Jon Lovett and Tim Miller on Losing Primaries (Inside 2024 - Extended Preview) 23:11

Hey everybody, it's Lovett here. We have something a little special for you today, an episode of Inside 2024. This is our new show for members of the Friends of the Pod community, where we're joined by campaign and political experts from the Crooked family to tell behind the scenes stories of high highs and low lows and weird weirds that happen on campaigns and in politics. In this episode, our intrepid producer, Caroline Reston, who's here in this recording, looming over us like the Babadook,

joins me and my guest straight from the cuck zone, Tim Miller, to unpack our tear-stained, scotch-soaked memories of primary defeats past, like the one I witnessed when I worked for Hillary and the several Tim experienced, including when he worked for Jeb! Bush. Find out what liquor got Jeb cracking wise and how to spot a secret gay or simply pro-gay Republican by just how much their heart isn't in it. Take a listen, enjoy the conversation, and above all, please clap.

And subscribe to Friends of the Pod to hear this show and so much more at crooked.com slash friends. We're having a good time over there. Yeah. In the Friends of the Pod community. Was your first time inside Tim Miller 2034? All right. I think we all know where that was going. Third place is a ticket to ride, ladies and gentlemen. I have just called President Obama to congratulate him on his victory. If we can blast 50 women into space, we will someday launch a woman into the White House.

Welcome to Inside 2024. Every month, this show will take you behind the scenes of what it's like to work on a campaign and share stories from the people who've lived it. I'm John Lovett. I was a speechwriter for President Barack Obama and a speechwriter for then Senator Hillary Rodham Clinton. And joining us, he was communications director for Jeb Bush's presidential campaign in 2016. He's a writer and podcast host for The Bulwark.

Tim Miller, good to see you. I've never been more prepared for a podcast than this one, John Lovett. I am just very well suited to the topic of the day. And as always, moderating discussion is Cooker Media's favorite producer. What? Favorite? Caroline Rustin. Stop. All right. What are we here for? What we're doing today is talking about what it's like to be a big old loser in

and campaign primaries. So, so happy we were able to gather our two favorite losers.

Or you could consider it a podcast about making lemonade. Yeah, look at where you guys are both now. Producing pods. Or hosting pods. Even a step up. I mean, we're just pod... That's what everyone aspires to be. You know? A podcaster. Yeah. When I was sitting in my bed in my high school bed, dreaming about what I was going to be when I grew up, I was thinking, man, I would like to be an infrequent guest on John Lovett's podcast. Look, the way I think about it is, I don't think we've...

gone from the heights of politics to podcast hosts, I think that we do the job that Prince Harry, Barack Obama, and Bruce Springsteen aspire to. And have all failed. That's a great point, Lovett. Man, I love your spin so far today. Let's keep this up as we go through all my losing campaigns. Yeah, so I actually just want to first let listeners know what were the campaigns that each of you have worked on where you did lose.

Tim, do you want to go first? How long you got? Yeah, yours is a little bit longer. Let's start with you. Well, in 2005, I worked on Jerry Kilgore's Cupid's Order. I don't know if we're going all the way that deep, but we'll keep it at the presidential level. In 2008, I worked for John McCain.

I was his Iowa spokesperson. You might know Barack Obama's Iowa spokesperson at that time. He was a guy named Thomas Vitor. So he won in that one. And then 2012, I was on John Huntsman's primary campaign. We finished in last place. And then I begged my way onto Mitt Romney's losing general election campaign. Technically, I worked at the RNC. And then in 2016, I worked for Jeb Bush.

That didn't go so well. And then after that, I joined on to a super PAC aimed at stopping Trump from winning the presidency. And I don't really remember how that worked out. Well, you made a lot of great content. Yeah. I did. I did. Love it. You're famously on one campaign that lost. Yeah. Pretty big one, though. I worked for, so I was a speechwriter in Hillary Clinton's Senate office. From there, went to, sort of helped on her winning campaign.

2006 Senate campaign uh against uh who's even running against it was supposed to be Rudy Giuliani actually and then it ended up being Rick Lazio yeah Rick Lazio and then I worked on Hillary Clinton's 2008 primary campaign against Barack Obama actually we both worked on campaigns that lost to Barack Obama in a sense that's something that we have in common

Uh, and after Hillary Clinton lost in 2008, I went back, uh, to working in the Senate office full time and ultimately was hired by Jon Favreau to be a speechwriter in the White House for President Obama. So for me, I got the same job that I would have gotten.

Either way, you know? So that was a cool twist for me. So you weren't the lead speechwriter. Is that the correct terminology? I wasn't chief speechwriter. You weren't chief. So what does it mean when you're a speechwriter below the chief? And like, how is speechwriting different on a... What are you laughing at?

What does it mean to be like the low to mid-management of the speech writing department? I'm trying to have a through line here. So we, you know, the candidate has, you know, tons of events and you're working on a bunch of different speeches all the time. And so I ended up doing either comedy speeches or policy speeches nobody cared about. That was sort of my...

favorite thing to end up doing. What were your favorite Hillary comedy speeches? Well, she didn't do as many of those. She didn't do the correspondence dinners. She actually hated those famously. Anyway, I also worked on policy speeches. I remember one time I did on the campaign. She went to Iowa and...

Bill Clinton was very, at the time, focused on energy policy. I'm sure he still is. And so I remember sort of doing a draft of a speech for her to give on climate and energy in Iowa and then getting sort of late-night edits from Bill Clinton from wherever. How is he sending you the edits? Okay. I saw your face working on that. But he would basically do notes. He has a...

beautiful but incomprehensible penmanship, just this beautiful squiggle. And then one of his advanced people, one of his people that was always on the roads with him, you know, making sure that the island had sprites or whatever, would call and kind of help

be a Rosetta Stone for his incomprehensible notes. And yeah. I feel like boomers plus are the last generation of good handwriting. So my last question on like the time on the Hillary campaign is, I feel like famously Hillary has had a harder time landing a joke. You may have seen that I recently launched a Snapchat account. I love it. I love it. Those messages disappear all by themselves. Oh,

What's it like to speech write for someone who very publicly has that kind of reputation? I think most, I think Barack Obama was exceptionally good at telling jokes. He just had a natural rhythm that made him very good at events like the Correspondence Center. Hillary Clinton is more, I think, in the standard deviation of a typical person.

in that they're not inherently very good at doing stand-up. It's just tougher. Yeah. She got them all into a UCB 101 class. Yeah. I mean, I don't know, Tim, how was Jeb with comedic material? Jeb was bad at jokes. Jeb was really funny after a couple scotches, you know,

in the hotel lobby, but not a natural joke teller. I did do a little, because we ran out of money, I did end up doing a little speech writing for Jeb at the end, and I had our election night losing speeches. So do we have that in common on this Losers podcast? Did you do Hillary's New Hampshire? I did a couple. I guess she won New Hampshire, like South Carolina losing speech. I did a couple. I don't honestly, it really is hard to remember now because there were so many people

Primary nights. There were so many losing speeches. I had so many more losing campaigns, but you had each one of those primary nights add up. You have to run. You run every time. That's such an important point. We packed in a year more losing than you did in a decade. The thing that we figured out, I remember as the 2008 primaries were unfolding, you could basically guess what was going to happen because what would happen is the results would

would be bad enough to not change the dynamic, but good enough to justify staying in the race that there was like a, but basically you couldn't hope for results good enough so that suddenly there's a chance that this fucking thing is going to turn around, but never could you get a result so dispositive that we could all go home.

So we just, that's why we ended up in this thing till June. We ended up in, we ended up in this primary till June, but it was a lot of training doing kind of, I think in the end, because the race was so static, we kind of, you know, Al Gore has that joke, you know, there's wins and there's losses. And then there's that third category. I feel like we did a ton of third category speeches. A lot of speeches were like,

You know, America's ready for change and strength plus experience equals change. And the fight goes on. Yes. Yes. Thank you, Michigan. And thank you a little less, Nebraska. Yes. Depending on the demographics of the next few contests, we'll see what happens. Tim, so you were the comms director for Jeb. Yeah.

But once he was, you know, losing and everyone wasn't working, you were saying that you wrote the speech. We do have a clip of the speech, and there is one line I specifically want you to answer to. Finally, I am so grateful to Senator Lindsey Graham of South Carolina here for his steadfast support and his amazing humor.

Amazing humor, Lindsey Graham. Did you write that line? Yes, I did. And I do not have to. You can tell I wrote it because he read it for some reason. Usually the thank yous you can just riff on. But every candidate has their strengths, you know, and Jeb was an on script kind of man.

Uh, Lindsay is hilarious. I think that at his core, he is a kind of funny wingman, you know, and he needs a daddy and he needs a front man and he's the sort of funny side character. And when the front man is John McCain, uh,

Like that, you know, that's not, it's kind of minimal damage, except maybe some of the bombings. And when the front man is Donald Trump, like you go to a very dark place, I think. That's probably the best coherent Lindsey Graham theory I've got. Yeah, I think that's right. So before we get into like really the bigger flops of Trump,

different candidates in Jeb's 2016 primary run and in Hillary's 2008 run. Both were campaigns that felt like had a lot of promise and were likely going to be the nominees, at least early on. So when you joined those campaigns, like what was your attitude going in? Were you like excited? Were you feeling confident? Were you like, holy shit, this might go all the way? Like where were you before things started heading in a different direction? Yeah, sure. I really, I really liked Jeb.

And so I was feeling excited to work for him, and I thought we had a chance for about a week. We had a really good first day of the campaign. Like our first day was really strong. And yeah, I mean, I knew probably by the fall that things were going a different direction. Oh, pretty early on.

Yeah. Oh, yeah. I remember where I was when I knew. Where were you? I was at my brother's bachelor party. I took two days off the campaign. I was really hungover, and we had a private poll coming.

And I had asked the pollster to put one question on for me, which was, what do you like least about Jeb Bush? And I'd saved it. I didn't want to ruin the bachelor party weekend, so I had an open poll. And I looked at it, and we were like, Trump's killing us. Marco's killing us. And then I scrolled all the way down to my question, which was the last one. And it was like, 45% didn't like him because he was a Bush fan.

You know, 48% didn't like him because he was low energy. And then there was like four other random things. And I was like, oh, so they don't like his name or his personality. And we're in a distant third. I don't think there's going to be a path back from that. When did Please Clap happen? At what point in the campaign was that? Very end. Very end. And that's all Ashley Parker's fault.

But that happened at the very end. I think the next president needs to be a lot quieter, but send a signal that we're prepared to act in the national security interests of this country to get back in the business of creating a more peaceful world. Please clap. Yeah, there's also, I think, a habit of like, please clap or the dean scream were not causes. They were

They were moments basically, you know, if you're in a bad mood and it's raining out, you blame the rain. If you're in a bad mood and it's sunny out, you look for another explanation. And I do think that like camp when campaigns are at a kind of downward slope, when things like that happen, they get they get they get sort of outsized attention because they are.

fulfilling the narrative. Yeah, people are looking for things to sum up Jeb being sad. Like, Jeb's sad. Our numbers are going down, right? Like, it was self-deprecating, right? In a room where we had just won New Hampshire...

And he kind of gets interrupted and he's like, go ahead, please clap. Like, nobody remembers that. Like, people, you know what I mean? But it was, like, because we were sad, people were looking for a meme, a gif. Yeah, I never took it as, like, a please clap. I always thought, like, he understood, like, just come on, work with me here, guys. It was charming. It was charming. So, Tim, here's a question that I wanted to ask you about this, which is, so, obviously, in 2016,

There was a kind of like, I think, a wider range of ideological outcomes, let's say. Right. Jeb becomes the kind of for a time, the main alternate. So the main the main sort of place you could go if you didn't want to go to Trump in 2012.

It's a narrow ideological band, right? Like what you and Sarah Longwell, you have, you have a podcast with Sarah on the bulwark. And I thought that was it. You, you, you do have like an interesting discussion the other day about what it was like being gay people in the Republican party, listening for clues, listening for people who, whose heart really wasn't in it. Can you talk a little bit about that and how it factored into how you ended up with John Huntsman in 2012? Yeah.

Yeah, sure. I mean, so in 08, I worked for McCain. He loses. And then I took a break from being an active politics, came out of the closet and focused on myself for a while, did a little self-care, as they say. I didn't realize it was that late that you're coming out of the closet. It was late. Yeah. Well, I mean, it was during McCain, really.

So anyway, I was kind of happy. I was at a PR firm, and I was attracted to Huntsman's campaign because he was a Tim Miller, right? He was moderate. He was center-left. At the time, he was for civil – he basically has the Obama 08 position in the Republican Party four years later. Like, I'm for civil unions, and I think gay people have dignity and all that. So he was taking the most –

view among the candidates in that ideological band. It's in the Republican Party. And so to me, 2012 was like, I'm getting back in this for the most earnest reasons possible. I kind of know this is going to be a loser probably. Let's take the shot. Let's work for somebody that is really aligned with me politically. Because he's probably going to be a loser, I got to be the national spokesman. That's not a job I would have gotten for a candidate that was more likely to win

because I was young. And so to me, I reentered it for Huntsman. And then after that, I kind of got a little bit more careerist about things. Just to go back, when I went into politics, it was really very kind of cavalier. I had been doing math when I was in college. I was thinking about maybe being a lawyer. I was so unexamined and so...

anxious and insecure and unprepared for these responsibilities that like the idea that I was like,

thinking about like, oh, Barack Obama versus Hillary Clinton. I was just hanging on for dear life. Like this is where I was. I worked. It wasn't like I thought to myself, ah, Barack Obama, Hillary Clinton, I'm going to choose the one that'll be a better president. And that's the one I'm going to work for. It's like, this is just where my desk was. And I believed in her campaign. And I, and my, my, like the way in which, you know, Tim was talking about, like you kind of find

the justification, not the justification, but you kind of find the emotional reason you're investing so much time. You kind of do some cognitive dissonance. Like if I'm working this hard, it must be for a reason. What is the reason? Here are the reasons. But, and I'd had those reasons. And for me, a lot of it was rooted in the fact that that was a very rhetorical process.

their differences on policy were very, very minor. Obviously there was a big disagreement on Iraq. That was the core of it. But by the time they're running, their position isn't actually very different. His view is I, his view is I, I wouldn't have voted yes on the authorization. She had voted yes on the authorization and then came to view it as a mistake. That's sort of like the core kind of, uh,

a difference in their sort of approach to politics. And from that, a bunch of other things happen. But so much of that campaign was Hillary Clinton and like the consultants around her trying to make an argument that in an electorate that desperately wants change, experience is the thing that makes change possible. While Barack Obama is saying, if you want change, I'm change. And that was simpler and worked much better. Did you develop any animosity for him? There was some sour grapes.

Because I remember, I remember like, I think my frustration was actually not with him.

It was with the coverage. It was a very frustrating campaign to be a part of because you're like, wait a second. Like he is an inspirational figure, promising generational change. She is an establishment figure that represents the status quo, but her healthcare policy is to the left of his. Her energy policy is to the left of his. Why am I the only person who understands that? And so I think the only time it became a kind of, I think like frustration with

the Obama campaign or with Barack Obama, it was like when that was the message, it felt insulting to us inside the campaign because like,

It was really like, it was an unusual arrangement. Speech writing in the 2008 Hillary Clinton campaign ran out of policy. And here's something that you don't always hear enough of from Democrats. A big part of our plan will be unleashing the power of the private sector to create more jobs at higher pay. She really viewed speeches, to her detriment ultimately, as a means of conveying policy chops,

history and proposals. And obviously, I think Barack Obama put a lot more poetry on top of that prose and basically made the argument that like inspiration is what you need and inspiration is what I offer. People of every creed and color from every walk of life is that in America, our destiny is inextricably linked, that together our dreams can be one.

We cannot walk alone, the preacher cried. So I think that like the, like how can he be the one offering change if she's on the left? Like that doesn't make sense. That doesn't make sense. Of course, there was so little difference. It was, we were dancing on the edge of the pen. So you're losing bitterness was more focused on the fake news media than on Barack Obama. Yes, especially because like, I was in the convention in 2004 when he spoke. I went, I was at,

the Boston convention in 2004. And I saw that speech. Um, I was, uh, I was a, a like volunteer boom mic person for a documentary of, uh,

a bunch of left-wing, like, gadflies who were running around the convention calling Madeleine Albright a war criminal. And I'm just, like, chasing... Madeleine Albright was... I remember Madeleine Albright was sitting on a golf cart. You know the seats on the golf cart that face the back... Backward? And I just remember, I'm like, there's somebody chasing Madeleine Albright

with a, with a camera and I'm chasing behind them as the golf cart pulls away so that she didn't have to answer questions. I don't even remember what they were, what they were. It was a, it was a, I don't know what during the Clinton administration they were focused on at that time. Uh, so I was on the floor during that speech. And so I like, I remember like, you know, there's a kind of like team mentality. So you're, it's sort of, but it's like in quieter moments. I remember being on the Hillary campaign. You'd be like, you know, walking to your car with somebody and just talking about it and just be like,

Jesus, Obama's good. Like, oh, fuck. This is not good. I'm in the McCain office and I'm watching it on streaming, the Obama speech. I just walked out to the rest of the people and I was like, we are fucked. It does not matter if we win this primary. I was like, we are fucked. I remember saying like,

I don't know. What's it like to lose to Kennedy? It's like that. Is that what this feels like? Because I think this might be what it feels like. OK, so Tim was saying earlier that on Jeb's campaign, there was like a clear moment where he was like, oh, fuck, we're going to lose this. When did that happen on Hillary's campaign to Obama? I know you were saying like there kept being hope during the primary race, but not really enough to sustain. Was there one thing that happened where you were like, it's over?

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