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Bill Kristol
Welcome to Bulwark 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 has 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 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 everyone should go read the piece. It's on the Bulwark website. Anyway, Rob, thanks for thanks. Thanks for joining. Thanks for joining me today, Bill.
Rob Flaherty
Thanks for having me. Really appreciate it.
Bill Kristol
And thanks for the piece which is really interesting. So yeah, here's what I told the DNC autopsies if you want to 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 outsiders what 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?
Rob Flaherty
It Was it, was it was the inmates running the asylum.
Bill Kristol
What did you. I'm curious. I always tell young people, you know, 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 of. But 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 in a kind 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 agree with that? Was that, I mean, I've just. Is that good advice? And what did you learn from that?
Rob Flaherty
Campaigns are the best. They're pressure cookers. You build great relationships with people. You learn the softest skills of how to get, 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 shmoopy or whatever, but like working as 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 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
Bill Kristol
another one, but not after this, not after this article. No, that's not.
Rob Flaherty
You hit the ceiling, you know, now
Bill Kristol
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 that, you know, you have these theories and ideas and positions and, 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 have 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?
Rob Flaherty
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.
Bill Kristol
Yeah, well, both doing. They go together in a way. Right. I mean. But anyway, enough of that.
Rob Flaherty
So.
Bill Kristol
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 I supposed 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.
Rob Flaherty
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 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 gets us to. For other reasons, too, but it gets us to the outcome that we had in November 2024.
Bill Kristol
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. 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 gu. Yeah, I guess when you're in a college race with an unknown guy, you have. In a way, it's harder, but it's also easier.
Rob Flaherty
Right.
Bill Kristol
You have a lot of flexibility in a college town, you know, defining your brand. Whereas Kamala Harris, as the sitting vice president, less so, but you could have done more.
Rob Flaherty
Yeah, I think that a lot of this was baked. You know, 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. The. 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 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 better. A better result.
Bill Kristol
And so what in particular, I'm just curious what, you know, what do you wake up at night thinking, God, if only we had done either something you proposed that wasn' 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?
Rob Flaherty
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 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. And the thing is, you know, 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, ah, 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, you know, when your campaign feels like the representation of the institutions of America making their case, that's hard. And so, you know, the answer probably would have been in there. But again, I don't, I don't sit here saying that was the sure. That was the sure bet. So it's hard to say.
Bill Kristol
I mean, I was an advocate of Biden not running. And the first newsletter I wrote, actually, I took over from Charlie Sykes and remember, it was Lincoln's birthday. So 19, February 12, 2024, was calling on Biden not to run again and sketching out as somewhat fanciful, perhaps exciting primaries 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 1968 didn't work out so well and stuff. So it was a perfectly reason. Objection. 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?
Rob Flaherty
I think if President Biden doesn't run, there would be a contested primary.
Bill Kristol
Right. Certainly if he doesn't run in the first place. Right.
Rob Flaherty
And I, but I think, I think Harris probably, 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 decides to get in. And then you kind of look at,
Bill Kristol
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, Be healthy for the country. Let's have a contested, you know, primary. It would have to be arranged as a kind of in a Rube Goldberg way, because 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?
Rob Flaherty
I. 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 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 superdelegates. 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.
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Rob Flaherty
But again, you know, I'm on no
Bill Kristol
and 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, didn't feel into the Democratic convention. I don't think that 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 with 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 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, 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, that is important, isn't it? I mean it's just a stupid, it seems so simple minded to say, well, why are you running for this office? You know, but voters do kind of want to know what you're going to do if you win, right?
Rob Flaherty
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, 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, you know, 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, oh, 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.
Bill Kristol
What do you. 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, 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 for most of that year, I've got to say. And it was. I was Vice President Quail's 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, 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 health care, 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 they're attitudes and you have to, they're hard to change just with however much paid advertising or clever digital advertising you have.
Rob Flaherty
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, 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 in, 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,
Bill Kristol
you know what I mean?
Rob Flaherty
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 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 world. And those were made worse by some decisions that he made and some stylistic things and all of that. But I, you know, it is, I think, understandable that people feel that the status quo is, 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 outwardly saying he doesn't care about people's financial situations like he is now right behind the bull on this as folks are mad. And the question is, what do Democrats do with that in the midterm in the long term?
Bill Kristol
Yeah. So let's get to Trump, since people can read your piece for all kinds of interesting further details about the Biden and then Harris campaigns 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 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 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 collapsed in front of Trump. So we need to really have a fresh look at everything. And I feel like the, that's a bit of a tension, I think. Well, I don't know. I feel, I feel as some people like me defending some of this stuff against Trump's very, very important in practicality, in real time. We cannot have a justice the limit to Gish, 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 of talk talk. Give me your sense of it all.
Rob Flaherty
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, 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 an 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 can get things done. And, and, you know, and 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. 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 so to me, the question for Democrats is, 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, like, delivery is going to matter and people feeling like something is getting better. And I think that that is as much, you know, money going out and programs working better, and people feeling like when they call the government, they will get an answer. I mean, literally. And I mean, I even mean that, like, literally tactically, but on the ground. And, you know, I think that, you know, that is all part of it, but it's also a marketing and branding question, which is, do people feel like they are getting results? People feel like the world is getting better for them. And, you know, it's interesting because I actually see the most interesting arguments about this from, like, Tucker Carlson talks about this. Tucker Carlson says, you know, if young people feel like they can't buy a home, they're not bought into the economy. You know, like, these basic questions, I think, are things that are really ripe for Democrats and the left to be thinking about. Because. Because if you believe in these institutions, they have to work. And that's the big thing. We can't accept failing government institutions anymore. People won't buy it.
Bill Kristol
Do you agree that 2026 is mostly about Trump, though, and about whether you want a Congress that's going to continue to rubber stamp what Trump wants or check Trump? And that in a way, though, 27, 28 is a very different dynamic. I mean, I try to say that when I speak to, you know, political types and donors, they tend to conflate that we have to fix the Democratic Party right away. Well, for now, I think, honestly, just running that you're going to stop Trump from doing all these terrible things is probably. Democrats are not going to do it, run anything in 27, 28. Right. So I feel like voters kind of understand that and they want Trump checked. Am I overly complacent that Democrats don't have to fix themselves until after November 26th?
Rob Flaherty
I agree with you mostly. I mostly agree with that. What I will say is a midterm election is weird. Our coalition has changed the, like, Obama CW of the people who vote over Republicans, you know, in midterms, that's kind of gone. The people who vote and show up in midterms are like institutionalists who believe in civics and, you know what I mean? Like, it is. And so the people who are going to show up are going to be mad at Trump. And so in many ways, this is. This is an election about checking Trump and all of that. And also, like, you know, people say, well, the Democrats need a vision. But, like, realistically, like, if we're just talking in brass tacks, we're not gonna have a vision until voters vote in a primary and there's a candidate and a vision that people get behind that represents. So, you know, I think that's hard. Like, Hakeem Jeffries is not going to lay out what it means to be a Democrat, nor should he. But, you know, I do think, you know, 27, 28 is that. And what a political party represents, whether we like it or not, is largely defined by the presidential and the person that we nominate. And so I think that discussion is really important and the primary is really important for that. And so, yeah, like, that is the moment when we need to have really big, really interesting visions for what the future is going to be and not just reactive to what happened in 2024. You know, where we're, oh, I'm going to go on Joe Rogan and I'm going to say we need to close the border and whatever. But, like, where you have a big vision for the problems the country is about to face, and I think they are about to get much bigger. So, you know, to me, I agree with you that, you know, 26 is, you know, tactical. And I'll make one last point. I think that that fact that, you know, 26, you can kind of get away with it, you know, by not having this grand vision or whatever, sort of will paper over the fact that presidential, in a presidential context, like the coalition of the Democratic Party still isn't big enough to win. And so, you know, we do need to have some kind of vision that it can bring more people in and, and mobilize more people. And that is a problem we won't address in 2026.
Bill Kristol
Do you think the general. I mean, I guess there's two prejudices of mine. I'm curious whether please tell me if they're to the degree that they're wrong or certainly you should qualify them and make them say them more intelligently. I mean, generational change really is its time after Hillary and then Biden and then Harris kind of, but really still Biden, you know, the Biden administration. So I have a huge prejudice towards getting to the John F. Kennedy moment here, if I can put it that, you know, in, in 2028. But also I have a prejudice against a lot of the fighting I see among Democrats, like come to the souls, you know, somewhat fresh eyes maybe, you know. Yeah, welcome.
Rob Flaherty
Welcome to our health.
Bill Kristol
No, thank you. I mean you, you have fresh eyes because you're young. I have fresh eyes because I haven't been around the Democrats so much. But I find the progressive centrist fighting silly a lot of the time, honestly, backward looking. They're all litigating fights, relitigating fights they had in 2021 or 2016. Yeah. And half the time I think I personally am close to the centrist on actual policy. On the other hand, half the time I find myself agreeing with the left or the progressives that a lot of this stuff has to be rethought and it's a new moment and it's a new coalition. And also you do need to come to people where they are and they are rightly or wrongly and maybe rightly and certainly much more unhappy than institutionalist centrist institutions want to believe. So let's go to now.
Rob Flaherty
Let's.
Bill Kristol
Doesn't mean you accept the progressives answer on everything. But I don't know, I found myself a little bit torn on the not torn, but just a little bit frustrated, I'm going to say by the conventional progressive centrist split. So both the generational thing and progressive centrist. Where are you on that?
Rob Flaherty
Yeah, I feel like I have no, first of all, generational thing I think is super important. I think youth, vitality, newness, freshness, that stuff is just going to matter in 2028. And I think because it's a visual signal about. This is different this time. Right. I mean in the same way that Barack Obama in 2008 embodied a change. I think that there's a version of that that is true. And yes, I find the sort of progressive center fights to be pretty reductive and, and not useful and kind of backward looking and like, you know, we're all kind of trying to get to some version of the same thing and you may disagree with different parts of it and whatever, but you know, at some level like neither the center or the left are going to get what they want without the other. We have to figure this out. And I will say this like 2020, I think this is a thing that people have like memory hold is, you know, Biden I think did a pretty good job of still in the general election sort of being the Ashoks, you know, oh, that's Joe Biden. Of course, he's not crazy left and whatever. But also while having a real serious dialogue with the left about, you know, what parts of his platform, you know, and including them. Now some people would argue he over included, but I don't, I don't know if that's true. I think it was actually key to him enjoying over the course of 2020 a lot of latitude to do what he needed to be able to win an election. And so but I do think it also means that in many ways the person who wins the 2028 primary is going to be somebody who the sort of progressive side feels like they can trust and the center feels like they can trust. And so I sort of look at that lens, but I think in either direction, if you're a centrist looking at a super at many progressives or folks who are like to your left or someone who's on the left who's looking at someone at the center, it's like, you know, trying to just destroy them wholly and totally is, you know, counterproductive for, for what we need to do.
Bill Kristol
I mean Biden 2020 was such an unusual primary and then, and then the pandemic hit and then an unusual general because Trump was the incumbent and run and running for reelection it could be again I suppose, and I don't and it certainly will be a Trumpy someone who won't have repudiated Trump, I think on the Republican side and could well be someone from the administration or someone who's more Trumpy than Trump. So I think it remains sort of a referendum on Trumpism, as is always the case when even if you're not running personally. 2008 was a referendum on Republican governance to a considerable degree, Even though John McCain had disagreed with Bush on a ton of things. But I do think the Democrats. It can't be an accident that. Who are the Democrats who want just putting Biden aside for a minute. Obama in 084 year senator, mid-40s I guess was he. I can't remember 46, something like that. Clinton in 92. Younger than Obama actually had been. And when he won very much changed. Not a, you know, governor of Arkansas. It's very nice. But I remember in the Bush White House we thought you can really hammer him. He's not ready to be president. Just been governor of this tiny state. Doesn't have a terribly good record for that matter. If you look at the data did not matter. He was the candidate. Carter 76. We've forgotten this because the whole administration kind of went sideways. But he was total outsider. I mean a one term governor of Georgia, I mean who had not done anything wildly notable honestly as governor of Georgia that I recall. And then he comes from nowhere and defeats a whole bunch of pretty well established and senior and well respected senators and other governors. Kennedy in 60. I mean the Liberal party has to be the party of the future. And I do think it embodies that, don't you think? With I just, I just feel like people have sort of forgotten that those are the people who've won the presidency in the last Johnson I guess 64. But that was an incumbent obviously in unusual circumstances. So I don't know, I feel like,
Rob Flaherty
I think that's really well put. You know the Liberal party has to be the party of the future. I think that is 100% it. Right. If you, if it doesn't feel like your forward looking vision isn't going to make the country, isn't going to change the country for the better. Like you know, and if it is, if it is defending what is versus you know, identifying what will be, I think that that is like that, that is the road to nowhere. Right. For, for, for, for liberal parties across the world. That's tricky.
Bill Kristol
Yeah, it is. Any view on issues that are being neglected or that are going to be much bigger two years from now or I mean AI people talking about AI, other things like that.
Rob Flaherty
I have a whole. Artificial intelligence is the issue. It is the biggest issue. It is going to define 2028. I think it's very possible it defines 2026. The speed at which this technology is developing and is going to thrash through the economy. And it is already so potent. I mean there's the data.
Bill Kristol
Right.
Rob Flaherty
You know, Patrick Graffini, who's a really smart Republican pollster, did some research into Data centers. And he found that if you tell someone a data center is being used for AI, it is minus 23% approval. And if you tell someone that the data center is going to be for streaming video, it has plus 1% approval. It's the AI people are really mad. And it's the qualitative stuff too. You know the videos we've seen out of college graduations where when people mention artificial intelligence, they're booing and it's like a new thing that is happening in real time and you can kind of see it. You know, we talked about the despair that young people feel and the hopelessness that people feel in this economy. Well, you know, the CEO of Anthropic is saying that 50% of entry level white collar jobs are going to be eliminated within five years. By the time we hit 2028, this is going to be everywhere. And so, and by the way, I should just say when you ask voters what they want in response to artificial intelligence, the most popular issues are taxes on the wealthy, universal health care and a federal jobs guarantee. Like voters are seeking democratic socialism in response to what they see as a threat on their personal economies. That is before you get to catastrophic risk, the national security threats that might come from biorisk, like all these kinds of things. And so to me, I think that Democrats are just, it's an absolute jump ball in which party gets to own this issue. And voters are screaming out for a lot of things that Democrats like to talk about in response to this. And so it is just an absolute no brainer and the party needs to get its head on straight about it.
Bill Kristol
That's so interesting. I've been a little slow on this, but I very much come to this view and you would know it so much better than I was. You actually really intersects with your actual work world, right? I mean, you and what you do in digital campaigning and stuff, right? I mean, AI's got to be fantastically transformative just there, right? I mean, I mean not leaving aside the fakes and all that, but I mean, just in terms of processing data and ability to fine tune, this is the thing.
Rob Flaherty
AI has been part of political campaigns and part of marketing for a very long time. But like I, you know, I use AI agents in all of my workflows, you know, and it has allowed me to do a lot more in my own business than I would if it were just me. I think, you know, the efficiencies that people are going to find, you know, one of two things is going to happen, right? The valuations of this company. These companies are justified by the efficiency that they which means job loss that they are going to deliver to their enterprise clients or the market's going to crash. One of two things is happening here. So and and it's going to happen soon.
Bill Kristol
So we're some of both conceivably right
Rob Flaherty
or so 100 some above. And so you know we have to be out of the front foot of this.
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Rob Flaherty
No longer.
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Bill Kristol
I mean I was talking, I'll let you go to second, but I think there's also a lot of cross cutting, I don't know, cleavages or whatever way to say it is pressures on the AI issue. And someone told me in the South, I guess a couple of state legislatures have already passed legislation to prevent, you know, AI from the social consequences of, you know, exploiting young women and so forth or young people, you know, unclothing them and so forth on AI and violating their privacy and all that. Wildly popular. And apparently in these one or two states, at least this one one, the establishment, the Republican establishment was against the restrictions on AI because AI contributed a huge amount of money to these candidate pains. And of course Trump's been pretty a pro AI. That's kind of the official Republican position at this point. Entrepreneurship, you and apparently it just got steamrolled by true organic popular unhappiness. And a couple of Christian sort of religious conservative groups got involved on the side of regulating AI. But apparently it wasn't that they were so powerful. It was just genuine popular revulsion at the idea that these things are just utterly uncontrolled. It's the Wild west and they're doing a lot of social damage as well as economic damage. I think some of the discussions, but a little economic focus, obviously the jobs are very important, but. And I feel like that can cut every which way. Right. I mean, who's protecting our kids? I mean, that's, I don't know, is that liberal, is that conservative?
Rob Flaherty
You know, 17 Republicans in Connecticut just voted against a bill that would allow, that would ban sexually explicit chatbot AI conversations from with children. I mean, it's unbelievable. And I think that the accelerationism that the Trump administration has sort of, you know, the David Sacks accelerationism is a massive political mistake for them. And so it's, you know, and then it is great to see that they are finally taking the security impacts seriously. You know, the post Mythos hacking stuff. But there's an entire world of economic anxiety to your point, social anxiety that people feel around this and people are screaming out for action. And I think it's just the biggest opportunity. It's a no brainer 9010, 8020 issue that's sort of staring us right in the face.
Bill Kristol
Any Democratic politicians. I just, I got to start following it much more closely. Been to your mind, sort of at least beginning to address it and grasp the importance of it?
Rob Flaherty
Yeah, I think in a couple of different places. Right. You're seeing Bernie Sanders, who obviously is taking catastrophic risk and the economic impact seriously. I don't love that they're using just straight up data moratoria as the pathway or data center moratoria as the pathway. I think data centers are. There needs to be lots of controls and regulations, but they're going to get built somewhere. And so you need to have other, you know, take the issue more seriously on the economics. You know, Pete Buttigieg just talked about a new deal given what the economy is going to look like. And even Gina Raimondo has talked about sort of the, you know, transitional work stuff. I worry a little bit, you know, we're talking about job transitions for a lot of these people that are going to, you know, transition training for a lot of these people that, you know, we're going to find ourselves in a position where like what are you, what are you retraining them for?
Bill Kristol
Right.
Rob Flaherty
But I, on the whole, I feel like, you know, people are just starting to wake up to this. But, but there's a long road to go and I worry it won't happen until it's too late.
Bill Kristol
But I think it's such an important point and I think given the fluidity, don't you think of and rapidity of which things happen in our politics. Someone who's a backbench member of Congress. I'm gonna even go further. Someone who's even elected in 26 and is utterly unknown to everyone except the people in his or her districts. And 12 political pros like yourself. I don't know six months in, if that person really can show leadership on this issue. I don't know. Can that person be a national figure? I think so, don't you think?
Rob Flaherty
Nothing but upside. This issue. It is the fastest growing issue in terms of political salience in research. It is leapfrogging. So it is the time to get in and be early about this because I really do believe in 2028 it is going to define the race and by the way, it is going to define the attack against, you know, Republicans, you know, especially if J.D. vance or anyone from the Trump administration is at the top of the ticket. It is, it is the argument. And so no time better than the present to be, to be really good on AI.
Bill Kristol
Okay, well, I hope, a lot of hope we get off this, this podcast, this video and your phone starts ringing off the hook even more than it normally does from every Democratic, you know, candidate, senator, member of Congress, governor, mayor. I mean, this is one where you could also pick it up in different areas, right, because you have federal issues, city issues. I mean, it's not clear what level of government is what, what kind of office holder or candidate is, is best able to address this. It could be all kinds of different ones, right? I mean, someone running for state office, someone running for federal office and so forth.
Rob Flaherty
Yeah, absolutely right. I mean, it has impacts all the way up and down and it can't
Bill Kristol
be just a no, nothing kind of a, you know, I wish this weren't happening. Right. It has to be grown up about this is happening. And so how do we manage?
Rob Flaherty
You see this on the left, actually you see a lot of people like, who say, well, AI is a hoax. Stochastic parrots. It's these kinds of, if you talk about this issue, it's like NFTS or the Metaverse. But this thing is real, it can do a lot and it is going to replace a lot of jobs unless we set some rules of the road. And so you can't put your head in the sand. And voters certainly are not putting their heads in the sand on this. They are very, very nervous about it. And so that's the opportunity that's so interesting.
Bill Kristol
Okay, well, I'm glad we got on today. I didn't really plan on discussing where the Harris campaign and all that. But that, that was also very interesting. But no, no, it's a good example of how one has to be. Yeah. Adjust to what's happening in the real world. And again and not just, you know, the lessons of 24. Is that a little more talk about this, you know, lunch table? I don't know. I always feel like that's overdone the backward looking lessons.
Rob Flaherty
Well, 100% and it's 100% the way to think about it, which is I think the issue, if you are just trying to relitigate the issue set from 2024 and 2028, you are going to miss out on what is actually coming. And so, you know, you have to be thinking about what's around the corner.
Bill Kristol
But we'll have to continue this conversation every few months, maybe every few weeks the way things are going to really stay on top of both 26 especially I think you're right on 2728 where I mean 26 I think, don't you think some degree getting baked in here and. But 2728, not at all. Really. Right. Truly open. I mean it's going to be when you think about it, I mean you've had Trump on the ballot three times. Let's assume for a minute he's not on the ballot again. We've had Clinton, Biden, Biden's VP. I mean 2012 was Romney, who wasn't a fresh young person really. And Obama reelect. So really 08 was the last election that was kind of a fresh, fresh face.
Rob Flaherty
Right? Really?
Bill Kristol
Yeah. Think about it. And this time we could have two. Really. Because Trump has been so dominant that even Vance would be kind of. And he's young. Yeah, totally. And both parties with having some competitive primaries and stuff up in the air in terms of some of these big issues, pretty unusual moment for American politics,
Rob Flaherty
I think especially after what we've just gone through. You know, it's going to be, it's going to be a really fascinating election.
Bill Kristol
Okay, well we'll stay in touch on it. And Rob, thanks for the piece which everyone should go read and thanks for the very interesting conversation.
Rob Flaherty
Thanks for having me, Bill. Really appreciate it.
Bill Kristol
And thanks for joining us on Bulwark on Sunday.
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Host: Bill Kristol
Guest: Rob Flaherty (Former Deputy Campaign Manager, Biden-Harris 2024)
Date: May 17, 2026
In this episode, Bill Kristol interviews Rob Flaherty, former Deputy Campaign Manager for both the Biden and the Harris 2024 campaigns and author of a much-discussed autopsy on why Kamala Harris lost the 2024 presidential race. The conversation drills into campaign strategy, the critical importance of "brand" over a mere bundle of policies, and the lessons Democrats must learn from defeat. Flaherty analyzes the structural and messaging failures but also puts the Harris defeat in global and historical context. Finally, they pivot to the rapidly rising political salience of AI and what it means for the future of both parties.
"Campaigns are the best. They're pressure cookers. You build great relationships with people..." (Rob Flaherty, 02:55)
"The reality is it's about something bigger that is more than the sum of all of those parts...the overarching story of why are you in this race."
(Rob Flaherty, 05:31)
"I don't think anybody from the administration probably could have won...there were things we could have done [differently], but a decent amount of this was baked in."
(Rob Flaherty, 07:11)
"If you're a centrist looking at someone to your left...or someone on the left looking at a centrist, trying to just destroy them totally is counterproductive for what we need to do." (Rob Flaherty, 29:07)
"Artificial intelligence is the issue...the CEO of Anthropic is saying 50% of entry-level white collar jobs are going to be eliminated within five years."
(Rob Flaherty, 33:59)
On Democrats' future:
"If it is defending what is vs. identifying what will be...that is the road to nowhere, right, for liberal parties across the world."
(Rob Flaherty, 33:17)
On AI's opportunity:
"No time better than the present to be really good on AI."
(Rob Flaherty, 42:04)