The arch on the Mississippi that soars above St. Louis is a tribute to its historic role as gateway to the West.
But Missouri is also the midpoint of the river’s journey from north to south. It’s where America’s fractured history of racial segregation becomes central to the workings of political power.
In the 20th century, the state was a bellwether that voted with the winner in all but one presidential election. But after 2004, Missouri turned red, voting for John McCain, Mitt Romney and three times for Donald Trump, including by an 18-point margin in 2024.
For Missouri voters, gerrymandering – the art of shaping electoral districts to benefit one party – is a big part of the political debate ahead of Nov. 3's midterms.
It’s become emblematic of the Democratic Party’s struggle to make its coalition of urban liberals, social democrats and Black and Latino voters competitive outside the Northeast and coastal states.
When Mr. Trump asked last year for more winnable Republican seats in the House of Representatives, Missouri’s state legislators responded with a new, gerrymandered congressional map, threatening a House seat held by a Democrat in Kansas City and altering a potentially competitive seat in the St. Louis suburbs.
The battle over that map has become a defining issue of the midterm election campaign.
Richard von Glahn, a labour organizer, immediately set to work to get a referendum on the ballot to veto the new map. He thought gerrymandering might be too niche an issue to draw a crowd, but 5,000 people turned up for the campaign launch. Within hours, 2,000 had volunteered to canvass door to door.
“Voters don’t like this‚” Mr. von Glahn said. “If your vote can’t have impact because some lobbyist in D.C. redrew a map, then what are we doing? We’re hardly participating in a democracy.”
The gerrymandered map ended up in a series of legal challenges over the past year and ultimately at the Supreme Court three times in September. It was rejected each time, with the court holding that Missouri must use its 2022 map for this election.
On Nov. 3, voters will also cast ballots on Proposition A, a referendum on whether to override the state legislature and reject the gerrymandered map going forward. The last published poll showed a close race, but Mr. von Glahn is confident his side will win.
Holly Bernstein, 55, canvassed for months to ensure Proposition A would be on the ballot. Now she’s working to get out the vote ahead of election day.
“You want to make sure that a vote has the power to do something, and this gerrymander took away the power of many people,” Ms. Bernstein said. “It just infuriates me.”
The new map was intended to deliver Republicans seven of the state’s eight House seats, up from their current six-to-two margin, by carving up the Kansas City district of a former Congressional Black Caucus chair, Democrat Emanuel Cleaver.
It would also have made the map more favourable for Republicans in the 2nd congressional district, in the St. Louis suburbs, which polls have shown is close this time.
Then, in April, too late for this election’s manoeuvring, the Voting Rights Act was gutted by the Supreme Court.
That meant that the city of St. Louis, which makes up most of the Black-majority 1st district, could be the next gerrymander target. A Republican state senator posted “8-0” on social media, suggesting that was the goal.
There’s a street in St. Louis that marks a divide as stark as any in the United States.
On the south side of Delmar Boulevard, you’ll find some of the city’s grandest homes and neighbourhoods, where education levels and life expectancy are high and the population is predominantly white.
On the north side, where the population is predominantly Black, the district is visibly struggling.
There are thousands of vacant lots and abandoned homes – nearly 20,000 at last count. Schools sit abandoned, their playgrounds fenced off and windows broken.
The area is in the midst of a “demographic winter,” as St. Louis University demographer Ness Sandoval puts it, as population declines and residents move to the nearby suburbs of St. Louis County.
The divide is in part the product of a long history of segregation and economic marginalization perpetuated by laws and real estate covenants that steered Black and white home buyers to certain districts.
Delmar Boulevard marks a racial and economic divide in St. Louis. Parts of the city to the north have emptied out of people.
Charles Pearson, the executive pastor at Friendly Temple Missionary Baptist Church, moved to St. Louis in the early 1970s after finishing university in Arkansas. He was born at a time when schools were still segregated. He helps organize voter education events and says it’s important to remember that, not long ago, people died for the right to vote.
He says he’s profoundly concerned about the country’s direction and describes Missouri as one of a handful of states that are “true disciples” of the Trump administration, whose vision he describes as “rooted in 1955,” when women, Blacks and other minorities had little political say.
“I was a child when they finally got rid of the water fountain, so those issues are not theoretical to me. I truly believe that the individuals currently in power, that’s their vision,” Dr. Pearson said, referring to the separate drinking fountains for Blacks and whites.
Politics is about the allocation of power and resources, he says, but it is not moral. The disenfranchisement of Black voters in Missouri is dismaying but not surprising, he adds.
He says his church does not endorse any political party but is encouraging congregants to vote. Most will cast ballots in the 1st congressional district, which has elected Black representatives since 1968. The seat is currently held by Democrat Wesley Bell.
“Our job as a church has been to be sure we’re educating people.”
After the attempt to redraw the congressional map was quashed at the Supreme Court, only one House seat in Missouri is seen as a competitive race: the 2nd congressional district, a relatively wealthy seat based in the suburbs around St. Louis.
It’s currently held by Republican Ann Wagner, a seven-time incumbent who won the district by 12 points in 2024. She’s opposed by Democrat Fred Wellman, a former Army officer.
Republicans here face the same headwinds as elsewhere: Fuel prices have skyrocketed, the Iran war is unpopular, and some people are struggling to make ends meet.
Steven Rogers, a political scientist at St. Louis University who oversees the state’s largest political poll, said August’s results were the most critical of Republicans in the poll’s six-year history.
John Rice, a physician who lives in the 2nd district and describes himself as a moderate, said despite his opposition to gerrymandering, which Democrats have also done in California, he will vote for Ms. Wagner. He sees Mr. Wellman as a socialist, and although the Iran war has pushed up gas prices, he believes it was necessary.
“I still haven’t heard anything from the Democrats about what they want to do, except that they hate Trump,” he said.
Downtown St. Louis is part of the heavily Black 1st congressional district, currently held by a Democrat. The 2nd district, in the suburbs, is a more contested race this year.
Winning over voters in districts with a veteran incumbent can be difficult, but it was only a generation ago that Missouri was a swing state.
Oakville is a middle-class community of tidy bungalows and meticulous lawns adjacent to the Mississippi River south of St. Louis. It’s both a 20-minute drive and a world away from the city. It tends to lean Republican. On a recent afternoon, Democratic canvassers are knocking on doors to identify potential voters.
Joe Miskovic, who runs a local sports bar along with his wife, is leaning on his pickup.
“Let me stop you right there; I don’t want to waste your breath,” he says, interrupting the canvassers. He introduces himself as a politically middle-of-the-road guy from a blue-collar family.
“I struggle right now really bad with the Democratic Party launching so far left that I can’t relate to it any more,” he said. “We all voted Democrat my entire life, but the last five to 10 years I just can’t.”
He explains that his son is a police officer in St. Louis who has been shot twice in just five years on the force. He asks if Mr. Wellman wants to defund the police.
The canvassers assure him that Mr. Wellman – as a 22-year military veteran – understands the importance of supporting law enforcement.
“I’m torn,” Mr. Miskovic says at the end of the encounter. “I think the country is having a hard time finding anyone that’s in the middle any more.”

Democrat Fred Wellman hopes to win the 2nd congressional district from its Republican incumbent, Ann Wagner.Andrew Jansen/News-Leader/USA Today Network via Reuters Connect; J. Scott Applewhite/AP
A few days later, Mr. Wellman holds a town hall at a public library in O’Fallon, about 60 kilometres away. The room is full, and Mr. Wellman gives an energetic performance condemning what he calls the Republican pattern of chaos and corruption and the mounting costs that families face.
In an interview with The Globe and Mail afterwards, Mr. Wellman says Congress needs to take back control of the tariffs and normalize relations with Canada.
“You guys are our allies. I went to war with Canadians.”
He says Republican attempts to gerrymander the district have been destabilizing, but adds that the Democrats have some work to do to rebuild their reputation in the state.
“We lost our working-class roots in a lot of ways,” Mr. Wellman says. “We lost that rural voter.”
He refers to the 1899 speech by Democratic Representative Willard Duncan Vandiver that gave the “show me state” its unofficial motto. He told a naval banquet in Philadelphia: “I come from a state that raises corn and cotton and cockleburs and Democrats, and frothy eloquence neither convinces nor satisfies me. I am from Missouri. You have got to show me.”
That idea sums up the skeptical Missouri voter, Mr. Wellman says.
“What it means is you can talk a lot, but until you show me action, I’m not going to buy it.”