The counties of Waukesha, Ozaukee, and Washington—known, collectively, as the WOW counties—compose the bungalow belt of the city of Milwaukee, a suburban sprawl of Craftsman-style homes clustered neatly among dozens of lakes. Waukesha County, the largest of the three is, according to one analysis, the best performing Republican suburb in America. Although Republicans failed to win Wisconsin in the 2012 Presidential election, Waukesha delivered the highest turnout in the nation for Mitt Romney—Ozaukee and Washington were the third and fourth highest. But in 2016, when Trump secured a surprise victory in the state by a margin of twenty-two thousand votes, something peculiar happened. A post-mortem map compiled by the G.O.P. revealed that in a strip of counties running up the eastern edge of the state, from Kenosha to the Door Peninsula, and passing through the WOW counties, Trump underperformed Ron Johnson, Wisconsin’s Republican senator. One of the greatest discrepancies was in Waukesha County, where Johnson bested Trump by an eleven-point margin. That’s nearly twenty thousand votes that should have easily gone to Trump.
According to Nancy Kormanik, the president of the Republican Women of Waukesha County, there are now more Trump supporters in the WOW counties than in 2016. Kormanik, a seventy-three-year-old retired secretary, admitted that she, too, had been reluctant to vote for him. “I really didn’t believe him,” Kormanik told me. Dozens of her friends left the Presidential bracket on their ballots blank because they were unsure whether Trump was a real conservative. “I mean, he didn’t play his whole deck,” she said. “People literally took a gamble on him.” This year, however, she assured me that every last one of her friends would vote for Trump, and do so eagerly. “He has delivered, over and above,” she said. “They do believe his performance has been incredible.”
As suburban areas across the country have become more diverse, more educated, and more Democratic, the WOW counties, the story goes, remain a bright red firewall. In 2014, Craig Gilbert, a reporter at the Milwaukee Journal Sentinel, worked with Charles Franklin, a Marquette University pollster, to do an extensive survey of the region. Wisconsin’s contentious governor, Scott Walker, who had recently survived a recall election, had an approval rating in the area of ninety-two per cent among Republicans. More than half of WOW-county residents lived in neighborhoods that Romney won by thirty per cent or more. The gap between Obama’s support in urban Milwaukee County and the surrounding suburbs, meanwhile, was the second largest in the country, after New Orleans. “In southeastern Wisconsin,” Gilbert wrote, “you’ll find the most polarized part of a polarized state in a polarized nation.”
In early October, Terry Dittrich, the chairman of the Republican Party of Waukesha County, invited me to the Party office, squeezed inside a strip mall off State Highway 59, between a vegan-dietary-supplements store and a house-painting business. A flier taped to the door was addressed to uninvited journalists: “NO FILMING, NO PHOTOS, NO INTERVIEWS.” Inside, several elderly people milled around without masks. Dittrich was in isolation upstairs. He is a long-time Waukesha Republican, a native of Madison and an adviser at an international bank. Given that the county is so reliably Republican, I wondered whether the remaining weeks of the campaign might be fairly relaxed for him. “Let’s put it this way,” Dittrich said. “Waukesha is going red. I don’t think anybody would think we’re not. It’s just a question of what those margins are.”
Trump won Wisconsin four years ago owing to a confluence of factors, but a big one was depressed Democratic turnout in Milwaukee County. Dittrich does not expect that to happen again. To win this time, Trump needs to boost his numbers. One strategy has been to focus on the outer edges of Waukesha County, where the population is less dense. Dittrich is encountering a lot of new faces out there. “If you ask them, ‘Are you pro-Republican?,’ they’ll either say maybe or no,” Dittrich said. “But if you say to them, “Are you anti-swamp?’ “Yes.’ ‘Why do you want to vote?’ ‘Because I love Trump.’ ” He added, “I don’t know how you would model or identify these people in normal polling.”
Other indicators are less encouraging for Dittrich. According to recent surveys by the New York Times and Siena College, Trump is trailing Biden by an average of twenty-three points among suburban women in swing states. In 2018, Walker, another early Trump holdout who became a vocal supporter, suffered a drop in support in the Milwaukee suburbs, his home turf, and ultimately lost his reëlection bid. Dittrich told me that the outcome was, in part, owing to the wavering support of young moms who thought that Walker’s opponent, the former schools-superintendent Tony Evers, would boost education. “The bottom line is we did see a weakness among younger women,” Dittrich told me. These were “women that are in a district that should absolutely be going red and didn’t go red.”
Those districts are the inner suburbs that border Milwaukee, where younger women are invested in what’s happening in the city on issues like school funding, environmental policy, and social justice. Reclaiming these suburban women as reliable voters for Trump, and for the Republican Party, is key to the campaign’s chances in Wisconsin. “We won’t make that mistake again,” Dittrich said, “of not paying attention to them, talking to them, finding out what their real issues are, finding out what made them think differently the last election cycle.”
The parties are also using local elections as a proxy war for the Presidency. The Fourteenth District, which lies partly in Waukesha County and partly in Milwaukee County, is the site of a scorched-earth campaign for the State Assembly seat. Both parties are running moderate middle-aged women with children in local schools who are familiar faces to moms in the area. “So that’s where we are,” Dittrich said. “We have a real dog fight between two pretty good candidates.”
Trump, who has a campaign event scheduled in Waukesha on Saturday, has his own ideas about winning those women back. A week earlier, at a rally in Janesville, he told a crowd at Southern Wisconsin Regional Airport that the “most menacing aspect of the Biden-Harris agenda is their attack of [sic] law and order.” “Today I want to explain to you the threat that their far-left plans pose to the safety of your family, your community, and your country,” he said. “If you give the power to Democrats, the radical left will defund, disband, disarm, and dismantle police departments all across America.”
I asked Dittrich whether he thought Trump’s law-and-order messaging was working with women voters in the WOW counties. He conceded some skepticism. “Are they concerned enough, or do they believe somehow this violence is justified?” he said, referring to women who might sympathize with the goals of Black Lives Matter. “I don’t know.” But he suggested that at least some of these voters felt threatened: “You definitely get the feeling that people are on edge. They’re looking around and saying, ‘Holy cow, we’re next.’ ”
Milwaukee was my family’s Lower East Side, a hub of immigrant commerce where my great-grandparents arrived from Eastern Europe as teen-agers, sometime in the nineteen-tens. The city’s storefronts and places of worship were repurposed every few decades, by Germans, East-European Jews, Poles, and Latinos, with each successive generation adding a layer, like rings inside a tree. The Great Migration from the South came decades late in Milwaukee, not reaching its peak until the nineteen-seventies, when industry had already begun shedding jobs. The city’s Black middle class remained small, its economic frustrations compounded by vicious racism, both of which prevented them from moving out to the suburbs. Today, the city of Milwaukee is thirty-nine per cent Black. But the statistics in its suburbs remain astounding: across the Waukesha county line immediately to the west, every incorporated township is less than three per cent Black.
In addition to all its other ruinous effects, segregation breeds stark political polarization. “There’s really good political science research on the social psychology of segregation,” Katherine Levine Einstein, a political scientist at Boston University, told me. “Once you’re in a segregated place, you change the attitudes of white people in those communities, and entrench that segregation.” Some pollsters have observed that extreme segregation“radicalizes” white voters. Einstein is from Milwaukee, and recalled a years-long battle that took place after Waukesha discovered elevated radium levels in the area’s drinking water. The easiest solution would have been to pay the city of Milwaukee for access to water from Lake Michigan. But the residents of Waukesha would do just about anything to avoid giving their money to Milwaukee. “They would rather drink the water containing carcinogenic chemicals,” Einstein said.
Over the summer, Wauwatosa, a stately, old, white middle-class suburb, was the site of ongoing demonstrations against Joseph Mensah, a Black police officer who shot and killed three young men, two of them Black and one Native American and Latino, over the last five years. In February, Mensah killed seventeen-year-old Alvin Cole in the parking lot of Mayfair Mall, and over the summer, in anticipation of a ruling on the case, demonstrators repeatedly showed up at Mensah’s home. One occasion resulted in a scuffle in which shots were fired and three people were arrested for assault. In early October, the Milwaukee County District Attorney announced that Mensah would not be charged in Cole’s death. As protests broke out in Wauwatosa, the Governor deployed the National Guard, which set up a staging ground in the Mayfair Mall parking lot. The city issued a curfew, enabling riot police to make arrests. Among the protesters rounded up were Alvin Cole’s mother and two sisters. Several shop windows in Wauwatosa’s downtown were smashed, and the police deployed tear gas and rubber bullets on multiple evenings.
I asked Dittrich what he was hearing from constituents. “Very concerned,” he said. He complained about the violent faction that had aligned itself with otherwise responsible Democrats. I brought up the violent fringe that had aligned itself with the right. Dittrich took a breath. “They are not burning down cities,” he said, bringing his fist down on the table. “They are not indiscriminately going up and pounding out glass and car windows, and going around cities indiscriminately threatening people. Please tell me where.”
Kenosha is an hour’s drive south of Milwaukee. In August, after Jacob Blake was shot by Rusten Sheskey, a Kenosha police officer, demonstrations spilled out into the city’s streets and became destructive, resulting in multiple local businesses being burned down. Kyle Rittenhouse, a seventeen-year-old from Illinois, drove up as a self-appointed and illegally-armed defender of local properties; he is now charged with shooting three people, two fatally. (In Janesville, Trump had asked the crowd, “You ever hear of a place called Kenosha? Because if I didn’t get involved, there would be no Kenosha right now.”) Dittrich told me that he and other Republicans in the area would not pass judgment on Rittenhouse until due process was done. “If there’s an isolated case where you have a person who goes crazy and goes shooting people, first of all, they’re subject to arrest. Second of all, we have so many anti-discriminatory laws in this country that are going to send that guy up the river for a long time,” Dittrich said. Still, he added, it might turn out that Rittenhouse had acted within the limits of the law, in self-defense.
A couple of weeks after Rittenhouse’s arrest, his mother attended an event sponsored by the Republican Women of Waukesha County, where she received a standing ovation. “I think I can safely say that 97% of the households in Waukesha County have firearms,” Kormanik told me, “and they will use them.” Robin Moore, a former president of the Republican Women of Waukesha County, who ran unsuccessfully for the Fourteenth District seat two years ago, told me that Black Lives Matter had put out a schedule of protests planned in around twenty Wisconsin towns this summer. “We know it was meant as intimidation,” Moore said. Most, in the end, remained small. “I think they knew, had they shown up in force, that the people of Brookfield would have made sure that it stayed peaceful,” she said. “It would have been handled. Luckily, we never really had to find out.”
Moore, who is fifty-seven, works as an executive wine consultant and resides in Brookfield, a wealthy, serene town in eastern Waukesha County. She lamented that the governor—despite having sent in the National Guard there as well—had aligned himself with looters in Kenosha. She said there was concern that, if the wrong people got into office and reduced funding for law enforcement, their communities would be affected. “They’ve seen what happens when we don’t have police on the street, we’ve already been through that, especially in Milwaukee,” Moore said. “So whether Joe Biden is aligned with them or not, it does shine a light on the Democrat Party, at least from the elected officials we have here in Wisconsin. They seem to want to stand with those who want to tear down our cities, rather than build them up.”
In early October, I went to see Matt Mareno, a twenty-nine-year-old organizer who chairs the beleaguered Waukesha County Democratic Party, at the Party’s office in downtown Waukesha. It was empty but for Mareno and one volunteer making phone calls, both wearing masks. “Honestly I was very nervous during the Kenosha timeframe, when Trump came out,” Mareno said. Trump’s message, that Democrats can’t control anything, that they support rioting and looting, “has worked really well for Republicans in this county historically.” In the absence of in-person canvassing, which they have decided to curtail during the pandemic, Democrats have moved to a “relational organizing” model, in which, in addition to making phone calls, volunteers reach out to their own networks on social media. Mareno’s impression was that many women in the area didn’t want Trump to come to Kenosha. “We just kept hearing feedback that people don’t want more division,” he said. “They want to heal, they want someone to unite the country. So that gave me comfort.”
Myron Orfield, the director of the Institute on Metropolitan Opportunity at the University of Minnesota Law School, is writing a book about the Fair Housing Act in the nineteen-sixties. “Civil disorder in 1968 helped Richard Nixon a lot, especially when there was violence,” Orfield told me, “but it feels like the polling is different now. A lot of white people see this differently than they did in the sixties.” His data suggest that people now are much more ambivalent, more likely to see both sides, and, although they might be fearful of violence, they may also agree with black grievances and believe in a need for reform. “I don’t think the violence ever helps, I think it hurts the Democrats,” Orfield said. “In those really white suburbs of Milwaukee, I wouldn’t be surprised” if people are scared, he noted, “but I think they’re already kind of built into Trump’s base.”
Compared to 2016, when the Party gave out about seven or eight hundred Hillary signs, Mareno said, there were now nearly four thousand Biden signs circulating in Waukesha County. “If you would have told me in 2016 that there would be four thousand people who are willing to tell their neighbors that they’re Democrats,” Mareno said, “I would have laughed in your face.” He has encountered other forms of support, too. “We’ll be phone-banking, and we’ll call a house, and a husband will pick up, and we’ll be, like, ‘Hey, is Emily there?’ ” Mareno said. “And they’ll be like, ‘She doesn’t want to talk to you.’ And then we get a call back an hour later being like”—he switched into a whisper—“ ‘I’m voting for Biden, but my husband, he’s a big Trump supporter.’ I’m, like, Oh, cool. Shy Biden voter.”
