great at kind of weaving these things together. But basically, we try to find the balance between the two poles of dad jokes and super mean, hard-hitting jokes, and self-deprecating. And I think the end result was really fun in finding the right balance.
But Barack Obama had such incredible timing and was such a great performer. Like, even when he would laugh as he was reading, it was all part of the fun of him telling these jokes. He just was so, so easy. He made us look so good as writers.
Nicolle Wallace: I mean, he’s so good.
Jon Lovett: So good.
Nicolle Wallace: He’s so good, and he seems to keep getting better. You know, I worked for Bush and half the country absolutely hated his guts. And now people see him with the Clintons or the Obamas and they’re like, oh my God, he wasn’t that bad. I worked on the campaign against President Obama and I don’t know that there’s any better person that’s been in the job. I wonder what you think of all the nostalgia for what we had before this time.
Jon Lovett: I’ll just be honest with you, Nicolle. I have no nostalgia for George W. Bush. I have none. I have none. I’m sorry.
Nicolle Wallace: At least, you’re honest. I’m not sure the people that say it mean it.
Jon Lovett: Look, my personal view, I believe him to have been one of the worst presidents in American history. He has benefited from the fact that Donald Trump has somehow managed to be worse. I also do think I had criticisms of George W. Bush at the time as a speaker and communicator. But I go back and look at him now and I’m like, well, he’s fucking Socrates, compared to what we’ve got now. So I see the comparison.
I am sorry. I am not on board with the George W. Bush nostalgia. I am very eager and excited and happy that you and I, for whatever reason, have come to understand the threat of Trump in the same way. I think it speaks so well of you. I think it speaks so well of the kind of Republican whose eyes were open, and whose values and morals were able them to avoid a kind of groupthink and collective mania that has caused them to embrace something so heinous. I think it speaks so well of you as a person, but I will not re-evaluate George W. Bush and I have no nostalgia for that era. Thank you for allowing me to say that.
Nicolle Wallace: I feel like there’s more.
Jon Lovett: No, that’s it. That’s all I got.
Nicolle Wallace: That’s good. I mean, look, I appreciate the honesty. I think part of the toxic moment is thinking everything before this was fine. So I try to own that, not just in my work, but in my life. And I wanted to ask you about your life. The thing about a podcast is there’s so much more of you out there, you know, right? Like, it’s just you, and everyone listening can tell if you’re full of shit, which I think is why you guys are so wildly successful. Like, it feels like there’s no space between, like, what you really think and what your lives are really like, and the stuff you talk about. Like, do you keep anything for yourself? And I’m asking more in terms of, like, I’m looking for self-salvation and survival skills. I’m not trying to pry.
Jon Lovett: Yeah, I know. It’s a good question. Like, to me, I think the harder part for me is not like, oh, what parts do you not talk about? Like, I don’t really feel like there’s much I’m not talking about. It’s more actually like what you say on the microphone and what you say when the microphone is off should be different, not because you’re not being honest about who you are, but because you’re making sure you have something to offer —
Nicolle Wallace: Right.
Jon Lovett: — and making sure that you’re not just filling the space between the mattress sets, you know? And so, like, for me, I think sometimes in the crush of things, when I’ve looked back on shows or even periods where I felt like, you know what, I don’t know that I’ve been offering as much as I could. It’s not because I wasn’t being honest. It was because I felt like it was like a half warmed overtake. I didn’t really have enough of a perspective. And yet, you’re having the conversation, so you’re sharing what you think.
Like, I’m sure I’m being very self-critical, deserved or not, whatever. But, like, to me, that’s the challenge, right? It should feel authentic. It should feel real. It should feel like you’re just having a conversation. But, also, like, make sure you’re not wasting people’s time. Like, yeah, it should be free-flowing and open. And there’s a glut of these, right? Just like a celebrity interviewing another celebrity, whatever it may be. And it’s like, how do you make sure, you know, you’re giving people something of value?
Nicolle Wallace: Or that it doesn’t become shallow.
Jon Lovett: Yeah.
Nicolle Wallace: But I feel this way in Trump 2.0. Like, if I’m not ready on a story, like we’ve got four fucking years of this. Like, if I’m not ready, I’ll wait a day. Like, if I haven’t read enough, or if I haven’t done my own reporting, I’ll do it tomorrow, you know? I mean, there is like this moment where I feel like the risk of being shallow is even more than the risk of being uninformed.
Jon Lovett: Yeah. Yes, I think that’s totally true. Like, how do you make sure you’re covering what’s important and, you know, without allowing Donald Trump to be the world’s assignment editor, even though —
Nicolle Wallace: Totally.
Jon Lovett: — in many ways, he is, right? Like, that’s just the truth of it. And then there’s just —
Nicolle Wallace: Yeah.
Jon Lovett: — you know, the people like, oh, you know, don’t talk about the federalizing of the police in D.C. It’s a distraction from these other issues. And like, in some sense, I think you’re right. But, also, it matters when the President decides —
Nicolle Wallace: Totally.
Jon Lovett: — he’s the police chief of a city, and what the harbinger it is for what he could do in the future. And we should talk about it because we need to win people over on our views about it. and why it’s dangerous and why it doesn’t represent an actual kind of tough-on-crime position, whatever the response is. Like, you have to go to where the news is.
Nicolle Wallace: Totally. I guess the last thing I wanted to ask you about is how you cover systematic dehumanization, either of immigrants or of maligned groups.
Jon Lovett: I do think one of the reasons Trump’s numbers in immigration have dropped is because it’s one thing to hear about mass deportations or imagine it’s going to be going after criminals. And then you see moms being arrested on the street. You see people being —
Nicolle Wallace: Yeah.
Jon Lovett: — hounded at Home Depot. And all of a sudden, it taps into something deeper. It was heartening. You know, Democrats were all over the place in immigration for a long time. Donald Trump had been hammering the issues for years. And yet, in polling, despite the fact that there really weren’t very many people making the argument, the American people remained in support of immigration.
And I’ve been thinking about that and what Trump does. And what Trump does, if he has one great skill as a political person, it is he takes the worst thing about you and he makes it more true. He takes the worst thing about you and he’ll make it more true. He takes the worst thing about America and he makes it more true. He takes the worst thing about his base and he makes it more true.
Leadership matters. That’s what politics is. It is about leaders. And he takes what’s worst about people, their sense that life is unfair, that when it comes to America, there aren’t six boarding groups. There’s just winners and losers, right? So I got to get to the front of the line. That everybody is corrupt; that our cities are riddled with crime; that immigrants are taking jobs, whatever it may be, and he kind of appeals to that worst instinct and he makes it more real. That’s what he’s doing right now. He’s making those qualities more true about America.
But, like, there’s an opposite to that. There’s an alternative to that. That’s what Barack Obama does at his best. That’s what Bernie Sanders does, and AOC. You have to make the good parts more true, right? The pro-immigrant, the big and generous version of America more true. And these things have existed in our politics forever. They’re always duking it out.
But our job is to offer a vision that is appealing and inspiring to make the good parts of our nature, of our instincts as individuals, as a culture, make those more true. And I think that does involve looking at some of the dehumanization and the ways in which Trump is making life work for real, flesh and blood people. That is, in part, how you bring alive that better part of who we are. And if we can do that, we can start building political power and send these people back to their fucking mediocre shrimp cocktails in Mar-a-Lago.
(Music Playing)
Nicolle Wallace: Thank you so much, Jon, for doing this. Really, I’m such a fan and it’s so nice to have such a big chunk of your time. I really appreciate you.
Jon Lovett: It was good talking to you. I’m really glad I got to do it. Thanks for having me.
Nicolle Wallace: Thank you so much for listening to “The Best People.” Be sure to subscribe to MSNBC Premium on Apple Podcast to get this and other MSNBC podcasts ad-free. As a subscriber, you’ll also get early access and exclusive bonus content like my recent conversation with novelist Daniel Silva. All episodes of the podcast are also available on YouTube. Visit msnbc.com/thebestpeople to watch.
And a reminder to get your tickets for MSNBC Live ’25, it’s an all-day event. It happens October 11th at the Hammerstein Ballroom. I’ll be there along with some of your favorite MSNBC hosts and special guests. Tickets are on sale at msnbc.com/live25 and we’ll have a link in our show notes.
“The Best People” is produced by Vicki Vergolina and senior producer Lisa Ferri, with additional support from Max Jacobs, Delia Hayes, and Alison Stewart. Our audio engineer is Bob Mallory, and Bryson Barnes is the head of audio production. Pat Burkey is the senior executive producer of “Deadline: White House.” Brad Gold is the executive producer of Content Strategy. Aisha Turner is the executive producer of audio, and Madeleine Haeringer is senior VP in charge of audio, digital, and long form.