“Gun to Your Head, Who’s Going to Win?”: Dan Pfeiffer, in Conversation With Sarah Longwell

As we inch closer to one of the most crucial elections of our lifetime, we decided to team up with our friends at Substack, who over the last month have been facilitating dialogues between influential political figures, writers, and commentators. This week, we’ll publish several of those dialogues on the Interview website. The second, edited for length and clarity below, features former senior advisor to Barack Obama and Pod Save America co-host Dan Pfeiffer in conversation with the political strategist and publisher of The Bulwark Sarah Longwell. Read on for their discussion about both candidates’ closing arguments, Trump’s ploy for disaffected young men, and the state of the presidential race —and remember to vote!

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DAN PFEIFFER: We just finished watching Vice President Harris’s closing argument speech from the Ellipse, the place where President Trump delivered his infamous January 6th speech. Sarah, what did you think of Vice President Harris’s closing argument?

SARAH LONGWELL: I thought it was great. I don’t like pumping people up on hopium. I promise I will tell you the truth, but I really thought the closing was extremely strong and new. There were some parts in the middle where you could tell that their team had sat down with each other and been like, “Do we pack it full of some policy things?” I started to go into the visuals of it all. I thought she looked amazing. And I don’t mean amazing like, her hair looked nice. I meant that she just looked presidential. Owning the stage, clear in purpose, lots of clarity. Anyway, I thought it was an excellent closing argument. What do you think?

PFEIFFER: Right. That was my take. There was a private debate within the Democratic Party and the anti-Trump Coalition for a while now and that spilled down to The New York Times over the weekend. You either had to talk about the economy or about fascism, and whichever choice you made was going to determine the election. And the truth is, she had to do both. She did that in the speech. It was a false choice. She’s just in a very tough position, because she’s only been in this race for four months and no one knew anything about her beforehand. And I thought she tied them really well together. It did feel like in the CNN Town Hall, which she used again tonight with the to-do list, and it sort of unlocked how you tie the two of them together. Because it’s not about the word “fascism”; it’s about Trump being in it for himself and for his own power, and then getting to the consequences [of that]. So I thought that was a very good speech. I happened to have CNN on, fortunately or unfortunately, so I saw a little of the panel afterwards and there was some Republican on there I’d never seen before. But his take was that having the White House in the background was a huge mistake in a change election. I find that to be absurd, but…

LONGWELL: Listen, first of all, there’s always going to be some lug nut on a CNN panel looking for some reason to take points away, especially when she does a great job. I think that on the theme of having to balance many things, she was doing this with her words as much as the visuals: “I am the current vice president and I have the chops, take me seriously.” And also, “I am something different and new. And I’m in this place where the last footage you’ve seen from there was the time Donald Trump did the darkest thing that’s ever happened in our country around elections and politics.” And I would say she has, for a long time, done a good job explaining why Donald Trump is bad, and she’s sort of hit or miss on who she’s going to be and why she’s going to be better. I thought she did it tonight. And, look, after he kind of crapped the bed at Madison Square Garden, to have him ending on that note and her ending on this note, that’s a strong contrast.

PFEIFFER: She’s used the phrase “new way forward” and “turning the page” since the convention. But today, she kind of painted the picture of what that new way forward was. Not just in policy, right? Obviously, she’s going to do the price gouging thing and the housing credit and the $3 billion and all that. That is great and important and people love that. But meeting with experts, sitting down with people you disagree with, inviting them to the table and not demonizing them, that’s the part of Trump’s era that has gotten a little bit lost over the last four years. David Axelrod, my old boss, has this thing that people are always looking for the replacement, not the replica. And she’s essentially running against Trump as if he was the incumbent president right now, as if people’s minds are in 2017 to 2020. It’s just like how Barack Obama was not running against George W. Bush, but everything that Barack Obama represented was a change from Bush, right? That’s how we thought about our messaging and our position in that campaign. For people who are looking for something different, she gives them an opening there. 

LONGWELL: I also thought, she’s not running against Biden at all, but she is also trying to say she’s different from Biden. And I think that she walked that line of, “I am the vice president and I was proud to serve with Joe Biden, and also I’m going to be my own person with my own agenda and my own way of doing things.” I was glad she put some meat on the bones. I interviewed her at one of these town halls with Liz Cheney and I kind of asked her, “Hey, you talk about turning the page. Tell me what’s on the other page.” At that moment, her answer was fine but not superb. And I thought tonight it was a much clearer, “Here’s what you can expect from me as a president and here’s some policy stuff, but also here’s some big picture American thematic stuff. I know how to compromise. This is a lost art. I know how to listen to other people. These are things Donald Trump can’t do.” 

PFEIFFER: Yeah. Did you take anything from the closing message and the ad traffic about who their top targets are over the last seven days?

LONGWELL: Obviously, there’s this question at the end of, do you make a play for the disaffected Republicans? Which they feel like she’s been doing. There’s been some Democratic criticism like, “Why are you focused on doing this stuff with Liz Cheney? You’ve got to turn out the base.” And, again, I thought tonight was about her ability to do both. I was writing them down—she did insulin caps, price gouging, building homes, child tax credits, senior care covered by Medicare. Then she called out the Trump abortion ban, which maybe she’s been doing, but I hadn’t heard before. That was the stuff for the base, the popular stuff. But then she did the stuff for the center-right people. She’s like, “We are just going to stop using immigration as a political football. We’re going to focus on solving it.” She was getting cheers. I thought she made her pitch to the disaffected Republicans and to the base.

PFEIFFER: And the same day or day before, she’s on the Breakfast Club with Charlamagne, And she’s doing Shannon Sharpe’s podcast in a way to reach out to young Black men. She’s kind of doing all the things because you really are stitching together people from all these different parts to get there. David Plouffe estimates it’s 4% [that are] truly undecided, then about 10% if you include people who might change their mind and people who are low propensity voters thinking they may or may not vote. And when you look at that, the easiest votes to get are theoretically the Nikki Haley Republican Independents, because they’re definitely voting.

LONGWELL: That’s right.

PFEIFFER: They’re going there. And they’re either going to vote for Kamala Harris, Donald Trump, or they’re going to leave the top of the ticket blank. A lot of these other people, you’ve got to convince them to do two things: to vote, and then to vote for you. And so can you squeeze more out of that group than you were already getting? And if you can, then you have a very, very good shot of winning Pennsylvania, Michigan, Wisconsin, because of the numbers.

LONGWELL: I completely agree with that analysis. We’ve been getting politically realigned out of the Republican Party, Bulwark Republicans, the Red Dog Democrats. We’re mad, we’ve hated MAGA for a while. But I talk to and listen to the focus groups all the time. And sometimes people forget this, but I was talking to this group of young voters at Kenyon today, my alma mater, and I was like, “young people who come to the Republican Party are coming for Donald Trump, right?” Donald Trump’s all they’ve known. Since these kids were 10, Donald Trump’s been on the scene. But if you’re 65 and you came to the Republican Party for Ronald Reagan, you’re like, “Wait, what is this party?” So old white voters, it may sound counterintuitive because you think that’s not really normally a target-rich environment for Democrats, but those are actually the voters that have been kind of hanging in with her. And the good news is that in Pennsylvania, Michigan, Wisconsin and Nebraska too, there are a lot of old white voters.

PFEIFFER: Yeah.

LONGWELL: That’s what she’s been capitalizing on. And every cycle, more of these center-right voters look up and say, “Man, I did it once, but I’m not doing it again. And then there was January 6th, and I’m out.” The other thing I take away from the focus groups that gives me optimism is that these swing voters really hate Donald Trump.

PFEIFFER: Yes.

LONGWELL: Even if some of them are like, “Yeah, he’s better on the economy and maybe I’ll vote for him,” they just hate his guts and think he sucks. They don’t hate her that much. They’re tribally not used to voting for Democrats, but they don’t hate her. She doesn’t fill them with dread about what’s happening to the Republican Party. And they must have data to support this. They’re not doing this road trip with Liz Cheney if they’re not looking at the numbers and thinking, “The biggest pool of gettable voters for us right now are these center-right independent disaffected Republicans.”

PFEIFFER: Yeah. I talked to David Plouffe on Pod Save America a couple of weeks ago and I asked him, “There’s always one thing in the public polling that the public polling misses, right?” Trump’s Latino share in 2020 was a thing that did not show up in the public polling. And he said the place he thought the public polling was likely to underestimate her performance with was the Republicans and Republican-leaning Independents. And for weird, nerdy polling reasons, those people are not getting captured because they are jamming the polls into this 2020 frame. Something changed in these four years. The models miss it. A lot of stuff has happened since 2020, and it was going to be Biden-Trump. It’s 2020 all over again. 

LONGWELL: I mean, obviously with Republican voters against Trump, we’ve been banking on these voters now for multiple cycles. It’s paid off every time. I keep believing that there’s more of them. The other group that I think is going to matter a lot is non-college white women.

PFEIFFER: Yeah.

LONGWELL: Working-class white women in these states vote for Trump at a high rate, but it feels like she’s been doing slightly better with them than Biden did, right? So there’s been a little bit of a trade where she does slightly less well with non-college white men than Biden did, but she’s doing much better with non-college white women and working-class women. And I think a lot of that is Dobbs [v. Jackson Women’s Health Organization]. That’s a place where there could be an under-sampling and there’s more breaking for her than people might think. And we talk about this at The Bulwark a lot. People have made a lot of the gender gap this time. I think that sometimes people are like, “I don’t know, gender doesn’t look so different from 2020.” The reason I think it’s so different is that as you come down generationally, the gap gets really, really big.

PFEIFFER: Yep.

LONGWELL: It’s not as pronounced up high. But if you were going to stake your election on those young women turning out versus the young men that Donald Trump is trying to put rocket fuel behind, I’d bet on those young women any day just from who’s more likely to turn in their homework and who’s more likely to show up and do the thing that needs to get done.

PFEIFFER: Right. And that’s exactly the group that Michelle Obama was talking to in her rally last weekend, these women who are married to MAGA men. She made the very explicit point that your vote is secret, they don’t have to know who you voted for, it’s your choice. And, yeah, that is a very interesting group to watch because of Dobbs. And it’s why the campaign has an ad out now that uses some of the language from Project 2025 on abortion. They just put a ton of money in. There’s some Future Forward ads that are hitting that group very specifically. So that’s a group to watch. And then there’s young men, who obviously Trump was courting very aggressively and probably somewhat successfully on [Joe] Rogan. I don’t know what you thought of the Rogan appearance.

LONGWELL: I am not as reliable as I could be on evaluating Trump because I always listen to it at a fast speed because I can’t tolerate it that much.

PFEIFFER: Me too. 

LONGWELL: And I don’t think he sounds that good, but I heard a lot of other people be like, “No, he was pretty good on Rogan.” But I think he’s frequently flat. I mean, sure, three hours is a long time, so I guess he held up for three hours. But I mean, I’m not his target audience for that. Whatever. It was fine.

PFEIFFER: Yeah. I mean, there were 36 million views on YouTube last I checked, and it’s the biggest podcast in the world, so lots of people heard it. Now, 50% of Rogan’s audience is outside the United States, for what that’s worth. I watched the whole thing, I also watched it at a fast speed because that’s how I watch all my YouTube content. I thought it was better than the portrayals from folks on our side. He obviously did weird Trump stuff. He was flat sometimes, largely incoherent. But to an extent it helps. It’s probably just his presence there and then the gazillion clips on TikTok of him, which are usually his best moments, not his worst moments. Particularly if you have a TikTok algorithm that looks like mine, as a white male in my mid-to-late forties, TikTok has a real view of what they think I would like, and it’s very Joe Rogan, Donald Trump-y, which at least is a reminder to vote. Like with all things Trump, he did not maximize his opportunity. And unlike at Madison Square Garden, he probably didn’t shoot himself in the foot here, so it was kind of a mixed bag. Do you think she should do it if she got the opportunity?

LONGWELL: I think that she should do it. But I saw today that Rogan’s like, “Well, you’ve got to come to me and you’ve got to give me the three hours.” Because the campaign had been like, “Fly out here, she’d love to sit down with you for an hour.” And he’s like, “No, you’ve got to come to me.” And I’m like, “Fuck, Joe Rogan.” I don’t know.

PFEIFFER: Yeah.

LONGWELL: I’d like to see her do it. I want her to do all the non-traditional media. I loved when she went on Bret Baier because I think people respect the hustle, they respect you’re going into the lion’s den. I think you can reach people you might not otherwise, and you can pick off some people at the margins or at least earn some respect. I think it’s fine, but I don’t think it’s a do-or-die. What are you, Joe Rogan? The Pope? She’s got to fly to you? It’s silly.

PFEIFFER: Yeah. I think if this was three weeks ago or a month ago, sure. Go to Austin for a day, do a fundraiser, do the podcast. It’s actually probably high-reward and relatively low-risk because he is not a contentious interviewer, and I think she would do very well in that environment. But with six days to go, I would not choose losing an entire day to go to Austin to do three hours of Joe Rogan instead of barnstorming Michigan, Wisconsin, Pennsylvania, Georgia, et cetera.

LONGWELL: Especially after tonight. I mean, Donald Trump earned himself two days of negative press, and a lot of people weren’t watching that rally, but it lit a fire under a bunch of Latino and Puerto Rican influencers. I didn’t know who Bad Bunny was, but I went and figured it out. Tim Miller made me look at some shirtless photos of him. And it’s like, “Okay, this guy’s super influential, and if it costs him the 450,000 Puerto Rican votes that are in Pennsylvania, good.” This is lousy for him as his narrative for the close. I don’t know how anybody watched that speech tonight and thought anything other than, “Wow, that was a great night for her.” 

PFEIFFER: Yeah, I agree. And the Trump thing has an opportunity cost, right? Obviously you have this very specific group of voters in Pennsylvania in particular who are among the voting eligible age, which is nearly four times Biden’s margin in 2020. That’s how many voters there are. So that’s obviously problematic for him, but also it ruined his rally. Not that his speech was good, but the press kind of gives you a freebie on your closing argument speech, so you have to work really hard to screw it up. And they really did a phenomenal job of that. Because even if it hadn’t been Tony Hinchcliffe, it could have been the guy who called Doug Emhoff a crappy Jew, the guy who called Kamala Harris or Hillary Clinton a sick bastard, or all the other terrible things that were said.

LONGWELL: Steven Miller saying that America is for Americans.

PFEIFFER: Yes.

LONGWELL: And you’re like, “Okay, say it to Elon’s face. Say it to Melania’s face.” What are we doing here?

PFEIFFER: But then he goes to Pennsylvania today in Allentown, a place with a large Puerto Rican population, and the entire coverage and narrative is around this. And I can’t speak to the higher powers in politics, but the fact that Kamala Harris was doing an event in a Puerto Rican neighborhood in Philly on Sunday announcing her plan for Puerto Rico, and hours later this comedian at Trump’s event says this thing about Puerto Rico, and then two days after that Trump is flying to Allentown for a previously scheduled event is a sign that maybe if there is a higher power, it is on a side here. Luck matters in the end in a close race, and that’s a little bit of luck there.

LONGWELL: I think, if you’re like, “Gun to your head, Longwell—who’s going to win?” I think it’s her. And a lot of it has to do with late-breaking Independents. People are like, “Who’s undecided at this point? Who are these insane people who are undecided?” And I’m like, “I don’t know. I hear from a lot of these people, and a lot of them are the center-right folks.” And people who are just political Independents, maybe they just tuned in. They literally are like, “I’m going to check out their closing arguments and call it a day, or I’m just working on vibes,” or whatever. This is why Hillary Clinton, whether it was the flu plus Comey plus the bad headlines, she couldn’t catch a break there at the end. 

PFEIFFER: And the other reason Hillary lost is a lot of them who voted, voted for Jill Stein and Gary Johnson in the end because they thought she was going to win. But she didn’t end on a strong note. So it’s like, “Well, I can’t vote for Trump, and I’m not going to vote for Hillary, so I’m going to cast the vote for Jill Stein.” Obviously, it’s been helpful that a lot of the leaders from the Uncommitted Movement have endorsed her. The Uncommitted Movement itself has been supportive in some ways. But that’s the one place where you could still get that third-party number that could be problematic.

LONGWELL: Hey, talk to me for a second about that uncommitted vote because I get this question a lot.

PFEIFFER: Yeah.

LONGWELL: I did focus groups on this back when it was Biden’s. My sense is that with the degree of animosity around this, you’re kind of down to a few diehards, and most people, especially the white allies, once Joe Biden stepped off stage, they were all like, “This is cool. We’re fine now.” Is that your sense, or do you think there’s still a big movement out there to sit it out?

PFEIFFER: I mean, it’s a question of how big the movement is, right? There was that huge debate after the Michigan primary when it was like 100,000 people who voted uncommitted in that primary where Biden was largely unopposed. If she wins Michigan by what Biden won it by, maybe that’s not going to matter. If Michigan looks more like Wisconsin in terms of margin, or Arizona and Georgia in terms of margin, then that can be very problematic. Because I don’t think it’s the same as it was before, but it’s still something that the people I talked to in the campaign are very focused on and trying to deal with over the final six days here.

LONGWELL: I guess there’s no reasoning with people on this particular point. What is your view on the state of the race? We haven’t talked about this. You and I haven’t been on together. Obviously, I consume your stuff. But where do you think things are at the end here?

PFEIFFER: I think that we have reached a place where it’s sort of impossible to know what’s going to happen, right? The race is so close that polling is useless for predictive purposes. 

LONGWELL: I know.

PFEIFFER: There’s definitely been some movement in his direction since her peak, and you sort of always kind of knew that was coming because people always look at margin and not vote share. So her margin was three, but his vote share was two points under what he got in the last two elections. So he’s obviously going to get at least that, or close to that. It’s kind of narrowed back to where it was. Anything that happens over the last week could be incredibly decisive and it could be small things. Little things can make a difference here. Are there not enough voting machines in Maricopa County? Is there bad weather in Waukesha, Wisconsin? Is there traffic in downtown Philly? Having said all of that, and I don’t make predictions because of my brutal experience in 2016, but if I had to pick which candidate’s side I would rather be on, it would be Kamala Harris’s campaign for the following reasons. One, she’s much better liked, right?

LONGWELL: Yes.

PFEIFFER: There’s a nine to 10 point delta between their net favorability, and that matters with undecided voters. They tend to break to the person they like better, historically. This is a unique election, but history is on her side there. Two, I still think her easiest path to 270 is easier than his easiest path. Pennsylvania, Michigan, Wisconsin, three states the Democrats have won in 16 of the 18 statewide races since 2018. You have three Democratic governors who have built up the party structures there in really good ways, and this is a weird thing for me to say as an Obama alum, but Trump is depending on these low-propensity voters.

LONGWELL: Yeah.

PFEIFFER: And that was the argument people made about Obama and why he couldn’t win, because are these young people really going to turn out? But the difference is that Obama built a campaign to turn those voters out, and I’ve seen no evidence that Trump has done that. Maybe Elon Musk and Turning Point, those people have some secret sauce that I don’t know about, but it takes an organization to turn out the voters he needs and they haven’t built that organization. So she has the better hand to play over the next six days here, I’d say.

LONGWELL: Yeah, I agree with that. And the Obama years were sort of marked by this idea of having a better digital strategy.

PFEIFFER: Yeah.

LONGWELL: They figured out how to find the people they needed. And I’ve always been like, “What does Elon know that the rest of us don’t?” They’re running this very gross, “Okay, we’re going to run an anti-Israel message here. We’re going to run a pro-Israel message here. I’m going to try to scare these different subsets of voters. We’re basically going to say Kamala Harris is on both sides of an issue just to scare these voters.” And I’m always like, “Is it working? Does he have data? Does he know exactly how to pinpoint these people?” I don’t think Turning Point does, but I do always wonder what kind of data Elon’s sitting on.

PFEIFFER: The one thing that they have done, they didn’t build a field organization, but they have very strategically used Trump’s time to target their voters. He has done every podcast there is to do in the manosphere. Like I said, Trump always has bad moments in all of them, but in general they have had very friendly audiences and they’re where Trump’s at his best. And that has been very well done and strategic and disciplined, and it’s been an effective media strategy. Now, is that going to be enough to turn out the voters? Who the hell knows, but that part of their campaign’s been effective. But whether it works or not, is there someone calling? Is there someone knocking on doors? Do they have a relational organizing program where you’re getting the mom and the uncle and the grandmother to get the son to vote? I haven’t heard any evidence that they’re doing that.

LONGWELL: For me it’s like, what are you picking up in the focus groups? I’ve sort of had a pretty unsatisfying answer, which is that I could explain either outcome through the focus groups. And so I do tons of swing voter groups—not just undecided groups, but actually focusing on people who voted for Trump in ’16 and went to Biden in ’20—to figure out if she’s holding onto those voters or losing them. And I would say there’s good news and bad news in there. The good news is she holds most of them. The vast majority of them stick with her. In every group of nine or 10 people, she’s getting seven or eight or nine. But there’s always one or two that are going back to Trump. And it’s usually a guy, and it’s usually because they’re mad at Biden about the economy. And now I also do another group in my persuasion category which is two-time Trump voters who are out on Trump.

PFEIFFER: Yeah.

LONGWELL: These are new and gettable voters. But the thing that I can’t quite quantify is whether there are enough new two-time Trump voters who are out on Trump to offset the backsliding that I see a little bit among swing voters who were pissed at Trump over COVID and wanted a change with Biden, and then Biden got in there and they’re mad about it. They don’t think he did a good job. They’re unhappy about the economy. And so they say, even though they hate Trump, “I’ll close my eyes and ears and just enjoy his economy.”

PFEIFFER: Yeah. The other thing that makes me feel a little bit better is the blue walls. Every single battleground state, with exception of North Carolina, the demographic shift since 2020 has been in her favor.

LONGWELL: Yeah. And I saw something in the chat about North Carolina and how because they have such a repellent lieutenant governor, Mark Robinson, who’s running for governor, who had all the porn and paid for the abortion and is a Black Nazi and just really couldn’t be a more atrocious candidate. Like, [he’s] really taking Herschel Walker and saying, “Hold my beer, buddy.”

PFEIFFER: Yeah.

LONGWELL: And I was talking about the abortion ballot initiative in Arizona, and there’s a little bit of, “Well, won’t the fact that you have this ballot initiative hurt Trump?” And I’m never sure about this one because it allows a lot of these center-right voters who are pro-choice to basically bifurcate their votes.

PFEIFFER: Yeah.

LONGWELL: So they can be like, “Nope, I am going to vote for this ballot initiative to protect abortion rights because I care about that, and that gives me permission to vote for Trump over here.” Similar to Mark Robinson. I wish what he did was a reminder to voters of how vile Trump is, but the focus groups I’ve done in the state sort of show the opposite, where they’re like, “Oh, I’ll never vote for Mark Robinson, but Trump’s perfectly normal.”

PFEIFFER: The abortion ballot initiative is interesting. I mean, it’s not a political calculation in Arizona or Nevada. In Arizona, in particular, you had to do it to combat the law. But it probably would’ve helped Biden more than it’s helping Harris because Biden had tremendous turnout challenges. Harris doesn’t have those challenges, and so your hope is people who didn’t like Biden who were Democrats but cared a lot about reproductive freedom would turn out, and then obviously they’re going to vote Biden. Harris has probably gotten all those voters, and so there is this risk that it makes you split. 

LONGWELL: We’re looking rough. I use a lot of concealer right now. Guess what, guys? Don’t get tired. Authoritarians want you tired.

PFEIFFER: Yeah, that’s right.

LONGWELL: So don’t get tired, and let’s go hard these last few days. It’s right here.

PFEIFFER: Absolutely. Sarah, great to talk to you as always. Thanks everyone for joining us and listening to us talk. Good luck surviving this upcoming week.