Updated at 1:17 p.m. ET on June 7, 2022
DUBUQUE, Iowa—Megan Simpson was 3 years old when her family strapped her in a stroller and took her door-knocking for the first time. She was in elementary school when she began stuffing mailers for get-out-the-vote campaigns. Every Election Day during the 1990s and 2000s, Megan and her five brothers and sisters stayed home from school as the house was transformed into a staging area for the precinct. Her parents would blast Bachman-Turner Overdrive’s “Takin’ Care of Business,” and their living room would fill up with volunteers and stacks of walk packets.
In Dubuque County, full of Irish and German Catholics and dotted with manufacturing plants, Democrats outnumbered Republicans by the thousands. These were blue-collar people, most of them white, who voted for politicians allied with unions. The county hadn’t backed a Republican presidential candidate since Dwight D. Eisenhower in 1956. It was the seat of Democratic politics in northeast Iowa, maybe the strongest concentration of Democrats in the entire state. And the Simpsons were its first family.
The Simpsons had a passion for politics, and a family history of state and local political involvement that stretched back decades. The clan was a “political machine,” Greg Simpson, Megan’s father, told me. Led by their parents, or sometimes alone, the kids would trek around town, showing up on people’s porches to talk about health care and register them to vote. They marched and toddled in parades for Iowa candidates such as Tom Harkin, Tom Vilsack, and their own aunt and uncle, the well-known state lawmakers Pam and Tom Jochum. “Whoever the Simpsons were working for was who [people in town] wanted to be behind,” Kelly Simpson, Megan’s mother, told me.
John Kerry doted on Megan’s sister, little Madi Simpson, letting her ride along on his northeast-Iowa bus tour in 2004 when she was 5. A few years later, Michelle Obama told a group of supporters she hoped that Sasha and Malia would turn out as well as the Simpson girls. In 2007, Megan was an organizer on Barack Obama’s Iowa caucus campaign. She spent her days driving through town, and out to the county’s rural areas, trying to persuade thousands of white people to elect the country’s first Black president. When Obama won the caucuses, and later swept the county and the state, the Simpson family was thrilled. But they weren’t surprised: Dubuque County always chose Democrats. That was true, at least, until 2016.
On the evening of November 8, Megan and her siblings gathered at Happy’s Place, the local Democratic bar, to watch the results roll in. When they realized what was about to happen, Megan’s sisters began to cry. At home, Greg poured himself a glass of bourbon. By morning, Donald Trump had become the first Republican presidential nominee to win Dubuque County in Greg’s lifetime. Trump had beaten Hillary Clinton by roughly one percentage point in the county, but the swing away from Democrats was enormous: Obama had won by 15 points just four years before. Dubuque was one of 206 U.S. counties that pivoted hard and fast from Obama to Trump—and one of 31 in Iowa. At Happy’s, Kelly was sick to her stomach. “I felt like I had lost a connection with Dubuque,” she told me. “I felt like, Who are the people living in this town?” Four years later, Trump won Dubuque County again, this time by three points, even as he lost the election to Joe Biden. The Simpson family faced a devastating reality: A Democrat was headed to the White House, but a Republican had won their home turf by an even bigger margin than before.
After 60 years, voters in Dubuque County seem finished with Democrats. Nationwide, the trends are the same: Working-class voters without a college education are voting more in line with Republicans, while Democrats make inroads among more educated voters. The political winds that used to propel the Simpsons forward in each election are now blowing hard against them.
The Simpsons remain hopeful. Most of the clan insists that the party can still turn things around, maybe not in this year’s midterm elections—for which today’s primaries are being held—but in the next cycle, or the one after that. Megan wonders if Dubuque’s support for Trump was simply a Halley’s Comet that most Americans won’t witness again in their lifetime. Greg sees the GOP’s progress as the natural motion of the country’s political pendulum. “I don’t think [the county] is irretrievably gone. A lot of the people who voted for Trump might come around,” he told me. It makes sense that the Simpson family is optimistic. They’ve spent decades working to keep Democrats in power in Iowa. But Dubuque County has changed, and so has its once-ruling party. The voters who formed this reliable blue bastion on the Mississippi now seem to be sprinting away from it as fast as they can.
People say Iowa is flat, but Dubuque County is all lush, rolling fields and open sky. Your ears pop when you drive into the city’s downtown. A rickety funicular makes trips up and down the bluff, offering stunning views of the snaking Mississippi. Growing up three hours downriver, the only thing I knew about Dubuque was that a lot of Catholics lived there, and that’s still true. The county is home to three Catholic colleges, two seminaries, and six religious orders. (Joe Biden, during his various bids for president, used to take ice cream to the nuns.) John Deere employs nearly 3,000 locals at its factory in Dubuque, making backhoes and crawlers. For decades, this was a region full of progressive labor leaders and pro-life Democrats, a place where you could actually find people who identified as “socially conservative but fiscally liberal.” The county’s rural voters were always more conservative, but their votes were usually outweighed by the Democrats in town.
The Simpsons used to live on Prince Street in Dubuque, near Comiskey Park. It was a mostly Catholic neighborhood where many residents were active in unions, such as the local United Auto Workers and International Brotherhood of Electrical Workers. During Obama’s 2007 caucus campaign, Megan would go door-to-door in the area and talk with her neighbors about the Illinois senator. They’d tell her how much they liked him, and how excited they were to vote. Some of those same people became precinct captains, and reliable Obama volunteers. The Comiskey Park neighborhood went overwhelmingly for Obama in 2008; lines on Election Day at nearby precincts were longer than the Simpsons had ever seen.
By the fall of 2016, Megan had moved away. But during the general election, she traveled home to Dubuque with a few friends to volunteer for Clinton. They drove over to Comiskey Park to start knocking on doors. This time, though, few of her former neighbors seemed excited. Most didn’t answer, and the ones who did told her different versions of the same thing: We don’t like Clinton, and we don’t trust the Democrats anymore. They were deflated. One man’s words are cemented in Megan’s memory: “No one cares; none of them are good,” he told her with a shrug. “I’m over it.”
On the night of the election, Megan sent a volunteer to Comiskey Park to drop off snacks to voters in line outside the voting precinct at Sacred Heart Church. The volunteer called her cellphone a few minutes later: “There’s no one here,” they told her. Disappointed, Megan drove to a different precinct near the outer ring of Dubuque, where she’d heard there was a long line. She took water and granola bars to the voters there, relieved at the sight of them all, crowding outside the Assemblies of God Church on Pennsylvania Avenue. It wasn’t until later, after the results came in, that it hit her: “Those people were not voting for Hillary.”
During the four years of Trump’s presidency, Megan was advising Democratic candidates in Montana. Allison, the next-oldest Simpson sibling, started a Democratic volunteer group in Dubuque County called Girl Force. Kelly Simpson volunteered almost every month in 2020. But their neighbors’ lack of interest in voting for Democrats endured. Even “after Trump won, people didn’t want to be bothered,” Kelly remembers. She’d visit houses of loyal Democrats—former Obama and Kerry voters—and they’d dismiss her politely. “We’re not interested anymore,” they’d say. Meanwhile, Trump’s support grew. At a rally at the Dubuque airport a few days before the election, people walked for miles to hear him speak, leaving their cars parked along Highway 61. When Biden lost the county in 2020, the Simpsons weren’t surprised, exactly; they were disgusted. Hannah, the third-oldest Simpson, told me she felt betrayed. “I had a lot of hatred for people in Dubuque for a while after that election,” she said. Are we that county that I was raised to believe we were? she’d wondered.
Last fall, 10,000 John Deere workers across the country, including many in Dubuque, went on strike for five weeks while they negotiated a new contract. One of Kelly’s cousins was on the picket line, and she told Kelly about men who went on strike wearing their bright-red Trump 24 T-shirts. A decade ago, the thought of a UAW member in Dubuque openly supporting a Republican presidential candidate on the picket line was inconceivable. “Donald Trump wasn’t for you!” Kelly wanted to shout at them. “Not one of them should ever be wearing a Trump ’24 shirt. Because then we have failed them.”
Dubuque UAW members who swung to Trump didn’t do so because of his policy promises, though, Dan White, the former president of the union local, told me. Sure, they liked that he talked about keeping jobs in America, but mostly they really just appreciated the way he talked, and how he sounded like he was on their side. Fox News, talk radio, and social media helped reinforce that impression, Tom Townsend, the business manager of the local IBEW, told me. Many of his members have fully bought into the right’s portrayal of Democrats—that they’re all socialists who want to take their guns. They won’t listen when Townsend tries to tell them otherwise.
Changing the reputation that Democrats have in northeast Iowa right now will be a tough project. Early last fall, I visited a few of the neighborhoods where Megan had helped Obama win, and which had since swung to Trump. Democrats aren’t speaking to working people anymore, Lori Milledge, a 52-year-old social worker in one such precinct, told me. Even though Trump was “an ass,” Milledge said, “he really was ‘America First.’” Down the street, a retired John Deere employee and UAW member named Ronald told me he’s always voted Democrat, but he hasn’t actually liked a presidential nominee since Obama. The party “turned away from the working-class people, and [went] more to the upper-crust type—the college graduates and people in corporate offices,” he said. He’ll probably keep voting for Democrats, but he knows many others who won’t. His wife, another longtime Democrat, is so fed up with what she sees as the party’s elitism that she told Ronald she’d consider voting for Trump in 2024.
Union involvement was once a reliable way to discern whether someone was a Democrat. Today, education is a better predictor of party affiliation. The Simpsons sit at this complicated intersection of politics and identity. Greg earned his bachelor’s degree in history and, later, a nursing degree from a local community college. He is an educated professional, yet he still views his party’s leadership as elitist and entrenched: “I can’t think of two more stereotypically worse people than Chuck Schumer and Nancy Pelosi,” he told me. Schumer is “a coastal guy who doesn’t know what a loaf of bread costs. He’s got his glasses down on his nose; he’s been in the Senate for a million years. If I just got off my shift and saw his face come on TV, am I gonna say, ‘Hey, this guy gets me’?”
America’s growing education gap has led to an imbalance, some political analysts argue, in which the highest-educated, most-liberal members of the Democratic Party control its messaging—alienating less educated, less liberal Americans who might otherwise be open to voting blue. “I don’t think it’s a coincidence that the people we’ve lost are likely to be low-socioeconomic-status people,” the Democratic pollster David Shor, one of the leading proponents of this theory, told Ezra Klein in an interview last year.
Megan, who didn’t graduate from college but has made politics her full-time career, is hyperconscious of the risks of appearing to condescend to her fellow Democrats. When Trump won in 2016, she was living in San Francisco and working at Airbnb. At the Women’s March a few months later, she overheard a group of women talking. “How could anyone vote for Trump? Don’t they have a brain?” one of them asked. Megan was so frustrated by the way people spoke about Trump supporters—her neighbors and her friends—that she quit her job and moved back to Iowa. “I just felt like it was time for me to leave this bubble,” she told me.
The Simpsons insist that Democrats will start winning federal elections again in Dubuque County if they can convince voters that they’re true allies of the working class. They need to “show up at UAW meetings, to be out on the picket lines,” Kelly said. Voters need to know, Greg said, that “we want to fix bridges, and get the roads paved, and make sure kids are in school.” Yes, Democrats want gender-neutral bathrooms, he added, “but it’s not the only thing we care about.” Some of the same volunteers and organizers that the family worked with a decade ago are still active in Dubuque. That fact gives Megan hope. “It’s a long-term game,” she said. “They’re doing the work.”
Democrats have been trying to send this message through their policies—the American Rescue Plan; the bipartisan infrastructure bill. But changing people’s impressions of a party isn’t as simple as tweaking a platform, because the majority of Americans don’t hold strong policy views. In politics, personality is the product; policies are the fine print that most people don’t have time to read. “Individual people’s politics is so much more about who they think they are in the world as opposed to policy stances,” Kathy Cramer, a political-science professor at the University of Wisconsin at Madison, told me. “It’s about ‘Am I being heard? Am I being respected?’” To have any hope of clawing back their former terrain, Democrats need to make voters feel like the answer is yes.
Yet even local Democrats who have made powerful cultural appeals are in trouble in Dubuque. Abby Finkenauer, the energetic, folksy-sounding daughter of a local-union pipe fitter, who won the county in 2018, couldn’t make her win stick. In 2020, she lost her district to a Trump-endorsed Republican who campaigned on stopping the radicals and socialists in Congress. “To the extent that folks in Dubuque or anywhere else are getting messages from the [Democrats], they’re not coming from the messaging machine; they’re coming through various intermediaries, like Fox News and social media,” Lee Drutman, a political scientist and the author of Breaking the Two-Party Doom Loop, told me. Finkenauer is now running for U.S. Senate. If she secures the Democratic nomination in tonight’s primary, she will face longtime Republican Senator Chuck Grassley in the general election. She’s not favored to win.
Creating a message that can win back Trump voters is tricky. Resentment of elites and economic insecurity clearly helped fuel Trump’s rise, but support for Trump is also linked to racial resentment. Dubuque, which is 85 percent white, has a history of racism and discrimination. To make an effective cultural appeal and hold true to their principles, Democrats will have to figure out how to alleviate the anxiety that these white Americans are feeling while continuing to advocate for marginalized people, Ashley Jardina, a political scientist and the author of the book White Identity Politics, told me.
Republicans aren’t going to make their rivals’ task any easier. Voters now see the GOP as “reaching out to the working person without their nose in the air about being a hunter or a gun collector,” Jeff Kaufmann, the chair of the Iowa GOP, told me. Before 2016, Republicans didn’t have much of an advertising budget in Dubuque. Kaufmann used to visit the county annually, but he traveled there four times in 2021 alone. Each of his events has drawn massive crowds and even more money. He credits Trump. “I couldn’t have brought them over. It took a phenomenon, and Donald Trump was that phenomenon.”
Losing Dubuque County is not going to cost Joe Biden the presidential election in 2024. Iowa, with its six Electoral College votes, is not a necessary stepping stone for Democrats on the path to the White House. It’s no longer the purple state it once was. But the Simpsons’ struggle is a glimpse into the future for Democrats in different, more-contested parts of America. The voters abandoning the party here are much like the ones in places like Macomb County, Michigan; Kenosha County, Wisconsin; and Luzerne County, Pennsylvania. The question for Democrats is whether the first families of these counties can avoid becoming strangers in their own lands too.
The Simpson family is now scattered across the country. Greg and Kelly are divorced now, and Kelly moved to Wisconsin for a job. Greg still lives in Dubuque, but he’s less active in Democratic politics than he used to be. Hannah and Allison have moved to nearby Jackson County. Megan is in Montana, watching from a distance as her home state continues to move away from Democrats. Sometimes she can’t help but feel defeated. That feeling hits hardest when she’s driving through Dubuque County, remembering all the central-committee meetings, the door-knocking with her sisters, and the excitement of the Obama volunteers. It’s difficult, in those moments, to ignore the sinking feeling that people here aren’t on her side anymore. “It’s possible, right?” she said. “That’s what the trend looks like.”
An earlier version of this story misstated the year that Greg and Kelly divorced and Trump’s margin of victory in Dubuque County. We regret the errors.
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