Eating Pizza With a Cool Person
Volume Two - Sidney Madden
One of the things I was super excited about when I started this newsletter was something I’m obviously calling “Eating Pizza With a Cool Person”. The idea is pretty simple: I reach out to someone I admire who is doing helpful, unique or interesting things in Chicago, offer to take them out for pizza, and we have a conversation.
Sidney Madden is a writer and editor for the daily Chicago email newsletter from City Cast. In case you’re unfamiliar with City Cast Chicago, this is from their website:
There’s a lot to love about Chicago. We’re diverse, boisterous, and fraught with some of the most pressing issues of our time. None of that diminishes Chicagoans’ deep passion and pride for our city, whose story is still being written. Every day, you’ll hear from the team highlighting what makes this beautiful, complex city we call home just a little bit better.
I’ve been an avid reader since my family moved back in February 2021 and Sidney and I have been email buddies since I started writing in to guess the answer(s) in their weekly Chicago location trivia game (and FYI when I finally won and was able to provide my own clue I picked the house from Uncle Buck).
I met Sidney at her favorite pizza place, D’Agostino’s in Lakeview, and we talked about writing, growing up in a very distinctive part of the city, and what it’s like to cover Chicago for a living.
CPN: Where did you grow up?
Sidney: I grew up in downtown Chicago, in the loop/Maggie Daley park area. I wasn’t born on Michigan Avenue, but my parents’ first place was on Michigan Avenue, and then we moved down the street. And that area has changed quite a bit. The lakeshore and the park area. It’s changed a lot in my lifetime.
CPN: What was it like to grow up downtown?
Sidney: It was really fun. I enjoyed it a lot. With City Cast I think a lot about my relationship to Chicago, and so at the beginning my relationship was just with downtown Chicago. I didn’t really think, not that other places didn’t exist, but just my Chicago was from the South Loop to Old Town to the West Loop. This was the space I inhabited. And then when I went to high school at Whitney Young, it was magnet school, so now I had friends from all different neighborhoods and it got bigger. But growing up down there was really fun. I got to volunteer at The Adler in high school, which I wouldn’t have been able to do in the suburbs. I could hear Lollapalooza every year.
CPN: And that’s pretty unique. I know people who have lived there, but I don’t believe I’ve ever met anyone else that grew up down there.
Sidney: And that’s what people’s reactions usually are. Even in high school, people would be like, “What neighborhood do you live in?” I’d say downtown, and then they’d go, “Ooooh.” That’s what they’d always say! I think it’s just because of how downtown was my Chicago, and other people’s neighborhoods are their Chicago, that’s what makes it unique. Also, it’s such a transient area between workers and tourists. But there are people who live there! I took a school bus to school with other kids! We exist!
CPN: Have you seen the video that just went everywhere about the penthouse across from The Bean?
Sidney: No! But that sounds like something I’m going to have to Google.
CPN: Someone is cleverly trying to sell their apartment. It’s pretty interesting.
Sidney: I love a good viral video. I’ll have to check that out.
CPN: Do you remember what your first favorite pizza was?
Sidney: I used to live right by Giordano’s when we were on Michigan Avenue. It was right across the street. So I remember eating that the most as a kid. And that was probably my favorite. I remember we ordered from there until one time they delivered us a pizza, this is when we lived right down the street so we were being lazy, and they forgot to put the cheese on our cheese pizza, so it was just sauce. And then we were like, alright, time to find a new place. But it was good up until then!
CPN: Was it tavern or was it stuffed?!?
Sidney: Tavern. I’m a thin crust girlie all the way.
CPN: Do you remember your first time having D’Agostino’s?
Sidney: It was probably when I first moved to Lakeview, so more than two year ago. I don’t specifically remember the very first time, but we walked by enough where I was eventually just like, we should stop in. And my partner, he used to ride the Addison bus, so he would pass by it a bunch. Then it just became such a spot for us. Winter. Spring. Summer. One of the last times we went, do you remember over the summer when we had the really bad air pollution?
CPN: I do!
Sidney: We didn’t have any food! I was like, we’ve got to eat something. So we came out here in our masks, and it was not safe, but that’s what we ate that day.
CPN: So it’s gotten you through some stuff!
Sidney: We’ve celebrated things here. We’ve had some tough moments here. It’s a good spot.
CPN: So what makes it your favorite?
Sidney: You’ll see, once you try it. But you’ve had it before, I think?
CPN: Yeah. It’s just been a long time.
Sidney: I think it’s the sauce. It’s kind of sweet, and I haven’t had anything like it. And I just told my co-workers this a little while ago, there’s something about it - and I don’t know if it’s because I come here when I’m really hungry - but the more I eat it, the hungrier I become. And that experience doesn’t happen to me very often. So there’s something, quite literally, in the sauce here.
CPN: Have you been to any of the other D’Agostino’s? Is this one your favorite?
Sidney: So there’s one that’s more west, and I think I went there in middle school with a former friend. This is my favorite. This is my grown up, happy, adult memories. And that one is my weird, childhood, middle school memories. Nothing to do with the pizza. It’s just the vibes and the people.
CPN: Which is totally understandable. So what do you love about Chicago?
Sidney: This is a good question. A lot of things. I think, as someone who’s moved around a lot and come back, it’s fundamentally home. I went downstate for college, and I remember I would take the Amtrak back up - and of course it would be two or three hours late - but I would step out of Union Station and I would just be immediately hit by the buildings and this sense of home. I went to school in Champaign, and the buildings were just so small there. I felt too big. And there’s not noise there. I would step off the train and hear, what are they called, the guys who drum on the buckets?
CPN: The Bucket Boys!
Sidney: Yeah. I’d hear The Bucket Boys. And you hear people talking and laughing and chatting. There’s just so much life. So anytime I’m away for any extended period of time I come back and I’m just hit with that, that sense of home.
CPN: What do you think could be better about Chicago?
Sidney: A lot of things. And of course we focus on that at City Cast. One thing I think could be better in regard to what I was saying earlier is that I think people really have their bubbles. And I think it would be great if we got out of our bubbles more. But I also recognize that’s really hard to do, because it’s not super easy to get around right now. Going from Rogers Park to Logan Square feels very difficult. You have to take, I don’t even know how many buses. Chicago could be better at connecting people.
CPN: Have you always been a writer?
Sidney: I think so. My aunt is an author, so at a young age she really encouraged me to explore my creativity. I remember one of her books, I wrote an epilogue to it, and I was like, look! And you couldn’t even read the handwriting. But she was very sweet and she encouraged me. So to do it professionally as an adult is a blessing.
CPN: When did you first start writing?
Sidney: I think that I was six. I really struggled with reading when I was young. It didn’t come easy to me. But I had a teacher who really believed in me and spent extra time with me. And I think that if he hadn’t done that, and obviously reading is a precursor to writing, I don’t know if I’d be here.
CPN: You went to school in Champaign…
Sidney: Yeah. University of Illinois.
CPN: What did you go to school for?
Sidney: Journalism. But I was confused. I started off on a pre-med track. But then I joined The Daily Illini because a friend’s sister had a good experience on the sports beat. I was looking for things to do, and writing was always fun for me. So I joined the features team. It was halfway through my first year, and my parents really encouraged me by being like, “You should consider changing majors. You talk about falling asleep in chemistry. And you don’t really like biology. And you procrastinate doing your calculus homework so you can go cover things for The Daily Illini. That’s a pretty clear sign.” And I was like, that is a clear sign. So I made the switch. And I’m really glad I did. I had a much better experience once I did.
CPN: What kind of stories would you do for The Daily Illini?
Sidney: A lot of human interest stories. My first story was about The Marching Illini, and I only remember it because I was so proud of the title - The Marching Illini: A beat of positivity on and off the field. Which is very cheesy, but I was nineteen, so it’s fine. So I did stories like that. There were other interesting things going on in the area, like around Halloween weekend a bunch of alumni would come dressed as famous deceased University of Illinois coaches and athletes and professors. And they would do a walking tour, so you could walk around and listen to them all do their monologues. So little, weird, interesting stories like that were my favorite things to report on.
CPN: How would you describe City Cast to someone who’s not familiar with it?
Sidney: That’s another good question. And I need to work on my pitch for this, and we’re doing our first memberships right now so I should be quicker about it. City Cast Chicago is a daily newsletter and podcast and the whole idea of it is trying to connect people to the city they love. We’re a network of newsletters and podcasts across the country, and Chicago was the first to launch. So the way we think about the podcast is it makes you feel more connected. And then the newsletter is how to get more connected. So that’s why we share our neighborhood guides, and we share so many events. But on the podcast this week my colleagues interviewed this woman whose family started the big pilgrimage to Des Plaines, and it just captures more emotion, whereas the newsletter is able to provide more utility to our readers.
(Quick note on the neighborhood guides, whoever did the one for Oak Park is obviously an incredible talent. People should really pay them for their opinions more!)
CPN: Which makes perfect sense. How did you end up working there?
Sidney: Saw a job listing and got lucky. I don’t know that it’s some amazing story, but I felt lucky to land there, for sure. Especially my first big job and they really took a chance on me.
CPN: What’s it like to cover Chicago?
Sidney: I think it depends on the day. Sometimes it’s really rewarding. And to meet people like you, who I first met as a reader. The readers are definitely the best part. You’ll probably find this interesting, we had someone write in to share their deep dish recipe because we did a podcast about who on our team liked deep dish and who didn’t, and I tried to make a deep dish and it was a fail. And he was like Sidney, try my recipe. And I haven’t yet but I’m going to! So we get really nice messages like that. Like, wow, you really took the time to sit here and write this all out and it’s very thoughtful. Another time someone wrote in to say, let me back up…we shared this fund for survivors of domestic abuse and we were like hey, if this applies to you you can get a thousand dollars (here is a link to the Survivor Crisis Fund, though their applications are closed at the moment). And this person wrote in and was like, “Thank you so much for sharing this, my friend really benefitted from this when she applied. And we only know because you told us.” So that is the best part, the very tanglible ways you’re hearing about how you make people’s lives better. So it feels like we’re really fulfilling that mission of connecting people to the city they love. And other days it’s really hard. Chicago politics is no joke. It’s fast moving. And everything going on with the migrants right now is disheartening. It’s hard to see so much human suffering. So it has its highs and its lows, but it also reflects the city we live in. Which is very complicated.
CPN: When you’re looking at stories, what’s your personal criteria for what you think is newsworthy or important?
Sidney: Great questions. I think something we ask ourselves a lot is how can we move a story forward? What’s the City Cast spin on it? Why are we talking about it now? Those are some of the things we’re looking at when it’s like, is it newsworthy? And then sometimes too, we do quite a big mix of stories, so it’s not always about doing the hardest hardest news. Sometimes we just want to give people a break from the really hard stuff. And I think we strike a really good balance. I’m trying to think about what we even talked about today. Daily news is such a trip. One day we might be talking about the Brighton Park migrant shelter, which was a big, big story last week and we covered that quite a bit. Then this week we talked all about snacks from Chicago. And I think it’s nice that people can get both in one place.
CPN: Do you feel like that makes it easier? That you don’t just have to talk about serious things. And you don’t just have to talk about more fun things all the time.
Sidney: Yeah, it’s a good balance. A when we go back to news selection, sometimes I think about it like; you want people to eat their vegetables, but you also want to give them a treat.
CPN: That’s a great way to put it.
Sidney: This is what you definitely need to know. But also, here’s something that’s fun to know. And I love to find things that are fun to know, which makes sense because of the features background. But yeah, anything that’s weird.
CPN: What are some of your favorite stories that you’ve done?
Sidney: Earlier this year I talked to this person who was at the Highland Park parade. She’s a survivor. And since then, even though it was only a year and a half ago, she’s become such an advocate against gun violence. And that was a very moving conversation. Just to hear what she’s been through. It’s super personal. There was this other one I really liked…I’m blanking on the artist’s name, but I can tell you later (Sidney did tell me, it’s JeeYeun Lee). She did this really interesting three part audio series about the lakefront and whether the City of Chicago technically owns it. Because it’s up for debate. And that was really fascinating. She spent a long time making these podcasts, and then she lead these walks with people. And they would all listen to them together walking from point a to point b. And I like I said to you earlier, I spent my whole life by the lake. So I told her during the interview, this has made me reevaluate my relationship to the city and where I live. Those are some of the standouts from this year. But then there’s fun stuff too. Any sort of reader engagement stuff is so fun. Right now we’re doing this Christkindl Market mug bracket. And so many people are participating! And it’s not going the way I thought it would go! But it’s really fun.
CPN: There’s a hockey writer who I talked to over the summer, and he generally writes more serious stuff, but he said his most read article of all-time was ranking alternate jerseys. So anytime you think you’re doing something important, then you do something kind of silly and see the way people react to it, it’s always interesting.
Sidney: It’s search engine optimization! I don’t get it. But whatever comes up first on Google I guess.
CPN: Is there a kind of story, or maybe even a specific instance you can think of, where you’d never want to cover anything like that again?
Sidney: I don’t know if I’d never want to cover it if it’s about Chicago. But I remember a really tough news cycle, and I might be getting some of the details wrong, but I think it was last spring. There was a lot of gun violence. A bunch of teenagers were in Millenium Park, and I think a 16 year-old got shot by The Bean. And I remember there was this quote, and he said his dream was to live until he was 21. Which is so depressing to begin with. And that was happening while there’s mass shootings going on all around the country. At Uvalde in Texas. And I believe something had happened in New York as well. There was a lot back to back. So we broke format that day, and we explained why we were breaking format. “This is really hard. So let’s all take a breath.” We also shared “some good news to get you through”. And that’s something my co-worker Jacoby says a lot on the podcast. So we were just like, hey, this is a really hard time right now but here’s some good things going on in the city.
CPN: What do you see as the future of newsletters, or ways of delivering community-based news?
Sidney: People have been asking me this a lot lately and I don’t have a good answer. It’s just so hard to answer. We’re seeing a newsletter boom right now, because there’s something very inherently personal about newsletters in ways that articles are less so. You know, I’ve corresponded with readers like you for a really long time, and so there’s almost like a relationship in that way because of the nature of the medium and the ability to reply. It feels like there’s a person on the other side of it, and people like that. Especially in the age of AI and ChatGPT, which is threatening to replace all of us. And I also think, with newsletters especially, that readers are choosing to show up there. They’re signing up. People are electing to be there and read the newsletter. It’s ultimately their choice in that way.
CPN: So City Cast Chicago recently launched a subscription model, how does that play into the future of your newsletter?
Sidney: That’s something I’m still learning. And we just launched it. We have two different tiers; the ‘friend’ level is $8 a month, and the ‘cousin’ level in $15 month. And each level unlocks different perks.
(If you have any questions about becoming a City Cast Chicago member you can also hit them up on email at: membership@citycast.fm)
CPN: Do you have any advice for anyone who’d like to do what you do?
Sidney: Anyone can start a newsletter now. It’s very accessible. More specific to Chicago news, and I’m really passionate about helping students, for people wanting to get into Chicago news there’s this really great program through City Bureau called Chicago Documenters. They train you, and they’ll pay you, to cover city council meetings. It’s a good way to figure out who the big players are in the city. It’s a good way to get some money. It’s a good way to build up some live tweeting skills. And I think they do blog posts as well after the fact. With Chicago media the hardest part can be getting your foot in the door, and this is such an accessible way. And they’re always looking for people to join. It’s pretty robust. And I subscribe to their newsletter. It’s so thorough, and so good.
CPN: One more. On a scale of one to ten, how sick are you of talking about The Bear?
Sidney: I actually haven’t watched that much of The Bear. I tried to watch the first couple of episodes and I got really stressed out! So I personally haven’t talked that much about it. I would actually like to talk more about it! So, I’m not sick of it because I haven’t really watched it.
CPN: I forgot to qualify what the scale meant anyway. Like if one meant ‘a lot’, then ten would mean ‘not at all’. So let’s say that. And then you’re a ten?
Sidney: How about a seven. Ten seems a little agressive.
Huge THANK YOU to Sidney for taking the time out of her busy schedule to meet up with me. I’m a big City Cast Chicago fan and I believe exactly what she said; it’s a great way to feel connected to everything going on in Chicago.
Now as for the pizza, I glitched and thought I’d eaten D’Agostino’s before only to realize I hadn’t, so this was officially my first time. Once again, Sidney was spot on. The sauce is slightly sweet, and like all good tavern-style, you want to keep eating it so long as there’s pizza left in front of you. The crust is super thin (like the pepperoni), but without being dry at all. If I lived closer to a D’ags, I would definitely add it to the rotation (and I’ll probably hit the Lakeview location up in the future whenever I’m going to the Music Box for a movie).
Sidney is awesome!