In the weeks between President Joe Biden’s disastrous debate performance and his decision to step aside, no one in political media was making the case against his candidacy louder than the former Barack Obama staffers and co-hosts of Pod Save America.
In his third appearance on The Last Laugh podcast, Crooked Media co-founder Jon Lovett returns to talk about his unexpectedly prominent role in the Democratic Party’s existential crisis and how he’s feeling now that Vice President Kamala Harris has emerged as the presumptive nominee who will take on Donald Trump in the fall. We also discuss how the political comedy world handled both Biden’s decline and Trump’s assassination attempt, how he navigates writing jokes for his own podcast Lovett or Leave It, and how on earth he ended up as a contestant on the upcoming season of Survivor.
When I begin our conversation congratulating the “Obama pod bro cabal” on a successful coup against Biden, Lovett takes a long pause before saying, “Yes, your facetious tone noted,” before giving a more serious answer than I was expecting.
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“Everybody understands the stakes, understands the importance of defeating Donald Trump,” he says. “And on the Democratic side—unlike on the Republican side—we can talk amongst ourselves. And yeah, there’s going to be ego and pride and some harshness, because it is so important, and people do rightly have a lot of emotion around the outcome of this election. But it speaks well of this very large and inclusive movement that we could get to this point and unify behind a candidate. And a lot of people had very strong views about what should happen, and I suppose we were among them.”
During our talk, Lovett expresses “profound and genuine gratitude” towards Biden, both for making his “selfless” decision to step aside and for the “successes” of his administration. Now that Harris will almost certainly be the nominee, he is feeling a mixture of “anxiety and uncertainty,” on the one hand, about how the rest of the race will play out and, on the other, the type of “hope” that has been in short supply amongst Democrats in the years since his old boss Obama left office.
As he thinks about balancing those two feelings, Lovett likes to remind himself that “being too cynical is not more sophisticated than being too hopeful.”
“We have a really good case,” he says. “Both for what we want to do in the future and against Trump's failures as a president. We have a great case. Let’s fucking make it.”
Below is an edited excerpt from our conversation. You can listen to the whole thing by following The Last Laugh on Apple Podcasts, Spotify, Google, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Wednesday.
In terms of making the case, the thing that you guys were really hammering on Pod Save America after the debate was that it’s not necessarily when Biden confuses two names that was your biggest concern, but rather a fundamental inability to make the case against Trump. And I think we’re already seeing that with Kamala Harris, the bar was so low that the fact that she can go out there and speak clearly and forcefully, that’s what people have almost forgotten was possible in a candidate for president.
Yes, it is exciting to have a candidate out there prosecuting the case effectively. And to imagine not just making it through, but doing so in a way that feels like we’re taking the fight to Donald Trump, that is inspiring. That is meaningful for people. The country had been saying for two years now they want a different option. And that’s not to have anything but respect for Joe Biden and the kind of president he’s been. But that's what the voters were saying. It’s not what elites were saying, it’s not what pundits were saying, it’s not what insiders were saying. In fact, they were trying to say the opposite. It was the voters that had this great concern. And yes, changing candidates at this point is unprecedented. It’s risky. It’s nerve-wracking. It’s uncertain. But it’s amazing what happens when people discover that they’ve gotten something that they wanted.
Before we get too far into this, I did want to get your take, as someone who briefly wrote for The Newsroom, on Aaron Sorkin’s op-ed in which he made a very strong case for Mitt Romney to become the new Democratic nominee.
Yeah, he withdrew it.
Yeah, he did. He said, “Never mind.”
You know, there was a lot of talk about how people who felt like it was worth making a change, even though it was risky, were having some kind of Sorkinesque fantasy. And then we discovered that the actual Sorkinesque fantasy was worse.
Now that we’re on the other side of this decision by Joe Biden, I’m curious how you think about the outsized role that you and Crooked Media and the other Pod Save America guys played in all of this. I mean, I think it’s probably the biggest spotlight you’ve had to date.
I think that’s a lot…
You think it’s an exaggeration?
Yes. We talked about how we felt watching the debate. And the value proposition of Pod Save America has always been that we’re going to be honest while trying to be helpful. There are plenty of places you can go that are entertaining and pretty cynical. There’s a lot of serious and self-serious coverage of politics—especially the kind that treats politics like a game. But this is a place where we’re going to be honest and open and try to not take ourselves seriously, but tell you what we really feel. And in that moment, we just described what we felt watching that and what we think it meant for politics, and what it meant for the listeners, and what it meant for those of us who care deeply about the fight to defeat Donald Trump and to defeat MAGA Republicanism. And I don’t think our doing so is what mattered at all. What mattered is that a lot of people felt the same way.
Well, it’s validating, right? We watched the debate and then listened to you guys and thought, “Oh, it wasn’t in my imagination. This is as bad as it seemed to me.”
Yeah. The calculus was always, Joe Biden’s biggest liability is his age. He’s an incredibly successful president, incredibly capable politician, but the voters are saying they have a deep concern about his age. So that creates a certain amount of risk. The other side is the risk of pursuing something new, and all that that entails, whether that was a primary over the last two years, or a change in the last few weeks before the convention. You can do a risk assessment, and people landed on different sides of it. Certainly what I felt in seeing that debate is, they’re reasonable arguments, but that’s an argument we need to have. That’s all. We have to have this conversation.
You can’t ignore it anymore.
You can’t ignore it. And because of how that debate went, it means that this conversation has to be had and has to be had very, very quickly. I think it’s worth noting that the only reason the debate was worth having at all, the only reason people felt like they needed to voice how they felt, is because at root, people believed, myself included, that Joe Biden ultimately was in this because he cares about the country. And yes, every person has ego and pride. But ultimately Joe Biden would be motivated by what was best for the country. If he was persuaded that the best thing for the country was for him to stay in, he might have, and then we would have gotten behind him and made the best case. But he looked at this and assessed it, and decided that what was best for the country was for him to do this incredibly noble and patriotic act. And the argument was worth having because people believed in Joe Biden as a man, as a person, that he had the character to make the right call. And people didn’t necessarily agree on what that right call was, but the whole debate was premised on the idea that Joe Biden loved his country.
Do you have any regrets about not speaking out after you attended that fundraiser that George Clooney later wrote about, and that you all talked about on the podcast weeks later, but not right after?
I mean, there are a bunch of Republicans out there saying, like, all these Democrats should have spoken out sooner.
“They were hiding something.”
Yeah. And then you go back and you look at [House Speaker] Mike Johnson leaving the White House after a meeting about negotiations over the budget with Biden. And what does he say? He doesn't say Joe Biden shouldn’t be president. He doesn’t say, “I have concerns about Joe Biden.” He doesn't say, “What I saw with Joe Biden is worrying me.” He says we had a very productive meeting with the president. Was Mike Johnson motivated by a desire to protect Joe Biden? Of course not. The only question was, is Joe Biden the most effective messenger to take on Donald Trump? You see the State of the Union, you say, that was awesome, that messenger can do it. You see the debate, you say no, that was a really poor performance that makes me doubt that he’s the right person. But between those is a one-off event after the president arrives from a multi-day international trip. That wasn’t the most effective I’ve seen Joe Biden. So I’m not sure. I think everybody was trying to figure this out, whether or not the president was going to be in the position to have the fight we needed to fight. And ultimately even he, I think, came to the conclusion that collectively, people decided it would be better to make change. But I don’t think that was an easy or obvious decision.
Through all of this, there was some criticism that you all received, even from within the Biden White House, anonymous sources who were talking to The New York Times, including being labeled an Obama “pod bro.” How did you take that?
I don’t know how much gayer I need to be to stop being called a “bro.” Look, I really respect people that fight hard for their candidate and for their campaign. And I don’t begrudge anybody who does that, especially when it becomes uncertain. Especially when you’re not necessarily fully apprised of what’s going on at a higher level behind closed doors. So I have nothing but kind words for anybody working on this campaign. And, by the way, one of the only reasons we’re now in such a strong position is because they built an incredible campaign. They have a great operation with great people that can pivot and help Kamala run an incredibly effective race with the hundred million dollars that just came in through the door. So I understood it. You’re in a campaign, you’re fighting for the person you believe in, who you’ve made this decision to work long hours and fight on behalf of.
That to me was a hard part about all of this, because I’m well aware that I’m just some schmuck sitting here talking. I’m not doing the work. They’re doing the work. We’re trying to help, we’re trying to raise money, we’re trying to get people to knock on doors through Vote Save America. But we’re not inside of these campaigns. It must have been just such an incredibly stressful and anxiety-provoking couple of weeks, to just want to be contributing and feeling like you’re trapped in this maelstrom where you don’t know what the next day will hold.
Listen to the episode now and follow The Last Laugh on Apple Podcasts, Spotify, Google, or wherever you get your podcasts to be the first to hear new episodes when they are released every Wednesday.
