A Certain Shade of Purple: Can these Democrats win local races in Waukesha County?
In Waukesha County's two largest cities, unabashed Democrats Mike Hallquist and Alicia Halvensleben are each running for mayor. A special feature story on the purpling of the former GOP stronghold.
The Recombobulation Area is a 19-time Milwaukee Press Club award-winning opinion column and online publication founded by longtime Milwaukee journalist Dan Shafer. The Recombobulation Area is now part of Civic Media.
Brookfield Square Mall is empty. And not just because it’s a weekday morning in February.
The emptiness is felt the minute you walk into the food court and there are no food vendors operating — the last one moved out in November. Vacant storefront after vacant storefront with vacant kiosks in between, with only a few anchor tenants hanging on, Brookfield Square Mall is now a ghost town — a relic of the once-bustling space it was, now struggling to re-invent itself.
When I go meet with Mike Hallquist, the Brookfield alderman now running for mayor, and he bristles. He knows this “empty husk of a different generation,” as he’d refer to it as, is not a particularly shining example of the evolution of the city where he’s served on the Common Council since 2020, and that it is clearly not currently in great shape. But, he tells me I should go visit on Saturday, where the Brookfield Farmers Market takes over the hollowed-out food court.
Hallquist is passionate about Brookfield, he’s an optimist, and he’s pragmatic. He’s very action-oriented, saying he’s “passed more ordinances and amendments” than anyone on the council, combined. He’s focused on results, and touts initiatives like the redevelopment of Wirth Park through a public-private partnership (officially reopened with an inclusive playground last week) and piloting the use of universal changing stations at city libraries (a concept since adopted by other Waukesha County communities) as top accomplishments in his current role. He champions public safety, and celebrates that in Brookfield, every firefighter in the city is also a paramedic — “a higher level of service than other communities provide.” He wants to get things done, and get them done well.
“How do we stay a great community?” he said. “You look for constant improvement in everything you do. And even when the answer is hard, you figure it out.”
The 40-year-old second-term alderman recognizes the need for this community of just over 40,000 people to “continue to adapt” and change with the times.
When it comes to development in a “built-out” suburb like Brookfield, Hallquist said, “It’s very easy when you are in expansion mode, when you have limitless fields of green to expand, to build houses…It’s much harder when you are now 40, 50, 60, 70, 80 years in the future and you’ve had to rebuild that road three or four times, and your property tax revenue will not go up high enough to cover that cost. So, the City of Brookfield has to find a way to remake itself as a modern suburb that is sustainable.”
Brookfield Square, he added, is a “natural location” for new housing, including affordable and mixed-income housing, and larger mixed-use developments that reinvent the space.
Housing and development is one of the top issues in Hallquist’s campaign for mayor — along with modernizing the way the city communicates by embracing digital media and being “radically transparent” about the way government operates. That also means being more hands-on and proactive about redevelopment — like at Brookfield Square Mall, where he’s critical of the current administration’s efforts there.
“The city should’ve been far more proactive in changing the zoning and indicating what it wants that property to be and the value it would provide,” he said. “And then, heaven forbid, we actually go out and try to find those projects to come into our community and we try to market those opportunities to people capable of building them, because that’s a win-win.”
Taking action on development projects is something a recent study from the nonpartisan Wisconsin Policy Forum shows that Brookfield is struggling with. Of several southeastern Wisconsin municipalities analyzed, Brookfield has by far the longest “median project timeline, “ of 467 days.
“We have to be more open to housing and providing what the market will provide,” he said, because “at some point, it’s death by a thousand cuts. We’ve made it so hard to build in this area that nothing will be built, and the best projects will look at Menomonee Falls, they’ll look at New Berlin, they’ll look at Waukesha, they’ll go to the Lake Country area and they’ll look at every area but us because we’ll be too hard to work with.”
Issues like housing and redevelopment or updated communications practices or responsible budgeting amid inflationary pressures and under-funding from the state are the types of challenges cities across Wisconsin are facing. In that respect, Brookfield is no different from so many of the municipalities where folks will be heading to the polls in the nonpartisan Spring Election on April 7.
Perhaps what sets this race apart, though, is that Hallquist is an unabashed Democrat running to be mayor of one of the largest cities in what was once the GOP’s unequivocal stronghold — Waukesha County.
He’s also not the only Democrat running for mayor in a Waukesha County municipality. Alicia Halvensleben, a second-term alder and Common Council President, is running for mayor in the city of Waukesha.
A generation ago, Democrats running for office in Waukesha County would’ve been unheard of, but the longtime base of Republican politics in Wisconsin is in a period of significant and rapid political change.
While 68 of Wisconsin’s 72 counties shifted to the right from the 2020 to 2024 election, one of the four counties to shift toward Democrats was Waukesha. Waukesha is the third most populous county in Wisconsin, so a shift of a few percentage points in the county’s overall margin matters a great deal in the overall calculus for statewide elections.
In Brookfield, for the 2000 presidential election, George W. Bush won in the city by a more than 40-point margin, winning more than 70% of the vote. In 2024, Donald Trump carried the city by just over 5%, winning just over 51% of the vote. It’s not just Trump, either, as the shift has been seen in state level races like ones for governor, too. In 2014, Scott Walker won by a more than 45-point margin in the city when he was re-elected — 72.4% to Democratic candidate Mary Burke’s 26.9%. In 2018, Walker’s margin of victory slipped to about 28% (63%-36%) in his loss to Tony Evers. When Evers was re-elected in 2022, defeating Republican Tim Michels, the Democratic governor narrowed the gap to about 8%. That’s a nearly 40-point shift in just eight years. The reddest of red suburbs has significantly purpled.
“I feel like we’re close to a realignment where things happen quickly and change dramatically,” said Hallquist.
Partisan politics have seen several flashpoints in Brookfield in recent months, most recently with a Trump administration effort with the U.S. Department of Education coming to Brookfield Central High School, inviting significant pushback from parents and the community, and even some protests — even if the event itself was fairly benign, unlike some previous events in this “History Rocks!” tour, which featured Linda McMahon and Erika Kirk.
So, what would it mean if a Democrat won the race for mayor in Brookfield?
“It would be a paradigm shift,” said Hallquist. “This is the canary in the coal mine…There is a different way to lead in this county — and that’s not directly tied to partisanship, necessarily. But it is tied to challenging the way we’ve always done things in Waukesha County and understanding that to survive, all of the suburbs are going to have to adapt and change.”
Like Brookfield, the city of Waukesha is experiencing dramatic political shifts. The swings in presidential races haven’t been as pronounced as in Brookfield — Bush won by a 21-point margin in 2004; Trump by a 6-point margin in 2024 — but in gubernatorial races, shifts have been significant. In 2014, Scott Walker won the city by a 32-point margin. In 2022, Republican Tim Michels carried the city by less than 4%. And just a year ago, in the 2025 Spring Election race for Wisconsin Supreme Court, Democratic-aligned candidate Susan Crawford won outright in the city of Waukesha with more than 51% of the vote against Elon Musk-backed conservative Brad Schimel, whose home county is Waukesha, where he served as a judge and as District Attorney.
For decades, said Halvensleben, Waukesha “wasn’t just ‘lean Republican,’ this was strong Republican territory. It’s hard to change out of that mindset. That shift is still slowly happening. I think people are starting to pick up on it. It’s changing.”
The second-term alder and second-term Council President has long been active with Waukesha County Democrats and is currently the party’s chair for the 5th Congressional District.
Like the race between Hallquist and incumbent Steve Ponto in Brookfield, this mayoral race in Waukesha is formally a nonpartisan one, but this contest has an even more partisan underpinnings. That has a lot to do with Halvensleben’s opponent in the race — Scott Allen.
Allen is a Republican state representative, who has served in the Assembly for more than a decade, first elected to the position in 2014. He has the reputation of being one of the furthest-right members of a particularly far-right caucus, (occasionally challenging hard-line conservative Assembly Speaker Robin Vos from the right). Allen has sided with election deniers on a number of occasions post-2020, expressed outlandish views on reproductive rights, proposed arming teachers, and also made national news in 2019 by putting forth a list of 10 people to honor for Black History Month, most of whom were white. He seems to meld the most extreme views of the religious right and MAGA factions of Republican politics.
Halvensleben wasn’t planning to run for mayor until she heard the news that Allen would be the one running, and her phone “blew up” with people encouraging her to run against him.
“Our community deserves better than Scott Allen, and I know that I’m going to be better than him,” said Halvensleben. “If the incumbent had run again, I would not have run against Shawn Reilly. I think Shawn has done an amazing job; I have loved working with him.”
Reilly has been the mayor of Waukesha since 2014, and had been a lifelong member of the Republican Party — up until Jan. 6, 2021. In a Facebook post that evening, he said he was “ashamed” that he was a member of the party, disavowing his allegiance, saying it could be the “end of my political career, but I have to put this out because I am so upset.” He would win re-election in 2022 with nearly 64% of the votes, despite the Republican Party of Waukesha County endorsing a late-entry challenger. Reilly would go on to endorse Kamala Harris for president in the 2024 presidential election, telling The New York Times, “I’m very afraid of the direction our country will head in if Donald Trump becomes president. I think we’ll be heading down a road of authoritarianism and fascism.”
Also in that 2024 election, Shawn Reilly’s brother, Kevin, ran against Scott Allen as a Democrat. Allen won that race, but under new maps, it was the closest contest he’d faced in a decade of Assembly races, where he mostly ran unopposed in a deep red district.
While Allen’s candidacy may have been the impetus for the 36-year-old Halvensleben’s run, she’s been getting more and more involved in politics over the last decade, following Donald Trump’s upset victory in 2016. In 2022, she took on an incumbent for an aldermanic seat and won. When re-elected following a three-year term in 2025, she became Council President. She said these weren’t wins “by a landslide” in the typically Republican city, but “I’m typically outperforming,” she said.
Working with the Waukesha County Democratic Party over the last 10 years, Halvensleben helped start a team to do canvassing for local candidates, and has seen a political shift unfold right from the street level.
“We knew there were always Democrats in Waukesha County, but we’ve had to (tell people), no, you’re not the only one,” she said. “Over the last 10 years when I’ve been knocking on doors, so many people are like, ‘Don’t tell anybody, but I’m the Democrat on the street.’ And I was like, ‘Actually, there are five of you.’”
So, what’s driving this shift? Hallquist and Halvensleben’s answers to this question have a lot in common. For one, both see a trend of people perhaps leaving for college or to start careers, only to return home to start a family. That’s part of Hallquist’s own story — he went to graduate school at the University of Southern California on a partial scholarship, and also played in a punk rock band that went on tour — and it’s something he sees in Brookfield.
“There are a lot of people who grew up here,” he said. “(Maybe they) lived somewhere else, probably for a job or educational reasons. And then oftentimes when they have children, they decide to move back. It’s their home. It’s where people grew up. This is, I think, a very Wisconsin thing.”
“People are born here; they grow up here,” said Halvensleben. “Maybe they move away for college, but they’re coming back to raise their families,” adding there’s been an “influx of millennials with their young families” in recent years, and that “their politics are different.”
There are generational aspects at play here, certainly. There’s also a growing diversity in the region with changing demographics, and for some, an acceptance and celebration of that diversity.
“We are becoming more diverse, statistically, in the city of Brookfield, and that’s a good thing,” said Hallquist. “People should not feel threatened by that…I think it’s going to be better in terms of building a more inclusive city with better outcomes and understanding,” adding that he thinks Waukesha County is “more open to things that, historically, it was not.”
But some of those old tensions are still there, and it can often manifest in the suburbs’ fraught relationship with the city of Milwaukee.
In 2014, the Milwaukee Journal Sentinel published a series on political divides in the Milwaukee metro area, characterizing the region as “the most polarized part of a polarized state in a polarized nation.” The deep red suburbs and dark blue city were worlds apart.
But the extremes of that polarization have softened, with the suburbs becoming a bit bluer, and parts of the city becoming a bit redder. The region as a whole is far more purple, overall, than it was in the early to mid-2010s.
“I think, in many ways, both sides are operating on 20-year-old data and stereotypes,” said Hallquist.
It can take time for public perception to catch up to new realities. People are perhaps growing tired of these same old divisions.
“I know you’ve got some old school people who are like, ‘Don’t Milwaukee my Waukesha’ or whatever, but I think overall, people have a slightly different attitude than they used to,” said Halvensleben. “I think people are recognizing that we need to work together, that we don’t need to be at odds with each other.”
From the archives: Marquette professor Phil Rocco’s Dec. 2024 essay on Waukesha County encountering the limitations of Wisconsin’s 2023 shared revenue reform law.
Still, there can be examples of the ugly side of these simmering tensions boiling over, like when Brookfield Alderman Kris Seals opposed an affordable housing development in the the city, saying, “If you can’t afford those units, then you live in Wauwatosa or West Allis until you can afford to move into Brookfield.”
Hallquist, who led an effort to censure Seals after those comments in 20231, sees this come up all the time on social media in response to his advocacy for affordable housing in Brookfield.
“Look at my social media posts about housing,” said Hallquist. “It’s very much that narrative, which is, ‘we don’t want those people,’ or they post things like, ‘we don’t want Milwaukee values.’” They’re just blatant dog whistles … There are ones that are just like, I think you forgot to put your klan hood on in your profile picture, I said to one commenter, because it’s just abject racism. It must be hard for those folks walking around being so afraid of everything and everyone.”
And yet, despite this, Hallquist remains an optimist.
“Here’s the positive side: That’s not the prevailing narrative,” he said. “That tide is shifting. The community’s attitudes are shifting to be more open.”
But as the campaign has unfolded, Hallquist has encountered more and more of the uglier side of social media that can also be present in the suburbs.
The incumbent who Hallquist is running to unseat is Steve Ponto, who is seeking a fifth term as mayor, at the age of 78. Ponto has not had the reputation of being an especially fiery or divisive politician — he was challenged from the right, in 2022 — but throughout this campaign, his daughter, Stephanie Ponto, who lists her role as the campaign manager, has been all over social media with a high volume of Facebook and Instagram comments about the campaign at all hours of the day and night. She’s attacked a nonprofit Hallquist is involved with (he’s an active volunteer at multiple organizations). She’s also sent numerous direct messages to Hallquist and some of his supporters, like District 1 Alder Sara Monty. Hallquist has characterized some of this behavior as “harassment” that crosses a line.
Per documents shared with The Recombobulation Area, in early January, Hallquist emailed Mayor Ponto directly, saying he had “legitimate concerns” about Stephanie Ponto’s social media presence, sharing several attachments with examples, to which the mayor replied in a separate message, “I asked Stephanie not to contact you and she agreed.” Weeks later, Hallquist sent another email, saying the “harassing behavior never stopped” and became “more extreme,” writing, “her harassment is now making me and my family feel physically unsafe.”
This week, Hallquist said in a message to The Recombobulation Area, “I’ve wanted this campaign to be about issues and vision for the City of Brookfield, but after four months of constant harassment from Steve Ponto’s daughter and campaign manager that includes: constant social media harassment, comments mentioning my children, deeply troubling false allegations sent to a fellow colleague, harassing resident supporters in private messages in the middle of the night, and now targeting my apolitical non-profit affiliation, I’ve had enough. I am quite fine with disagreement and trolling, but this behavior continues to cross a line. It’s been disappointing to see the mayor embrace this style of campaigning and harassment head-on.”
More documented examples of this behavior will soon be available at The Recombobulation Area.
These races for mayor in Waukesha County are nonpartisan. Most of what I talked to Hallquist and Halvensleben about are issues facing local government across Wisconsin — budgeting, transparency, development, etc. The redevelopment of Brookfield Square Mall is not exactly an issue steeped in your typical Red vs. Blue partisan politics.
But as the suburbs continue to grow more and more purple, the new politics emerging can have a certain dark side. A Waukesha County native myself, I am very familiar with the duality of this landscape, and how there can be a certain ugliness lurking beneath the surface of a charming suburb like Brookfield — an ugliness our current fraught political moment tends to exacerbate.
But one thing is for sure, if either Hallquist or Halvensleben manage to pull off an upset and win one or both of these mayoral races, it will send shockwaves through the political universe in Wisconsin — and could prove to be a flashing warning sign of what’s to come for Republicans in the midterm elections this fall, and yet another sign that the suburbs are not what they used to be.
Dan Shafer is a journalist from Milwaukee who writes and publishes The Recombobulation Area. In 2024, he and the publication joined Civic Media, where he is currently a Contributing Editor. He’s written for The New York Times, The Daily Beast, Heartland Signal, Belt Magazine, WisPolitics, and Milwaukee Record. He previously worked at Seattle Magazine, Seattle Business Magazine, the Milwaukee Business Journal, Milwaukee Magazine, and BizTimes Milwaukee. He’s won 23 Milwaukee Press Club Excellence in Journalism Awards. He’s on Twitter at @DanRShafer.
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Follow Dan Shafer on Twitter at @DanRShafer and at BlueSky at @danshafer.bsky.social.
I can’t say in words how excited I would be for Terry Dittrich to see both cities go blue
Exciting good news. Waukesha the city has certainly had progressive politicians in the past, including mayor, but Brookfield moving leftward would be a sea change. Hopefully Hallquist can win. And of course Halvensleben, too.