Episode 16: L3 IRL • Anne

[00:00:24] Tonight we're speaking with a woman who knows what it's like to be in the room where decisions are made, big decisions. Anne Caprera has been called Governor J.B. Pritzker's indispensable right hand. She's run campaigns, worked at the highest levels of democratic politics, and since 2019 has served as Pritzker's Chief of Staff, helping lead Illinois through some of the biggest political challenges in the country. She's a strategist, she's a powerhouse, she's a social media

[00:00:54] savvy political insider and because politics isn't stressful enough, she's also a Philadelphia Eagles fan and an avid surfer. Who knew? Tonight we're going to go behind the scenes. We're going to talk about politics, power, women in leadership, Illinois grassroots organizing, and what it takes to keep going in today's political climate. Anne Caprera, welcome to Left Leaning Ladies.

[00:01:20] So happy to be here, ladies. I'm just thrilled to be on a podcast with a bunch of women who are involved in politics and feel the same way I do about the world. So. Absolutely. Well, thank you so much for taking time out of your very busy schedule during an election year to sit with us tonight. We're going to jump right in with some questions. Sure.

[00:01:43] Anne, you've said that you knew that you were going to be in politics at just 13 years old. You wanted the life in politics. What happened to little Anne that made you think, this is the life I want? And then how much of that, how much of the woman that you imagined in your brain at 13 is sitting here with us today?

[00:02:04] Oh my God, that's such a good question. Well, a couple of things happened. Like I would start by saying I'm the eldest of five. And if any, if I have any other eldest daughters on here, you know that like, you just go through your life, right? Organizing people like my siblings joke that I'm just constantly hurting them places even now. You know, we're all in our 40s and late 30s.

[00:02:31] So, so that probably started at a young age, but there was actually a catalyzing event and it's my funniest like origin story. So I do tell it, but I was in the eighth grade.

[00:02:47] I grew up Catholic. And so we, I went to Catholic school pretty much through till I got to college. And I, in the eighth grade class and sister Mary Debra's class in the eighth grade, we, she decided she wanted to do a mock presidential debate. And this was in 1992.

[00:03:06] And so it was Bill Clinton, Ross Perot and George H.W. Bush who were running for president. And she's like, we're going to do this mock debate. I got really excited because I was, even at that age, I was like a debater and I liked to talk about politics.

[00:03:21] My family, by the way, it was all Republican. So like, I, you know, I grew up hearing about George Bush and she was like, okay, I'm going to select three students to play the president, presidential candidates. And she picked three boys.

[00:03:38] And I was like, I was like devastated. Cause I was like, I figured I'd get to play George H.W. Bush or something. So I raised my hand and I was like, what about the girls basically? Like, can we, you know, can we participate? And she kind of thought about it for a minute. And then she goes, you know what? We'll have the president's wives participate as well. Um, yeah, it's crazy.

[00:03:59] But like, and I, everybody, by the way, who hears this story now thinks this is where I tell you that I played a young Hillary Clinton and I did not. I played Barbara Bush. Um, and, uh, Patrick Scanlon, who was the quarterback of the football team was George H.W. Bush. And I was Barbara Bush. And we did the mock debate. And, uh, George Bush did not speak at all during that debate. I explained the Bush tax plan.

[00:04:29] And she talked about the economy, like the whole thing. And at the end, I like, she awarded somebody like winner of the debate and I won the debate, which is very funny. But I remember thinking like, this is so cool. This is what I want to do. And, um, I, when I got to high school, I had a champ, we had, we had AP classes and I had an amazing AP government teacher, uh, Mrs. O'Connor. She was like, it went. And that, at that time is when

[00:04:59] the moral majority, Newt Gingrich, they were taking over Congress. And there was this like whole, I mean, gosh, it feels like we just rerun this over and over again. Um, you know, send women back to the home movement. And I can remember even like, as a sophomore in high school, being so offended by this idea that that's what we were, they were advocating for. Um, and so I got really interested in politics and started to think like, this is something like, I love to write.

[00:05:27] I, I was on the debate team. Um, you know, I, I loved to argue about politics and ended up going to American university in DC, which just, I had a chance to like, basically live and work on Capitol Hill and be involved in all sorts of politics from the time I was in college till after until now. Um, but yeah, there was this, this eighth grade presidential debate got me both interested in it.

[00:05:55] And also like kind of outrage that the idea was that they were, they were going to, that my teacher was going to pick three guys and that I wasn't going to get to debate. And the debate was just, I couldn't even stand the idea of it. So, um, JB loves this story, by the way. He thinks it's very funny. I can see why that is an excellent story. That's amazing. Yes. I love that. I'm going to tell people that story.

[00:06:19] But you know, it's funny because years later I, I ran Hillary Clinton super PAC in 2016. And so every time I start that story, everyone thinks, Oh, I'm going to say that. I was like, I played Hillary and I didn't play Barbara Bush. Yeah. So that's awesome. Barbara Bush was very well liked. I remember when, you know. She was a tremendous, I mean, honestly, tremendous first lady. And she gave, I'm a, I, my passion is speechwriting. I don't get to do it as much as I would like, but I do do some of it still.

[00:06:47] Um, Barbara Bush years and years ago gave a commencement speech. I'm forgetting it was at one of the Ivies. Um, and the, the students at the time didn't want her to speak because there was some controversy going on with her husband.

[00:07:03] And she ended up coming in and giving like a really tremendous commencement address, which I respect immensely. It's worth going and looking up because it was like funny and heartfelt. And she talked about, you know, women going out into the world and, and being professionally successful. She was a really remarkable woman. And, and, you know, especially to think about right now as a first lady, like who she was and what she stood for, um, really mattered at the time.

[00:07:31] And I remember like, I remember liking her, even though I was becoming more and more liberal as I got into college and everything else. So that was going to be, I was going to ask you that. How did you go from being a Republican to a Democrat?

[00:07:48] It was also a funny story. Um, so I, I, I was at American and every student at American is like knee deep in politics. I mean, it just, you're, you're interning. You're following what's happening on the news. I was, um, a senior in college and, uh, that, that was 2000. So that was when, uh, the Gore other Bush, uh, presidential election was happening.

[00:08:18] And CNN actually was filming. We had a class that would go for about three hours and they had divided it equally between Democrats, Republicans. And then we had like four independents in the class and they would film us for like three hours. And then they would put seven minutes on newsstand on Thursday nights.

[00:08:35] And, uh, I was always featured on this class because I was just, I would say a lot of crazy things. And, um, but that was like the environment I was going to school in was like, you know, that we were really involved in politics and everything else.

[00:08:50] And I, you know, I, you know, I always, I started to realize my like sophomore, junior year. I'm like, no, no, like I I'm pro LGBTQ rights. I'm, you know, very pro choice. Um, obviously pro like I'm a feminist. I'm like a raging feminist. And, um, and so my, my values weren't really lining up with the Republican party anymore.

[00:09:13] But the, the, the moment that like switched everything, I took a class, uh, junior year where, uh, it was about the politics of choice. Um, and the, the, the professor who I'd worked under at the Women in Politics Institute at American, um, she was like an expert and is an expert on reproductive rights, had argued in front of the Supreme Court, like all sorts of stuff.

[00:09:37] And she basically did this two weekend class where she went through all of the things that were happening around abortion at that time. And she brought in people from really all sides of the debate to talk to the class. Uh, and there was, so we had a, you know, a pro choice panel that had like Planned Parenthood and NARIL and like all the stalwarts of the choice community.

[00:09:58] And then she had another panel where she brought in a bunch of anti-choice organizations to talk about their politics and like why they felt the way they did. And I'll never forget, there was a guy that came in and I don't, I can't remember the, what organizations they were, but he walked in representing one of these organizations and he had his pregnant wife with him. I mean, she was like eight and a half months pregnant and she was sitting next to him the whole time, didn't say a word, but like sat next to him the whole time.

[00:10:24] And then sitting right next to him was a woman from another anti-choice organization. She was, I remember actually like looking at her thinking she looked a little frail and they, my professor was asking them, okay, like what are your parameters? Like, are you anti-choice in all situations? Are you pro choice if a woman has a medical condition or life is in danger or rape and incest, like kind of went through the scenarios.

[00:10:50] And the guy was talking about, no, we, we are anti-choice in any situation. Like even if the mother's life is in danger. And I remember the woman from the other organization, remember she's from like, this is, I think it might've been like pro-life America or something like that. She literally looks at him and says, you know, I have cancer. And if I got pregnant, I would die. Like I couldn't survive the pregnancy. And he was like, well, we're, we would still be against the abortion. And I literally, like, I remember sitting in the back of the room and I was like, well, I'm a Democrat.

[00:11:20] Like, you know, like, I mean, and that was it. Like I went out the next day and changed my voter registration. So, so yeah, I mean, it really, for me, actually, that was like the catalyzing event that moved me. But it's, you know, we study this in political science. Like, you know, people are brought up. My, my parents were Republicans and my family was Republican, not Trump Republicans, but they were Republican. And, and so I, you know, I moved away from that through college.

[00:11:48] And then the funny thing was my dad was a Republican for a long time. And in 2010, I was working for a female member of Congress. I had helped elect her. I was her chief of staff on Capitol Hill. And I was talking to him and he was complaining about something with like the Obama tax plan or something like that. And it was right before the midterm elections. And I said to him, you know, dad, like if Obama, like if we lose, like if the Democrats lose, like I lose my job.

[00:12:17] And he was like, what do you mean? And I'm like, what do you mean what I mean? Like, you know, like I'm, I'm, I work for a member of Congress. Like she's up in, you know, three months. And if like there's a wave against the president, then she probably gets taken out in that wave. She's in a pretty Republican district. That means I no longer have a job. And he like was flabbergasted by this and hung up the phone. And the next day he called me and he was like, just got back from the DMV. I changed my voter registration. I love that.

[00:12:47] Like the financial situation finally kind of came home for him. And he's been a big liberal Democrat ever since. So that's awesome. That's a good dad. It is. But it's, you know, like the through line for all of this is like all politics are personal. And even, you know, they, I think when people see folks who work in this business, they think, oh, you know, we're certainly not doing it because you're going to become a gajillionaire.

[00:13:16] And it's not anywhere near as glamorous as like people seem to think it is. But you do it because it's personal. Like the things that you care about are on the line. And that's simultaneously what puts all the gray hairs in your head, but also like keeps you going. That's amazing. I have a question for you. So I also used to be more of a conservative.

[00:13:44] Did you find any correlation? Because I know that you said that you were raised Catholic and so was I. Was there any correlation between your religion and your political affiliation? Because for me, as I left Catholicism, that was kind of the catalyst for me to become more of a Democrat, honestly. So I didn't know how you felt. Right.

[00:14:10] So it's a really good question because I think there's a real schism, I mean, to use a Catholic school word, in the church right now. You know, I was raised very culturally Catholic. Like in the sense that, you know, you went to mass. We celebrated the holidays. You had your first Holy Communion. But like we didn't talk about it.

[00:14:36] I mean, it was, you know, nobody we didn't sit around the dinner table and like talk about Jesus like that. That was just not how Catholicism worked in when I grew up. We talked about it in religion class and that was kind of the end of it. And I would even say at the time, while the Catholic Church has always been political, like it was nowhere near as political as we've seen these things take shape over the last 20 so years.

[00:15:02] But, you know, I never connected with my faith in that sort of way. Like I was pro-choice from a young age and kind of rebelled against that aspect of the church. The only part that I did find comfort and I would say, you know, I lost my mom when I was 12. She was in a car accident and I can very vividly remember being in the church for the funeral.

[00:15:31] And that being the moment that I was like, OK, I have to believe in something that comes after because that's the only thing that's going to get me through this thing, this terrible thing that's happened. And over the years, I think that's morphed into like I see when religion is at its best, it's saying take care of people, be accepting of people, you know, go out and try to treat the injustices of the world.

[00:15:58] And I think that there is a movement inside the Catholic Church to get more back to that like social justice teaching. I think that's what you're seeing with this current pope and the previous pope.

[00:16:08] But on the other hand, you have I mean, if my grandmother, my sainted grandmother were still here, she would look and be like the converts, the new folks, the J.D. Vances of the world who have come in and brought more of an evangelical Christian aspect to Catholicism that Catholicism never really had on, you know, traditionally.

[00:16:30] So it's weird because I think in some ways I have found a little bit back to the church in terms of like they were the Catholic Church was enormously helpful to us when we were combating Operation Midway Blitz. I mean, they were really the folks in the communities in Chicago, especially who were communicating with the Hispanic community about how to stand up for your rights and how to be sheltered and like where to go.

[00:16:57] So the the cardinal here in Chicago is a friend like I would consider him a friend. We don't see eye to eye on every issue, but I see him as somebody who like is trying to figure out how to do the right thing and advises the pope on how to do the right thing. So it's it's I mean, I guess the answer to your question, Meredith, it's complicated, right? Like it's it's I don't go to mass.

[00:17:21] I'm not you know, I'm not what I would call like a devout Catholic, but it's still part of my life. Like I you know, I my brother. It's funny. My brother's like more of an atheist. He's like came out of it. He was the altar boy, too. Like and he's become more of an atheist. And a couple of years ago, we got into a fight about like the existence of God. And I started I was like yelling at him. And I'm like, how am I like arguing for this theological concept? It's never been like nobody would say I was the person that did that.

[00:17:50] But like but yeah, it's very interesting. I would say I'm a spiritual person. I don't know that I'm like a dogmatic religious person, though. So hopefully that answers your question. I did get to meet the group last year, which was one of the cooler things I've ever gotten to do. So that I would say just separate it apart from anything else. I was it was wild and very cool. So that's very cool. That is awesome. Yeah.

[00:18:17] My question is that we're seeing more women pursuing visible leadership roles in government right now. And especially in politics. And I think there's probably a lot of young women listening who would look at someone like you and think, how do I do that? Like, how do I become a governor's chief of staff? What would you tell them to pursue? Oh, so I love this question because I get to go every year.

[00:18:47] We have Girls State in Illinois and they always ask me to come talk to these 15, 16 year old girls. And I love speaking to them because they are they are like who I was at that time of my life. Like they're all dressed to the they have suits on and they're taking notes. And they're like I was like, I could tell every psychosis you kids have around homework and being a straight A student. And like, you know, all of the things.

[00:19:13] And I just love speaking to them because these are this is the type of question they ask. I look, if you want to be a governor's chief of staff, what I tell people is, and especially young women, get involved in a campaign like there is no better learning experience. And I actually think women do better on campaigns than anyone else because we are natural problem solvers. Like we we see a problem. We were looking for a solution.

[00:19:42] And those are the people that are rewarded on campaigns. And yes, there's still a lot of sexism and everything else. But in as much as there exists a like true meritocracy in this world, I would say campaigns are it. Even ironically, like the Trump campaign. I mean, Susie Wiles, like you would never think that Donald Trump would have had a female campaign manager.

[00:20:07] But like, I think we are kind of at our best when we're thrown into a chaotic situation that someone needs to bring order to. And so I always tell them, like, even if you're in high school and, you know, you're still figuring out your life, like just volunteer and get the taste of being around that kind of energy and the projects that we do on campaigns. Because I think you'll you I just believe people, you know, right away, you either love it or hate it.

[00:20:34] Like it's there's no you you're never mediocre about whether you like campaign or political life. And so that's the way to start. And then it's just once you get the first like foot in the door, each door is going to open after that. I mean, I could have never predicted the path that I took from, you know, graduating from American University.

[00:20:58] I, you know, totally on a whim sent my resume to Emily's list and I faxed my resume in literally. And they ended up hiring me to work as a research like coordinator on campaigns around the country. And I had no experience. Like, I really didn't even know what I was doing, but I learned on the job. And that one job enabled me to meet people.

[00:21:27] And then that job began another job, began another job. And even at the points in time when I thought, you know, I'm done with this, like I can't do it anymore. Then something would come along and change the course of what I thought I was going to do. And I think it's hard for the eldest daughter type A's. We're planners. Like we want to be like we have a five year plan and we have a 10 year plan. And what I always tell the young women I talk to is like throw that out the window a little bit.

[00:21:55] Like it's nice to be ambitious, like have goals, have things you want to do. But stop trying to think that you're going to be able to plot each point on the horizon because you're not. And, you know, the job that you thought you were going to have at 30 is probably not the job you're actually going to have. But you can make your way to the thing that you want to do. And if it's being a chief of staff or a governor, that's just time and experience and getting to know the right people. Not something, by the way, that I thought I would.

[00:22:25] If you had asked me 15 years ago, is this where you're going to be? The answer would not have been this job. So it's a little bit of a sometimes I sound like a successor. It's like, you know, love the journey sort of thing. But you should love the journey. Well, that that like as bends into my next question, what keeps you showing up every day? Rage. I mean, I'm passionate about a lot of things.

[00:22:52] But like it's funny because we, you know, I try to like take in an appropriate amount of social media. In this job, it's hard to like be all over social media because you will like you'll drown. But, you know, especially over the last two years, as we've been dealing with these things, it's funny because I'll have people occasionally will be like tweeting at me or blue sky me or sending me messages. You should be doing this. You should be doing that.

[00:23:17] And like what I want to say is like if you don't think I am as mad as you are about what's going on right now, like you got another thing coming. Like I, it can at times be difficult to deal with because I see it all the time. I see every aspect of what's bad about this government right now. And but I have to show up every day and figure out solutions. Like that's my job. And those solutions are always imperfect.

[00:23:44] But what I've learned working for JB especially is like you have to choose the imperfect solution over inaction every single day. Like you cannot get paralyzed by the moment and just be like, I don't know what to do. And I'm so mad about what's happening that I'm just going to stand here and rage. Like you have to you have to figure out a way forward.

[00:24:05] And then the other thing I would say is, you know, I when I think about politics and the history of politics and also what I've experienced over the last 25 years, a lot of our political history is really just a story of kind of a backlash and then a backlash to a backlash and then a backlash to a backlash. Like, unfortunately, that's what drives a lot of people is anger about different situations.

[00:24:33] There was one moment in my political career where that was not the case, really. And that was when we elected Barack Obama in 2008. And it was really this moment where there was hope. There was like this idea that we were doing something good for the country. And I believe that we can get back to that. I think that their road is hard. And I also think, you know, JB laughs at me because he's you know, he is the ultimate like happy warrior. Put him on the road. He's going to talk to everybody.

[00:25:02] He's going to have a smile on his face, everything. I am like, yes, happy. But I would like to win. And I have very little patience for people not having their eyes on the prize. Like, I cannot do anything to help the people that I care about if we don't win elections. And so, you know, for me, it's like that that drives me every day that I need to be part of a winning solution.

[00:25:28] And and then and then I also like to think about like these people being held responsible for the things that they've done. That's when I sit alone at night sipping a glass of wine. What I love that. I do, too. Me three. I highly recommend it. Anger is good fuel. Yeah. Well, my question's a little bit different.

[00:25:58] You spend a lot of time out in communities across Illinois talking with people well beyond the walls of the Capitol. When you get out of the state, what are you seeing or hearing that surprises you? And what are you seeing that genuinely excites you or gives you hope about Illinois and the people who live here? Well, I'd start by saying I love Illinois. It's my adopted home now. You know, I grew up in the suburbs of Philadelphia, spent a long time in Washington, D.C. But the last 10 years of my life have been here.

[00:26:26] And I never would have thought I'd move to Chicago and live here. And I love it. You know, I love the people. I love the state. I love everything about being in the Midwest. I would have told you 20, 15 years ago I was a coastal person, but I really, like, changed completely in terms of how I think about it. You know, one of the things that I love when I'm out on the road, whether it's with the governor or just me, is, you know, I think – I believe that people are fundamentally kind.

[00:26:56] Not everyone, but most people. And that when you really sit down and talk to them, they're not wishing ill on their neighbor. They're not, you know, they're not out being hateful in their community. That if, you know, if somebody they care about is suffering or going through something, they're going to try to help them. And I, you know, I could – we could do a whole podcast about how we've gotten to this moment in our country.

[00:27:23] But I think that there are a lot of nefarious forces around the country and around the world that are trying to pit people against each other. And trying to untangle that motivates me. And I watch it every day when we go places, whether it's in Chicago or outside of Chicago, where people are trying to have real conversations in their community.

[00:27:45] And are, I think, a little bit fed up with that kind of vitriol and hate coming from the federal government, coming from Trump. Like there is a – I think an active movement right now to find ways to dismantle some of that. And so I stay motivated thinking about that and thinking about how am I part of that? How is my boss part of that?

[00:28:10] Like what are we doing to make the conversation better at the same time that we're fighting for the things that we care about? And, I mean, you guys have my boss on. Like he's very much a fighter. We believe in that. But we also believe in like that politics shouldn't just be a miserable march towards an election. Like it should be about communities and about people. And it should be something that people feel like they want to be a part of.

[00:28:33] I mean, what you guys have created here, and I'm sure as you're out organizing in your own communities, like I think people are yearning for connection right now too. I think the phones and the online stuff, like they kind of hate how it's isolated them. And remember that a campaign or a political movement at its heart when it's really good and well run is a community endeavor. It's something you're doing with other people.

[00:28:58] And the best campaigns I've been a part of have – some have – I've won, some I've lost. But it's been like truly like the people that I got to spend time with. And I have these amazing memories of like being in the foxhole with those people. And so I think you create that through politics and through campaign. And the other thing I would say that I'm hearing from people, and I'm obsessed with this. My boss has heard me talk about it a lot. But, you know, I think people are really mad at a system that they feel is very rigged.

[00:29:26] And I think they're right to feel that anger. Like I think they have a right to that because I do think both in the Republican Party but also in the Democratic Party, we've abdicated a little bit of our responsibility to – you know, health care to me is like the best example of this. Like we should never let the health insurance lobbyists in the room to write health care legislation.

[00:29:49] And I don't care that like there are certain elements of the Democratic Party that are like, oh, we've got to raise money from these people or they've got to help us win elections. No, like we've got to get back to certain fundamental values around certain things. And health care is one of them. AI is another one. Yeah, absolutely. We're not like letting these people in to water down a bill when we need to try to figure out how do we deliver health insurance in a better way? How do we deliver health care in a more fair way for people?

[00:30:18] So I hear that a lot, and I hear it across the political spectrum. Like I think people are just really mad, and I think they have a right to be mad. And so figuring out how to fix that stuff really motivates me too. So what would you recommend for people like us living in these super rural communities of Illinois? What's the best thing we can do to affect change on a national level to get where we need to be? Well, what you're doing right now is important.

[00:30:48] I mean, honestly, I was saying this, I think, before we started taping. But like, you know, when people ask me, like, what can I do? You know, there's the traditional answers, right? You know, you can vote. You can organize. You can run for office. Like, we need to do all those things. But I think there's a third space that we all need to think about. And Democrats are not as good at this. Republicans are good at this. And that is, how are we creating community around the causes that we care about?

[00:31:17] One is hosting a podcast like this and talking about it, like being voices from a non-traditional Democratic area, as you guys are, and saying like, hey, we're out here and we care about this stuff. We're going to talk about it. I mean, I watched where you guys were talking through the hate comments you get and that sort of stuff. Like, I think that is really valuable. Like, I think people see that. And they, you know, and by the way, humor is the best way to combat that stuff.

[00:31:44] Like, and I think it makes people stop and reflect. I think it's also starting to get creative and thinking about how you bring people in. You know, I think when we campaign and political types, we're always thinking about organizing around like, oh, we're doing a phone bank or we're doing a door knocking effort or protesting. But I also think we need to find other ways to like suck folks in. Like, are you starting a book club?

[00:32:11] Are you, you know, are you creating some sort of event space or something that you're doing every week that, you know, people want to be a part of? I mean, you almost have to take a little bit of the lessons of like, I hate to say this, but like, it's true. Like the right wing evangelical culture. Like they don't start by recruiting people by going out and saying, you know, do you want to be a hard right evangelical? That's not how they, that's not how they draw people in, right?

[00:32:40] They say, come, come with me to this service. It's great. We're going to have a little social afterwards. And then there's a movie night or whatever. And that's how people start to be part of this. And so I think that the Democratic Party has to think about that too. And how are we being purposeful in creating community for people to come in and want to be around other people? And, you know, you bring politics into it.

[00:33:06] But I do think, especially in these rural areas, they also have to see that Democrats are not monsters. We're not crazy people. We care about our communities too. And there are common things that we all can be passionate about. And so that's my best recommendation now. And I'm also just engaging in the online conversation.

[00:33:32] Because I think that the right has really figured out how to infiltrate online spaces. And unfortunately, that's what gets served to a lot of people. So we need to be part of that conversation too. Yes. I agree. Great advice. Putting politics aside, if you had a plane ticket to go anywhere in the entire world, where would you choose to go serve? The Maldives.

[00:34:02] So I've been surfing. So the funny story about me surfing, I grew up in the surfing metropolis of the Philadelphia suburbs. I was always an ocean person. In the same way you guys all go to lakes here, we go to the beach out east. And I grew up boogie boarding. That was the thing that we, it was like the craze when I was a kid. And so I had always wanted to learn how to surf.

[00:34:31] And in 2014, I was the political director at the Democratic Senatorial Campaign Committee. We lost the Senate that year. And I just, it was a miserable election night. And I remember coming out of it thinking like, God, I just failed at this thing that I really wanted to succeed at. And I decided I needed to take a vacation. And I, on a whim was like, you know, I've always wanted to learn how to surf.

[00:34:57] So I literally Googled best surf camps. That's what I put into Google. And this place in Costa Rica popped up. And I was like, great. I went on, booked it, like pretty much sight unseen. Like I didn't know anything about it. And I got a plane ticket. Yeah, went down there. Had like the best week of my life. By the way, this place is called Pure Vida Adventures. They are still around. I go there every single year. I do a trip every year.

[00:35:26] I go to the same surf camp. I have surf friends. It's run by a woman who is from the Pacific Northwest. And she's great. And she has all these Costa Ricans who work for her down there. And they're amazing surf instructors. And the surf there is amazing. So anyway, I learned how to surf. And it's really, honestly, I'm not like, I'm like maybe a intermediate surfer at best. Because I only surf a few weeks a year.

[00:35:56] But it is truly one of the great things that exists in my life. Like it is so much fun. You go. So I have to put the phone away for, you know, however long we're in the waters. It's usually like two or three hours. You feel like a kid again because you're just like exerting all this effort. And you have to conquer fear, which is my favorite part of it. Like, you know, laying flat on a surfboard, those like one or two foot waves that you're from the beach, you're like, oh, no big deal.

[00:36:25] As you're paddling out, suddenly it looks like a tsunami coming in. And so you kind of have to figure out how to be, how to conquer fear. And I think as you get older, especially for women, like we kind of lose the muscle of conquering fear. Like we retreat into the places that are safe for us. And so picking up a hobby that forces you to stop and say, okay, like when you learn how to surf, they teach you first in the whitewater. So in the breaking water.

[00:36:53] And once you learn how to stand up and kind of maneuver, they'll be like, okay, we're going to go out to the green waves. And those are the unbroken waves. That's what you think of when you think of surfing. The first time you do that is terrifying. Like it's, you know, and it does not matter how small the surf is. It's just a scary experience. And almost everybody, the first wave you take, you wipe out. And then usually you're right in the crash zone, which means the waves are coming over your head. When this happened to me, I like freaked out.

[00:37:23] And I'm not a panicker by any stretch of the imagination. And I had a great surf instructor and she looked at me, she came paddling over and I thought she was going to like pull me out of the water. And she was like, Ann, get back. I hope I can curse on this. Get back on your fucking surfboard and get out. And like, that's literally what she said to me. Get back on your fucking surfboard. And so, and I like, I did, you know, I'm used to taking instruction.

[00:37:48] And, and I remember I like paddled back out and I was sitting in the waves in the lineup thinking to myself, I really want to go in. Like, I'm so scared. Like that was scary. And, and then I also was like, if I paddle in, I will never come back out and do the skim. And so I like communed with the ocean for like 20 minutes. And then she came back, my instructor came back and she's like, do you want to try another one? And I said, yeah. And so she pushed me to this wave. I caught a wave. It was the best experience of my life.

[00:38:17] That was 15 years ago. I've been all over the world surfing. Thank God, like I conquered this one moment of fear because it's led to this hobby that I just absolutely adore. And, and I will tell you a fun JB story. There are many reasons why I will never, like he has my undying loyalty. But on the, when I, when I managed this campaign in 2018 on election night, we were staying at a hotel in town.

[00:38:46] I came up, you know, we'd won. It's a big, great win. Election night when you win is the best thing in the world. And I went into my hotel room and on my bed was a custom surfboard. Surfboard that Ian had made. And he had a note on it that said, how can you ride the blue wave if you don't have a board? Oh, I love that. So that board is my house now.

[00:39:13] So it's, you know, but that's my, my long winded, but sincere advice is get a hobby. And if it's surfing, like it's a great hobby because you have an excuse to travel to a lot of exotic locations. That's amazing. Yeah. Very cool. So we have talked about a lot tonight. We've talked about politics and campaigns in Illinois, but I want to know more. We all want to know more about you.

[00:39:43] So we're going to do a left leaning ladies quick fire round. And so I don't want you to overthink this, like whatever first comes to your mind, it's nothing too serious. So are you ready? I love it. Yes, I'm ready. Okay. Coffee or tea? Coffee. Okay. Morning surf or sunset surf? Oof. Morning surf, but I will say there is nothing better than a golden hour surf. So.

[00:40:13] Okay. Summer or fall? I feel like I already know the answer to this. Summer. I'm a summer person. Okay. Deep dish or thin crust? Oof. I like deep dish. I really do. I actually had a piece. I had it for lunch today. All right. Road trip or plane? Plane. I don't want to be in a car. Dogs or cats? I have a bird. I love bird. Okay.

[00:40:43] So the third option, a bird. I love that. I love dogs and cats. Like I have a sister who has a dog and a sister who has a cat, but I've had lovebirds since I was 12 and I have one right now. So what's the bird's name? Marley. He is a, he's a neighborhood celebrity. I had a bird. I got, my parents gave me a bird when I turned 12, a love bird. And that bird lived for 22 years. Wow. I know.

[00:41:09] And when, when his name was Houdini, when he died, it was like the most devastating thing in the world. Oh, I bet. And, and then I had, and then I got another bird. I wanted a dog. And my sister was like, you're never home. When are you taking care of a dog? Um, so I got another bird and that bird died during COVID, which was equally terrible. And, um, and then I got Marley five years ago. It was literally like December of 2020. I, we were all in quarantine. I couldn't go home for Christmas. It was like a whole thing.

[00:41:38] And, um, my two previous birds, they only liked me. They did not like other people. Marley loves everyone. Um, Marley also lives in my like three bedroom condo here in Chicago. And I think he thinks I'm the night manager of a hotel. Like he just lives a glamorous life. I came home the other day and there was a little note under that had been slipped under my door.

[00:42:05] And it just said to the person with the cute bird on the first floor. And it turned out to be my neighbor. She was like, she wrote this little note about how she saw, she sees Marley in the window every day. And always like waves at him. And could she come over and meet Marley? And I was like, sure. So yeah, Marley's a celebrity. So that's so cute. All right. I have a few more. So do you like weekends in or weekends out and about? Oof. Mostly weekends in now, but occasionally.

[00:42:35] I like a, I like to travel or go somewhere for the weekend. So. And one last one, one word that gives you hope. JB. That was exactly what I was thinking. You would say. He does give me hope. I mean, I, I, I, you know, I'm not just saying this because I work for him. Like. I've worked for a lot of politicians.

[00:43:04] For women, for men, for organizations. And I think I could say this to a group of women. You know, when you work in a field that's dominated by men. You kind of get used to this. You probably have all been in a, in a meeting or on a conference call with a bunch of guys.

[00:43:22] And you get the impression that they are humoring you, you know, that you're saying something and they're kind of, you know, they're texting someone or there's a side look or whatever. And, and I had gotten used to figuring out how to navigate rooms like that. And JB was the first male politician I worked for that.

[00:43:48] I, I felt like I had his full attention and he thought I was smart enough to do the job I was doing. And he listened to me. And I have a thousand examples of this over the years, but like, you know, I, I remember, you know, I had, I had run Hillary Clinton. I had won super PAC in 2016. And that's how we met was election night, 2016. If you want to talk about an origin story, like JB Pritzker and I met at the Javits Center in 2016. Wow.

[00:44:16] And when I call it our sliding doors moment, cause like could have gone either way. Like our lives would have gone in a different direction if she had won that night. But so I, I'd run Hillary's super PAC. I'd never really spent any time with Hillary though. And when you run a super PAC, you're legally mandated not to talk to the candidates. So when I got here and I was managing JB's campaign, I remember it was like the summer of 2018.

[00:44:42] Hillary came into town and she was doing an event that can, might've been a book thing or something. And she said, she contacted JB cause of course he had shared her campaign and asked if, if he wanted to come to dinner. And he said, yeah. And it was him and MK and he invited me to come along. And I was like, you know, I'm not starstruck by a lot of people, but I, I love Hillary Clinton. And so I went to dinner and I, you know, I've been a staffer my whole life.

[00:45:12] And, and the staff mentality is like, you know, you're seen and not heard basically like, you know. And I remember we sat down at dinner and Hillary was asking him all about the campaign. You know, what was going on with the gubernatorial campaign? How was it going? What did the polling look like? What's the messaging? Blah, blah, blah. And he didn't answer a single question. He turned to me and he said, and you should tell Hillary all about the race. Like you should. And every time she asked a question and he would direct it to me.

[00:45:37] And I was so thrilled to be like, you know, here's this like iconic political figure to be talking politics with her. Like, you know, to be like, yeah, this is our theory of the case. And this is what we're doing with the TV ads. And, and so I, it always has stood out to me as an example, because like most political people and frankly, most men would want to hold the whole spotlight in a situation like that. And he just turned it over to me.

[00:46:07] And I've never been in a room with him where somebody will say to him, hey, that was a really great speech or that was a really great idea or you did this or that, where he knows I was part of it, that he doesn't turn and say that was actually Ann's idea or Ann did that. And I just, I have a, he's, he's my family now.

[00:46:28] I mean, even if he decided not to do anything else in politics for the rest of his life starting tomorrow, like we'd still, he'd still be somebody I talk to all the time and want to work with because I just, I, he's, he's got me to stick around. I told him I was going to do a year as his chief of staff. And that's. So he's the best. And I, I, I love him. I mean, like he's, he's really family. And I, I, you cannot say that about every political boss you've had in your life. So.

[00:46:59] And he's awesome. He's awesome. He's awesome. He's awesome. He's awesome. He's awesome. As the candidate. What's that? Instead of the person behind the scene. I said, would we ever see you as a candidate and the person behind the scene? No. I, you know, when I first got into politics, I thought I was going to run and I, I love what I do. Like I, you know, I, I love the, I love moving on. All the pieces on the, on the chessboard. You know, I love being able to sit and think about the strategy and the messaging and like,

[00:47:28] how, how are we getting something out that we need to get out? And I, I mean, I guess you never say never, but not, not, not anytime soon. But I, I love this stuff. Like I love talking about it. I love, I love talking about the man I work for. I love, I love getting into it about what's going on in the country and what the future of the party is. Like I, I care a great deal about that and have a lot of opinions on it, but running for

[00:47:57] office, probably not, not right. You know, and I, I think that we've learned so much from you tonight and thank you for giving us a glimpse, like behind the curtain, because we don't always get to see that. And we really, really enjoyed hearing about you and your journey to where you're at now. And we love hearing about the campaign and we only wish you the best of luck. I know that you are super, super busy right now. So thank you so much for joining us. We are thrilled, thrilled to have you.

[00:48:26] So ladies, this was a pleasure. Thank you for having me on. Hopefully I'll get to talk to you again and please thank you for what you're doing. Thank you for being so active in your communities. I love that you started this podcast. It gives me hope. And like, I, please don't lose that in like the next, you know, coming months and years as we are like trying to figure out what we got to win in November and then we got to win in 28.

[00:48:53] And, um, we're going to need you to, to be doing what you're doing in order to get that done. So thank you. Thank you. Thank you so much. Thanks guys. Thank you. Tell JB we said hi. He's like, oh, you're going on the left leading ladies. And I was like, yes. Awesome. He watches all of the stuff. Like he really does. So it's sometimes drives me a little bit crazy because he watches every single podcast that exists in Illinois.

[00:49:24] That's so awesome. Yeah. Awesome. Well, thanks ladies. Thank you. Thank you so much. Have a great night. You too. Talk to you later. Talk to you later. Bye. Bye. Bye. Bye.