MIKE SPAULDING: First of all, Mr. County Executive, congratulations on the election. I don’t think we’ve had a chance to speak since taking office, so congratulations.
COUNTY EXECUTIVE CROWLEY: Thank you so much. It was a — it was a weird election, but glad we all pulled through.
MIKE SPAULDING: Yeah, a little odd. I’m sure when you started running for county exec you never thought that “I’m going to finish this race while, like, sitting at home and in quarantine.”
COUNTY EXECUTIVE CROWLEY: No, never did I think that we’d be going through a pandemic, but to wait six days for the election results, I would wish on no candidate.
MIKE SPAULDING: So how’s week number one been? You just got sworn in on Monday, Tuesday of this week.
COUNTY EXECUTIVE CROWLEY: It was not your usual week during transition. We’re definitely taking things slow, so we’re looking at about a 60-day transition. We’ve asked many of the essential staff to stay on because, again, we’re in the middle of a pandemic. So it’s about making sure that we can flatten the curve, get this community back being healthy again and really start to focus on the road to recovery.
MIKE SPAULDING: So have you had a chance really to settle in yet? I just ask, have you gotten to go to the office, sit in the chair yet? Do you know where your stapler is, all that kind of stuff?
COUNTY EXECUTIVE CROWLEY: No, I mean, I don’t know where anything is. I mean, I’ve been to the courthouse, I used to work there, so I’m lucky I know where the bathrooms are. But right now it’s just been hitting the ground running. We have been a part of the daily COVID-19 briefing sessions looking at how Milwaukee County is being impacted by the COVID-19 crisis, but also making sure that we’re putting Milwaukee County in the best path forward to make sure that we can continue to provide the quality of programming that people currently need or that they will eventually need as the results of the coronavirus.
MIKE SPAULDING: I know you spent some time in the City of Milwaukee working and, obviously, living and stuff like that. What’s it been like interacting in your new position with some of these people you’re going to be working with on a day-to-day basis, like Mayor Barrett or someone like that? I’m sure it’s been a little bit odd even if you know them.
COUNTY EXECUTIVE CROWLEY: I mean, it is a little bit odd. I mean, you’re sitting here staring in front of these screens all day every day, but we are definitely increasing productivity not just here within the political realm but I think all across Milwaukee County.
You have to thank our essential workers. It is National Nurses’ Awareness — I mean, Appreciation Week, Correctional Officer Appreciation Week. And so we want to thank those folks who have been on the front line by combating this virus making sure that we have a healthy community, and so — but it has been different, but we are coping with the times, but hopefully we’ll be back to normal soon.
MIKE SPAULDING: You have such a great backstory, and I do want to spend a lot of this interview kind of digging into that a little bit and kind of getting to know where you came from and who you are, but you have mentioned the pandemic. I do just quickly kind of want to ask you just about it in general. In our newsroom, it’s taken up a lot of the airspace in our newsroom on our airwaves, how much time per day do you spend on COVID-19, like focused things?
COUNTY EXECUTIVE CROWLEY: A lot of my time. I mean, right now, I mean, you can’t have a healthy economy without a healthy community. A lot of people want to go out and enjoy, you know, going to see their neighbors, helping out with folks, and it’s kind of put a hamper on everything. You’re not able to do the things that we’re normally able to do, and so — but I think that, you know, folks here in Milwaukee — not just here but across the country understand the challenge that we are in. And a lot — and many of us have risen to the occasion, making sure that we flatten the curve and continue to practice, what I like to call, physical distancing, because I think it’s important that we socialize. Many people are in their homes, we have safer-at-home orders here in the state also in some places across the country, but it’s extremely important that we realize that, you know, we need to make sure that we’re there for our loved ones, for our family and our friends, mentally and emotionally because many folks are really throwing the brunt —
MIKE SPAULDING: I know you’re locked in to all of the information now for — throughout at least the City of Milwaukee, we’re doing the daily calls and all those types of things, how do you feel that the state and local governments have thus far responded to the pandemic?
COUNTY EXECUTIVE CROWLEY: Well, I mean, when you look at this, we can always be doing more. I mean, I don’t think anybody is happy with what we are doing right now. We could see, I think — we want to see an increase in testing, we want to see more contact tracing, but it all takes resources. And so we definitely need to continue to lean on our federal congressional members as well as the state legislature to see what resources we can provide, especially to local governments who are on the front lines providing many of those services.
Here in Milwaukee County, we have really taken the — taken the lead in making sure that we can convene all 19 different municipalities. We don’t have a robust health department within Milwaukee County, so we have to work with the 11 different ones. And so we’ve been doing everything that we can to make sure that this community is safe and informed, but also making sure that businesses know that we are looking at how we open. I don’t think that we can have a conversation quite yet, because the science isn’t saying that we can open right now. It’s not a question of when, it’s more of a question of how to make sure that we don’t go — we don’t slide back into having another safer-at-home order.
MIKE SPAULDING: What’s the biggest hurdle right now? Is it being able to manage the human element to this or is it the business element or is it just strictly being able to get finances in order? Because, as we know, this fallout does have such a large kind of economic impact in what we’re going through right now.
COUNTY EXECUTIVE CROWLEY: I mean, I would say it’s all of the above. I mean, we think about the human aspects of this, we need to — a lot of people are seeing the COVID-19, and we talk about the data, and the people are being hospitalized, these are real people. These are our friends, these are our neighbors, these are our family members. And so we need to make sure that we are doing everything that we can to keep them healthy; although, we do know that there is an economic issue to this. And so, you know, when you see all of the businesses that have closed and many of the people that have been put on unemployment because they don’t have access to funds right now, we need to do everything that we can to get this economy back up and running. But, again, it’s more so about how do we do that to make sure that we don’t slide back and have to redo this all over.
MIKE SPAULDING: How do you find balance in those two things? How do you reckon with, you know, kind of being able and wanting to keep you and your family and friends safe but also understanding that, “Hey, as the county executive in Milwaukee, you know, I’m going to be overseeing the business climate here, and, you know, that’s going to play a large role in what I’m going to be doing”?
COUNTY EXECUTIVE CROWLEY: Well, it’s a delicate balance, but it’s about making sure that you have open communication. You know, I know me and my family, we’ve been doing as much as we can to kind of cope with the safer-at-home order. And one thing that we like to do is we like to play board games. It gives us the opportunity to have fun, talk to one another intimately about what’s going on in our daily lives.
But we also need to make sure that we’re talking to businesses. I definitely understand that they are hurting, but many of them also understand that they cannot open up too quickly. They may open up and they may have a workforce, but how do you make sure that you keep that workforce safe? But more importantly, how do we make sure that there’s consumer confidence out there that folks understand that they can go out and go to different businesses?
And so there’s a delicate balance, but we need to make sure that we understand that we are all in this together.
MIKE SPAULDING: And one more final political question, I promise, of this interview. You just got out of Madison, there is a lot going on there right now: The Supreme Court case; the governor saying one thing, the legislature saying another. Can you kind of take us behind the scenes a little bit? What goes on when you’re in Madison and you’re actually going through that process?
COUNTY EXECUTIVE CROWLEY: A lot is going on. I mean, it’s a lot of conversations about what is going to happen. I mean, when you’re in the state legislature, you’re trying to figure out what can you do to work across the aisle to get things done. Right now, this isn’t a legislative issue, this is in the Supreme Court. So it’s really about how our local governments respond once we know what that order is going to be. And we’re trying to do our best to make sure that we’re coordinating with one another as counties, as local municipalities to make sure that we’re ahead of the game.
MIKE SPAULDING: So I want to take us into the way-back machine here for a couple of minutes. You grew up in Milwaukee, not terribly far from where our studios are here on Capitol Drive. What was it like growing up for you in the City of Milwaukee?
COUNTY EXECUTIVE CROWLEY: Interesting, to say the very least. I grew up in that 53206 zip code that we infamously talk about, which is one of the highest incarcerated zip codes in the country and possibly the world since the United States is the only one to use zip codes. But growing up, I mean, we seen different things. Growing up, we struggled as a family with drug addiction and mental health issues. And we found ways to really — really I guess, you know, take ourselves out of the neighborhood and really introduce ourselves to something more different. And I contribute many of that, if not all of that — and it’s not to say I didn’t have loving parents, because I did, but it was an organization called Urban Underground that really introduced me to this life of service.
And so I started community organizing at a very early age, at the age of 16, 17. And really started to pipeline and create new paths into different opportunities. And so I continued to work in the community here throughout Milwaukee County and then eventually decided I was going to throw my hat in the race to run for office.
MIKE SPAULDING: How did you come upon the Urban Underground? So I wanted to ask you about that program and why it is so meaningful and so impactful for you.
COUNTY EXECUTIVE CROWLEY: Absolutely. So I — it just — stumbled upon it, to be quite frank with you. I was a junior in high school, Bay View High School, and a friend of mine was just sitting at the table and he called me over. And he couldn’t remember why he even called me, but his cousin was recruiting for this organization. So I picked up the application and asked him a few questions about it. And I just said, you know what, why not? I was already transient. I had never — I never really committed to anything before other than sports. So I wanted to try something new and I got involved in that program, and it really — it really — like, it got me out of my own comfort zone, in a sense, right. And so I learned more about just the City of Milwaukee or the block that I was living in. I had an opportunity to see, you know, other people, you know, I had the opportunity to actually leave the state and see other African Americans in other places, doing things that I never would have seen here in the City or in Milwaukee County. And it really inspired me to get more involved and really instilled some values into me about making sure that we give back. But more importantly, one of the things that my dad used to tell me all the time is that, “You can’t take care of your — nobody else if you can’t take care of yourself.” And Urban Underground really taught me to really reflect, look upon myself, understand who I am, but make sure that I give back to this community.
MIKE SPAULDING: Bill Glauber wrote a great profile on you, I think it was — it came out in Sunday’s Journal Sentinel, and in that same piece where he mentioned Urban Underground, he also mentioned that your mom used to call you “Governor Crowley” when you were a kid.
Did that happen before you really got into the community organizing or was that something you came up upon as a young kid?
COUNTY EXECUTIVE CROWLEY: I was literally a kid. I mean, I was 6 — 5, 6 years old and my family would call me Governor Crowley. And I never really understood it. They used to tell me that whenever we had family gatherings, you would be the first one — first one to help out everybody, you would be the last one to eat. Because it was just life of service. And so, you know, when I got my first political start, that was one of the things I thought about in the back of my head.
I am not looking to be governor anytime soon, but, you know, it definitely motivated me to continue to stay involved in this work once I got a taste of it.
MIKE SPAULDING: And so you did the Urban Underground thing, 16, 17 years old, and then you went to work for Senator Russ Feingold, right? What — at what point did that happen? How did that transition happen?
COUNTY EXECUTIVE CROWLEY: So I was doing community work, working at different nonprofits, so I was working around. And I was — I think at the time, I was working for Safe and Sound Community Partners. Community Partners, working directly with Milwaukee Police Department to combat drug houses and drug deals and really doing everything we can to bring real resources to those who need it. And an opportunity presented itself for the — Russ Feingold was looking for an African American statewide organizer, I had no clue what I was getting myself into, but I definitely gave them my resume. I will never forget it, it was George Aldrich who interviewed me, and two days later he hired me. Let George tell it, he’s responsible for all of my success. And I give him a piece — I give him a piece of that, but it was a really good opportunity. I got a taste of what it meant to be outside of Milwaukee County, do some organizing politically. I quickly realized not only did I love it, but people thought that I was really good at it. And that’s what really kicked off my political start.
MIKE SPAULDING: So you went to UWM, right?
COUNTY EXECUTIVE CROWLEY: Yes.
MIKE SPAULDING: You didn’t graduate though.
COUNTY EXECUTIVE CROWLEY: No.
MIKE SPAULDING: Why not? It just wasn’t for you?
COUNTY EXECUTIVE CROWLEY: No, it wasn’t that. The thing was is that we were having a lot of family issues, and so my last semester while I was attending UWM, I was actually there, online classes. My mother was having her own health crisis. And so unfortunately, I had to — I had to drop everything that I was doing. I moved from Madison back to Milwaukee, moved my mother in to help her get her back on her feet, which was not only therapeutic for her, but therapeutic for me, because were able to have some mother/son time that was desperately needed, and some conversations for us to get over for us to even be at the point that we are now.
And so looking — definitely will be going back to finish the degree. I don’t have that much time left, but once this work in the community, I have a — I have a family of five, and definitely had some challenges growing up, but we’re going to get there.
MIKE SPAULDING: So on the timeline of you, you know, moving your mother in with you; you moving back here to Milwaukee; and your time with the Russ Feingold campaign, did that all kind of coincide with one another?
COUNTY EXECUTIVE CROWLEY: So Feingold was 2010, and then I when I — I had moved to Madison actually December of 2012, I was still in school still —
MIKE SPAULDING: Okay.
COUNTY EXECUTIVE CROWLEY: — when I was — when I was actually working for Russ Feingold, and then I had to back out.
MIKE SPAULDING: So what was it about the community organizing for Senator Feingold’s campaign that — you said you fell in love with it, almost a love at first sight-type thing, what was the draw?
COUNTY EXECUTIVE CROWLEY: Well, you know, you get to meet a lot of different people, but when you meet a lot of different people, you get to hear about their different experiences, you get to learn about different geographical areas, different history. And, for me, you know, I’m a sponge. I like to get to know about different types of people. And I live by a motto which is, “Nobody cares what you know until they know how much you care.” And my thing was is that, you know, we have a lot of — a lot of problems, a lot of issues, not just here in Milwaukee County but throughout the whole state, throughout this country, throughout this world, and if we’re going to fix these issues and solve the problems, we have to be able to have some real conversations. And that’s what I love most about this. No two days are alike. I get a chance to really talk to people who are not just doing well but also suffering, learning from their experience, and also delivering them the best services that we can deliver to them to help them out at the end.
MIKE SPAULDING: And so you decided to run for office yourself, you got elected back in 2016. How did that decision come about, was it just a natural progression?
COUNTY EXECUTIVE CROWLEY: No, it was not. It’s funny that you say that, because the whole time — ever since that I worked for Russ Feingold, so many people would say, “David, you’re going to run for office,” or, “David, you should run for office.” And I would tell them, “No, not ever.” But I got bit by that bug.
And I first ran for city alderman, and I had lost that race. And, for me, I’ve always been a local guy. The closer you are in politics, the closer you are to the people. So when I lost that race, you know, the opportunity came for me to run for state rep. And, you know, I had a lot of friends who I’ve, you know, worked for or got elected. So I never seen myself running at any point, but when that seat opened up, it was — I knew that it was my time.
And so I ran and had the backing of a lot of different individuals, a lot of different organizations. But once I won, I also became chair of the Milwaukee Delegation and chair of the Black Caucus because many of the members and my colleagues understood that, you know, I may have — I may have been a freshman legislator, but I wasn’t a freshman to the building. And so I understood the process, I understood how to work with many of the folks in the assembly because of not only my personal experience but my professional experience being in the Capitol.
MIKE SPAULDING: We learn so much from our failures, and I wouldn’t even say running for office and not getting elected your first time is even a thing of it, more as a setback. What did you learn from the first time to the second time that changed and obviously changed your — changed the course of what you were doing?
COUNTY EXECUTIVE CROWLEY: Well, I mean, just — just thinking about what you said, failures, you know, I think about this quote that I got from Yoda, which is, “Try means to fail with with honor. Don’t try, do.” And if you want to be successful, you must double your failure rate. And so the only time that failure is a bad thing is when you don’t learn from it. And so it’s important that, you know, you pick yourself back up and you get back up on that train and try to move whatever objective you’re working towards. And so, you know, one thing that I have learned is that you have to continue to take a — take a chip off the block and it may not — the only way to eat a whole elephant is one bite at a time. I’m not — you know, I’m not trying to, you know, come at this and — you know, I understand, you know, what steps I need to make in order to get things done, but I also understand the process throughout all of that.
MIKE SPAULDING: So I don’t know if you remember it or not, but the day after the election in 2016, you came here early in the morning, sat where I’m sitting right now and we got to do an interview together. And I was a big fan ever since then just being able to sit down and talk to you. It was kind of a breath of fresh air, someone who you knew was going into something new, which was — which was awesome. But one thing — I listened back to it this morning, one thing you said to me was that you wanted to give Milwaukee a voice in Madison. So over your four years or, you know, a little under four years, do you feel like you accomplished what you set out to do on day one?
COUNTY EXECUTIVE CROWLEY: No, because I’m still doing it. You know, and I say that because as a state legislator, yes, you’ve been able to make some end rows, but, you know, we haven’t totally changed the trajectory here in the city or within Milwaukee County. And that’s one of the reasons why I ran for county executive. We need somebody who can be a bridge builder here for Milwaukee County. We have 19 different municipalities, we have 19 different urban unique needs. And when I think about what we need as a county is more cohesiveness and better partnerships to make sure that we’re getting the resources we desperately need and deserve here.
MIKE SPAULDING: Did you like your time in Madison in the state house?
COUNTY EXECUTIVE CROWLEY: Absolutely. I loved my time. I’m definitely going to miss many friends on both sides of the aisle up there, but they also know that I won’t be going anywhere anytime soon. They’re definitely going to see me a lot more.
MIKE SPAULDING: So both sides of the aisle, that means you don’t, like, despise each other like the — like we make it out to seem, right?
COUNTY EXECUTIVE CROWLEY: No, I don’t — I don’t despise anybody. I mean, look, you know, we may differ politically, but, you know, personally we may have a lot in common. I think a lot of the times, again, a lot us don’t take the time to really get to understand one another. And so we can’t just focus on our differences. And so it’s important that we understand what the similarities are. And once you start to have that conversation, you actually realize that you agree on a lot more than you disagree on, you may just differ — you may just differ on process.
MIKE SPAULDING: At what point did you know that you wanted to leave and to do something else? And was it — was county executive on your mind the whole time?
COUNTY EXECUTIVE CROWLEY: So, I never thought about, quote/unquote, leaving. I wanted to make sure that we continue to do the work of the people, but when the county exec office, this opportunity presented itself, it just — for me it was about taking on more responsibility and continuing the work when I first got elected in 2016.
MIKE SPAULDING: What’s your relationship like with former County Exec Chris Abele?
COUNTY EXECUTIVE CROWLEY: We’ve always had a good working relationship. He actually came, and practiced social distancing here during my inauguration, so I definitely appreciate him. But we’re also going to continue to work with him, he started a lot of good things here within Milwaukee County and look at what he’s been able to do with chronic homelessness. Also, personally for me, when you think about the declaring racism as a public health issue, something that we have to continue to focus on. But I look forward to working with him, but also, you know, my opponent Chris Larson as we move forward and making sure that we do everything that we can for Milwaukee County residents.
MIKE SPAULDING: Did he give you any advice upon your election to his former office?
COUNTY EXECUTIVE CROWLEY: “Be you.” I think that, you know, since the beginning of this race, we’ve always talked about being a bridge builder, and that’s the one thing that I’ve always focused on with him, whether we had disagreements or not. And so he thinks that I’m the best person for this seat, because what we need is someone who can bring more people together instead of tearing us apart.
MIKE SPAULDING: You’re from Milwaukee, you grew up here. That’s just one thing that separates you from the past several county executives that we’ve had. How does this — how does that shape your view of what your role is going to be moving forward, that you have such an intimate relationship with the city itself?
COUNTY EXECUTIVE CROWLEY: Absolutely. I mean, we’re going to have to work well with the City of Milwaukee, but I’m keenly aware that, you know, I am the county executive of 19 different municipalities, and so it’s extremely important that not only that I work with the city but all of the other cities and villages throughout Milwaukee County. So we’re going to do exactly that. The City of Milwaukee is the largest city within Milwaukee County, so we know that there is going to be some closer alignment there in making sure that we can provide the services and give the folks what they need. But I’m representing everybody, and so you’re going to have — you’re going to see me having conversations with those that agree with me; those who don’t agree with me; you know, union members; business owners to make sure that we can find alignment for Milwaukee County. Because if we’re going to move this community forward, we’re going to have to do it together. And I think COVID-19 has shown us that. When you look at the health data throughout Milwaukee County, we’re going to continue to fight for this to be the healthiest place, but the health disparities largely falls along racial lines. And so the COVID-19 crisis has exacerbated that, but we need to make sure that we continue to have this conversation, ongoing conversations to make sure that we are the healthiest county and that’s about working together.
MIKE SPAULDING: You’re the first African American to be elected to this position. How do you — how do you carry that with you? What does that mean to you?
COUNTY EXECUTIVE CROWLEY: It means a lot. You know, I remember, you know, learning about folks like Lloyd Barbee, Vel Phillips, and you know, they’ve been trailblazers here in the City of Milwaukee. And so, you know, back then when I learned about them, I probably didn’t know much what I was learning, but now I’m very aware of who those individuals are but also how to stand on their shoulders. And so for me it’s about making sure that we continue to push Milwaukee County forward, but I also understand that as the first African American elected to this seat, we’re probably going to have a microscope on everything that we’re doing. So we’re going to have to be better and badder at everything that we’re doing, but more importantly creating better partnerships, sustainable partnerships to make sure that we’re doing everything that we can for every resident.
MIKE SPAULDING: While it’s awesome to be the first person to do something, to break that ground, what do you think took so long for us to get to this point?
COUNTY EXECUTIVE CROWLEY: Well, you know, I think, again, it was going back to this message about bringing more people together. For the longest time, I think sometimes we may forget, especially during this crisis, that Milwaukee County is one of the most segregated places in the country. And so, you know, some of the conversations that we were able to have during this campaign, you never had before. The fact that racism was a public health crisis and was deemed that at the Milwaukee County level is unprecedented at that time. And I think that many people were starting to ask themselves “what needs to change?” But I don’t think people just came out to vote and said we’re going to vote for him because he’s black, it was because of the work that I put in as a state representative but also as a community organizer. But this is not just about, you know, being the county executive, this is also about how do we inspire, how do we bring hope to these communities while also doing a good job of administering the great services that we have to do.
MIKE SPAULDING: You’re also the youngest person to hold this office. How do you — how do you go about capitalizing on that ability? Is it being able to connect with the younger constituency? Is it being able to go out and inspire a young person to maybe get into public office or get out there and, you know, be a community organizer?
COUNTY EXECUTIVE CROWLEY: I would say absolutely. You still have those folks between the ages of 18 and 35 who may not participate and go to the polls and vote on a consistent basis. Although, eeing somebody closer in age to them may actually encourage them, but I think that this is going to again inspire not just folks who are the millenials or are my age and those who are younger, but I also think that this gives those — our older generation, our elders, some room to breathe, to know that we are looking to step up, are ready to step up, and that we’re willing to work with them. A lot of times when you see young people moving up in the ranks, a lot of the times it may feel like we’re trying to take the baton or steal the baton, but I want to let young — other young folks know across this state, quite frankly across this country, that we really need our elders. They have the wisdom. We need to create partnerships with them. But it’s a two-way street when we — once you start to understand that you not only can teach them but you can learn from them as well and that doesn’t matter what age you are.
MIKE SPAULDING: I can imagine that growing up in Milwaukee, still having obviously friends, family here having sort of a
legacy here already that some of the things you mentioned in your campaign, whether it’s addressing, you know, disparities in education, housing inequality, is it more of then — is it more than just a campaign slogan for you? I mean, do you kind of hold that closer to your heart knowing that you’re from here, you have had blood, sweat, and tears in this city and in this community as a whole?
COUNTY EXECUTIVE CROWLEY: Absolutely. So, I don’t think that these are campaign slogans. These are goals that we need to be reaching and obtaining, and we have to put the stake in the ground at some point as community leaders and as elected officials. And so as a person who’s experienced addiction, you know, three times within a year-and-a-half span, making sure that our young people and families have access to housing is near and dear to me. But we need to continue to fight for that. And so, you know, we’re going to — we’re going to continue to inspire and encourage this community, but this is not about pandering to anybody. We want to make sure that we are having open and honest dialogue and providing some transparency there so folks understand what my vision is for Milwaukee County, how they fit within that vision, and how we can move forward together.
MIKE SPAULDING: Along that same vein, and I know you have young kids, you have friends here, having that idea of being able to go out and see people in the community in which you’re serving, does that — does that bring with it more of a sense of obligation? Because you will see people who you’re speaking to politically but you’re also going to see them at the grocery store or, whenever see them at the parks and places like that, does it just add that extra layer of accountability; you’re not detached at all?
COUNTY EXECUTIVE CROWLEY: Oh, I’m not detached at all. And absolutely, that level of accountability is definitely there. Especially because I am the first African American elected. And so especially being in the African American community, I want to say that day two, after we learned that we won this race and I had to go grocery shopping, many people wanted to set — talk to me, wanting to let them know that one, they support me, but, two, I need to make sure I’m doing a good job and they’re willing to hold me accountable for that. Because again, it’s not about just being the first African American or being the youngest or being the first of anything, this is about, I think for many people, will you be the first to actually to do something that we can say that Milwaukee County has benefitted our lives especially during this time of pandemic.
MIKE SPAULDING: A couple of rapid-fire questions for you. Why do you think people with your background aren’t more represented in politics? Is it just a lack of a desire? Is it some other sort of barrier?
COUNTY EXECUTIVE CROWLEY: I would say, you know, it’s — the biggest one, I would say, is the access to resources. You know, when I first ran for, you know, city council, I didn’t have any resources. When I first ran for — I then ran for state representative, I didn’t have the resources. And so we don’t have the types of networks, in particular communities of color, to be able to get the necessary resources to run for office.
But I think a lot of the times also we tell people what they need to do in order to get in office, but we don’t have any training for folks once they are already in office. And I think that sometimes no matter — no matter who you are, that can be very overwhelming. And so we have to make sure that you’re not only preparing people to run for office, we’re actually preparing them to govern.
MIKE SPAULDING: Over the past four years since you first got elected to the state assembly, personally in your life, what’s changed the most since then?
COUNTY EXECUTIVE CROWLEY: I got a bigger family. I have a bigger family. So, you know, I just celebrated four years with my wife, Ericka Crowley.
MIKE SPAULDING: Congratulations.
COUNTY EXECUTIVE CROWLEY: Thank you.
So we have my 12 year old stepdaughter, Alyssa Anderson; I have a 2 — almost 3 year old, Ava; we have a 6 month old, Autumn.
So the biggest change is, you know, when I first got into this, doing this type of work is that, you know, I was a stepfather, and don’t get me wrong, I love my stepdaughter, but that family sense of, until I had children, really understanding who I’m really doing this for didn’t set in until I had my first daughter. And I have all girls. So, you know, me being an African American man, you know, for me it’s about setting the tone to make sure that my three girls have the same opportunities that I’ve been afforded to and even more. So, I mean, the biggest change is, you know, I have a vivid image of who and what I’m doing this work for.
MIKE SPAULDING: Being a new father, did that play a role at all in your decision to want to seek doing something back closer to home in Milwaukee?
COUNTY EXECUTIVE CROWLEY: I mean, it — if anything, it almost convinced me not to run, you know, but if it wasn’t for me having the awesome wife that I have, there’s no way that I’d be able to do this work in general. And so for anybody who is a CEO, working in the community, running any type of department, or any type of leadership position, definitely needs a partner that has their back no matter what.
And so if it wasn’t for my loving, dearing wife Ericka, there’s no way I’d be able to do this work. And so I would say that it didn’t — it didn’t have a bearing on it, you know, let my wife says — she was — and she told be flat out, she said, “David” — because I asked her on four different occasions if I should run for the seat, and the last time she said, “If you don’t run for this seat, me and you are going to have some problems.”
MIKE SPAULDING: It’s always best —
COUNTY EXECUTIVE CROWLEY: So I don’t know if she was — maybe she was just tired of looking at me at that point.
MIKE SPAULDING: She knew that you would be regretting it for the next four years if you didn’t do it. And she didn’t want you moping around at home for four years.
COUNTY EXECUTIVE CROWLEY: For sure.
MIKE SPAULDING: You probably don’t have a ton of free time, but when you do have some free time, when we’re not all, you know, forced to stay at home, what do you like to do?
COUNTY EXECUTIVE CROWLEY: So, I’m a big sports fan. I like to play sports. I played semi-pro football back in the day. So, whenever I can get out and play some basketball, that’s what I like to do. But me and my family are really big on board games. Again, so whenever we can play — you know, everybody likes to play Monopoly, we like to play Milwaukee. And so that’s what we do. We spend time and chat and have some time to really focus on, you know, the emotional side of things whenever you got games.
MIKE SPAULDING: Now you spoke very fondly of your now extended family, do you have someone that you looked up to that helped shape you in to get to you — where you’re at?
COUNTY EXECUTIVE CROWLEY: Oh, I mean, absolutely. I mean, I still look up to my parents even though when you think about their trajectory, but I outside of my family two — you know, I guess three people kind of come to mind. One of those people is Reggie and Charlotte Moore, those two who started Urban Underground. They have been literally a beacon of light in my life in helping me navigate, you know, all of the obstacles that were in front of me.
But I would also have to say one other person, she’s no longer here with us, is Tamara Grisby. I got to know Tamara when I was 18 years old, former state representative here from the City of Milwaukee. And, you know, my first time walking into the state capitol was because she asked to speak at a hearing when I was 18 years old. And I always remember the tidbits that she gave me. I would also have the opportunity to work with her former chief of staff, Cindy McGinnis, who’s in Madison, who also helped me learn the ropes as a staffer.
And so, you know, there are a lot of people. And, you know, usually I don’t like to give names because there’s literally so many people who have touched me in so many different ways that I could never thank them enough for what they’ve done.
MIKE SPAULDING: I want to thank you very much for giving me some time today. One more question for you: What are you —
COUNTY EXECUTIVE CROWLEY: Okay.
MIKE SPAULDING: What are you looking forward to doing most in your new position?
COUNTY EXECUTIVE CROWLEY: Actually, traveling across the county. Traveling across the county and really getting to get to meet as many of the constituents as possible and making sure that Milwaukee County continues to deliver the quality services that we do.
MIKE SPAULDING: County Executive Crowley, thank you so much for giving me some time. I appreciate it and hope we get to connect again soon.
COUNTY EXECUTIVE CROWLEY: Absolutely, anytime.
MIKE SPAULDING: Appreciate it. All right.