Milwaukee Has Elected Two Socialists, Reviving the City’s Pro-Worker Political Tradition

Milwaukee is sending two socialists to the state legislature for the first time in over 80 years. It’s the fruit of an impressive canvassing operation — and it marks the revival of working-class politics in Milwaukee, once a bastion of socialism.

With the elections of Ryan Clancy and Darrin Madison, Milwaukee will send two socialists to the state legislature for the first time in decades. (Darrin Madison for State Assembly website / Ryan Clancy's website)

It is a warm August night, and the sidewalk in front of Art Bar — tucked away in Milwaukee’s tree-lined Riverwest neighborhood — is crowded with young socialists radiating nervous energy. After nearly two months of canvassing thousands of doors, they are waiting to see whether history will be made.

On the ballot in today’s August 9 primary is Darrin Madison, a twenty-five-year-old community organizer who, if elected, will be the first black socialist to serve in the Wisconsin State Assembly. If he wins, he will also join County Supervisor Ryan Clancy — running unopposed in the 19th District — to become the first socialists the Wisconsin State Assembly has seen in over eighty years.

Some in the crowd are not simply milling about, but pacing apprehensively in between sips of ginger old fashioneds (which someone has deemed tonight’s “lucky” cocktail). The polls begin to close and — via the county clerk’s glitchy Facebook feed — the wards slowly report their results. Madison leads, but Bryan Kennedy — who is the mayor of Glendale, a northern suburb added to the 10th District this year, and who has outspent Madison seven to one — appears close behind. For an hour or so, there is more tension, more pacing; every few minutes, the latest numbers are announced over a portable PA system.

Finally, as the last wards trickle in around 10 PM, the outcome becomes clear: Madison has won with a resounding 58 percent of the vote.

This victory, which comes five years after the refounding of the city’s Democratic Socialists of America (DSA) chapter and more than half a century after the last “Sewer Socialist” left office, is emblematic of Milwaukee socialists’ struggle to build an independent base of working-class power in political terrain that is tilted in favor of a powerful few.

Sewer Socialism, Redux

To find the lineage of Milwaukee socialism, you only need to look at the infrastructure that defines everyday life here.

Parks and bridges are not simply named after socialists, socialists were instrumental in their construction. Milwaukee County’s extensive system of parks and beaches was the product of visionary socialist city planner Charles Whitnall. Socialist mayoral administrations ushered in the eight-hour workday, created Milwaukee’s first public higher-education institutions, and vastly expanded the quality and extent of city services, from streetlights and sewerage to libraries and museums.

Yet Milwaukee’s built environment also offers potent reminders of how the political power of the working class was contained and compromised in the latter half of the twentieth century. The city’s freeways — first planned by the County Expressway Commission in the 1950s — displaced tens of thousands of residents, leveling black working-class neighborhoods. In the process, numerous local cultural institutions were wiped out, from Sicilian churches in the Third Ward to the Walnut Street corridor that housed the black commercial district to the socialist epicenter of Brisbane Hall, home to the long-running Milwaukee Leader newspaper.

By the time those freeways were built, Milwaukee socialism had already been undergoing a slow decline. Beginning with the New Deal, and with increasing intensity during the early Cold War years, Wisconsin’s political system realigned from a multiparty democracy into a duopoly. Following a decade of policy success in the 1920s, Milwaukee socialists in the state legislature gradually began running on the Progressive Party’s ballot line as part of a fusionist strategy. Yet with Democrats’ growing dominance, alternatives to the two major parties began to disappear.

As his political support structure decayed, Frank Zeidler, Milwaukee’s last socialist mayor, found himself increasingly politically isolated. The 1948 mayoral election, which Zeidler ultimately won, was dominated by a campaign of red-baiting that only intensified when his administration approved racially integrated housing projects on Milwaukee’s all-white west side. Zeidler’s final election to office in 1956 found him battling a racist smear campaign and a Common Council dominated by allies of the Wisconsin Property Owners’ Association, which vigorously opposed public housing.

Milwaukee Socialists in State and Local Office, 1905–1959; source: Authors’ analysis of data drawn from Jack Ross, The Socialist Party of America: A Complete History (University of Nebraska Press, 2015)

The election of Zeidler’s successor, Democrat Henry A. Maier, marked a turning point. Maier’s virulent opposition to fair-housing proposals authored by Vel Phillips, the city’s first black alderwoman, fueled a wave of protest that would define the city’s politics in the late 1960s. Maier leveraged his confrontations with black leaders to consolidate support among both the city’s business elites and white working-class voters. Meanwhile, deindustrialization pummeled the city, driving down unionization rates and creating the racial and economic inequalities that still plague Milwaukee today. Working-class African Americans, most of whom had arrived during and after World War II, were hit the hardest.

The desperation and resentment produced by this process animated state and local politics throughout the 1980s and 1990s. In 1986, Republican Tommy Thompson won his first of four straight gubernatorial contests by stirring up rural and suburban anger at taxes and social welfare spending, while Democrats abandoned pro-worker rhetoric in favor of a lifestyle-based appeal to the white middle class. Elected in 1988, Milwaukee mayor John Norquist sought to draw professionals back to the city through a set of “new urbanist” investments in walkable neighborhoods and entertainment districts that didn’t even gesture at working-class voters.

Deprived of the tax base and state-level aid needed to address its increasing social ills, the city continued to shed population and wealth throughout Norquist’s mayoralty and that of his successor, Tom Barrett. The 2008 financial crisis dealt still another blow, setting off a firestorm of foreclosures.

The deterioration of working-class politics, the immiseration of the urban poor, and the middle-class anxiety produced by the housing crisis created the opportunity for the antidemocratic pirate regime of Governor Scott Walker. Elected in the 2010 Tea Party wave, Walker used his victory in to remake state politics. His signature piece of legislation, Act 10, destroyed the power of public sector unions, his redistricting plan ensured a permanent conservative majority in an otherwise evenly divided state, and his economic development policy provided a no-strings-attached slush fund for corporate interests.

The legacy of the neoliberal era in Milwaukee is a familiar one, just in more vibrant hues: racialized poverty, rural and suburban resentment, the foreclosure of working-class politics, an eroded democracy. Wisconsin, once a progressive bastion, has become a desolate landscape for the Left. And that’s why the coalition Darrin Madison managed to construct is so striking.

Ryan Clancy and Darrin Madison at the Wisconsin State Capitol.

While the August 9 primary was Madison’s first bid for state-level office in Wisconsin, he is by no means a newcomer to Milwaukee politics. In 2021, he ran a strong race for county supervisor, losing in the general election by only twelve votes. His involvement in political struggle goes back further still. By the time he turned fifteen, Madison had already been mobilized by the fight over Act 10, which decimated finances for public schools, leading to an exodus of educators and a significant decline in school quality throughout the state. Not long after the Act 10 protests, Madison joined Urban Underground, a youth-led social justice organization, as a community organizer.

A critical figure in Madison’s political development has been David Bowen, who has represented Assembly District 10 since 2014 and, notably, was the only Wisconsin DNC superdelegate to endorse Bernie Sanders in his 2016 presidential run.

When Bowen first ran for the Milwaukee County Board in 2012 — becoming the youngest county supervisor and one of the youngest black elected officials in the city’s history — Madison took notice not only of the vast array of county services, but the structural limits on local government in Wisconsin. It soon became clear that the state was choking local governments’ access to revenues while preempting cities and counties from imposing meaningful workplace and housing regulations.

“What happens at the local level — especially when it comes to the ability of the working class to lead a decent life — really hinges on the work of the state,” as Madison puts it.

In turn, Madison’s platform proposed leveraging state resources to strengthen the quality of local services — reversing the retrenchment of state aid to education, supporting public housing and transportation, and legalizing the sale of marijuana to finance schools and workforce development programs.

But to advance these ideas at the state level, Madison would first have to build a winning coalition in District 10.

Organizing Across City Limits

The boundaries of Milwaukee politics are a series of doors pretending to be walls.

With the decline of local party organizations and the implosion of organized labor, mass participation in Milwaukee politics experienced a long, slow decline beginning in the 1970s. Today, organizations attempting to mobilize working-class voters face great odds and must labor across a deep set of political trenches: the city tends to top the list of most segregated metropolitan areas in the United States, and its revenue and regulatory authority have been increasingly hijacked by a gerrymandered state legislature.

If these conditions can create a sense of despair, they have also opened up an important set of coalitional opportunities for Milwaukee socialists. Over the last two years, Milwaukee DSA has helped elect two socialists to the County Board: Ryan Clancy (in 2020) and Juan Miguel Martinez (in 2022). Clancy’s reputation and organizational capacity has evidently made him difficult to beat. In 2022, he ran unopposed in elections for both County Supervisor and State Assembly District 19. This is particularly surprising, given that Clancy’s district tends to attract among the highest levels of fundraising and voter turnout in the state.

Yet, perhaps better than any other election, Darrin Madison’s State Assembly race illustrates how socialists have organized across the Milwaukee metro’s stark racial and economic divides.

Assembly District 10 is composed of three distinctive clusters. First, the district includes several black working-class neighborhoods on Milwaukee’s north side. To the east and bordering the University of Wisconsin Milwaukee campus, there is Shorewood, a village with a majority white population, progressive political leanings, and a median income nearly double that of Milwaukee’s. Finally, as the result of 2020 redistricting, the 10th now includes the northern suburb of Glendale — also wealthier and majority white — whose mayor was Madison’s opponent. The newly drawn district, as Madison put it, “was designed to keep people of color and leftists out of office.”

Seen from one angle, this was one of the most challenging races Milwaukee socialists have run in recent years. Kennedy not only held elected office, he outspent Madison seven-to-one, according to state campaign finance reports. (The average individual contribution for Kennedy was $475, compared to $48 for Madison.) The primary in District 10 also received little media attention. With less than a week to go before the election, only one story on the race had been printed in the Milwaukee Journal Sentinel (the print edition of the article conveniently left out Madison’s numerous endorsements). Local voter guides focused almost exclusively on statewide races, ignoring assembly contests entirely. The Shepherd Express — an alt-weekly turned less-than-alt-monthly — made no endorsement in District 10.

Wisconsin State Assembly District 10, following 2020 redistricting cycle.

On the other hand, Madison had a few political and organizational advantages, including support from the two prior District 10 representatives (including his mentor, David Bowen), several additional members of the Wisconsin state legislature, and eventually Milwaukee’s Democratic congresswoman, Gwen Moore. Even before announcing his candidacy, it was clear that Madison would garner the endorsement of the Milwaukee DSA chapter, which had supported his 2021 run for County Supervisor. By mid-June, the chapter’s Electoral Working Group had come to be a primary source of mobilization capacity; by the end of the campaign, over sixty volunteer canvassers had reached out to over eighty-seven hundred voters, roughly a quarter of those registered in the district.

The canvassing efforts paid off in two ways. First, canvassing helped consolidate and mobilize the vote in black working-class neighborhoods, where turnout rates in primaries are roughly half of those in Shorewood and Glendale. A look at the two graphs below illustrates the strength of Madison’s performance in majority-black wards with traditionally lower levels of voter turnout.

Ward-Level Race and Madison Vote Share.
Ward-Level Turnout and Madison Vote Share.

There is evidence that canvassing helped mobilize these voters. Milwaukeeans accounted for nearly half of the yard signs distributed by Madison’s campaign. And while 62 percent of Milwaukeeans canvassed by DSA volunteers either supported or leaned toward Madison, he won 72 percent of Milwaukeeans’ votes, claiming a supermajority in each ward.

A relevant message, an ability to speak to the concerns of black working-class voters, and support from key local political leaders clearly aided Madison in Milwaukee wards. Yet given his fundraising deficit, limited media coverage attention to District 10, it is unclear how residents would have received information about his campaign if not for the DSA-driven canvassing effort.

Darrin Madison Ward-Level Vote Share.

Second, canvassing efforts also tapped into the base of left-leaning voters in the high-turnout Shorewood. In this densely packed progressive village, Madison provided a message that resonated, focusing on — among other things — fixing the state’s defunct education equalization formula. By contrast, Kennedy’s campaign relied on bromides about the need to compromise and work with both sides of the aisle — messages that seemed increasingly incongruous with state Republicans’ legacy of undermining electoral democracy and obstructing popular reforms. The campaign also appeared to lack the organizational infrastructure to defend this message to voters one-on-one.

DSA canvassing data helps illustrates the scale of its own persuasion campaign. At their doors, 52 percent of canvassed Shorewood voters supported Madison, while 39 percent were undecided. In the end, however, Madison claimed 61 percent of Shorewood’s votes — a figure that helped put him over the top on August 9.

Clinching Shorewood and Milwaukee gave Madison the victory. What made that victory even more decisive, however, were canvassing efforts in Kennedy’s hometown of Glendale, where Madison won 41 percent of the vote — far more than anyone involved with the campaign anticipated.

In District 10, the city limits proved to be lines on paper. At the street level, there were simply doors waiting to be knocked.

Elected Socialists in a Democracy Desert

With the elections of Ryan Clancy and Darrin Madison, Milwaukee will send two socialists to the state legislature for the first time in decades. The question, however, is how socialist elected officials can use their positions to build an enduring working-class coalition.

Madison and Clancy should have no illusions about their ability to drive policy in the Wisconsin Assembly. An April decision by the Wisconsin Supreme Court forced the use of Republican-drawn state legislative maps that will guarantee continued GOP control of both houses, giving conservatives a significant shot at a veto-proof majority. With rigged rules, Democrats — let alone socialists — will play little direct role in formulating policy.

Clancy and Madison will have to play a different game.

Legislatures, as the political scientist David Mayhew suggests, are not simply the site of lawmaking — they are public spheres that allow for a wider array of political actions to unfold. Elected socialists can use their offices to organize and mobilize working-class voters. Despite ample evidence of discontent, state Democrats have largely confined their political work to the statehouse. With formal avenues of political work eliminated, opponents of the minoritarian Republican regime have no real option other than to galvanize popular resistance to the GOP’s blatantly pro-corporate agenda.

Recent political developments in Milwaukee may highlight a path forward. In the last two years, Milwaukee DSA has mobilized members and other supporters to testify and agitate in support of socialist County Board Supervisors Ryan Clancy and Juan Miguel Martinez, as well as organized political pressure campaigns in support of teachers unions and a coffee shop unionization drive.

Even with only two members on an eighteen-person board, DSA-affiliated supervisors have already spearheaded several legislative initiatives including winning “right to shelter” and “right to counsel” for Milwaukee County tenants, moving $2.4 million from the sheriff’s office budget into infrastructure and human needs spending, and improving life for prisoners in the county jail by capping commissary prices and providing free video calls for remote visitation.

Recent political upheavals around the murder of George Floyd, the school shooting in Uvalde, and the overturning of Roe v. Wade have shown the Democratic Party to be unable or unwilling to catalyze popular political action into meaningful legislative achievements. Unlike their Democratic Party colleagues, Madison and Clancy may be able to directly coordinate their legislative activities with a cadre of committed and organized activists throughout southeastern Wisconsin. A close relationship with local chapters could allow them to mobilize popular action in support of policy and will directly connect Madison and Clancy to popular movements as they emerge on the ground.

Second, Madison and Clancy now have the opportunity to build a statewide socialist platform and generate capacity across Wisconsin’s geographical divides. DSA currently has five chapters in Wisconsin, but its reach remains largely confined to urban areas. Nevertheless, the systematic looting of the state by a minoritarian conservative government has produced broadly shared grievances that could be the foundation of socialist organizing. Agribusiness is poisoning residents and pricing out small farmers, the Wisconsin Economic Development Commission has failed to hold grantees accountable for their use of state tax dollars, and towns and cities throughout the state face shortages in teachers and affordable housing. Using their statewide platform, Madison and Clancy could open doors for socialist organizers by taking up issues with statewide salience and engaging with local activists in ways the Democratic Party does not.

A hypothetical might show the potential of this strategy. Currently, approximately 8 percent of Wisconsinites are employed in the tourist industry. Many are in the Milwaukee area, but many others reside in rural Northern Wisconsin. Most jobs in this industry are precarious, low-wage, and have little or no health care benefits. Further, many tourism workers are immigrants on short-term work visas, making them exceedingly vulnerable to hyper-exploitation and abuse. Yet most statewide tourist policies focus exclusively on marketing and economic development projects. A concerted effort to instead focus on wages and unionization would not only benefit Milwaukee workers, but also provide socialist organizers in more conservative areas of the state with a basis for building chapters and pressure groups.

Finally, the election of Madison and Clancy offers a unique opportunity for DSA chapters to develop a closer relationship with unions. The powerlessness of the state-level Democratic Party means that labor has little to lose in backing socialist organizations, but this is only likely if socialists prove useful. Madison and Clancy might be able to use relationships with labor leadership at the state level to guide local activists in such activities as worker outreach, community education, strike support, and salting. There is no path forward for socialists without a vibrant labor movement, and that requires work within unions to ensure workers control the organizations and can move them toward a more thoroughgoing confrontation with capital.

Socialists no doubt face tremendous odds in states like Wisconsin, where the reality of democratic decline can feel impenetrable.

But on a warm August night last week, the sidewalk in front of Art Bar was humming with radical energy.

“Folks didn’t believe a rose could grow out of concrete,” Madison told the crowd in his victory speech, “but it did.”