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A
Hi, Bill Kristol here. Welcome to Bull work on Sunday. I'm very pleased to be joined today by Rob Flaherty wrote a terrific piece for the Bulwark on Thursday. I think it was Thursday morning and it's gotten a lot of well deserved attention. Rob was deputy campaign manager of the Biden campaign and the Harris campaign, particularly in charge of digital media. And this was a piece in which Rob laid out what he would have told the. What he did tell, I guess the DNC autopsy, which, however, has never appeared. So good to have your thoughts memorialized in the Bulwark. A very interesting piece on many accounts, actually, in terms of digital media, the future of a lot of aspects of campaigning. But I thought we'd focus today on some of the bigger picture conclusions. You draw the first part of your piece, but I want you to go read the piece. It's on the Bulwark website. Anyway, Rob, thanks for joining. Thanks for joining me today, Bill.
B
Thanks for having me. Really appreciate it.
A
And thanks for the piece, which is really interesting. So, yeah, here's what I told the DNT autopsies, if people want to look it up and should read it. So let's talk about some of the things you've been around. I should say you're very young, but you've been involved in politics for quite a while. I think you began as a student, right? At Ithaca College. I remember reading about this Ithaca mayor's race where some outsider won an upset victory and there were a couple of key student players and helping organize that. And that was now I discovered. That was you, right?
B
It was, it was the inmates running the asylum.
A
What did you. I'm curious. I always tell young people this is a bit of a diversion, but why not? I don't know. I was not involved that much in campaigns when I was young and you know, I was academic, getting my PhD and all this nonsense. But the. I always advise young people to go work on campaigns. I think you can learn a ton. And also they're so fluid and you can rise much faster if you're good and you're not in a little box the way you are of corporate structure. That's not quite so much true of a presidential campaign, obviously, but certainly a local campaign. I'm curious, do you, do you agree with that? Was that, I mean, I'm just, is that good advice? And do you, what did you learn from that?
B
Campaigns are the best. They, they're, they're pressure cookers. You build great relationships with people. You learn like the softest skills of like how to like, you know, work with a lot of sort of people who are both different and the same as you. So I tell everybody it's like the best thing you can do. And I think that like, you know, it sounds shoopy or whatever, but like working as, you know, an 18 and 19 year old on a campaign where the oldest person was 22 to win a mare's race in a college town, like to me it sort of did show like anything really is possible. And, and so it was sort of the first little bite I got of it and it's what got me hooked. So anyone who wants to do a campaign, go do it. It is, it is great. And now maybe I may not do
A
another one, but not after this, not after this article. No, that's not ceiling. You know, now for me also, the thing I learned is someone sort of coming from the study of political philosophy and all this stuff is, you know, the kind of recalcitrants of reality. I mean, you know, you have these theories and ideas and positions and issues and then you actually deal with human beings out there at a certain time and place and they have their own interests and views and prejudices and, and it's very, it's a good wake up call for especially maybe younger people who are, I don't know, you know, who are like me who had been in limited circles, honestly. Right. You know, I'm not saying I, I was aware of other, God knows, I think I read up a lot of history and stuff. But the campaign is a real, could be a real, real cold water in the face, don't you think?
B
Oh, 100. I mean, you know, you have to actually go talk to real people and put your ideas in front of them and they will say, I don't like it. And so you do get sort of hit with the, you know, the wall of pragmatism, but also like the, you know, you have to, at a certain point when, when you were able to make the case for something and drag people along, it is also sort of uniquely thrilling. Right. So, yeah, in a lot of ways it, it can both be, you know, like, you know, like you said, you know, splash of cold water in the face, but it can also be really transformative in ways that are, are amazing. And so, you know, you get, you get all of it. Which.
A
Yeah, well, both doing, they go together in a way. Right. I mean, but anyway, enough of that. So. Well, let's talk about your lessons of from 2024. One very striking feature of your pieces, you stressed us right at the beginning is the importance of brand, as they say these days, the brand as opposed to. Or maybe as opposed to too strong, but by contrast with the normal focus on, you know, issues. And so say, what do you mean by that? And what is. Yeah, explain that.
B
Yeah. You know, it's funny, I think if you. One of the things, if you look at the data that the campaign put together, we found that the tactics, the individual tactics, were reaching the voters that we wanted to reach, and the voters, when they were reached, said we liked it, but obviously something wasn't gelling. And I think that so often Democrats, and I certainly think this was the case in 2024, approach politics as sort of the culmination of a laundry list of popular policies. And the reality is it's about something bigger that is more than the sum of all of those parts. And so, you know, it's the overarching story of why are you in this race? For what reason are you in this race, and what are you going to do? I think that that is the thing that had to be defined, and I don't think that we necessarily had a very clear story there, which allowed everybody else to put their biases about the status quo, their feelings about President Biden, the attacks that were coming in from Trump on Vice President Harris. And that, you know, gets us to. For other reasons, too, but it gets us to the outcome that we. We had in November 2024.
A
And do you think it was fixable in a sense, or how much of this is just driven by some realities? Kamala Harris was Joe Biden's vice president. People were water change. You know, she was stuck. She was the defender, had to be a defender of the Biden administration, et cetera. How much can one work to define one's own? I mean, I guess when you're in a college race with an unknown guy, in a way, it's harder, but it's also easier.
B
Right.
A
You have a lot of flexibility in a college town defining your brand, whereas Kamala Harris, as a sitting vice president, less so, but you could have done more.
B
Yeah, I think that a lot of this was baked. I think President Biden getting into the race was sort of the beginning issue. You know, I don't want to say original sin, but it was sort of the, The.
A
The.
B
The sort of foundational issue. And then, you know, that just makes it really hard to dig out of. And this is true. It's not just true of President Biden. It's true of incumbents across the world. You Know, everybody had a hard time if you were in power. And we've seen that for conservative governments across the world in this environment. You know, we've just seen people are mad. And so I just think being the party in power, I don't think anybody from the administration probably, probably could have won. I think it was possible. You know, I think if, you know, there were a couple of things that were done differently, maybe it does lead to a different outcome. You know, I think that if the election happened the day after the first debate, we might have won, or the only debate that we had in the general, we might have won, but a decent amount of this was. Was a little bit baked in. But, you know, there were things that we could have done that might have led to a. A better. A better result.
A
And so what in particular, I'm just curious what, you know, what do you wake up at night thinking, God, if only we'd done either something you proposed. It wasn't an idea that wasn't accepted or an idea of yours that was accepted that didn't work out well, or what sort of. What are the regrets?
B
Well, it's funny, I mean, I think looking back, there were things where I think if people had listened to my suggestion, there would have been a better outcome. I think there are things that if people had listened to my suggestion, it would have been even more catastrophic. So, you know, it kind of goes in either, you know, it's hard to say, I think that, like, you know, it's hard not to look at the success of affordability messaging and in the time since and sort of say that that might have been a more successful tact if the. And the thing is, is, you know, this is. This gets at this question about brand. Like a lot of our paid media, when we were advertising at people, was about middle class economics and the economy and all these things, but it wasn't the thing that people thought about when they thought about Kamala Harris. And that, to me, I think, was like the thing that was missing. On the other hand, though, let's say you run a campaign that's like, I am in this because life is too unaffordable for Americans. Does that stick when you're the sitting vice president of the United States? And that kind of gets at the thing about, gosh, I don't know if. I don't know if anyone from the admin could win. And so to me, there's this baseline question, though, of Americans were really mad at the status quo, and they're really mad about the institutions of America not delivering from them. And when your campaign feels like the representation of the institutions of America making their case, that's hard. And so the answer probably would have been in there. But again, I don't sit here saying that was the sure bet. So it's hard to say.
A
I mean, I was an advocate of Biden not running, and the first newsletter I wrote, actually, I took over from Charlie Sykes, and I remember it was Lincoln's birthday. So 19, February 12, 2024, was calling on Biden not to run again and sketching out a somewhat fanciful, perhaps exciting primaries of, you know, among many candidates and a contested convention in Chicago. And I remember how that would work out fine. And many people told me that the last contested Democratic convention in Chicago in 1960 didn't work out so well and stuff. So it was a perfectly reasonable object. I mean, was that always. I mean, so I think Biden not running wasn't fanciful. He could have made that decision. Was the notion that if he pulled out at some point once he was running, that one could have avoided to some degree the incumbency problem by having a contested primary? I would say even one that Vice President Harris might have won. I still think it would have felt differently. Or was it just impossible to do, given the timing?
B
I think if President Biden doesn't run, there would be a contested primary, Right?
A
Certainly if he doesn't run in the first place. Right.
B
And I. But I think. I think Harris probably wins. I mean, this is the thing is that, like, voters are voters, you know, and, you know, I think it's. It's very possible she would have had, you know, the sort of leading position. But I think the unique. The uniqueness of our system is, you know, you can have a campaigning party and a governing party and. And, you know, I think a economically populist person who comes out of a primary teeing off the Biden administration, which was enormously unpopular, I think would have been better prepared to win a general election. You know, I think the. The challenge for Biden deciding to stay in is at that point, you know, voters. Voters at the time were like, yeah, we'll stick with President Biden in the Democratic primary. And so it was hard for people to kind of break in against him. And so that's why, you know, it gets complicated from there once he, you know, decides to. To get in. And then you kind of look at
A
how about when he decides to get out? Would it have been crazy for him and Obama and five other people to say, you know, what It'd be healthy for the country. Let's have a contested, you know, primary. It'd have to be arranged as a kind of in a Rube Goldberg wave as the primary dates had gone by and so forth. But it wouldn't have been crazy to do something like that and have an open convention. Or is that just too late, too impossible?
B
I think there's sort of two things here, which is one, you know, a contested convention decided by insiders. I think the things that you would do in that period would probably look, look bad to anti status quo voters generally. But there was also like more of a, there's like a true campaign brass tax question which is, you know, at that point Biden's campaign is 200 million cash on hand that can't go to anyone but Kamala Harris. And so there was sort of a cash deficit question as well. I just think of a, a short, I mean at that point it would have been what, two weeks, three weeks primary run. You know, I don't think it would have done, it wouldn't have done folks a lot of favors especially because I think the kind of campaign that you need to run in order to win probably is not the kind that would appeal to super delegates. And so, you know, I worry that that would have been sort of a more damaging outcome than Harris, you know, being in the position that she was in. But again, you know, I'm no, and
A
you, and you could be right. I mean, she got off to a good start. After all, it's not as if she was, you know, it didn't feel that bad after going into the Democratic convention. I don't think things were so, were so bad. I mean I, the 68 thing, I mentioned the convention there and that was the first presidential race I had any real knowledge about. I was incredibly minor league 15 year old volunteer at the Humphrey headquarters. And actually in, in New York, I mean, well, I was, I was, you know, I was an anti communist liberal. Anti communist. So on the one hand I was for Humphrey, I was for Humphrey as opposed on the other hand to Kennedy first before he was shot and then McCarthy, you know, so I was not on the left, so to speak. Humphrey was unpopular obviously with all of the new left. On the other hand I was for Humphrey because I admired him for civil rights and Fred for his anti Communism actually throughout the 20 preceding years. Liberal anti communism wasn't a huge fan of Nixon. And then there was of course Wallace. So the Humphrey camp is interesting if you look at, I mean he lost because he couldn't escape Johnson's very great unpopularity in Vietnam by that point. Much greater incidentally, bigger problem than Biden had. On the other hand, he rallied from, you know, 20 points down to almost win. And it's for me it's a bit of a lesson that I don't know, maybe these things aren't quite as big. You know, he was able to make it much closer than he might have by running a certain, I don't know, maybe a certain kind of campaign that maybe, maybe Harris could have done a little bit more of some of what Humphrey did. But anyway, who knows. It's interesting. I don't know if the analogy, how much, how helpful the analogy the analogy is. I mean I think why she was running. Yeah, that is important, isn't it? I mean it's just stupid. It seems so simple minded to say, well why are you running for this office? But voters do kind of want to know what you're going to do if you win, right?
B
Yeah, it's like a pretty. I do think this is like a politics as it has always existed. It was fine to kind of hand wave that question, but in the world in which you're communicating now, you are up against a wall of people who like directly create the content that they are making. Right. And so you know, you are seeing a person who has real conviction all the time and then you go up against politicians who are like I exist and I'm here, you know, and you should just accept that I'm here for whatever reason and you know, say what you will about Zoran, like I think that was sort of the brilliance of the marketing of his campaign is you knew he was in it for affordability. He had specific three very easy to remember policies as to why. And you know, he came into office and sort of everything fell or before he came into office sort of everything fell from that. To me I think there's like a little bit of that that's missing and you know it's our tactical stuff like our super tactical paid tried to answer this question, you know, it's middle class economics, that's what she's here for. But she wasn't talking about it as much. It wasn't like the reason, it wasn't the thing she led with and, and so it just didn't kind of gel. And that to me is the thing. And so I think voters have an expectation of you really believing what you're saying and talking about it and making that case really compellingly. And I think all too often I think we Sort of glaze over that when we, when we launch a campaign, what do you.
A
Why the, you know, super hostility to the status quo? I mean, I guess it just is a fact. I mean, I went through this in 92 with, I thought George H.W. bush were a pretty good president. And I remember realizing at some point, early mid 92, I really thought we were going to lose most of that year, I've got to say. And it was. I was Vice President Quail Chief of staff, so I was there in the White House involved in most of the senior campaign meetings. And I mean, you just couldn't. People understood at some point from the polling that, gee, people were very unhappy and Bush's approval drifted down to about 38%. But. And there were all these tactical attempts to overcome it, which none of which really made much difference, but it was always at some point I just realized, you know, what if people want change, they want change, right? I mean, and here was 12 years of Reagan, Bush and some legitimate complaints and, and, and a little bit of you did a good job Vice President Bush winning the Cold War, but now President Bush. But now we want to move on to someone who focuses on economics and healthcare, you know, and that wasn't crazy of voters to think that, I suppose. But this is where I kind of come back to. You know, you do have to. The voters have their views, right, and their attitudes and you have to. They're hard to change just with however much paid advertising or clever digital advertising you have.
B
You know, they, they are a bit what they are. And you have to think about, you know, we come out of COVID which was a, I think, a sort of generationally, you know, psyche altering event for a lot of people. You know, I think you come out of, you know, the sort of false start that we had of things are getting better. Oh, we're out. Oh, no, wait. Covid is actually a thing that is going to stick around. You know, you look at the rising costs that were coming and inflation. You look at the sort of like honestly the, the like crime bump that we saw coming out of COVID I think people just had like pent up energy, you know what I mean? Like all of that. And I think people just had a sense that the wheels were coming off a little bit and that they couldn't afford things. And that sort of intersects with like some of the big structural stuff that I think that people have in, in their lives. I mean, if you look at young people, you know, they are, they think they'll never buy a home and they won't be able to, you know, they're saddled with debt, either credit card or college. Like, there is this sort of pervasive sense that I can never quite get ahead that I think the pandemic and the post pandemic economy made people feel and sort of the environment post pandemic made people feel. And so I think Biden in many ways, you know, was a, was a, you know, a victim of the same forces that were bringing down incumbents all over the. And those are made worse by some decisions that he made and some stylistic things and all of that. But, you know, it is, I think, understandable that people feel that the status quo is not working. And I think you're seeing Donald Trump on the other side of this now, right. That, you know, he's in these wars of choice and he's, you know, that are materially making costs go higher in the country. He's, you know, outwardly saying he doesn't care about people's financial situations. Like, you know, he is now, you know, right behind the bull on this as folks are mad. And, you know, the question is, what do, what do Democrats do with that? And in the midterm in the long term?
A
Yeah. So let's get to Trump, since people could read your piece for all kinds of interesting further details about the Biden and then Harris campaigns and, and especially, as I say, the very interesting discussion of the digital future and how to organize campaigns and stuff, which anyone who's involved in politics would be interested in. But, yeah, let's talk about the current moment. I mean, Trump, I feel, well, just I'll frame it this way and then take it whichever way you want. I mean, yeah, it feels to me like the tension for Democrats, I feel this personally is on the one hand, one wants to defend important institutions, important norms, important laws against Trump's utter lawlessness and recklessness and disdain for the rule of law and for, and for so much that has made America, you know, a decent country. And, and so one wants to be, one has to defend in a certain way the past against Trump, but then one doesn't want to be the simply the defender of the past. And we can't restore the past anyway. And you want to accommodate or not accommodate, you want to respond to people's legitimate also sense that, well, those institutions were good. On the other hand, they've collapsed in front of Trump. So we need to really have a fresh look at everything. And I feel like that that's a bit of a tension, I think. Well, I Don't know. I feel as for some people like me defending some of this stuff against Trump's very, very important in practicality, in real time. Cannot have a justice. The limit the two. We can limit him from turning the Justice Department into a totally, you know, Trump department that prosecutes everyone he doesn't like and so forth is important. On the other hand, that can't just be the message for 2028. Maybe it could be the message for 26. Talk, talk, talk. Give me your sense of it all.
B
Yeah, I listen, I, I, I share your lens that, you know, democracy and the rule of law are two of the things that make this country amazing. But the other thing is that, you know, we are asking voters to buy into a system that they are feeling isn't benefiting them, and that is what opens them up to fascism, and that is what opens them up to reactionary extreme politics. And, and so for those of us who believe in liberal democracy and all of that, you know, it is, is it incumbent to make sure, you know, people see that it delivers? And it was funny, you know, President Biden would talk about this in the foreign policy context, which is needing to show that, you know, democracies, things done and, and, you know, and it's, it's America versus China and all these things. But I think that that sort of starts at home. And so, you know, for the sake of a democracy, you have to, you cannot have this insane wealth inequality that we have seen in this country. For the sake of liberal democracy, you cannot have people feeling like things in their neighborhood are getting worse. But we're sending all of this money to, you know, a war in Iran and, and, and, and, and, and so to me, the question for Democrats is both a question of, okay, how do we take advantage of this moment where we are on the outside of the status quo and we are the change agents and we are not really responsible for governing. But then once we govern, delivery is going to matter and people feeling like something is getting better. And I think that that is as much.
The Bulwark Podcast
Episode Title: The Real Reason Kamala Harris Lost (w/ Rob Flaherty)
Date: May 17, 2026
Host: Bill Kristol
Guest: Rob Flaherty (Deputy Campaign Manager, Biden and Harris Campaigns)
This episode features a candid conversation between host Bill Kristol and Rob Flaherty, who recently published a widely read Bulwark piece analyzing why Kamala Harris’s 2024 presidential bid was unsuccessful. Flaherty, with insider experience at the highest levels of recent Democratic campaigns, explores not just tactical missteps but big-picture, structural realities about branding, incumbency, the electorate’s mood, and the limits of political messaging. The discussion is frank, reflective, and aims to draw key lessons for Democrats in the digital age.
On campaign ‘brand’:
“It’s about something bigger that is more than the sum of all of those [policy] parts…what are you going to do? I think that that is the thing that had to be defined, and I don’t think that we necessarily had a very clear story there…” —Rob Flaherty (04:33)
On structural obstacles:
“The challenge for Biden deciding to stay in is at that point, you know, voters...were like, yeah, we’ll stick with President Biden in the Democratic primary. And so it was hard for people to kind of break in against him.” —Rob Flaherty (10:14)
On post-pandemic political psychology:
“I think people just had a sense that the wheels were coming off a little bit and that they couldn’t afford things...the pandemic and the post-pandemic economy made people feel [that].” —Rob Flaherty (17:22)
On defending democracy and moving forward:
“We are asking voters to buy into a system that they are feeling isn’t benefiting them, and that is what opens them up to fascism, and that is what opens them up to reactionary extreme politics.” —Rob Flaherty (20:23)
The conversation is reflective, direct, and informed by firsthand campaign experience and political historical perspective. Flaherty is honest about missed opportunities and structural limits, while Kristol keeps the questioning sharp and engaged.
For the full article and more, visit The Bulwark.