How to Mock Trump and Win

Democrats are lately employing a strategy against Donald Trump that he has been using effectively against his opponents for years: mockery. It started with the vice-presidential candidate Tim Walz calling Trump “weird” and then bloomed into a bouquet of insults at the Democratic convention: unserious, self-involved, entitled, obsessed with crowd sizes, “fell asleep at his own trial.” Where did this strategy come from? Will it remain effective? And can it backfire?

In this episode, we talk with the Atlantic staff writer David Graham, who was at the Democratic convention and also covers Trump. And we talk with a surprising muse for the politics of mockery: Conservative lawyer and activist George Conway has been using targeted mockery against Trump for years, with unusual success. He reflects on what it means for Democrats to adopt this strategy.

Listen to the conversation here:

The following is a transcript of the episode:

Hanna Rosin: The sight last week at the Democratic National Convention of Barack Obama, the dignified statesman and 44th president of the United States, up on stage, looking down at his two hands as he made a joke about Trump’s, ahem, size.

Rosin: That was a revelation to me. In 2016, as Donald Trump was doling out belittling nicknames and insults, Michelle Obama famously told her fellow Democrats, When they go low, we go high.

And then in the last month, it’s like a whisper campaign went out among Democrats: Climb on down. Just say it. Say on a national stage that thing that you’ve been saying to your friends, Michelle.

Rosin: In fact, if you want to, you can even rhyme it, Bill.

Rosin: It’s not that politicians haven’t insulted each other for centuries. They do, and they have. Some insults stick; some don’t. It’s part of the game. But with the exception of Trump, I’ve never seen a political strategy of insults dominate an entire party and take off so thoroughly and quickly and gleefully. It’s like ever since Democratic vice-presidential candidate Tim Walz said the word weird—Trump is weird. J. D. Vance is weird. Their policies are weird—a door opened up, and Democrats rushed right through it.

Now, in other countries that deal with authoritarian leaders, mockery is a known strategy, a way of deflating a leader’s too-big ego. It can be really effective, also possibly dangerous. And of course, it can backfire.

Here in the U.S., though, it’s something we haven’t fully explored yet. So today is a two-part show. First, we’ll talk to Atlantic staff writer David Graham, who was at the convention and covers Trump and so is the perfect person to help us dissect the politics of mockery, where they came from, how they might roll out in the next few months, and how they can go wrong.

And then, it turns out there’s a surprising muse for the new dump-on-Trump approach. He’s a conservative who’s written for The Atlantic: George Conway. He used to be married to Trump campaign manager Kellyanne Conway. And during his years of observing his ex-wife’s boss, he gathered an arsenal of insights about how to make fun of Trump in a way that gets under his skin.

And he tried them out before anyone else was doing it.

Rosin: These days, Conway is looking prescient. But before we hear from him, I want to understand how Democrats are using this new strategy and what it might do for their chances in November.

With me to explain is staff writer David Graham. Hey, David.

David Graham: Hello!

Rosin: Hi. So in 2016, as you know, Michelle Obama famously declared, “When they go low, we go high.” We all know that lately we’re in a “we go low” moment. And I have found it just fascinating to watch, just anthropologically, how this line coalesced and became so effective, in what seems to be, instantaneously.

I’m curious, as a political reporter, what you’ve seen.

Graham: I think, maybe, just going high kind of ran out of usefulness. I don’t think it worked for a while. It didn’t work in 2016 for Democrats. You know, they lost that election. But in 2020, you had Joe Biden going out with this kind of soul-of-America, Jon Meacham–written speeches thing, which I think was a variation on that—you know, very high-minded and lofty rhetoric and “we’re going to save the soul of the nation” stuff.

And that worked. And then at some point, people got sick of it. It sort of lost its novelty. And, suddenly, you see Democrats ready to throw some punches, and that seems to be working for them now.

Rosin: Was it a spontaneous occurrence that just happened when the word weird came out of Tim Walz’s mouth? Or do you get a sense it was more of an orchestrated campaign?

Graham: I think there’s a little bit of both. I mean, Walz clearly hit on something with weird. And it was interesting, even—you could see him sort of developing it over a series of TV hits and recognizing that it was working and then being like, Oh, I’m going to do that. Push that button more.

But I think even outside of that, kind of from the moment that Biden stepped down, you saw the nascent Harris campaign taking a little bit more aggressive approach and being less like, We’re going to stand back. We’re going to tell you about how important the stakes are, with a very deep voice, and more like, Yeah, let’s bring it. Let’s go. Let’s mix this up.

And so I think those things are all kind of connected and have coalesced to form a sort of go-low strategy, I guess.

I mean, what blew me away—and this sort of gets to the shift, I think—is the back-to-back speeches by the Obamas at the DNC, because they have been so much the avatars of this. You know, it was Michelle Obama who used that phrase in the first place.

You know, they’re very dignified. They try to sort of stay above the fray. And so Michelle comes in and gives one of the hotter political speeches I think I’ve ever witnessed live and throws some punches in that one, talks about not expecting things to be given to us, sort of stuff.

And then Barack Obama comes up after that and makes—I’m not even sure how I can refer to this—makes an unsubtle joke about Trump’s manhood.

Rosin: Yes. That was good. That was good. Good job there. “Manhood.” I like it. Very 19th century. Yeah.

Graham: And of all the people to say that—Barack Obama. You know, he’s a funny guy but, man, I almost couldn’t believe it. So that’s the one that sticks with me.

Rosin: You know what was astonishing to me about that moment? I did believe that, probably, when Michelle and Barack talk to each other, they talk like this, in the same way sort of people talk like this. It’s not that you’ve never heard Trump referenced or described in these ways.

It’s just out loud in an official proceeding. It was the saying out loud of things that, you know, people normally just say to their friends. That’s the breach that I was curious about. Like, how did everyone decide this is politically acceptable to say in public?

Graham: Right. Right. Totally. Well, I think also there’s—Democrats, either intentionally or unintentionally, coupled the idea that democracy is important and there have to be guardrails and there have to be rules to the idea that also you can’t say mean things.

And I think what we’re seeing from them now is you can actually decouple those things. You can talk about democracy being important. You can talk about guardrails. But it doesn’t mean you can’t also ridicule Trump.

Rosin: Yes. And, in fact, I noticed that it was an order of operations—that the mockery would come first, and then, But to be sure, we should take him seriously.

Graham: Yeah. A Spoonful of Mockery Makes the Medicine Go Down, or whatever.

Rosin: Yeah, something like that. Now, I have been reading, I mean, at least back to 2020, maybe 2015—there are often an op-ed or two, often from people who are either from other countries or have experience reporting in other countries that say, Mock the dictator. Like, Dictators are deflatable. In general, one thing I have learned from living slash reporting overseas is that dictators have big egos, and you just have to puncture them.

And then they quote George Orwell, who’ll say, “Every joke is a tiny revolution.” And it does seem to be a strategy that’s been out there and that nobody’s plucked or used before.

Graham: Yeah, I think part of that is it doesn’t come naturally to the people who the Democrats have had atop their tickets.

Rosin: Mm-hmm.

Graham: It’s just not a Hillary Clinton thing, and it’s not really a Joe Biden thing, either. And I think Harris just feels more naturally at home doing that.

Rosin: Do you have a theory about why weird worked? It’s such a casual, nothing word.

Graham: I mean, I think it’s a couple things. One, J. D. Vance says some things that are pretty weird. I mean, I think it just resonates because it feels accurate, and it resonates because it was coming from Tim Walz, who feels so much like your high-school geography teacher. And so it feels like something he—it doesn’t feel calculated coming from him.

It feels really genuine and like he’s the right messenger for that. Maybe that’s it. I mean, I don’t know. It’s so simple. It seems like it ought to be—it’s hard for me to believe that just a single word this simple has permeated so quickly. And I’m sure we’ll get over it quickly. But, like, even this much?

Rosin: But the way it permeated is fascinating because, in my mind, the word weird—I do think of it like a series of literal dominoes. So you could have called J. D. Vance scary. Instead, they settled on weird, and weird is actually a way to reclaim the silent majority. Like, it is a flip.

Graham: Mm-hmm.

Rosin: It’s like: You’re the weird ones. Like, We’re the regular ones. We’re the majority. And then the campaign kind of builds on top of that little word and reclaims freedom and then builds on top of that and reclaims patriotism. So this kind of dumb, nothing word becomes the cornerstone of an entire strategy of role reversals, you know?

Graham: Yeah, and it’s also tied to them—you know, Harris sort of trying to run as an insurgent against an incumbent, even though she is the vice president, and he’s not in office. All of these things tie together, totally.

Rosin: Right. There’s just a flip. Okay, now I want to talk a little bit about the dangers of this strategy. You and I both work at The Atlantic magazine. I would argue that The Atlantic magazine has been very invested in taking Trump’s threat to the future of our democracy very seriously. And so there is a way in which minimizing the threatening aspects of it makes it seem silly or like the person isn’t really powerful, and it seems like there’s some danger in that.

Graham: Yes, I think that totally is right. But I do think there’s a danger of minimization. And, like you were saying, you saw them sort of trying to do this, like, make the jokes and then kind of, But seriously, folks. This guy’s going to tear down democracy. And it’s tough to make those things go together. I also have questions about whether it really will be effective over an extended period of time. And I think about Republicans in the 2016 primary trying to ridicule Trump and use that against him, and mostly they all flopped.

Rosin: What do you mean? Can you give me an example?

Graham: Oh, yeah. So Marco Rubio made another sort of suggestive, phallic remark talking about why Trump was so defensive about having small hands and got a response from Trump, but it didn’t really work for Rubio. He ended up looking sort of like a middle-school kid trying to make a rude joke, and obviously he did not win the nomination.

Rosin: I think it’s the many against the one. I’ve thought about that too, because obviously this is not the first time anyone’s, you know, used their hands and made the Obama joke. But it has to be everybody.

It’s like that moment in the high-school movie when, at first, it’s one kid against the other kid, and the bully always wins. But then, suddenly, the entire school comes up with the line, and then the entire school all of a sudden represents joy and goodness, and they’re the ones singing on top of the desks, and the former bully is hiding under the desk. Like, it can’t be one-on-one. And that’s what’s the sort of amazement of this moment, is how it coalesced and took form all at once.

Graham: Well, I think Trump has lost something, too. He seems to have lost some of his speed. So you know, I think Axios had a story a week or two ago about his failure to come up with a nickname for Harris and listed all of the things that he’s tried, and just none of them are taking. And it’s hard for me to remember the last time he came up with a really good nickname, or at least a really catchy nickname.

And so I think, maybe, Democrats sense some weakness and sense that he can be attacked in a way that he just can’t defend as well as he once could. I also wonder if maybe he’s just—we’re used to him. He’s not as novel, and that takes some of the power out of him.

Rosin: Yeah, some of it is novelty. I mean, that’s cheesily poetic, like an O. Henry story that the metaphor is his inability to come up—like, the last one was “communist Kamala.” Like, his inability to come up with a nickname that sticks, that’s the moment when he crumbles. So interesting.

Okay. Back, though, to regular strategy. So here’s another danger, just strategically, if you’re running Kamala’s campaign. If you’re making fun of Trump, there’s an implied audience to your message. Like, you are signaling, I am speaking to people who make fun of Trump. That doesn’t seem to be the people that she needs to be speaking to right now. Those people are already with her.

Graham: I don’t know. I mean, I think that if it works—the kind of ridiculing strategy works because it actually reaches other people. I mean, the high-minded approach, I think, has reached all the people it can. If you think that democracy is under threat from Trump, you’re probably already supporting Harris.

So that’s kind of a base play at this point, in a weird way. But, you know, if you’re not sure—maybe you’re one of these voters who voted for Trump once or twice but maybe not with a lot of enthusiasm, and then you were kind of appalled by January 6, but you also haven’t loved the Biden-Harris administration.

If you make this guy seem small and weak and ridiculous, I think it can appeal to some of those people, in the same way that the schoolyard bully, by being undercut, suddenly loses his power over everyone. Like, once someone recognizes that he can be punctured, there’s no one who can be bullied, because they’ve seen that he just doesn’t have the mojo anymore.

Rosin: So you’re a political reporter who’s been covering Trump for a very long time. What do you imagine he’s saying and doing now? We’ve had dribs and drabs from the campaign, but I wonder, where do you think he’s at now?

Because we’ve been talking about the strategy aimed at him. But I’m curious—and I know this is speculation—how is it landing on him?

Graham: Right. You know, he tends to rage whenever he’s down. He gets really upset. And I think even in his public pronouncements, we can see a little bit of this. Like, threatening to pull out of the debate is a gesture of frustration with the way things are going, frustration with the coverage. And, you know, those things come and go, but I think the fact that those rumors are circulating is a sign of the kind of backbiting inside Trump headquarters that we remember well from previous campaigns but hadn’t seen until now.

Rosin: This private raging and campaign chaos, it’s not just a side effect of this kind of messaging. It’s a strategy unto itself. And it’s one that my next guest has spent years thinking about. George Conway’s efforts to publicly mock Trump often get the result he’s after.

But he’s also well aware of the risks.

Rosin: All that, after the break.

[Music]

Rosin: George Conway is a well known conservative lawyer. During the Trump administration, he was considered for jobs in the Justice Department, and his then-wife, Kellyanne Conway, was, of course, Trump’s very visible advisor.

But at some point, Conway started to sour on Trump while his wife was still working for the president. And then one week, in March 2019, Conway tweeted a few things about Trump’s mental stability, including a picture of the official definition of narcissistic personality disorder. Trump, who you could argue had other things to do, tweeted back that Conway was a stone-cold loser, the husband from hell.

Rosin: But he didn’t. And Conway took Trump’s inability to ignore him as proof that he was right because one of the hallmarks of narcissism is extreme sensitivity to criticism, an inability to ignore it.

Rosin: That year, Conway wrote a story for The Atlantic that said Trump’s narcissism made him unfit for the presidency. And he decided he would do something to help make sure he wasn’t reelected. Conway had an idea—a really specific, out-there idea, which came to him one day when he was listening to some strategists talk minutiae about which campaign ads to run in which markets.

Conway: It occurred to me that all you needed to do to drive the guy nuts was to run ads on the cable provider to the White House.

And one day I was in my office at 52nd and 6th in New York, and my friend Molly Jong-Fast said, Hey, I’m having lunch with Rick Wilson.

And I said, Oh, can I join you? Because I wanted to meet Rick. I knew he was an ad guy. I knew he was an amazing troll of Trump, and he wrote a book about Trump. And so we had lunch. It was, like, three in the afternoon at Quality Meats on 6th Avenue. And I told him my idea.

And he looks like his eyes lit up, because he understood immediately. And we started talking about the kinds of things you could run as audience—you know, we didn’t call it audience-of-one ads, but basically that’s what we were talking about.

You don’t have to run these ads all over the place. You don’t have to run them in swing states. You could run ads that just drive him nuts by just, basically, running it in the White House.

Rosin: So he tried it out. It was surprisingly easy.

Conway: And what happened when we formed the Lincoln Project later is we took that idea, and we started running ads in Mar-a-Lago. It cost, like, $5,000 for just one spot on—it was Tucker [Carlson] I think it was, or [Sean] Hannity—just to run it in a very, very narrow place.

Rosin: That’s amazing. And what were the ads?

Conway: The one ad that I remember he responded to was called “Mourning in America,” M-O-U-R-N-I-N-G.

Conway: The ad was a contrast to the “Morning in America” ads, the positive messages that Reagan did in 1984, except it was “Mourning in America.” And it was like, How terrible. Everybody’s out of work because of COVID, and Trump’s an idiot.

And Trump went out after watching that. I think he must have been watching it in the White House. It was on Fox News. And, like, the next day, he’s at Andrews air base about to get on Air Force One, and he starts yapping about the Lincoln Project to the media, that they’re calling us a bunch of losers.

And then, you know, the next day, Lincoln Project has $4 million in contributions, or some figure like that. And it was like, that was the proof of concept.

Rosin: Conway has kept it up over the years. More recently, he started the Anti-Psychopath PAC, which runs these quick-cut, trolly kind of ads specifically about Trump’s mental instability. There are a lot of mentions of Trump praising Hannibal Lecter, for example.

They, too, are targeted at an audience of one, and the aim is to elicit a very specific cascade of reactions.

Conway: Trump is somebody who could be manipulated. But you cannot control him, at the end of the day. And that’s why it’s just so important for people to keep hitting him with truthful descriptions of his behavior that conflict with his personal self-image, the image he wants to create.

And it deeply wounds him. I mean, it deeply wounds him, to the point where he responds to it in a manner that, instead of talking about economics in his speech that he’s supposed to be talking about economics, he’s talking about who’s weird and who’s not weird, which is weird.

Rosin: All right. So you’ve been doing this for a while. You’ve, like, road tested the strategy that the Democrats are now using. Were you surprised, starting from the weird moment and then going through the Democratic convention, how suddenly mocking the president was politically acceptable on a stage by very dignified people?

Conway: Yes and no. I mean, I think they finally get it, the Democrats.

The way you win this election, I thought, is Trump has to become the issue. And once Biden stepped aside, Trump became the issue because he was the old guy in the race. And the Democrats had a fresh face, and all of a sudden people were looking more at Trump.

You know, I’d like to think I had something to do with encouraging all of this, but I think they figured it out, and one way or the other. But it’s something. I mean, I’ve been banging the drums on this for years, and it’s sort of gratifying to see it finally happen.

I mean, in 2020, I was tweeting that the Democrats should hire a team of psychological professionals to advise them how to get under Trump’s skin. They didn’t do it then. They don’t have to do it now. You don’t really need shrinks to do this. You just need to, basically, you know, make fun of the guy.

And he gives you thousands of things to make fun of, from Hannibal Lecter to sharks to electrocution to injecting bleach. You know, the guy is endlessly—I mean, he’s absurd. And pointing that out, you have to do it in a way that reminds people, though: He’s dangerous.

Rosin: Yeah, that’s the subtext.

Conway: Right.

Rosin: So the text is kind of a joke, mocking, trolling. The subtext is: He’s dangerous. Got it.

Conway: Right. But it reminds me of this—there’s this Star Trek episode where the Enterprise is kind of held hostage by some incorporeal being, if that’s the right word, that was basically causing, through its telepathy or whatever, the crew of the Enterprise to engage in conflict with one another, literally fighting each other in hallways in the various decks of the starship.

Star Trek episode: The rest of our lives, a thousand lifetimes, senseless violence, fighting, while an alien has total control over us.

Conway: And Kirk and Spock, or one of them, realizes that the way to defeat this evil being was to start laughing at it.

Conway: And they started laughing at it, and all of a sudden, the being shriveled away back into space. And that’s kind of like the way Trump works.

Rosin: Yeah. That’s really good.

Rosin: Well, thank you so much for walking us through that. That was really interesting. I feel like you’re a prototype for what we’re now seeing on a big stage. So it’s just interesting to hear about your experience.

Conway: Thanks for having me.

Rosin: This episode was produced by Kevin Townsend and edited by Claudine Ebeid. It was engineered by Rob Smierciak and fact-checked by Sam Fentress. Claudine Ebeid is the executive producer of Atlantic audio, and Andrea Valdez is our managing editor. I’m Hanna Rosin. Thank you for listening. Live long and prosper.