Q&A: The Candidates for Milwaukee County Executive

Theodore Lipscomb, Chris Larson and David Crowley talked with The Recombobulation Area about expanding transit, the proposal to raise the sales tax, addressing racial inequality, and much more.

The Recombobulation Area is a weekly column by veteran Milwaukee journalist Dan Shafer. Learn more about it here.

Left to right: County Board Chairman Theodore Lipscomb, State Senator Chris Larson, State Representative David Crowley. Photos via Facebook.


The next election being held in Wisconsin is on Feb. 18, when voters will head to the polls to cast their ballots in the Spring 2020 Primary. So first, head over to myvote.wi.gov to a) make sure you are registered to vote, and b) find out what’s on your ballot. 

There is an effort underway in this state that’s making it more difficult for some people to vote. Don’t let that stop you. Be prepared. And vote every time they let you. 

Early voting in Milwaukee is from Feb. 3 to Feb. 14, so don’t hesitate.

And in Milwaukee, Chris Abele’s unexpected decision to step down from his role leading the state’s largest county has upended the spring election, making the County Executive campaign the race to watch in local politics. 

While two candidates will emerge from the primary to compete in the general on April 7, the larger field of six candidates running for the office has already been narrowed down to four. The state Elections Commission removed Jim Sullivan, a former state senator who most recently was director of Milwaukee County’s Child Support Services, and Bryan Kennedy, the mayor of Glendale, after finding an issue with their nomination papers. Milwaukee County Board Chair Theodore Lipscomb, another candidate for county executive, flagged the Commission and urged them to remove Sullivan and Kennedy from the ballot. Sullivan and Kennedy appealed, but lost

Another candidate, Purnima Nath, was recently kicked out of an event held by the state’s largest immigrant rights group, Voces de la Frontera, for “verbally attacked multi-racial youth” and insultingly calling the students “illegal.” Nath, who has never held elected office, is also a conspiracy theorist, who, called climate change “nonsense,” questioned where President Barack Obama was born and made vicious anti-Muslim comments on social media. It’s very difficult to see her as a serious candidate.

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So it’s already been a bit of a weird race.

But now, with the Feb. 18 primary fast approaching, the field has essentially been narrowed to three candidates. There’s State Sen. Chris Larson, State Rep. David Crowley and County Board Chairman Theodore Lipscomb

The Recombobulation Area interviewed the three candidates. The interviews were all conducted separately, all by phone, largely asking the same questions, Q&A style. These were all recorded, and paying subscribers will soon have access to an audio version of each of these interviews. 

In the coming days, The Recombobulation Area will endorse one of the three candidates. You’ll be able to read the endorsement for free.

Here, you can read through what Lipscomb, Larson and Crowley had to say about many of the big issues facing the candidates and the County. These responses have been edited and condensed.

Why do you want to be Milwaukee County Executive?

LIPSCOMB: I’ve really been living Milwaukee County issues — budget, services, etc. — for some time now, and I’ve been really active and passionate about reinvesting in our parks and strengthening our transit system and really building a stronger Milwaukee County.  I grew up here, and my wife and I are raising our three kids here, and would like to make sure they inherit a county that’s as strong as the one we grew up in and our ancestors before us invested in. 

LARSON: I was born here, raised here, lived here my whole life, and as long as I’m raising my kids here, I’m going to make sure to fix our problems. I worry that if we continue on this same path, there will just continue to be the same cuts, the same decreasing of services, the same risk to our future at the County. 

CROWLEY: I was born and raised here in the city of Milwaukee, Milwaukee County. I’ve been here my whole life. And growing up here, I definitely understand the tale of two counties. Like many struggling families, my family relied on Milwaukee County services in order to survive. 

Whoever is going to be the next Milwaukee County Executive has to be a person that can be a bridge builder, and that’s been what I've built my reputation on. 

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What would be some of your top priorities as County Executive?

CROWLEY: First and foremost, it’s going to be about bringing back resources to Milwaukee County. We need to make sure that we can continue to provide quality programming for our most vulnerable communities. We have to make sure that we can continue to invest in our park system as well as build our transportation infrastructure. 

Racial equity also has to be one of those priorities. One of the worst places to live for African Americans is here in Milwaukee County and in the state of Wisconsin. It’s really about finding ways to make sure that when the tide rises, all the boats rise as well, and making sure that no matter where you live, what you look like, who you love in this County, that you have access to opportunity. 

LIPSCOMB: Fundamentally underlying most of the work is a need to secure a “fair deal” from the state of Wisconsin for Milwaukee County. And while there’s been a lot of talk about that being just a sales tax, it’s really about a lot more than that. It’s about the fact that most of what Milwaukee County provides is state-mandated services. Oftentimes, the lack of funding for those state-mandated services is what’s crowding out the ability to pay for things that people often care much more about, like transit and parks. 

LARSON: The big one is to end family homelessness in our first term. Homelessness is something that’s pervasive and it ends up impacting and scarring people’s lives, even those who aren’t homeless. 

It’s on us as a community to step up and help (people experiencing homelessness). If one of us were in that situation, you’d hope someone would step in for you. We can do that by working together at the County and make it a high priority.

That’s one, and we have a ton. On our website, we’ve got more plans and platforms and things than all the other candidates combined. It’s important to be transparent where you stand.

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Anyone stepping into this job is going to be compared to Chris Abele, who’s been the County Executive since 2011. What from the Abele administration would you want to continue or build on? 

LARSON: Ending family homelessness builds off of one of his big initiatives which is ending chronic homelessness. We have the ultimate goal of ending homelessness, full stop. 

Chris Abele has also embraced the sales tax shift, which I’m very welcome to. Considering he spent a few million dollars beating us up over it a few years ago, I'm very glad that he’s on board with shifting to a new sales tax, and allocating the funds for parks, transit and reducing property taxes. That’s something we want to continue to build on.

CROWLEY: There’s two things I would like to continue. Making sure that we can end chronic homelessness, I think that’s something that we have to continue to work on. Growing up here in Milwaukee County, my mother struggled a lot, and we were evicted on at least three different occasions. It wasn’t because she didn't want to pay rent, she wasn’t getting enough hours to pay rent, and she had three sons, and was going through a divorce. So making sure folks like my mother 20 years ago and people who are still struggling (can) find housing is something that we have to continue to do. 

Another thing I really appreciate County Executive Abele doing is really putting it out there, being the first County to say that racism, racial equity is a public health crisis here in Milwaukee County. As a black man, I really appreciate it and I think it’s a really good opportunity for us to really move the community forward. Because when anybody does better, we all do better.

LIPSCOMB: What he’s always talked about that I’d recognize him for is that he has always tried to put things in perspective of building a sustainable County for the long term. We haven’t always agreed on how to do that, and that’s where some of our arguments have come in — in terms of the wheel tax or the parking meters in the park, which I opposed. Obviously, at one point, that earned me about a $1 million of his spending as he tried to get rid of me. But after that election was over, we put that behind ourselves and worked together on the Fair Deal and we worked where we had common ground. We both recognized that this funding system, as it’s laid out currently, isn’t sustainable. It’s not a course we can remain on much longer.

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In what ways would you want to go in a different direction from the Abele administration?

LIPSCOMB: The areas where I’ve been most critical of him were the multiple pieces of legislation that he sought that were to increase his own power, or to increase the power at the County Exec, oftentimes at the expense of the County Board — but really, in my view, at the expense of citizens. In areas like contracts, where he can now write contracts for $100,000 with no review and up to $300,000 with very limited review, that he can sell anything that’s not parkland without any public process, without County Board oversight. We essentially find out after the fact that they’ve ventured into these contracts to sell public assets. Those things are outside of the norm in American democracy and I think they’re wrong. 

LARSON: I think it’s about returning power closer to the people. I pledged to reach out to each of the municipalities every single year and hold public listening sessions. This is something that I’ve done (as a State Senator), making sure that the people can actually have access to the office, which is very different from the County Executive, who is a lot harder to get ahold of, he’s a lot more distant. That’s one of the key differences. 

We’ve also pledged to visit each and every one of our county parks. I'm pledging to not sell any of them.

I think it’s important to set a clear path about where we need to head as a community, and that’s in contrast with where we've bounced back and forth the last couple decades.

CROWLEY: When you think about the relationship between the Executive's office and the Milwaukee County Board, not just within Abele’s office but even within when Scott Walker was in office, we need to make sure that we’re repairing those relationships. 

But also, (continuing) to invest in our transportation infrastructure. We can’t talk about workforce development without talking about transportation and I think we have to start working with our local partners and our neighboring municipalities and counties in finding ways to strengthen our transportation system. 

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What is your plan to address the County’s funding issues, and where do you stand on the issue of the sales tax?

LARSON: We do not have the flexibility to actually raise revenue to the point where it’s needed. We don’t have agency over our own destiny. We rely way too much on property taxes, and of 33 peer cities, we are among the highest, and we’re the only one that doesn’t have dedicated funding for transit and does not have the ability to raise the sales tax or raise a different kind of tax to be able to address needs. And unfortunately, we need that permission from the state. 

I would say that we are going about it a little bit wrong  by having Milwaukee County being the only one with its hand up saying it needs special attention. I think the way to go about it is to form a coalition around the state. Every other municipality and a lot of other countries are getting snubbed too and are recognizing they need flexibility. 

In the meantime, (we need to make) sure we’re leveraging as many federal dollars as we can get, and leveraging the fact that we’re a swing state and there is federal attention to our state. I think that’ll help in the short term, but it’s not a long-term solution.

CROWLEY: I am a supporter of (the sales tax). I think it’s a perfect example of getting folks to the table. You have the business community, you have Republicans and Democrats as well as organized labor saying that we need this in order to have some money locally to fix our own issues, our local issues. 

But we know with the current makeup, it’s not going to happen. And I think the only reason it’s not going to happen is that we’re only fighting for Milwaukee County. And I think we (need to) start to galvanize everybody around this state to say, look, we’re all hurting for shared revenue, we’re all hurting locally. You have many school districts that went through referendum, you have many municipalities going through referendum in order to just provide basic services. We have to talk about this as a whole. If we talk about this from a Milwaukee County perspective only, we’re doing ourselves a disservice and we’re continuing to put ourselves on an island.

LIPSCOMB: We have a very tiny window in terms of getting anything done this (state legislative) session, but we’ve at least begun the discussion, and we’ve begun to build a coalition. We now have other local officials speaking up and recognizing that they, too, are in tough financial straits. The business community (is) coming to the table, many prominent folks (are) lending their voice to this effort and saying that for Milwaukee County, the current setup is unsustainable. There has to be a real conversation about additional resources and broadening the revenue options available for local government. 

I certainly do hope (this discussion) leads to a referendum on the sales tax, but I also believe it’s not just about that. It’s about the idea that state formulas should be indexed for inflation. There has to be a recognition that costs increase. We can’t be stuck with a funding formula from 20 years ago. And that’s essentially what we have.

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What is your plan to expand public transit? 

CROWLEY: We have to build some relationships. A lot of folks don’t understand how vital our county transit system is to many different types of people. So that (means) building relationships with Racine, if Foxconn is going to happen. We know this region is going to change and we need to be looking at economic development regionally. We need to be talking to those WOW counties — Waukesha, Ozaukee and Washington — and figure out how we can get our workforce here in Milwaukee County to those jobs. 

But it’s going to take more than just partnerships. We’ve got to go after grant dollars. We’re going to create an office focused on seeking out and applying for federal, state and foundational dollars, not only to strengthen our transportation system but also to reinvest in our neighborhood parks. I also think the way we do this is partner with municipalities and take a different fight to the state of Wisconsin. We have to look at how we’re funding local municipalities. 

LIPSCOMB: There again, I think the Fair Deal intersects with all of these things. Milwaukee transit has long been recognized as one of the most efficient systems of its peer group. Nationally, though, it’s an outlier in that it’s one of the few or only systems of its size without dedicated funding. Until there is dedicated funding for transit, I think transit remains precariously positioned. I happen to think (transit is) one of the most important things we can provide for economic development and quality of life, and it should be a top priority. But from a legal standpoint, it falls below a lot of the state-mandated services that we have to provide. So it remains in jeopardy until there is a broader solution. 

That’s a big opportunity for us to try to work with our neighboring communities. It doesn't have to be a Regional Transit Authority. These things could be accomplished through intergovernmental agreements, but there has to be a recognition of our shared benefits. Many of those communities have employers who say they need workers and we have citizens looking for work who need to access those job opportunities and there should be cooperation on connecting employers to workers and vice versa. 

LARSON: First, you have to get dedicated funding to actually build it into the system. So, honestly at this point, where we are with the system is that there are probably going to be cuts. The transit system is on the chopping block. Realistically, we’re going to have the system we have until we get dedicated funding or until there’s an infusion of federal dollars. That’s the reality of it. If we have the funds to be able to expand to the point of what’s needed, then I think it becomes a lot easier to sell the system to people. We have way too many folks who drive and are paying for parking and would rather not given another option, but I think people are reluctant to use the transit system because of the risk of cuts. 

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Milwaukee County is part of one of the most racially unequal and most segregated metro areas in the country. What would you do in this office to address that issue?

LIPSCOMB: The historical patterns of the past still have effects today. Certain communities do not feel as welcoming. I think there’s a lot of work to be done to bridge that. I think I offer an opportunity to do that as someone who has represented both the suburbs and the city, and I think there’s a lot of work the County could do. I’m interested in us not just talking about it as an issue, but spending a lot more time diving deep into the ways in which County departments often are following the policies of the past without thought as to whether they should be rethought or re-examined for modern times and in recognition of issues like this. 

As an example, we were just talking about transit and the transit cuts that the Exec and the transit system were offering initially last year, they said they used a racial equity lens. And yet those cuts essentially cut the routes that extended out of the central city. The argument was that they would preserve the core system where riders are, but I think it’s a misapplication of the racial equity lens, that you would actually harm people’s opportunity for access to live other places, to work other places, and I think all of that deserves to be reexamined. 

I really think there are opportunities in departments across the County, from the airport to the zoo. Even within our parks, there was an analysis a few years back by the Policy Forum about the tale of two systems, that there is a different park system depending on where you live.

LARSON: I think it’s important to make sure that the Executive’s office, the administration and the entire County workforce reflect the diversity and background of our entire community. We’re going to make sure that’s a priority in our hiring practices, we’re going to make sure that the executive staff is majority-minority and we’re going to continue to reach out and listen across all communities. 

Another piece is how do we go about ending racial segregation. I think part of that is making sure that there is not housing discrimination. Through the County Executive’s office we can make sure that folks are empowered if there is housing discrimination. It’s something I’ll admit we’re not going to be able to snap our fingers and change immediately, but we sure have to begin. 

CROWLEY: One is finding more ways to bring more resources back so we can continue to invest in our Office of African American Affairs. Taking a hard look at all of our policies, how we’re hiring, but also how we’re contracting, (and) really forcing the conversation in the private sector. It’s (also) utilizing the Office of African American Affairs to look at our policies, how can we start to partner up with other municipalities and business to find ways to plug people into a particular position.

And I say that because there are not many times where you have an African American like myself actually running for Milwaukee County Executive. Let’s look at many of the companies even in the private sector as well as the public sector, you don’t have a lot of African Americans or people of color in many executive positions. This election has the potential of moving the needle forward and actually changing the narrative for Milwaukee County. I'm not going to say we’re going to end segregation in four years because it took a lot longer for us to get in this place, but we have to start having some tough conversations and talk about race in a constructive manner that actually moves this whole community forward.

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There’s going to be a lot of turnover on the Milwaukee County Board. Last I checked there’s going to be at least five supervisors who are going to be resigning at the end of their term. How do you approach that change?

CROWLEY: It’s going to be about building relationships. You look and we still have some institutional knowledge there with folks like Supervisor Willie Johnson who’s been there for a few years, Supervisor Moore Omokunde, Supervisor Marcelia Nicholson, Supervisor (Felesia) Martin is pretty new, but you’ve had some folks who have been there. I think what’s really going to be important is how well we work together. And I think that’s what this community wants to see, whether they see what’s been going on within Milwaukee County for the past few decades or they’ve been seen at the national level for the past few years, it’s really going to be about building relationships with each Milwaukee Bounty Board supervisor to make sure we know what our priorities are and how we can move forward together. I’ve worked for Milwaukee County government. I definitely understand what goes on within the Board, but also understand they have communities they represent, so I think it’s going to be extremely important to bring them to the table.

LIPSCOMB: (There will be) tremendous turnover. I believe two-thirds of the board will have less than four or five years of experience. There will only be two people with more than 10 years of experience. 

It’s one of the reasons that I think, coming from the Board, my experience with County government would be an asset in the Exec’s office, both the idea that I can hit the ground running, but also the idea that I can immediately bridge what has historically been tough relationships between the Exec and the Board. I do still have strong relationships there with those who remain and with some of those who are coming in. That’s an asset I bring to the office that my competitors don’t equally bring. 

LARSON: I mean, it’s some (turnover). But I think 15 seats are uncontested, including two people who are coming in uncontested. And what that tells me is the office has been denigrated to the point where people recognize that there’s not a lot of power there. The salary was slashed in half, the staff was slashed to a third of what it was, the ability to make decisions and represent this community was diminished and broken down. But if you’re going to make sure that there are good people committed to the County, you have to elevate that office again. 

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Reflecting on your career in public service, what’s an accomplishment you’re especially proud of? 

LIPSCOMB: The most underrated, under-known thing that I would point to that I am quite proud of is the fact that we continue to have a public, nonprofit transit system. There was an effort a few years back to contract our transit system to a for-profit out of Texas and essentially put the nonprofit that had been managing transit out of business and put a profit motive in between service and taxpayers. I was instrumental in pointing to a different path, which is that we should bring that nonprofit in house, that we should essentially absorb them and they are now a quasi-governmental instrumentality. I would compare them, and I did at the time, to the City having the Housing Authority or the Redevelopment Authority as a part of city government, and the same with transit to the County. 

CROWLEY: One of the things I am proud of that is also an example of me building bridges is when we were able to pass a piece of legislation that schedules Lincoln Hills to close in 2021. It was a huge topic for a number of years that we couldn’t get any traction in bringing Democrats and Republicans together, but I was able to facilitate a conversation within my first term, bringing folks like Robin Vos and Evan Goyke and David Bowen and Lena Taylor as well as Van Wanggaard and some of the other Assembly Republicans to the table to find something that we could actually pass to bring these young people back closer to home so we can actually rehabilitate them, because we’d seen what was happening at Lincoln Hills. So I'm really ecstatic and proud that we’ve been able to do that. We still have a way to go in making sure that everything goes off without a hitch, but to even get that through, it was a big deal for me. 

As an elected official who’s been in the Assembly for two terms, I'm the only person who has really passed some bills. I passed the most bills out of anybody at the state level in this race, so I'm excited about the fact that I have examples of being a bridge-builder. We’ve been able to get things off the ground and get things passed with bipartisan support. I'm dedicated to bringing that to Milwaukee County. 

LARSON: We’ve done a heck of a lot. Granted, I’ve been in the minority in all but five months during that time, and so while the victories don’t look as sweet as being able to stand at the top of the mountain and fly the flag and say, “Look at all the bills we’ve passed!” You could look at a number of things we were able to sideline or prevent from happening. That list is important, at the very least to make sure the public understands the most egregious things that are happening at the capitol, making sure that they have as much time as possible to digest what’s happening in our state’s name. And that list is long. 

You look at (when) Act 10 passed. That blatantly was an attack on public sector workers to diminish their power politically by cutting their pay, cutting their benefits and making it that much harder for them to organize. We went away for a few weeks to make sure the public had as much time as possible to digest what was going on. To that end, the largest protests in Wisconsin history materialized at the Capitol and that wouldn't have happened if they said “OK, they’ve got the votes, we’ll let them do whatever they want.” We were able to expose the move to right-to-work as nothing more than a right wing effort that’s organized by special interests. The list goes on. 

We’ve made small gains in some of the bills that I care the most about, and we continue to push on those. And in that regard, we push against our own party sometimes. One of the biggest issues I’m fighting for is drunk driving (laws). We are the only state in the country where your first drunk driving offense is a civil forfeiture, it’s a moving violation, you pay a fine. It’s ridiculous, and we have the highest rates of drunk driving as a result of it. People get killed every year, we lose anywhere from 160 to 185 of our neighbors and that’s something where I pushed against both parties and partnered with members of the other party who agree with me to get things done. (While) we’ve advanced a number of laws, we haven’t got legislation to actually tackle first time offenses, but we’re still making that effort. 

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Is there a candidate you are supporting in the Democratic primary?

LARSON: Yes. I’m in Elizabeth Warren’s camp. I think she's fantastic. I was part of a group that was trying to recruit her to run for U.S. Senate back when that happened. I was hoping she would run four years ago. And was very excited to see her step into the race and very shortly after her getting in, I had her yard signs in front of my house. I think it’s important now more than ever to make sure that we’re remedying not just the current administration or the current things that are in front of us, but thinking wholesale about the decades-long stacking of the deck. I think it’s important to finally have somebody in that position to shuffle the deck so the middle class has a fair hand.

LIPSCOMB: No. I’m going to keep my head down on that one, and I’m working my own race and I will support whoever is the nominee over Trump.

CROWLEY: I’m actually looking at all the candidates right now and haven’t made a decision about whoIi’m going to support, but to be quite frank, right now I’m trying to be the executive of this county. I had supported Cory Booker early on, but he dropped out and I haven't made a decision who i’m going to support moving forward just yet.

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What do you think differentiates you from the other candidates? Why should I vote for you?

LIPSCOMB: Being nonpartisan and the depth of my experience really do differentiate me from the other two with elective experience, both of whom are friends of mine. But they just don’t have the same deep understanding of county government, its issues, what we’ve done, what we’ve tried, what we’re yet to do. I believe I'm ready to hit the ground running in ways they are not. 

LARSON: The other candidates are great. We were the first ones out to make sure that we were running a clean, positive campaign focused on the issues and not on personalities. I think the community demands that, it’s essential, so we’ve done that. Put side by side, I’ve been in office for 12 years and have been very clear with where I stand. I’ve served as a County Board Supervisor, served in the State Senate, (and) if you look at the depth of my experience, it’s important to have somebody in that position who has got a line of sight of where we need to go long term, and I think i’m the best candidate for that. 

CROWLEY: I’m the only one who’s been able to actually get anything done in state government and build genuine relationships to get things done in state government. I’m a bridge-builder, and so when you think about making sure that we can tackle racial equity, bringing those resources back and also engaging some of our most marginalized communities, I have the ability to do that. But I'm also the only one who has not only provided these services, but was a recipient of many of these services. I bring a very unique perspective. I know how people feel about Milwaukee County. I know what it means to people, and I think that’s what sets me apart from everybody else.

You should vote for me because I'm the best candidate (laughs). When you think about the Milwaukee County Executive’s race, we need to think about what all we deal with. We're thinking about the House of Corrections, the parks, the transit system, mental health services, services for people with disabilities, services for our seniors, and I totally understand that these are the most vulnerable folks. When I think about who we are serving and what we do, but also more importantly where we want to go, I think I'm the most qualified candidate in this race, who not only has a vision, but has a plan in getting there. 


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