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Hey everybody, it's love it here. We have

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something a little special for you today and

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episode of Inside Twenty Twenty Four. This is

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our new show for members of the friends

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of the Pod community. We were joined by

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campaign and political experts from The Crooked Family

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to tell behind the scenes stories of high

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highs and lows and weird weird that happen

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on campaigns and in politics. In this episode,

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our intrepid producer Caroline Reston. Who's. Here

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in this recording looming over as like the

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Baba Duke joins me and my just straight

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from the cock zone Tim Miller to unpack

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are tear stained scotch soak memories of Primary

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defeats past like the one eyewitness when I

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worked for Hillary and the several Tim experienced

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including when he worked for Jab exclamation Point

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Bush find out what liquor got Jeb cracking

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wise and how to spot a secret gay

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or simply pro gay republican my just how

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over there? Yeah and the at the front

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of the Potter. First time inside to Miller

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to two different our it that we all

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know where that was going. Third,

1:05

blaze is a ticket to ride.

1:07

Ladies and gentlemen, I. Present

1:10

Obama to congratulate you about his

1:12

victory. If we can blast fifty

1:14

women into space, we will someday. Lots

1:17

hey, Guam and Hansen, the. White House.

1:21

Welcome to Inside Twenty Twenty Four! Every month

1:23

show will take you behind the scenes of

1:25

what it's like to work on a campaign

1:27

and share stories from the people who have

1:29

lived it. I'm John. Love It! I was

1:32

a speechwriter for President Barack Obama and a

1:34

speechwriter. For. Then Sen. Hillary

1:36

Rodham Clinton and joining Us. He

1:38

was communications director for Jeb Bush's

1:40

presidential campaign and twenty six seen.

1:42

He's a writer and podcast host

1:44

for The Bulwark. Tim. Miller.

1:46

Good to see I I've never been

1:49

more prepared for podcast and this one.

1:51

Com on it and chests. And

1:54

if your life either area well suited

1:56

to the topic of the day and

1:58

as always moderating discussion. is

2:00

COOKRID MEDIA's favorite producer. What?

2:03

Favorite song? Caroline Reston. All

2:06

right. I didn't write that. What are we here

2:08

for? What we're doing today is talking

2:10

about what it's like to be a

2:12

big ol' loser in

2:16

campaign primaries. So, so

2:18

happy you were able to gather our

2:21

two favorite losers on the

2:23

COOKRID MEDIA universe. Or you could consider

2:25

a podcast about making lemonade. Yeah, look at

2:27

where you guys are both now. Producing pods. Or

2:30

hosting pods, even to step up. I

2:33

mean, we're just, it's what everyone aspires to be.

2:36

A podcaster. That's when I was sitting in my

2:38

bed, in my high school bed, dreaming about what

2:40

I was gonna be. When I grew up, I

2:42

was thinking, man, I would like to

2:44

be an infrequent guest on John Lovett's podcast. Look,

2:46

the way that I think about it is, I

2:49

don't think we've gone from the heights

2:52

of politics to podcast hosts. I

2:54

think that we do the job

2:56

that Prince Harry, Barack Obama, and

2:58

Bruce Springsteen aspire to. And

3:01

have all failed. Yeah, you know? That's

3:04

a great point, Lovett. That is a great point. Man,

3:06

I love your spin so far today. Let's

3:08

keep this up as we go through all my losing

3:11

campaigns. Yeah, so I actually just wanna

3:13

first let listeners know what were the

3:15

campaigns that each of you have worked

3:17

on where you did lose. Tim,

3:20

you wanna go first? How long you got? Yeah, your list

3:22

is a little bit longer. Let's start with you. Well,

3:25

in 2005, I worked on Jerry

3:27

Gilgore's. I don't know if we're

3:29

going all the way that deep,

3:31

but we'll keep it at the

3:33

presidential level. And oh, and I

3:35

worked for John McCain. I was

3:37

an Iowa spokesperson. You might know Barack

3:39

Obama's Iowa spokesperson at that time. He was

3:42

a guy named Thomas Vitor.

3:44

So he won in that one. And

3:47

then 2012, I was on John Huntsman's

3:49

primary campaign. We finished in last place.

3:51

And then I begged my way onto

3:53

Mitt Romney's losing general election campaign. Technically,

3:55

I worked at the RNC. And

3:58

then in 2016, for

4:00

Jeb Bush. That

4:02

didn't go so well. And then after that,

4:04

I joined on to a super PAC aimed

4:06

at stopping Trump from winning the presidency. And

4:08

I don't really remember how that worked out.

4:11

Well, you made a lot of great content. Yeah, I

4:13

did. I did. Love it. You're famously

4:16

on one campaign that lost. Yeah, pretty

4:18

big one. I worked

4:20

for, so I was a speechwriter

4:22

in Hillary Clinton's Senate

4:24

office. From there,

4:27

went to sort of helped on

4:29

her winning 2006 Senate campaign against

4:31

a person. Yeah,

4:34

who did it even run against? It

4:36

was supposed to be Rudy Giuliani, actually.

4:38

And then it ended up being Rick

4:40

Lazio. Rick Lazio. Rick Lazio.

4:43

And then I worked on

4:45

Hillary Clinton's 2008 primary

4:47

campaign against Barack Obama. Actually, we both worked

4:49

on campaigns that lost to Barack Obama in

4:51

a sense. That's something that we have in

4:54

common. And

4:56

after Hillary Clinton lost in 2008,

4:58

I went back to working in

5:02

the Senate office full time and

5:05

ultimately was hired by John

5:07

Favreau to be a speechwriter in the White House

5:09

for President Obama. So for me, I

5:11

got the same job that I would have

5:13

gotten either way.

5:15

So that was a cool twist for me.

5:17

So you weren't the lead speechwriter. Is that

5:20

the correct terminology? I wasn't too speechwriter.

5:24

So what does it mean when you're a

5:26

speechwriter below the chief? And

5:28

how is speechwriting different on

5:33

a... What are you laughing at? What

5:35

does it mean to be like the low to midman? I'm

5:38

trying to have a through line here. The

5:44

candidate has tons of

5:46

events and you're working on a bunch of

5:49

different speeches at all the time. And so

5:51

I ended up doing either comedy speeches or

5:53

policy speeches. Nobody cared about that was sort

5:55

of my favorite thing to end

5:57

up doing. So what were your favorite Hillary comedy speeches?

6:00

speeches? Well she didn't do as many

6:02

of those. She didn't do the correspondence

6:04

dinners. She actually hated those famously. Anyway,

6:06

I also worked on policy speeches. I

6:09

remember one time I did on the campaign.

6:11

She went to Iowa and Bill Clinton

6:14

was very at the time focused on energy policy.

6:16

I'm sure he still is. And so I remember

6:18

sort of doing a draft of a speech for

6:21

her to give on climate and

6:23

energy in Iowa and

6:25

then getting sort of late night edits

6:28

from Bill Clinton from wherever. How

6:30

is he sending you the edits?

6:32

That's the claim. Yeah, okay. I

6:34

saw your face working on that.

6:36

But he would basically

6:39

do notes. He has

6:41

a beautiful but

6:43

incomprehensible penmanship. Just this beautiful

6:45

squiggle. And then

6:48

one of his advanced people, one of his people that was

6:50

always on the roads with him, you

6:53

know, making sure that the island has sprites or

6:55

whatever, would

7:00

call and kind of help be

7:03

a Rosetta Stone for his incomprehensible notes.

7:06

And yeah. I feel like Boomers Plus

7:08

are the last generation of good handwriting. And

7:10

so my last question on like the time

7:12

on the Hillary campaign is I

7:14

feel like famously Hillary has had

7:16

a harder time landing a joke.

7:18

You may have seen that I

7:21

recently launched a Snapchat account. I

7:23

love it. I love it. Those

7:26

messages disappear all by

7:28

themselves. What's it

7:30

like to speech right for someone who

7:33

very publicly has that kind of

7:35

reputation? I think most, I think Barack

7:37

Obama was exceptionally good at telling jokes.

7:39

He just had a natural rhythm that

7:42

made him very good at events like

7:44

the correspondent center. Hillary Clinton

7:46

is more, I think, in the standard

7:49

deviation of a typical

7:53

politician in that they're

7:56

not inherently very

7:59

good at doing

8:01

stand-up, it's just tougher.

8:04

Yeah. She gets them all into a

8:06

UCB 101 class. Yeah, I

8:08

mean, I don't know Tim, how was

8:10

Jeb with comedic material? Jeb was bad

8:12

at jokes. Jeb was really funny after

8:14

a couple of scotches in

8:18

the hotel lobby, but not a

8:20

natural joke teller. I did do

8:22

a little, because we ran out of money, I

8:24

did end up doing a little speech writing for Jeb

8:26

at the end. And I had

8:29

our election night losing speeches. So

8:31

do we have that in common on this Losers

8:33

podcast? Did you do Hillary's New Hampshire? I guess

8:35

she won New Hampshire, like South Carolina losing speech.

8:37

I did a couple, I don't honestly, it really

8:39

is hard to remember now because there were so

8:41

many primary nights. There

8:44

were so many losing speeches. I

8:46

had so many more losing campaigns, but you

8:48

had one of those primary nights at a

8:50

time. That's such an

8:52

important point. We packed in a year

8:54

more losing than you did in a

8:56

decade. The thing that we

8:58

figured out, I remember as the 2008 primaries

9:02

were unfolding, you could basically guess

9:04

what was gonna happen, because

9:06

what would happen is the

9:09

results would be bad

9:11

enough to not

9:13

change the dynamic, but

9:15

good enough to justify staying in the

9:17

race. That there was

9:19

like a, basically you couldn't hope for

9:22

results good enough so that

9:24

suddenly there's a chance that this fucking thing

9:26

is gonna turn around, but never

9:28

could you get a result so dispositive

9:31

that we could all go home. So

9:34

we just, that's why we ended up in this thing

9:36

till June. We ended up in this primary till June,

9:38

but it was a lot of training doing kind of,

9:41

I think in the end, because

9:43

the race was so static, that

9:46

we kind of, you know, Al

9:48

Gore has that joke, there's wins and there's losses,

9:50

and then there's that third category. I feel like

9:52

we did a ton of third category speeches. A

9:55

lot of speeches were like, you

9:57

know, America's ready for change

9:59

and it. and strength plus experience equals

10:01

change and the fight goes on. Yes,

10:05

yes. Thank you, Michigan. And thank you a

10:07

little less, Nebraska. Depending on

10:09

the demographics of the next few contests,

10:13

we'll see what happens. Tim, so you

10:15

were the cons director for Jed,

10:18

but once he was losing and everyone

10:20

wasn't working, you were saying that you

10:22

wrote the speech. We do have a

10:24

clip of the speech and there is

10:26

one line I specifically want you to

10:28

answer to. Finally, I am so

10:30

grateful to Senator Lindsey Graham of South

10:32

Carolina here for his steadfast support. And

10:41

his amazing

10:43

humor. Amazing

10:46

humor, Lindsey Graham. Did you write that

10:48

line? Yes, I did. And I did not have to. You can

10:51

tell I wrote it because he read it for some reason. Usually

10:53

the thank yous you can just riff on. But

10:56

every candidate has their strengths. Jeb

10:58

was an on-script kind of man. Lindsey

11:02

is hilarious. I think that at his

11:04

core, he is a kind

11:06

of funny wingman. He

11:09

needs a daddy and he needs a front

11:11

man and he's the sort of funny side

11:13

character. And when the front man is John

11:15

McCain, like that's not

11:18

kind of minimal damage except maybe

11:20

some of the bombings. And

11:22

when the front man is Donald Trump, like you

11:24

go to a very dark place, I think. That's

11:27

probably the best coherent Lindsey Graham theory

11:30

I've got. Yeah, I think that's right. So

11:32

before we get into like really the bigger flops of different

11:35

candidates, in Jeb's 2016 primary run and

11:39

in Hillary's 2008 run,

11:41

both were campaigns that felt like had

11:43

a lot of promise and

11:46

were likely going to be the nominees, at

11:48

least early on. So when you joined those

11:50

campaigns, like what was your attitude going in?

11:52

Were you like excited? Were you feeling confident?

11:54

Were you like, holy shit, this might go

11:56

all the way. Where were you before things

11:58

started heading in different directions? Yeah,

12:00

sure. I really like Jeb. And

12:02

so I was feeling excited to work for

12:05

him. And I thought we had a chance

12:08

for about a week. We had a really good first day of the

12:10

campaign. Like our

12:13

first day was really strong. And

12:17

yeah, I knew

12:19

probably by

12:21

the fall that things

12:23

had gone, we're going a different direction.

12:25

Oh, pretty early on. Yeah.

12:28

Oh, yeah. I remember where I was when I knew. Where

12:30

were you? I was my

12:32

brother's bachelor party. I took two days off

12:34

the campaign. I was really hung over. And

12:37

we had a private poll coming.

12:40

And I had asked the pollster to put

12:42

one question on for me, which was

12:45

what do you like least about Jeb Bush?

12:48

And I'd saved it. I didn't want to

12:50

ruin the bachelor party weekends. I had an

12:52

open poll. And I looked at

12:54

it and we were like, Trump's killing us. Marco's killing

12:56

us. And then I scrolled all the way down

12:59

to my question, which is the last one. And it was like,

13:01

45% didn't like him because he was a Bush. You know, 48%

13:03

didn't like him because he

13:09

was low energy. It was like four other random

13:11

things. And I was like, Oh, so they don't

13:13

like his name or

13:15

his personality. And we're in a distant third. I

13:17

don't think there's going to be a path back

13:20

from that. When did Please Clap happen? At what

13:22

point in the campaign? Very end. Very end. And

13:24

that's all Ashley Parker's fault. But that happened at

13:26

the very end. I think the next president needs

13:29

to be a lot quieter, but send a signal

13:31

that we're prepared to act in the national

13:33

security interests of this country to get back

13:35

in the business of creating a more peaceful

13:37

world. Please Clap.

13:42

Yeah, there's also I think a habit of like,

13:45

Please Clap or the Dean scream were

13:48

not causes. They were

13:52

moments. Basically, you know, if you're in a bad mood and

13:54

it's raining out, you blame the rain. If you're in a

13:56

bad mood and it's sending out, you look for another explanation.

13:58

And I do think. I think that

14:01

like when campaigns

14:03

are at a kind

14:05

of downward slope, when things

14:07

like that happen, they get

14:10

sort of outsized attention because

14:12

they are fulfilling the

14:14

narrative. Yeah, people are looking for things to

14:17

sum up, Jeb being sad. Jeb's sad. Our

14:19

numbers are going down, right? Like it was

14:21

self-deprecating, right? Yeah. In a

14:23

room where we had just one New Hampshire and

14:25

he kind of gets interrupted and he's like, go

14:27

ahead, please clap. Nobody remembers that.

14:29

Like people, you know what I mean? But it

14:32

was because we were sad, people were looking for

14:34

a meme that Jeb just didn't come up with

14:36

a sad. Yeah, I never took it as

14:38

like a please clap. I always thought like he

14:40

understood like, just come on, work with me here

14:42

guys. It was charming. It was

14:45

charming. So Tim, here's a question that I wanted to

14:47

ask you about this, which is, so

14:50

obviously in

14:52

2016, there was

14:55

a kind of like, I think a

14:57

wider range of ideological outcomes, let's

14:59

say, right? Jeb becomes the kind

15:01

of for a time, the

15:03

main alternate, the

15:05

main sort of place you could go if you didn't want to

15:08

go to Trump. In 2012, it's

15:12

a narrower ideological band, right? Like what

15:14

you and Sarah Longwell, you have a

15:16

podcast with Sarah on the bulwark and

15:19

I thought there was a you, you, you do

15:21

have like an interesting discussion the other day about

15:24

what it was like being gay people in the

15:26

Republican party, listening for clues,

15:29

listening for people who whose heart really wasn't in

15:31

it. Can you

15:33

talk a little bit about that and how it

15:35

factored into how you ended up with Jon Huntsman

15:37

in 2012? Yeah, sure. I

15:40

mean, so in only that word for McCain,

15:43

he loses. And

15:45

then I like took a break from being

15:47

an active politics came out of the closet

15:49

and like, you know, focused on myself for a

15:51

while did a little self care, as

15:54

they say, and I didn't realize it was that late that

15:56

you're coming out of the closet. It was late.

15:58

Yeah. during McCain

16:00

really. So anyway, I was kind of

16:02

happy. I was at a PR firm and

16:05

I was attracted to Huntsman's campaign

16:07

because he was a Tim

16:10

Miller, right? He was moderate, he was center-last at

16:12

the time. He's for civil union. He basically has

16:14

the Obama 08 position in the Republican party four

16:16

years later, like I'm four civil unions and I

16:18

think gay people have dignity and all that. So

16:20

he was taking the most progressive

16:24

view among the candidates in that

16:26

ideological band in the Republican party.

16:29

And so to me, 2012 was like, I'm

16:31

getting back in this for

16:35

like the most earnest reasons possible. Like I

16:37

kind of know this is gonna be a

16:39

loser probably. Let's take the shot. It's worked

16:41

for somebody that like is really aligned with

16:43

me politically, you know, because

16:45

he's probably gonna be a loser. I got to

16:47

be the national spokesman. Like that's not a job

16:49

I would have gotten for a candidate that was

16:51

more likely to win because I was young. And

16:54

so like to me, that was re-entered,

16:56

I re-entered it for Huntsman. And

16:58

then, you know, after that, I kind of got

17:01

a little bit more career-rest about things. Just

17:03

to go back, when I went into politics, it

17:06

was really very kind of cavalier. I

17:09

like had been doing like math when

17:11

I was in college. I was

17:13

thinking about maybe being a lawyer. I

17:15

was so unexamined and so anxious and

17:19

insecure and

17:21

unprepared for these responsibilities that

17:24

like the idea that I was

17:26

like thinking about like, oh, Barack

17:28

Obama versus Hillary Clinton. I was just hanging on

17:30

for dear life. Like this is where I was.

17:32

I worked, it wasn't like I thought to myself,

17:34

ah, Barack Obama, Hillary Clinton, I'm gonna choose the

17:37

one that'll be a better president and that's the

17:39

one I'm gonna work for. It's like, this is

17:41

just where my desk was. And I believed in

17:43

her campaign and my, like

17:46

the way in which, you know, Tim was talking

17:48

about like, you kind of find the justification, not

17:50

the justification, but you kind of find the emotional

17:52

reason you're investing so much time. You kind of

17:54

do some cognitive dissonance. Like if I'm working this

17:57

hard, it must be for a reason. What is the reason?

17:59

Here are the reasons. And I

18:01

had those reasons and for me, a lot of it was

18:03

rooted in the fact that that was

18:05

a very rhetorical primary.

18:07

Their differences on policy were

18:10

very, very minor. Obviously there was a

18:12

big disagreement on Iraq. That was the

18:14

core of it. But by the time

18:16

they're running, their position isn't actually very

18:18

different. His view is that- That's the

18:20

same. His view is I wouldn't have

18:22

voted yes on the authorization. She had

18:24

voted yes on the authorization and then

18:26

came to view it as a mistake.

18:29

That's sort of like the core kind

18:31

of difference

18:33

in their sort of approach to

18:35

politics. And from that, a bunch of

18:37

other things happen. But so much of

18:39

that campaign was Hillary Clinton and

18:42

like the consultants around her trying to

18:44

make an argument that in

18:46

an electorate that desperately wants change, experience is

18:49

the thing that makes change possible. While Barack

18:51

Obama is saying, if you want change, I'm

18:53

change. And that was simpler and worked much

18:55

better. Did you develop any animosity for him?

18:58

There was some sour grapes because

19:00

I remember, I

19:02

remember like, I think my frustration

19:04

was actually not with him. It

19:08

was with the coverage. It was

19:10

a very frustrating campaign to be a part of

19:12

because you're like, wait a

19:14

second. Like he is an inspirational figure,

19:16

promising generational change. She is an establishment

19:18

figure that represents the status quo, but

19:21

her healthcare policy is to the left

19:23

of his. Her energy policy is to

19:25

the left of his. Why

19:28

is Maya the only person who understands that? And so

19:30

I think the only time it became a

19:32

kind of, I think like frustration with the

19:35

Obama campaign or with Barack

19:37

Obama, it was like when

19:40

that was the message, it

19:43

felt insulting to us inside the campaign because

19:45

like, it

19:47

was really like, it was an

19:49

unusual arrangement. Speech writing in the 2008 Hillary

19:52

Clinton campaign ran out of policy.

19:54

And here's something that you don't always

19:56

hear enough of from Democrats, a big

19:58

part of the campaign. of our plan

20:01

will be unleashing the power of

20:03

the private sector to create

20:05

more jobs at higher pay.

20:08

She really viewed speeches to her detriment

20:10

ultimately as a means of conveying policy,

20:14

chops, history

20:16

and proposals. And obviously I

20:18

think Barack Obama put a

20:21

lot more poetry on top

20:23

of that prose and basically made

20:25

the argument that like inspiration is what you

20:27

need and inspiration is what I offer. The

20:30

title of every creed and color from every

20:32

walk of life is that in America

20:35

our destiny is inextricably linked.

20:38

That together our dreams can

20:40

be won. We

20:42

cannot walk alone, the

20:45

preacher cried. So I think that like the

20:48

like how can he be the one offering change if she's

20:50

on the left like that doesn't make sense that doesn't make

20:53

sense. Of course there was so little difference it was it

20:55

was we were dancing on the edge of the pen. You're

20:58

losing bitterness was more focused on the

21:00

fake news media than on Barack Obama.

21:02

Yes, especially because like I

21:04

was in the convention in 2004 when he spoke. I

21:08

was at the Boston

21:11

convention in 2004 and I saw

21:13

that speech. I

21:15

was a volunteer

21:18

boom mic person for

21:21

a documentary of

21:25

a bunch of left wing like gadflies

21:27

who were running around the convention calling

21:30

Madeleine Albright a war criminal. And I'm

21:32

just like chasing Madeleine Albright was I

21:34

remember Madeleine Albright was sitting on a

21:37

golf cart. You know the seats on

21:39

the golf cart that face the face

21:41

the back backward and I just remember

21:43

I'm like there's somebody chasing Madeleine Albright

21:46

with a with a camera and I'm chasing behind

21:48

them as the golf cart pulls away. So

21:51

she didn't have to answer questions. I don't even remember what

21:53

they were what they were. It was it was I don't

21:55

know what during the Clinton administration they were focused on at

21:57

that time. So I was on the during

22:00

that speech and so I like would oh I

22:02

remember like you know there's a kind of like

22:04

team mentality so you're it's sort of but it's

22:07

like in quieter moments I remember being on the

22:09

Hillary campaign you'd be like you know walking to

22:11

your car with somebody and just talking about it

22:13

and just be like Jesus

22:15

Obama's good I'm in the McCain

22:17

office and I'm watching it on

22:19

streaming the Obama speech I just

22:22

walked out to the rest of

22:24

the people I was like we

22:26

are fucked it does not matter

22:28

if we win this primary I was

22:30

like we are fucked I remember saying like I

22:33

don't know what's

22:35

it like to lose to Kennedy it's like that

22:38

is that what this feels like because I think

22:40

this might be what it feels like okay so

22:42

Tim was saying earlier that on Jeb's campaign there's

22:44

like a clear moment where he was like oh

22:46

fuck we're gonna lose this when did that happen

22:48

on Hillary's campaign to Obama I know you were

22:50

saying like we there kept being hope during the

22:52

primary race but not really enough to sustain whether

22:54

one thing that happened where you're like it's over thanks

22:58

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