Wisconsin Democrats built a winning machine. Now comes its greatest test.

State party chair Ben Wikler has built a formidable fundraising and organizing operation ahead of a potentially tough midterm election.

MILWAUKEE — Cavalier Johnson, Milwaukee’s Democratic acting mayor, is expected to glide to a full term on Tuesday. But he was still energetically rallying volunteers at a banquet hall this week — not just for his own race, but “for the big ones coming up in November.”

“This is the trial run for the races that decide control of the United States Senate. That will help the president get his agenda implemented,” Johnson told a crowd of 50 who gathered for an organizing training ahead of Wisconsin’s spring elections for local offices. “And that will make sure we protect democracy here in Wisconsin with Gov. Tony Evers.”

Hovering a few feet away from Johnson was Ben Wikler, the chair of the Democratic Party of Wisconsin. He’s also the reason why a heavily favored mayor was rallying volunteers for an election six months away. Wikler — a bespectacled 6-foot-4, with a notebook seemingly glued to his hand — has built a rare thing in the era of super PACs and dark money: making his state party not only relevant but a powerhouse of organizing and fundraising.

Since taking over as chair in 2019, he’s raised nearly $100 million, believed to be a fundraising record for a Democratic state party, and helped President Joe Biden win the tipping point state of the 2020 election, which helped Democrats rebuild their Midwestern “blue wall.” Now, Wikler’s machine is facing its biggest test, one that will ripple into 2024. That’s why the party is using this moment as a critical warm-up exercise for the midterms.

Evers, a Democratic governor whose authority includes certifying elections, is up for another term in 2022. GOP Sen. Ron Johnson, who has amplified disinformation around the 2020 election and the coronaviruspandemic, will be on the ballot, too. Wisconsin Republicans are currentlyconsumed by denying the results of the 2020 election, built on baseless claims. But while public polling shows Evers remains marginally popular and Johnson’s personal numbers aren’t great, it’s all playing out against Biden’s sagging approval ratings, sky-high gas prices and historical data that strikes against Democrats, as the party in power.

“I see this election as a clash between the national momentum and atmosphere against us and everything in Wisconsin, more than I could’ve hoped for, breaking our way,” Wikler told POLITICO while seated in the back of a minivan, bumping down a two-lane road in rural Wisconsin. “An organizing machine, a party operation and candidates themselves, on the Democratic side, are bringing the party together and energizing people, and Republicans are involved in a civil war.”

“The question is: Will the national dynamics or the in-state dynamics prevail over the other?” Wikler continued. “It’ll probably tilt by a tiny bit, one way or the other.”

Wisconsin is trending dead-even. In 2016, former President Donald Trump won it by 23,000 votes. In 2020, Biden won it by 20,000 votes. Brian Reisinger, a top Republican consultant in the state, said Wisconsin Democrats “had their back broken during the [GOP Gov.] Scott Walker years, and they never got back up again until Ben Wikler came.”

“But the true test of the party is whether you can win big when the wind is at your back and still eke out wins when the wind is in your face,” Reisinger said. “The Wisconsin Republican Party has done that. But Democrats haven’t yet, so this is his big test.”

Now, in preparation for yet more races that could be decided by thousands of votes, Wikler and the Democratic Party of Wisconsin are using Tuesday’s elections — a hodgepodge of local races, from school board to city council to circuit judge — to experiment with their tactics and messaging.

For the first time since the coronavirus pandemic started, the party returned to in-person door-knocking statewide in September 2021, combined with virtual phone banking and relational organizing — a tactic that empowers voters to talk to their friends and family about elections instead of talking to strangers. Democrats are also proactively chasing absentee voters, who can request mail ballots for both the spring and the fall elections. So far, they’ve already reached out to 350,000 voters.

“We’re already talking about what’s working and what’s not working, what it is that we still need to do,” said Gloria Reyes, president of the Madison Metropolitan School Board and co-founder of Adelante, a group focused on recruiting and supporting candidates of color in the state. “I think, in the past, what we used to do, is that once the election was close, then we’d reach out. … But now, we’re establishing relationships.”

They’re also message testing, collecting valuable data on what might move independent voters back into their column amid dire public polling for Democrats. The Wisconsin party’s paid communications focus on infrastructure and education. On Johnson, Wikler said, they plan to “spend a lot more time talking to voters about how Johnson gave himself a tax cut and wants to repeal the Affordable Care Act than we do on mouthwash” — a reference to Johnson’s promotion of mouthwash as a defense against Covid-19.

Threats to democracy and disinformation around the pandemic are animating issues for the party and for the base but not part of its message to swing voters. “We talk about democracy a lot, it’s just not the center of TV ads and mailers,” Wikler said.

“If you care about democracy, talk about roads,” he added.

The state party is also running a broad turnout program, rallying voters of color and reengaging rural voters. National Democrats don’t “pay enough attention to rural America,” said Bill Crawford, the former chair of a four-county coalition of rural communities. “I think Ben and the DPW are going to be teaching the national Democratic Party something in these elections.”

The fuel for change: A huge fundraising leap

Only a very well-funded state party could run this kind of a statewide, year-round operation testing tactics and messaging. That was Wikler’s goal when he first ran for chair in 2019: raise money to professionalize the operation with better-paid staffers; build on the neighborhood organizing program started by his predecessor; and stand up an all-year organization so that “candidates don’t need to make everything from scratch every election cycle,” he said.

It’s a big strategy, and it requires a big bank account. Wikler, a former senior adviser at MoveOn and a podcast host, brought a national fundraising network to tap, as well as a fluency with Twitter that drove small-dollar donations. His long Twitter threads, unspooling the stakes and narratives around elections, often go viral. A single Twitter thread has raised six figures in small-dollar donations, he said.

“Facebook is how you talk to voters,” Wikler said, “but Twitter is how you talk to influencers in politics.”

In 2020, at the height of the coronavirus pandemic, the Democratic Party of Wisconsin hosted virtual, grassroots fundraisers that featured celebrity TV shows and movie reunions, including “The West Wing,” “Veep” and “Parks and Recreation.” Its biggest get, though, was a table reading of “The Princess Bride” with most of its original cast, a virtual event that raised $4.25 million.

At the same time, Wikler’s become a star of the high-dollar donor set. Scott Anderson, a Democratic strategist who coordinates major donors around state races, called Wikler “the best state chair in the country, and the drop off to the next tier is pretty steep.” Dmitri Mehlhorn, who works with LinkedIn co-founder Reid Hoffman on his political giving, said the “local Wisconsin operation is good enough to survive a national red wave … and that’s because of Ben.”

“He’s completely redefined what a party chair, what a state party, can be,” said Mike Tate, Wikler’s predecessor as chair from 2009 to 2015, who credited Wikler for maximizing fundraising from big and small donors alike.

It’s a far cry from where Wikler’s fundraising career started: at a park in Madison, Wis., for an event benefiting then-state Rep. Tammy Baldwin’s 1998 run for Congress. Four people showed up, including Wikler and Baldwin.

Twenty-three years later, Wisconsin Democrats significantly outraised their Republican counterparts in 2021. In an emailed statement, Mark Jefferson, the executive director of the Republican Party of Wisconsin, said in part: “There's no question they need to tout ‘victories’ — no matter how small — if they want to keep those out-of-state dollars flowing in for November.”

“They have a tough job, and they need to toot their own horns as much as they can before they start the unenviable task of defending a weak governor who it's clear isn’t really up to the job, while Senator Johnson is in [a] strong position for re-election,” Jefferson continued.

Some of Wikler’s changes haven’t met with unanimous acclaim in-state. One Wisconsin Democrat, an elected official who was granted anonymity to speak candidly, complained that Wikler has ignored homegrown talent, hiring staffers who weren’t from Wisconsin and “who didn’t know how to pronounce the names of our elected officials, or pronounce the names of our cities.”

Critics did concede that the party “for the first time [isn’t] totally starved for resources,” but some felt they weren’t seeing early or big enough investment in state legislative races and in county parties.

“Inevitably,” Wikler said, “people second guess resource decisions,” noting that the state party is doubling its funding for county parties for the two months leading up to the spring elections.

“The thing you have to do is have an actual theory for how you’re going to invest resources, not just based on which wheels are squeakiest, but also have an ability to listen and see where there are opportunities that folks have detected in their areas that may not be obvious.”

He also added that the majority of the staff’s leadership team hail from Wisconsin, and they’ve “put a lot of work into these processes to change the culture of ‘who you know’ hiring practices — and the result speaks for itself,” Wikler said in an emailed statement.

“It’s a hard, thankless job. No one’s ever happy with you,” said Brad Courtney, the former chair of Wisconsin’s Republican Party. “He has his difficult people, we have our difficult people, but I have a lot of respect for him.”

The first Black mayor in Wisconsin history pointed out Wikler’s ability to take input and criticism and then do something constructive with it as one of the key ingredients of his — and the state party’s — recent rise.

“The party either listens or they don’t listen. Word gets around,” said Frances Huntley-Cooper, the former mayor of Fitchburg, Wis. But with Wikler, Huntley-Cooper said, “every time you saw him, he had his notebook and he was taking notes. And he wasn’t just taking notes, he was following through.”