OSHKOSH, Wis. — Donald Trump’s romp through white, working-class America in 2016 was nowhere more traumatic for Democrats than in Wisconsin, which flipped Republican in a presidential race for the first time since 1984.

Now, two years after his stunning victory in the state, shell-shocked Democrats are beginning to pick up the pieces, pouring money and resources into Wisconsin in a test run for a rematch with Trump in 2020.


Interviews with nearly two dozen local party officials, candidates and operatives here describe an ongoing effort marked by unprecedented organizing and millions of dollars from out-of-state donors — a reflection of the party’s urgency in reshaping the 2020 landscape in the upper Midwest, a Democratic bulwark that Trump toppled in 2016.

“We’ve all played with the calculator,” said Joe Zepecki, a strategist who worked on President Barack Obama’s 2012 campaign and on Democrat Mary Burke’s unsuccessful run for Wisconsin governor in 2014. “The number of paths that are back in play for Democrats if you can count on Wisconsin and Michigan — there’s a hell of a lot of ways to 270 [electoral votes].”

Already, more than $7 million has been committed this year toward efforts to reclaim Wisconsin. In recent months, billionaire Democrat Tom Steyer’s NextGen America has designated $2.5 million to register and turn out young voters. Eric Holder’s National Democratic Redistricting Committee has spent $675,000 on the midterm elections so far. The Democratic Governors Association has reserved about $4 million in air time in preparation for a top-of-the-ticket brawl with Gov. Scott Walker in the fall.

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Mocking the Republican governor at the state Democratic Party’s convention recently, Pete Buttigieg, the mayor of South Bend, Indiana, told a cheering crowd that Wisconsin Democrats could “use Scott Walker to send a message” to the rest of the country. The midterm elections in Wisconsin, he said, are the “canary in the coal mine” for the party’s improving prospects nationwide.

The intensity of the Democratic Party’s focus on Wisconsin stands in contrast to 2016, when Hillary Clinton did not campaign in the state at all during the general election — a slight still grumbled about by many Democrats.

Prospective 2020 presidential candidates appear determined not to make the same mistake. Buttigieg, Steyer and Holder are all potential candidates, as is Sen. Kamala Harris (D-Calif.), who trekked to Wisconsin this month to conduct a full day of campaign appearances with the state’s Democratic senator, Tammy Baldwin.

Yet the Democratic Party was ailing here long before Trump captured the state. Walker, a conservative reviled by Wisconsin’s once-powerful union interests, won election statewide three times, including in a recall election that demoralized Democrats who had spent millions of dollars in defeat.

“That took a lot of the wind out of people’s sails … That was huge,” said Randy Bryce, the ironworker-turned-Democratic-celebrity running in outgoing House Speaker Paul Ryan’s district.

For several years, Wisconsin Democrats approached elections with a sense of trepidation, culminating in what Kelda Roys, one of several Democrats running for Wisconsin governor, called “the catastrophe of 2016.” One of her rivals, Tony Evers, lamented months following the election in which he said there was “a lot of recrimination, a lot of people going below the surface and kind of hunkering down for a while.”

Now, said Evers, Wisconsin’s state schools chief, the “switch has been flipped a little bit here.”

In a special state Senate election in January, Democrat Patty Schachtner carried a western Wisconsin district that Trump won in 2016, beating a well-funded Republican by more than 10 percentage points. Three months later, Democrats claimed a rare statewide victory when Rebecca Dallet, a Milwaukee County Circuit Court judge, won a seat on Wisconsin’s state Supreme Court in a race that drew national attention. In a special election on Tuesday, Democrats picked up a state Senate seat long controlled by the GOP.

Brian Weeks, political director for the American Federation of State, County and Municipal Employees, said that if Democrats in Wisconsin this year can build and sustain an effective political operation, “I think that could be a road map for 2020.”

In a bid to compete with the Wisconsin Republican Party’s vaunted organizational advantages under Walker, the state Democratic Party hired an organizing director in early 2017 — an unprecedented move for Democrats here in an off year — then added seven full-time staffers. The party now employs more than 30 people statewide and will keep staff on following the midterm elections in preparation for 2020, said Martha Laning, chairwoman of the state Democratic Party.

“If you compare this to 2016, a presidential year, even at this time we had like one or two people in the coordinated campaign,” Laning said. “In 2014, we had nobody … So this is a huge difference.”

In previous years, Laning said, “there were areas of our state that we just never reached out to.”

The Democrats’ efforts have been aided by the Democratic National Committee, which has invested $190,000 in the state this election cycle for organizing, training and voter registration activities. Steyer’s group said it will hire at least 53 organizers on at least 35 college campuses throughout Wisconsin by November, while Holder’s organization campaigned for Schachtner and Dallet and is supporting two Democrats running in special state legislative elections next week.

Holder, Obama’s attorney general, described his group’s work in Wisconsin, which is focused on redistricting reform, as “a multicycle effort that is designed to have an impact … not only in 2018 and 2020 and 2021, but even beyond that.”

Republicans have reacted to Democrats’ advances with alarm. While Democrats rallied in Oshkosh, the state’s GOP lieutenant governor, Rebecca Kleefisch, urged Republicans at a local party office several blocks away to guard against complacency, saying victories by Schachtner and Dallet were “not OK.”

“We spent a long time turning the Titanic around,” said Kleefisch, touting Wisconsin’s unemployment rate of less than 3 percent and a “terrific story of prosperity” she said Republicans could tell.

Offering a variation on a criticism that Walker has leveled against Democrats in Wisconsin – that they are motivated by anger, suggesting an inability to govern – Kleefisch said of the Democrats down the street, “They’re mad just to be mad. They’re mad for mad’s sake.”

Mark Morgan, executive director of Wisconsin Republican Party, scoffed at Democrats’ organizing efforts, saying the GOP is “signing leases as we speak” on field offices throughout Wisconsin, with close to 20 already open.

Yet Republicans are aware that they are now on defense in Wisconsin, with a Marquette University Law School poll in March quantifying an enthusiasm gap that political consultants of both parties acknowledge: Nearly two-thirds of Democratic voters in Wisconsin say they are very enthusiastic about voting in this year’s elections, compared with 54 percent of Republicans. In the midterm elections in 2014, the advantage went the other way.

“There’s no doubt we are trying to overcome a lethargic base and a gap in enthusiasm among Republican voters here in Wisconsin,” said Luke Hilgemann, a Madison-based Republican consultant and former CEO of Koch brothers-supported Americans for Prosperity.

Hilgemann, who worried Republicans had been “lulled to sleep” by successful elections in recent years, said that in the special Senate and Supreme Court elections, “I think the base didn’t show up … We just can’t allow this to happen again.”

Still, Hilgemann and other Republicans point to signs the GOP in Wisconsin will be difficult to break. In the latest Marquette poll, Walker’s public approval rating stood at 48 percent, while Trump’s approval rating in the state ticked up incrementally from 2017, to 43 percent.

Baldwin’s public approval rating, meanwhile, dropped to 37 percent. While delegates at the state convention screamed “Tammy, Tammy” as the senator walked on stage to speak, political consultants in Wisconsin have become fearful of a massive influx of Republican spending opposing Baldwin. Outside groups so far have spent more than $3 million against her reelection, according to the Center for Responsive Politics — a stark reminder to Democrats of Republicans’ ability to raise and spend money in the state.

In a call and response with Democratic Rep. Gwen Moore at the weekend convention, delegates screamed “Yes!” when Moore asked, “Are you ready for a blue wave?” But she cautioned them that first, “We’ve got to part the Red Sea.”

