Ben Wikler, Chairman of the Wisconsin Democratic Party, runs what is touted by many to be the single most effective Democratic state party in the country—with no close second place. Wikler, 43, was born and raised in Madison, Wisconsin. He attended Harvard College and pursued a career as a progressive activist working in Democratic politics for the past two decades. Prior to returning to Wisconsin with his wife and three young children, he played a crucial part in defending the Affordable Care Act in his role as the Washington DC Director of Moveon. He was elected Chairman of the Wisconsin Democrats (‘WisDems’) in 2019, a team that’s been racking up one electoral success after the other: Trump lost the state in 2020, Democratic Governor Evers won a second term in 2022, and Democrats achieved a majority in the Wisconsin Supreme Court with the election of two Democratic candidates in 2020 and 2023—but Wikler is not yet done. The outcome of the 2024 presidential race, as well as control of the US Senate, will likely be decided by the outcome of November’s election in Wisconsin—not to mention several high-stakes down-ballot races as well. Wikler is building on the organization built with the prior electoral successes, but he is leaving nothing to chance. His days are long, yet his energy is high and upbeat. BPR had the chance to sit down with him to discuss his priorities, motivation, and plans.
Matthew Kotcher: So why does Wisconsin matter? Can you walk us through the math of the role Wisconsin will play in the outcome of the 2024 presidential election and Wisconsin’s role in determining control of the US Senate?
Ben Wikler: Wisconsin is the most closely divided state in America, which consistently makes it the ‘tipping point’ state in the fight for national power. We’re the only state where four of the last six presidential elections came down to less than one percentage point. In every election, the Electoral College has a ‘tipping point’ state. This is the state where, if you arrange states by the margin of victory—from the biggest win for the leading candidate to the narrowest—it’s the point where the winning candidate reaches 270 electoral votes. Wisconsin was the tipping point state for Trump in 2016, and the tipping point state for Biden in 2020. What that means is that there’s a good chance that whoever wins Wisconsin becomes the next president and that there’s not a path to the White House without winning Wisconsin. Whoever wins here will probably win nationwide, which is a lot of responsibility to put on the roughly 3.3 million Wisconsin voters—it essentially means that a margin of just over 20,000 votes could handily determine our next president.
Meanwhile, in the US Senate, Tammy Baldwin’s seat is essential to the Democratic majority. It’s hard to find a path to 50 US Senate seats for Democrats without holding Wisconsin. And Tammy Baldwin is within the margin of error in public polling against her opponent, Eric Hovde, who’s a massive self-funder who runs a bank in California and is moving to Wisconsin to run against her. Wisconsin also has two competitive House races—in its 1st Congressional District and its 3rd Congressional District—which, given the razor-thin House majority Republicans currently hold, could put Wisconsin in the position of tipping the House majority, the Senate majority, the Electoral College, and adding together the White House and the Senate seat could determine the future of the US Supreme Court. So, whether you live in Wisconsin or never even thought about traveling to Wisconsin, you have to care about what happens in Wisconsin politics in 2024.
MK: So with that said, the Wisconsin State Democratic Party was very successful during your time as state party chair, to say the least. It’s widely considered the most effective Democratic state party in the country. Trump lost the state, Governor Evers was re-elected, and the Wisconsin Supreme Court has a Democratic majority all during your time as chair. What did it take to make this a reality in such a divided state?
BW: Wisconsin has a long progressive history. It also has a long history of far-right politics, from Joe McCarthy to John Birch Society activity to Scott Walker, Ron Johnson and the Tea Party wave in 2010. That year, Wisconsin went from a blue trifecta to a red trifecta. And when Republicans took power, they immediately set about demolishing the political infrastructure and laws that allowed Democrats to be competitive. They smashed unions; they instituted right-to-work policies; they eliminated caps on political donations and eviscerated the campaign finance system; they gerrymandered our state to high heaven. We adopted the most partisan gerrymander in either direction in the country to ensure Republican control of our state legislature. And they changed their voting laws to make it especially hard for young voters and voters of color, especially black voters, to cast ballots in our state. That launched a period that lasted for eight years of Republican trifecta control in Wisconsin. And they were aided all the way through by a far-right majority in our state Supreme Court.
Wisconsin Democrats were able to elect Tammy Baldwin and re-elect Barack Obama in 2012. Those were important fights. There was a huge effort to try to recall Scott Walker. There was also a fight to recall Republican state senators that briefly led to a Democratic majority in the state Senate. But Republicans kept flooding the state with GOP money and hammering Democrats. And finally, in 2016, Trump won by 22,748 votes. My predecessor, Martha Lanning, decided to try to figure out how to turn things around after Trump’s 2016 victory. And she went looking for the most effective organizing strategies that had helped Democrats achieve outsized performance and found the Obama model of hiring organizers early to build neighborhood teams that could work to turn out voters in their own communities, led by volunteers.
That system created a greater level of buy-in and empowerment for volunteers, which meant that people who wanted to make a difference were excited to get involved. In the spring of 2018, using this neighborhood team neighbor-to-neighbor organizing system, Democrats helped support a landslide win in a state Supreme Court race and in special elections. And in November, Democrats swept every statewide race in Wisconsin for the first time since 1982. I was elected that year. I spent months volunteering with Democratic candidates, knocking on doors of neighborhood teams all over the state, and falling in love with this ground-up, grassroots system of organizing and prosecuting campaigns. So I ran for chair in 2019 and picked up the torch and threw myself into the work of expanding that neighbor-to-neighbor system while bringing in digital organizing techniques and communication skills that I had built in my work with MoveOn and other advocacy groups. When the Covid-19 pandemic hit, we were able to adapt our neighborhood team-based organizing system to a fully virtual system and won a Supreme Court race in the spring of 2020.
By training more than a huge number of voters to cast absentee ballots for the first time in our state and developing organizing techniques that were adopted across the country in the Biden campaign in 2020, we won that presidential election. And when Republicans tried to overturn the presidential election, our Supreme Court victory that spring gave us the tie breaking vote in our state Supreme Court that prevented Trump from stealing the election. All of that rocketed us into the midterm election cycle where we built trust, excitement, and a collective sense that we could indeed win, even in extraordinarily tough circumstances. We funded local elections all over the state. We won a superintendent of public instruction race. And that November, we were able to win a governor’s race during a Democratic presidency for the first time since 1962, in Wisconsin.
From there, we went to the Supreme Court race in 2023 which was defined by the fight for reproductive freedom and the fight for democracy. And now here we are in 2024 with an infrastructure we’ve been building continuously, for eight years. We have an approach to organizing that doesn’t shut down after elections, but rather uses every election to prepare itself to get stronger for the next one. We have the chance to potentially flip our state assembly and lay the groundwork for flipping the Senate majority to become a Democratic trifecta again in Wisconsin for the first time since 2008.
MK: What is a typical day in the life of Ben Wikler on the job? What motivates you to go to work every day and does anything ever get you down about this work?
BW: The more involved in politics I get, the more I fall in love with democracy itself, the idea that, in this country—even though it’s fragile, bruised and battered—we still have a system of self-government where people in communities of every size can decide who should make the rules. And the rules reflect, in some measure, the will of the people. I work with a staff that inspires me every day. I work with volunteers in every corner of our state. When I’m firing up volunteers, raising money, or speaking at a press conference, I’m always essentially making the case that we should fight for our most fundamental values. That’s the kind of work that makes it easy to go to get a good night’s sleep, when you’re done with the workday.
I think of a state party chair as having five core jobs. The first is setting the overall vision, mission, culture, and strategy of the state party in consultation with partners, party members, volunteers, and staff. The second is hiring and managing the executive director of the state party, who oversees the team to carry out that strategy and vision. The third is raising the funds to make sure that the team has the resources to actually carry out that strategy. The fourth is communicating everywhere all the time to your staff, to the volunteers who power the work on the ground, and to the general public to whoever else might need to hear the party’s message. The fifth is resolving political problems that require the state party chair’s involvement.
MK: Fundraising is a big part of the job, and you’ve used new and creative strategies to use low-dollar fundraising as a grassroots organizing tactic, such as readings of The Princess Bride with its original cast and the same with casts of The West Wing and Veep (my two favorite shows, by the way). How did you come up with these events, and what might be next?
BW: The new tradition of pop culture reunions and virtual get togethers started with a great Wisconsinite named Bradley Whitford, who was on West Wing and a number of other shows. We had planned to do a fundraiser with him during the Democratic National Convention in 2020. But when the Covid-19 pandemic hit, the convention went virtual and our team worked for them to come up with the idea of an online fundraiser where he would tape a virtual recording of the podcast West Wing Weekly with Josh Malina, fellow West Wing alum. And the host of the podcast has a Zoom event where anyone could donate any amount of money to watch the live conversation. We thought that might raise $40,000; we raised $160,000. After the success of that event, our team started brainstorming furiously for another idea; it turned out that someone on our team had a close friend from growing up who knew the actor who played the Man in Black from The Princess Bride. She reached out to Kerry Ellis immediately and Kerry had been thinking about how important Wisconsin would be in the election and was tremendously excited to be of service. He reached out to Rob Reiner, the creator of the movie, and together they started connecting with all their fellow West Wing cast members.
Almost the entire cast got together and did a live script reading, which, for me, was an absolute dream come true because The Princess Bride is my single favorite movie in the world (I’ve memorized it in its entirety). It reached the stratosphere after Senator Ted Cruz (R-TX), who famously loves The Princess Bride, tweeted how sad he was that the cast members were supporting Democrats, which led to responses from the cast members and a flood of press coverage. So that event wound up the most successful fundraiser in the history of our state party.
MK: So now I want to talk to you more about young voters. Madison is home to 49,000 University of Wisconsin students. What are Democrats in Wisconsin doing to mobilize college students at Madison and in Wisconsin’s other college towns, and to reach and energize young voters in general? What role has your team of youth organizers played in this work?
BW: Wisconsin has 320,000 college students, which is more than ten times the margin of victory in four of the last six presidential elections here. So students specifically, and young people more generally, are consistently the decisive factor in statewide elections that have enormous national consequences. For that reason, the Democratic Party of Wisconsin takes youth organizing and campus organizing incredibly seriously, which means making sure that it’s actually fun. We have worked with several dynamite youth organizing directors who’ve worked with us to build up a network of full time youth organizers and half-time campus organizing fellows across the state. That team is steadily growing right now. I expect we’ll have dozens by the election in November. Their job is to not only ensure that students are knocking on other students doors and reaching out to students through their social networks, but also to figure out how to have great visits by surrogates, including major candidates, to have public events that address that the the issues that are most motivating to young people—reproductive freedom is at the top of that list at this point.
MK: With respect to finding candidates to run, how do you do it and what qualities do you look for?
BW: Recruiters tend to be people in their own communities, working with people in the relevant body of government. We now have a deep bench. We try to recruit and support candidates as they start their political career and move up the chain so that once we get to a statewide fight, we have a ton of candidates with deep experience. Across the board, we look for people that can develop and communicate a clear message; build a coalition; work the politics to bring people together around that message and vision. We look for people that are deeply rooted in their communities, that are running in order to do something, rather than just to be something.
MK: So now for a short but sweet lightning round. When was your last day off?
BW: I took Monday off because my kids were out of school for the day, and I wound up doing some work. But I was going to be away for the next five days and had worked the previous six days. And I wanted to, I guess I took Sunday and Monday off, and I wanted to have some real time with them.
MK: Veep or the West Wing. Which do you prefer?
BW: I think politics is such a mix of people. There’s a constant level of absurdity that you have to laugh about. And at its best it’s driven by deeply held values, which is something that you see in the West Wing. I think often Veep is closer to the truth of what it feels like in the political system day-to-day. But the real heart that’s at the core of the West Wing is often what sustains people through a lifetime in public service and in politics. And a lot of my job is to remind people why we’re doing this work which ultimately is to serve and make a difference, to make our communities better.
MK: Favorite place to enjoy nature in Wisconsin?
BW: The arboretum around Lake Wingra. The Northwoods, especially Dallas County, where I went every summer when I grew up. Our amazing state park system which spans every corner of the state. They are probably tied for my top three.
MK: Your favorite pro sports team?
BW: Green Bay Packers. No question. The great community-owned team leads the way for the whole country.
MK: Okay, finally to wrap us up, bringing it back to The Princess Bride to close. Channeling your best Wally Shawn, what do you think is inconceivable?
BW: It’s inevitable that the princess will be murdered and that the Man in Black who was killed by Count Rugen and by Prince Humperdinck in the pit could come back and save the day. And likewise, people think it’s inconceivable that states that turn bright red can come back and become progressive powerhouses once again. And yet, in the same way that everything that Wally Shawn said was inconceivable turned out to happen in The Princess Bride, I think Wisconsin is going to turn blue and love will win the day.
*This interview has been edited for length and clarity.