MILWAUKEE — The Cape Cods and other modest homes in the Nash Park neighborhood of Wisconsin’s biggest Democratic city were decked out with skeletons and pumpkins in anticipation of trick-or-treaters, but the knock at the door came from 70-year-old Loretta Jackson of Evanston.
The retired state employee and Navy veteran arrived on a recent Saturday afternoon, having traveled with nearly 500 others Illinois Democrats across the state line — past the Mars Cheese Castle — to push voters in this key swing state to cast their ballot for Vice President Kamala Harris.
Although her house visits often went unanswered, when Derrick Williams opened his front door, Jackson had two main jobs: Make sure Williams’ name matched the voter listed in an app on her smartphone and get him to commit to voting for Harris, Wisconsin’s full Democratic slate and, ideally, to do so early.
“Kamala, all day,” Williams responded, holding a nearly empty carton of eggs because he was in the middle of baking cakes for a party. But he wasn’t voting until Election Day because he was “too busy at work.”
It was still a win for Jackson, though before she left she encouraged him one more time to reconsider his voting plan. “Vote early so people … like me stop bothering you,” she said.
All across southeastern Wisconsin and southwestern Michigan, conversations like the one between Jackson and Williams have been playing out this fall, the result of a new, coordinated program from Illinois Democrats and aligned groups to work their political muscle in nearby states that don’t vote as reliably Democratic as Illinois and will be critical to the 2024 electoral outcome.
Called Operation Swing State, the get-out-the-vote initiative aims to build on inter-Midwestern ties strengthened by this summer’s Democratic National Convention in Chicago. While Illinois Democrats have put boots on the ground in neighboring states going back well before Barack Obama’s surprise victory in the 2008 Iowa caucuses, Operation Swing State is larger in scope and scale than previous efforts and viewed by some Democrats as even more vital.
Illinois Republicans too have been heading north as the GOP nominee, former President Donald Trump, aims to crack the Midwestern “Blue Wall” that secured President Joe Biden’s victory in 2020. But while the former president’s campaign says its Trump Force 47 effort involves numerous volunteers from Illinois, the state GOP has no formal role.
Regardless, with solidly blue Illinois expected to go strongly for Harris, Wisconsin and Michigan have become the crucial presidential battlegrounds for Democrats and Republicans from the Land of Lincoln. Polls show the race essentially deadlocked in both states less than a week before Tuesday’s election.
“We know these things are going to be tight,” said Patrick Hanley, president of the north suburban New Trier Township Democratic Organization and one of the leaders of Operation Swing State. “They’re going to come down to the wire, come down to … two votes per precinct. And so I think a lot of our volunteers recognize the responsibility that Chicago-area Democrats have in the national context.”
Wisconsin and Michigan have played key roles in the past two presidential elections, with Trump winning both states in 2016 and Biden taking them back in 2020.
Indeed, there’s been overlap between Wisconsin and Michigan going back decades. They’ve gone for the same presidential candidate every election since 1992, when Democrat Bill Clinton first won the presidency, and they’ve picked the winner six of the last eight times. Only Republican George W. Bush since then has won the presidency without needing either state.
Wisconsin, in particular, has played an intriguing role. In losing her 2016 presidential bid, Hillary Clinton infamously didn’t visit Wisconsin in the lead-up to the general election — a mistake Harris has not made. She held the first rally of her abbreviated campaign in suburban Milwaukee, and she’s visited the state more than half a dozen times since. Harris and Trump both were in Wisconsin on Wednesday and are scheduled to be back Friday, four days before Election Day.
As Hanley said, the margins in Wisconsin, with 10 electoral votes at stake, have been narrow. Four of the past six presidential elections — the ones without Obama on the ballot — were decided by less than a percentage point. Each of the past two races was decided by fewer than 23,000 votes out of about 3 million ballots cast.
In Michigan, with 16 electoral votes at the time, Trump won by less than a point in 2016, outperforming Hillary Clinton by fewer than 11,000 votes out of about 4.8 million ballots cast. Biden achieved a nearly 3-point victory in Michigan in the last election, a margin of more than 154,000 votes out of nearly 5.5 million cast. The state now has only 15 electoral votes after losing a congressional seat following the 2020 census.
So, with Illinois a relatively short drive away from both states, Democrats in and around Chicago are trying to pour on their support to secure victories they think are essential.
“Usually Chicago does not have a tremendous ability to impact the presidential election,” said Ben Head, who is Operation Swing State’s other co-leader as well as the political director for Democratic U.S. Rep. Jan Schakowsky, of Evanston, and national organizing director for Men for Choice. “This year is really sort of a once-in-a-generation opportunity to do that.”
While Gov. JB Pritzker and other top Illinois Democrats have bounced around Wisconsin, Michigan and the five other swing states that will likely determine the presidential outcome, it is grassroots volunteers like Jackson who have powered the Operation Swing State effort.
As of this past weekend, organizers said, volunteers have worked more than 4,000 canvassing shifts in Wisconsin and more than 1,700 in Michigan, knocking on roughly 150,000 doors and talking with more than 35,000 mostly Democratic voters — exceeding Trump’s combined margin of victory in 2016.
Jackson, who’s spent part of her weekends all fall trekking to Wisconsin or Michigan, said her grandmother instilled in her an appreciation for the importance of participating in the democratic process.
“I was always taught by my grandmother that voting was important, especially as a person of color,” Jackson said. “She’s from the South and a woman and born 1908.”
Going door to door in Milwaukee, Jackson made sure voters knew where they could go to cast their early ballots and helped one person figure out that she might not have been registered to vote.
When her door knocks went unanswered in Wisconsin, she rolled up a flyer touting Harris and U.S. Sen. Tammy Baldwin — a Democrat facing a tightening reelection race against businessman Eric Hovde — and wedged it between the door handle and doorjamb before moving on to the next address.
Jackson’s group from Evanston was one of several that took off from the Chicago area Oct. 19, with the effort picking up pace in the weeks since. On the final weekend before Election Day, groups are scheduled to depart from more than a dozen locations across the Chicago area and northern Illinois. Operation Swing State also has organized weeknight phone-banking sessions throughout the fall.
Whether all those blocks walked, doors knocked and phone calls made pay off for Democrats should soon become clear.
So far, the polls in Wisconsin, as elsewhere, continue to tighten.
A pair from Quinnipiac University released Oct. 23 showed Harris and Trump dead even, 48% to 48%, in Wisconsin and Harris with a 3-point lead over Trump in Michigan. The polls of about 1,100 likely voters in each state were conducted Oct. 17-21, and each had a margin of sampling error of plus or minus 2.9 percentage points.
The latest Marquette Law School Poll, released Wednesday, showed Harris leading Trump 50% to 49% among likely voters in a head-to-head matchup and 46% to 44% when third-party candidates were included. The previous poll in late September showed Harris with a 52%-to-48% lead head to head. Robert F. Kennedy Jr., who suspended his independent campaign in August and backed Trump, remains on the ballot in both Wisconsin and Michigan.
The latest poll, the last from Marquette before Tuesday’s election, surveyed 834 registered Wisconsin voters, including 753 likely voters, Oct. 16-24, with a margin of sampling error of plus or minus 4.4 percentage points.
The poll’s director, Marquette law professor Charles Franklin, said that unlike 2016 and 2020, when Trump trailed throughout the campaign, “this year, we really have shown that nip-and-tuck race.”
In determining the outcome of a close election, “boots on the ground are an important thing,” Franklin said.
But the quality of the conversations taking place on the doorstep is an important factor in determining whether the canvassing effort provides an actual boost to the candidates on the ballot, he said.
“The evidence is that personalized conversations on the doorstep are the most potent form of door-to-door canvassing,” Franklin said. “So a knock, ‘Hi, I’m working for Candidate X; here’s some literature; hope you’ll vote,’ it doesn’t move the needle very much.”
Canvassers who directly address individual voters’ concerns can have a larger impact, Franklin said, but having those conversations with outsiders isn’t always as effective.
“In some ways, I think those are better done with locals,” he said.
On the Republican side, Trump Force 47 “captains and volunteers from Illinois” have been reaching out to voters in Wisconsin, Michigan and other battleground states by knocking on doors, sending postcards and making phone calls on behalf of the former president, Rachel Reisner, director of regional and battleground communications for the Republican National Committee and the Trump campaign, said in a statement. “The GOP has also recruited Illinois volunteers to become poll watchers in Wisconsin,” Reisner said.
The Trump campaign did not provide any details on the number of Illinois volunteers involved or the number of Wisconsin and Michigan voters they’ve reached.
The Harris campaign, meanwhile, said it appreciates having backup from Illinois on the ground in hotly contested states.
“We’re grateful to have folks spending their time fighting for our democracy together,” Timothy White, Wisconsin press secretary for the Harris campaign, said in a statement. “We know Wisconsin is going to be close, which is why we’ve built a historically strong coordinated campaign across our state to put our record numbers of volunteers knocking on doors and connecting on the issues that matter to them.”
For some Illinois Democrats, the effort has become a key focus, even with contested races on the ballot back home.
Cook County Board President Toni Preckwinkle, who also leads the county Democratic Party, recently said she was putting her effort more toward Operation Swing State than the countywide races on the ballot, including state’s attorney, circuit court clerk and county clerk, all of which have been in Democratic control for decades.
Democrats need “to support our brothers and sisters (in Wisconsin and Michigan) in the effort to secure our democracy,” she told the Tribune Editorial Board.
Preckwinkle’s preferred state’s attorney candidate, Clayton Harris III, was defeated in the March primary, making Eileen O’Neill Burke — someone Preckwinkle once referred to as a “de facto Republican” — the party’s nominee against Republican Bob Fioretti.
Nevertheless, state Rep. Elizabeth “Lisa” Hernandez, who chairs the Democratic Party of Illinois, said her organization hasn’t taken its eye off the ball at home.
The state party has been holding events for legislative and congressional candidates across the state while also offering its support in Wisconsin and Michigan.
Hernandez, of Cicero, swung down to Illinois State University in Normal last week to back first-term U.S. Rep. Eric Sorensen, of Moline, in his reelection race against Republican Joe McGraw, a retired judge from Rockford, in the 17th Congressional District before heading to Kenosha on Sunday with Pritzker, Schakowsky and others.
“We’re doing our homework here in Illinois, but I would say our extra credit is absolutely helping out our neighbors,” said Hernandez, who’s facing a challenge for her Illinois House seat from Brookfield Republican Laura Hruska.
The Operation Swing State effort is, in some ways, an outgrowth of the relationships party leaders in Illinois and its neighboring states built in the lead-up to the DNC, Hernandez said.
Wisconsin Democratic Party Chair Ben Wikler said his organization has been “grateful” for the help from across the border.
“It’s all hands on deck for democracy, and the Illinois Dems are welcome reinforcements here on the front lines of one of the nation’s most critical battleground states,” Wikler said in a statement. “We may have rival football teams, but we know that when we work together, freedom wins in the Midwest.”
Hernandez is not the only Illinois lawmaker who’s spent time canvassing in Wisconsin despite facing a challenge back home.
The same Saturday Jackson was knocking on doors in Milwaukee, Illinois state Rep. Lindsey LaPointe also was making the rounds. LaPointe, who represents a portion of Chicago’s Northwest Side, is running for a third full term against Republican John “JZ” Zimmers.
LaPointe’s been knocking on many doors in her own neighborhood but she said she thought it was important to devote some time to helping out in Wisconsin as well.
“I can’t wake up on Nov. 6 knowing that I didn’t do everything I could in my power, and being here in a swing state in person, going door to door, having those conversations, is a part of that,” LaPointe, who’d never previously canvassed in another state, said at a Democratic field office after finishing her shift.
Midway through Jackson’s shift that Saturday afternoon, she knocked on the door of a corner house with a Harris yard sign.
When Ashley Groth opened the door, Jackson asked about her biggest concerns heading into the election.
“I mean, I think just the state of democracy,” said Groth, who told Jackson she’d be voting for Harris and other Democrats on the ballot.
If Harris wins, Jackson said, “we can take a rest for a day or two, and then put the boxing gloves back on.”
Afterward, Groth said she doesn’t have a problem with people from another state coming to her door to try to help candidates she supports because she takes issue with the Electoral College system that gives places like Wisconsin an outsize influence in presidential races.
“I do feel like it is that way, which I don’t think is how it should be,” she said. “I do feel like my vote matters more.”
