For Wisconsin liberals, upcoming Supreme Court race is first test of ‘lessons learned’

Angela Lang is about to send her canvassing teams door knocking. But first, a moment to outline the stakes: “Fair maps, abortion, voting rights,” is Lang’s list. “It’s not a seat we can afford to lose because if Republicans and conservatives gain control of the court, that’s Elon Musk and that’s a through line to the Trump agenda.” On paper, the April 1 election pits Susan Crawford against Brad Schimel for a vacancy on the Wisconsin state Supreme Court. Liberal Justice Ann Walsh Bradley is retiring, and the election will determine the court’s ideological balance. Crawford currently serves as a Dane County Circuit Court judge and is a former prosecutor and legal counsel to a past Democratic governor. Schimel is a Waukesha County Circuit Court judge and was the state’s GOP attorney general from 2015 to 2019. The court race is a reminder that Wisconsin isn’t just a 50-50 state in presidential races. Close contests for Supreme Court seats have been common in recent years, and liberals are fighting in this one to maintain the 4-3 edge in the court they won in 2023.President Donald Trump’s weekend endorsement of Schimel only elevates the national stakes of the contest. They’re even bigger for Lang and organizations like Black Leaders Organizing for Communities, of which Lang is executive director. She preached a version of that “can’t afford to lose” argument five months ago, but Trump won Wisconsin on his way to a swing-state sweep and the White House. Now, with November’s bruises still tender, she faces another giant organizing and turnout challenge. “There’s always the finger-pointing after an election,” Lang said in an interview. “This would be the first true local test to see if there are lessons learned.” Trump increased his vote total and vote share in Milwaukee in November, including in the predominantly Black neighborhoods where BLOC operates. Lang’s way of doing things is among the points of post-election debate. Pro-Trump groups were nowhere near as visible or active as BLOC when it came to door knocking and community meetings. Yet Trump increased his share of the Black vote and, with help from Musk and others, used digital tools to reach and activate voters. In this Supreme Court election, Musk has funneled nearly $7 million to a conservative group in the state that is trying to mirror the 2024 strategy to mobilize voters for Trump. It includes digital targeting as well as traditional canvassing operations. A super PAC Musk has supported in the past is also spending heavily on television advertising. It is not required to disclose its donors. Lang hears the criticism that old-fashioned door-knocking isn’t as effective or necessary anymore. But she dismisses it as uninformed. “We will definitely increase some of our digital stuff,” Lang said. But, “I will always take stock in listening to our team that is knocking all day every day and has more of a pulse on the community than any overpaid consultant that likely is not even from our state and hasn’t set foot in our community.” We visited with Lang several times last year as part of our All Over the Map project tracking the 2024 campaign through the eyes and experiences of Americans who live in key states and are part of crucial voting blocs. Lang was well aware, especially in the final weeks, that Trump was running stronger in her community, especially among Black men. “People didn’t feel the Democrats were addressing the needs and the issues of the average voter,” Lang said. “People wanted to try something different.” Now, despite the enormous stakes in the Supreme Court race, Lang and other progressives here told us turnout remains a giant worry. “There’s so much voter fatigue,” Lang said. “People don’t want to talk about politics right now. They feel completely checked out.” That voter fatigue is just one piece of a complicated challenge for Democrats. There are tensions between grassroots activists and consultants over what went wrong in 2024 and how to fix it, both on how to prioritize an issues list and how to then communicate it more effectively; over whether they can or should make Musk an election foil. There is also anger at Democratic leaders for not showing more fight – and having more success – as President Trump moves at a frenetic pace. “We need to hold our ground,” is how Democratic consultant Josh Klemons put it. “Then Senate Democrats cave and absolutely people are frustrated. There’s no question about it. … It’s very hard to keep asking people to give their everything when they don’t see real progress.” Klemons is trying, with frequent TikTok posts about the stakes of the court election. He is the first to admit that – at first glance, anyway – he might not look the part. “I’m not a camera guy,” Klemons said in an interview at his Madison home. “I didn’t grow up wanting to be a digital influencer.” But he posted a TikTok complaining about how Republicans drew Wisconsin legislative maps a couple of years ago. “And it blew up,” he said. “And I did another a few days later, and it blew up even harder.” Now, he posts one a day on average, some shot in his basement office, others on a woodsy trail near his home. “My whole message is that we are in this together,” he said. “No campaign is going to save us.” On our latest Wisconsin visit, we stopped by a Milwaukee Democrats monthly meeting where the discussion was mostly about the urgency of the court race. But one member offered a resolution urging the group to invest in new organizing offices in Black and Latino sections of the city where Trump improved his vote share in 2024. Klemons has no issue with more visibility and brick-and-mortar party offices. But he says Democrats and progressives need to think and act on a much grander scale. “Republicans have built a massive media infrastructure that allows them to get out their message in a way Democrats cannot compete with,” he said. “It doesn’t matter if our messages are better or not because they are not getting heard.” Klemons sees a 2024 replay in the final weeks of the Crawford-Schimel race: Musk pouring millions into advertising and turnout efforts. “Wisconsin has a real chance on April 1 to show money cannot buy elections,” he said in the interview – echoing one of his TikTok themes. “The world’s richest man cannot pick and choose who should serve in our government at every level.” Democrats are making Musk as much of an issue, if not even more of one, than Trump himself. “We live in Elon Musk’s world right now,” Klemons said. “I’m working very hard to make sure we don’t live in Elon Musk’s Wisconsin.” Kate Duffy, like Klemons, calls her path to Instagram accidental. She founded a group called Motherhood for Good back in 2022 and now posts regularly on issues she sees as essential to busy mothers like herself. “I try to make content that can be digested between bath and bedtime,” Duffy said in an interview at her home in suburban Milwaukee. “A quick video that somebody can watch in two or three minutes is going to do really well.” One Duffy staple is 60-second explainers of key issues and themes. She augments the posts with maps and graphics. But she is also now leaning into longer posts – for her, a key lesson of her 2024 experience trying to help Kamala Harris. “My biggest takeaway is to listen to my gut more,” Duffy said. “We can do a longer video. We can explain things more. We can add more nuance. People are craving that.” Messages from campaign consultants dissuaded her from doing more of that last year. “(I) kept hearing, well, ‘These are the messages. It needs to be quick and simple. And hit this.’ And looking back, I’m realizing that is probably what came off as inauthentic and didn’t really resonate with as many people.” Another takeaway: Talk more and smarter about the economy and the cost of living. “There’s so many women who make all the household purchasing decisions and are in charge of the budget and that is certainly somewhere where we can do better,” Duffy said. Democratic consultants, she said, urged a focus on abortion rights and women’s rights. “That’s foundational,” Duffy said. “I’m always going to believe in that. But we can’t discount somebody’s actual struggle they are feeling to put food on the table for their kids. That is a daily trauma they are dealing with. So I think we need to do a better job messaging towards the economy.” The barbershop was a daily town hall long before the internet, long before new media and social media and big data. Eric Jones stops by the Exodus Hair Studio in Milwaukee once a week for a trim and for crackling conversations about the Bucks and the Brewers, about the local economy and about everything under the sun when it comes to politics. Jones was part of our All Over the Map Project last year and repeatedly told us – in part because of the chatter at Exodus – that Trump was running stronger among Black men than he had in 2016 and 2020. He is, again, worried about Musk money late in a campaign. “Any political campaign is essentially an information war,” Jones said. “And any war needs a budget. The guy with the biggest budget tends to win.” And he is worried, again, about Black turnout. “I’ve asked a good amount of people,” Jones told us in an interview at Exodus. “It’s bad when you don’t know the candidates.” Jones was a reliable barometer of his community throughout 2024. Now, in the early days of the new Trump term, he has two takeaways. Jones hears some buyer’s remorse among Latino friends who shifted to Trump and now regret it because of the administration’s crackdown on the undocumented. “They are regretting it now – right now,” Jones said. “But his policies haven’t gotten to the Black community yet.” Many of Jones’ friends, for example, believe the federal government can be cut substantially and yawn when Trump critics complain about installing loyalists at the FBI and Department of Justice. “That doesn’t resonate with them,” Jones said. “Let him do something that affects their day-to-day.” So far, Jones said he sees little to nothing that convinces him Democrats have learned their 2024 lessons. That worries him some in the context of the Supreme Court election. “But it’s kind of unfair,” Jones is quick to add. “Because it just happened to them. I don’t know if anybody can learn a lesson that quickly. … The midterms will be a better chance to see it.” This story has been updated with additional information.