Teaching an old party new tricks

One week before Wisconsin’s November 1998 general election, about a dozen Madison-area high school students took part in a taping of Wisconsin Public Television’s show Wisconsin Kids Vote ‘98. Host Kathy Bissen asked if any of the students had general thoughts on the election, which featured races for Wisconsin governor and U.S. Senate.

Ben Wikler, then a 17-year-old senior at West High School, spoke up. 

“I think campaign finance is a critical issue because most people can’t run for office because they can’t raise the money,” he said. “I’d like to see a fair system where everyone can get involved,” the West High Regent added. “If I ever run for office, I don’t want to raise $3 million.” 

Nearly 25 years later, the utopia articulated by Wikler, now the lauded chair of the Wisconsin Democratic Party, is still just a vision. Money remains the driving force in politics and few have been better at raising it in recent years than Wikler. The nonprofit Wisconsin Democracy Campaign estimates that, between his election as party chair in spring 2019 and this spring, Wikler-led Democratic committees have raised a stunning $110 million.

That cash, and a Republican-passed change in election laws that lifted all limits on donations to parties and lets party leaders move that cash to candidates’ campaigns, helped Democrats carry Wisconsin for President Joe Biden in 2020, helped re-elect Democrat Gov. Tony Evers in 2022, and helped Milwaukee County Judge Janet Protasiewicz win a seat on the state Supreme Court in April.

Wikler doesn’t apologize for his record fundraising, which allowed his party to spend $9.9 million on Protasiewicz’s campaign — 59% of its total spending — before the election. The 42-year-old will raise all he can to play offense during next year’s elections for president, U.S. Senate and House and state Legislature.

Wikler justifies his fundraising by saying Wisconsin is “on the knife’s edge” of the nation’s future. A few thousand votes decide statewide elections, and Republicans are “obsessed” with Wisconsin — the first presidential debate and the GOP’s nominating convention will be held in the state, he notes.

Two months before the November 2020 presidential election, Wikler organized a celebrity-packed reenactment over Zoom of The Princess Bride that raised a record $4.25 million. He says such pop culture events are valuable because they attract both check-writing donors and anyone willing to give the party their contact information. “We found thousands of volunteers doing them,” Wikler says. “They’ve been transformative for us.”

He has used the cash raised to not just fund campaigns, but to invest in full-time staff and party infrastructure. There is now a payroll of about 60 employees, making the WisDems the largest party operation in the nation. UW-Madison political science professor Barry Burden says Wikler’s “astronomical fundraising has allowed the Democrats to hire and train a large and impressive team.” 

Four years into his tenure, Wikler is widely credited with turning the tide for Wisconsin Democrats, offering hope and light after the dark days of former Gov. Scott Walker. Says Charles Franklin, the veteran political scientist who directs Marquette University Law School polls: “We’ve seen the Democratic Party under Wikler make major advances in both the amount of money raised and — especially — the efficiency of the use of that money.”

Wisconsin’s national impact

When dialing for dollars, Wikler has a simple pitch for the people of Wisconsin: “If you care about the future of Wisconsin…we have the ability to take dollars, put them to work — and win in a way that can affect all of our lives.”

For those who live outside of Wisconsin, he adds, “we point out that what happens in Wisconsin doesn’t stay in Wisconsin. So, if you care about the future of American democracy, donating to the Democratic Party of Wisconsin is one of the biggest ways you can make an impact.”

Wikler, who was re-elected party chair in June at the party’s convention in Green Bay for a two-year term, says he no longer calls every election “the most important in your lifetime.” Instead, he stresses “why each election is important.”

Wisconsin will be one of the few states determining who is elected president next year. Re-electing Democratic Sen. Tammy Baldwin could decide which party controls the U.S. Senate in 2025. And reclaiming southwest Wisconsin’s U.S. House seat — won by Republican Derrick Van Orden in 2022 — would go a long way toward Democrats again controlling the House.

The nation’s richest 1% have responded to the call, writing large checks to both parties and candidates’ campaigns in Wisconsin. Reid Garrett Hoffman, of Mountain View, Calif., co-founder of LinkedIn, gave the state Democratic Party almost $3.6 million this year, WisPolitics reported. Jay Pritzker, the Democratic governor of Illinois and a billionaire, gave state Democrats another $1 million. In the first half of the year, the state Democratic Party raised $5 for every $1 donated to the state Republican Party, according to campaign-finance reports.

To state Republican Party Chairman Brian Schimming, that kind of out-of-state fundraising means that Wikler has “nationalized Wisconsin.” 

Wisconsin Democrats “put the ‘For Sale’ sign out front, and the money came rolling in,” he adds. “Democrats have dropped the old pretense of being all in favor of campaign-finance reform,” Schimming says. “He’s just got them — straight out — grabbing money whenever they can get it, wherever they can get it.”

Matt Rothschild, who just retired as executive director of the Wisconsin Democracy Campaign, says Wikler has done a “tremendous job” as party chair but adds a warning: “I don’t want him or anyone else to draw the wrong conclusions from his ability, in the short term, to beat Republicans at their own game — raising money from fat cats. There are more right-wing billionaires than left-wing billionaires out there, and it won’t take long for them to swamp us with their money.”

And, Rothschild says, “Super-rich Democrats may not have the same interests as working-class Democrats, especially when it comes to issues like wages, unionization and trade. It’s simply not true that left-wing billionaires are stand-ins for all Democrats and progressives. Most importantly, everyone’s supposed to have an equal voice in the political arena, but the money from the billionaires is drowning almost all our voices.”

Asked about Rothschild’s warning, Wikler says, “We have to be a party that can legislate based on our values. If that means a bunch of donors jump ship, so be it.”

Liberal politics at the dinner table

Growing up on Madison’s west side, liberal politics were part of Wikler family dinner discussions. Wikler’s father, Daniel, now an ethicist at Harvard’s School of Public Health, was a UW-Madison professor from 1975 to 2002. His mother, Lynn McDonald, founded the program Families And Schools Together and is now retired from UW-Madison’s Center for Educational Research. The two divorced when Ben was a child. 

Wikler got involved in politics at an early age, stuffing envelopes at 11 for the congressional campaign of his godmother, Ada Deer, a pioneering feminist and Native American leader.

At Madison West, Wikler began a statewide movement of high school students who lobbied legislators — successfully — for more state aid for public schools.

He went on to volunteer for then-Assemblywoman Tammy Baldwin and interned for progressive Democrat Ed Garvey and U.S. Sen. Russ Feingold. He met his wife, Beth, at Harvard University. The two “fell in love while putting up posters together for a protest” against the federal government’s tepid response to the global AIDS crisis.

In Washington, D.C., Wikler made high-profile connections with other activists nationally on climate change, poverty and human rights issues — contacts that now help him champion the causes of Wisconsin Democrats. He worked closely with comedian and then-U.S. Sen. Al Franken on his two books and a national radio show, served as press secretary for the successful 2006 U.S. Senate campaign of Ohio Democrat Sherrod Brown, and produced national podcasts.

Wikler joined the liberal group MoveOn.org in 2014, serving as Washington director. His job, according to his LinkedIn page, was to make sure “the views and values of MoveOn’s eight million members are impossible to ignore in D.C. and political media.”

When Donald Trump stunned Wikler and other progressives by winning the presidency in 2016, MoveOn leaders wrestled over which issues to focus on. Wikler fought to prioritize keeping the Republican majority in Congress from repealing Obamacare, and he led that national movement.

His message: Confront Republican members of Congress at every public appearance, tell reporters what you plan, capture those sessions on your phones, and post the video on social media.

Why was it so important? “These people were trying to rip away health care that people needed for their lives,” he says.

At about 5:30 a.m. on July 28, 2017, Wikler was leading a protest of people with disabilities outside the Capitol when he announced that Republican U.S. Sen. John McCain had cast the pivotal vote preventing the repeal of Obamacare. “It was an unforgettable moment that, to me, spoke to the power of democracy even when it bears so many cracks and scrapes,” Wikler recalls.

In 2019 Ben and Beth moved to Madison and into Ben’s childhood home. Their three children range in age from 5 to 11; Pumpkin is their 90-pound Bernese mountain dog. Wikler thought he would continue working for MoveOn but when former state Democratic Party Chair Martha Laning announced that she would not seek another term, he ran and easily won the job at that year’s state party convention.

Building relationships, gaining votes

Wikler, who said he was paid $198,000 last year, is not just the party’s star fundraiser, he is its chief strategist. And he pursues multiple avenues for winning elections. 

He challenges the party’s 12-member “digital team” to aggressively use social media and posts his own party-line messages to his 140,000 Twitter followers. He dreams up special events like bringing Pumpkin to the UW-Madison campus for a “pet out the vote” event that encouraged students to vote for Protasiewicz in April. Students missing their pets back home loved to meet Pumpkin, he explains. 

He also champions neighbor-to-neighbor organizing, especially in WOW counties (Waukesha, Ozaukee and Washington) and BOW counties (Brown, Outagamie and Winnebago).

Barack Obama’s neighbor-to-neighbor organizing “model requires early investment, which most parties usually don’t have,” Wikler explains. It’s what is considered a “relational” organizing model — the party trains volunteers to do outreach to their friends, neighbors and, if students, their classmates. 

In Outagamie County, one of several in eastern Wisconsin that Wikler says determines who wins statewide elections, the neighbor-to-neighbor effort has a name — OATS, or “Outagamie Action Teams.”

Wikler’s focus on neighbor-to-neighbor organizing, says Rep. Lee Snodgrass (D-Appleton), means “you have a person who is a Democrat who is talking to their neighbors, finding other Democrats, getting together regularly — building relationships in a fun way.”

In June UW-Madison students received an email from the Wisconsin Democratic Party asking them to sign up for its “Organizing Training Program: Road to 2024.” 

The program, an eight- to 10-week course running in the summer and fall, promises to train participants in “how to organize their communities for progressive causes, and build skills in political organizing.” Coursework includes how to recruit volunteers, organize volunteer and voter data, and how to persuade people on issues.

The party will once again be organizing hard in college towns like Madison. As Politico recently reported, “traditionally liberal college counties like Dane are flexing their muscles, generating higher turnout and ever greater Democratic margins. They’ve already played a pivotal role in turning several red states blue — and they could play an equally decisive role in key swing states next year.”

“Lose by less” is another Wikler core strategy. The idea is that in every part of Wisconsin, even “deep red” areas of rural Wisconsin, Democrats should turn out more votes than they did in the previous election. “We have to do a ton of work to ‘lose by less’ in a lot of places,” he says.

“In Wisconsin, if you get a percentage point or two, that’s exactly what you need. That paid off in 2020. Every single county in Wisconsin had more votes for Biden than it did for Hillary Clinton — every county. We didn’t see an exit from the Democratic Party.

“That gave us something to build on,” Wikler adds. “Then, in 2022, not as many Democrats fell off, and some Republicans crossed over, and we won with independents — enough to win” and re-elect Evers as governor.

In May, at a “Forward Together Dinner” in Appleton of Outagamie County Democrats, Wikler congratulated the party faithful for mastering his “lose by less” strategy. His reference point? Protasiewicz’s 51% winning margin in Outagamie County, which reversed a trend of Republicans winning the county by narrowing margins. In 2016, Trump won the county by 13% and in 2018, Republican Gov. Scott Walker won it by 11%; Trump’s margin of victory was 10% in 2020, and Tim Michels, the Republican candidate for governor, won the county by only 7% in 2022.

“What you’re showing is that change is possible,” Wikler told the crowd. “You changed history. For the first time, we’re not playing defense.”

Outagamie County Executive Tom Nelson, a former Assembly majority leader and U.S. Senate candidate, says he’s grateful for Wikler’s leadership. “And I speak for candidates, elected officials all across the state.”

Wikler has “dramatically changed the narrative of Democrats in Wisconsin,” Nelson adds. “In the dark ages, down-ballot candidates for Assembly were not just ignored but, if you had problems, if you needed help, you were pretty much on your own.”

Snodgrass agrees. It used to be, she says, that there was little coordination between local Democrats and the party — party contacts would change often and you didn’t know who to contact. Now, she says, “we know their names; we know who to call.”

Knocking on doors

Wikler has also transformed how those candidates are financially supported by the party. Assembly candidates who have a viable campaign plan that is cleared by the party are guaranteed a minimum of $2,000 in support; state Senate candidates, $5,000; if pre-election polls show the race is close, more money is forthcoming, along with staffers and volunteers. 

That is helping fuel the organizing being done by Assembly Democrats to recruit and support more candidates. 

Rep. Francesca Hong, 34, an emerging young leader of Wisconsin Democrats, is a critical part of that effort. After winning a 2020 primary in Madison, which gave her a “safe” Democratic seat, Hong began traveling statewide to work with other candidates, help local party activists organize, knock on doors, and listen to voters.

Hong says she does “candidate care,” because running as a Democratic Assembly candidate in rural areas — especially as a woman — requires “a lot of mental gymnastics and emotional labor.”

Hong is a Wikler fan. “He has infectious energy. He’s charismatic. He is one of the best messengers and speakers that I have seen come through the party. He can explain things and break them down, and not just on his Twitter posts. He knows how to articulate what the opposition is doing, and how we can fight back.”

But, in two election cycles of meeting with voters statewide, Hong has learned some valuable lessons. Democrats “don’t have a great message to send to white men in their 40s, 50s and 60s. Saying, ‘Hey, we’re undermining democracy…’ Folks aren’t always connecting with that,” she adds.

She says the party suffers from “elitism” and has “appeased” moderates and “left working people behind.” Also, “just having the metrics of how many doors [volunteers] knock on isn’t going to be a complete reflection of the type of relationship building we need to be investing in to get folks to trust our party again.”

While doing doors in Jefferson, a white male homeowner told her, “I’m not going to let anyone take my AK-47s from my basement.” 

Hong’s response? “I let him know the last time I shot trap, I thoroughly enjoyed it. Democrats aren’t here to take your guns away.”

Rural Wisconsin residents “don’t care about Princess Bride” fundraisers, which Hong calls a “triggering” event for her. “They care about internet access and going to college and not being in debt. Democrats are missing a huge opportunity as a party to let them know they are the essential voter — the essential future for Wisconsin.”

Echoing Rothschild’s warning, Hong says, “Investing in [rural] communities may not be what the largest donors in our state, and national donors, are looking for.”

Asked about Hong’s worries, Wikler notes that the $4.25 million raised by the Princess Bride re-enactment let the party give much-needed support — cash and other resources — to Democratic candidates for the Legislature.

And Hong’s “elitism” worry? “There are elites in both parties who try to advance a vision that does not resonate with most Americans,” he says. He sees no “elite cabal” when he attends party events statewide, but instead finds “teachers, firefighters, farmers, retirees.”

“We’re living in an era of record inequality when the power of money is unparalleled, and the Democratic Party’s commitment to fighting against the power of money has to be central to our politics.”

The rural challenge

The challenge in front of Wikler and his party to win back rural voters is great. The Republican Party has controlled both houses of the state Legislature since 2011 and gerrymandered electoral districts are not the only factors at play. 

Former state Sen. Kathleen Vinehout of Alma, who represented several western Wisconsin counties for 12 years and ran for governor, was surprised when her colleague, former Democratic Rep. Chris Danou, lost the 2016 election to Republican Rep. Treig Pronschinske. Danou told her “something happened,” Vinehout recalls.

So, Vinehout went to the clerk’s office in the city of Whitehall, in Trempealeau County, where she was stunned to discover that 25% of all votes in that city were cast by new voters.

Looking through new-voter registration forms, Vinehout says, “I could see the patterns — more men, older, in their 50s, family groups.” Asking about those new voters, Vinehout says she was told the new voters were largely men “you’d see at the recycling center, but not at the polls.”

Vinehout’s Trempealeau City Hall research reflects the huge increase in votes for Republican candidates for president, and the decrease in votes for Democrats, across northern Wisconsin.

Draw a line that divides Wisconsin into segments north and south of State Highway 10, and you’ll find that Wisconsin Elections Commission records show an average 22% increase in Republican votes for president between the 2004 and 2020 elections in most counties north of that highway. 

In those same northern counties, votes for Democratic candidates for president fell an average of 10% in that period.

This is not news to Wikler.

“This is one of the biggest megatrends in global politics. Across America, and in industrialized countries, there has been an explosion in political polarization that tracks geographic density and education levels,” Wikler says, adding: “Wisconsin is one of the rare states where that is almost perfectly balanced out by what you see in suburbs and cities.”

Elections Commission records support his claim.

In the same period between the 2004 and 2020 presidential elections, Democratic votes for president went up by 43% in Dane County, 41% in Waukesha County and 6% in Milwaukee County. Votes for Republican presidential candidates fell 12% in Dane County and 25% in Milwaukee County over that period; GOP votes for president in Waukesha County went up 9%.

Although one Ashland County Democrat accuses Wikler of having a “12-county” strategy that targets only Madison, Milwaukee-area and Fox Valley counties, Wikler shrugs off the criticism. 

“Forty-two percent of Democratic votes come from rural areas,” Wikler responds. “Democrats can’t cede a square inch of the state. We have to organize and show up everywhere.”

What’s next

Wikler is convinced that former President Trump will be the Republican nominee for president next year, despite the criminal charges pending against him. He also predicts that “the biggest issue is going to be abortion — the question about the freedom to make decisions about your own body.”

Trump inflamed rage and a sense of grievance among a group big enough to win the primary and take over the party, says Wikler. And he has continued to stoke that sense of fury. 

“That has really wrapped the whole GOP around this sense of dominance and bullying. So many Republican politicians say privately they detest everything Trump stands for, but it kills them politically if they ever came out against him,” Wikler adds. “They’re just demonstrating every day that there’s not a principle that they’re willing to hold above their own career.”

Schimming counters that Wikler and Democrats have to repeatedly attack Trump because their own presidential candidate could be in trouble: A national poll found only about 40% of Democrats, those who lean Democratic and independents, want the 80-year-old Biden to run again.

When so few voters “want Joe Biden to run again, you need a bogeyman to keep your base fired up,” says Schimming. “If I were [a Democrat], I’d be petrified that Biden is in such weak shape and so they need an enemy.”

But Schimming allows that Republicans must adopt the “vote early” strategy Democrats effectively used in the last three election cycles. “We’ve got to do early votes. We can’t be 100,000 or 200,000 votes down on Election Day and think we can make that up in 13 hours.”

“Republicans are wise to rethink a disastrous strategy,” Wikler observes.

No one thinks Wikler will leave the state before the pivotal 2024 presidential election, but, given his rising profile, what about after? Will he run for office? Become a gun-for-hire consultant? Return to Washington as a Democratic National Committee leader?

Asked where he sees himself in 10 years, Wikler pauses before saying his wife, Beth, who is a consultant for the Robert Wood Johnson Foundation, asks him the same thing. He then waves off the question. Yes, people ask him to run for office, and to consider other big challenges. But — for now — he has his eyes on the 2024 elections, ever mindful of Wisconsin’s key role.

“I’m honored by the speculation, but I’ve always dreamed of raising my family here in Madison, and that’s exactly what I plan to do.” 

Wikler acknowledges he’s part of a broken political system and still believes, as he did at 17, that money should not determine who can run for office. “I think we should have public financing of elections.” But, he adds, “I don’t believe in unilateral disarmament.”