Daring to winAnnie Howardon November 23, 2022 at 4:53 pm

Helen Shiller insists that the story of Uptown is not unique. After more than 50 years living in the neighborhood, it’s hard to disagree with her. In many ways, the most pressing concerns that Shiller first identified when she moved to the neighborhood in 1972 still haunt the wider city, and America as a whole: conflicts with police, a lack of adequate housing, and a deep-seated disconnect between the desires of working-class people and the politicians who represent them. In many cases, they’ve worsened.

But the story of Uptown is irreducible, and among Chicago neighborhoods, its history stands apart in many ways. Where gentrification crept north along the lake from the Gold Coast through Lincoln Park and Lakeview, Uptown’s lakefront today remains dotted by affordable high-rise apartments: buildings that could have easily become market-rate but didn’t, thanks to community organizing. Elsewhere in the neighborhood, countless institutions and even single apartment buildings testify to many different populations who fought hard to stay in place. 

Their identities are many: poor white families who migrated from abandoned Appalachian coal towns; Native Americans shoved in droves to cities due to federal resettlement legislation; scores of Southeast Asian families, displaced by American militarism in countries like Vietnam and Cambodia; people displaced from shuttered psychiatric clinics. There are countless others. No matter their specific identities, a common thread has united many who have called Uptown home: hardship. 

 Shiller first arrived in the community in 1972, called to move to the city from Racine, Wisconsin, by the Intercommunal Survival Committee (ISC), a cadre of about two dozen young, white organizers working under the guidance of the Black Panther Party (BPP). For the next 15 years, Shiller was a lively, committed community organizer who focused on the basic survival needs of the neighborhood’s most destitute residents. She lost a closely contested run for alderman in 1979. Eight years later, Harold Washington called upon Shiller to run again; she won, helping tip the balance of the City Council in Washington’s favor during his second term. Shiller remained in office for six terms before finally retiring in 2011.

Now, with the release of Daring to Struggle, Daring to Win: Five Decades of Resistance in Chicago’s Uptown Community (the title drawn from Illinois BPP chairman Fred Hampton’s call to action), Shiller looks back on her decades in service to Uptown, Chicago, and beyond. Shiller’s fundamental goal for the 46th Ward was to encourage development without displacing the ward’s low-income residents. Much of that approach has been swept aside under the past 12 years of Alderperson James Cappleman, who was a vehement Shiller critic for years before he took office.  

With Cappleman’s retirement ensuring that the ward will once more change hands, the question remains: will Cappleman’s pro-development approach, typified in the ongoing struggle around Weiss Hospital, endure? Or will progressive challengers reanimate the spirit of community activism that propelled Shiller’s work in Uptown? 

By the time Shiller won her aldermanic campaign in 1987, Chicago’s progressives were increasingly optimistic. After the narrow, bruising, racist vitriol that he faced in his 1983 election, followed by three years of “Council Wars” in which white, machine Democrats blocked much of his legislation, Mayor Harold Washington entered his reelection campaign that year on surer footing, boosted by a court-mandated ward remapping in 1986 that enabled the election of Hispanic progressives such as Jesús “Chuy” García and Luis Gutiérrez.

Daring to Struggle, Daring to Win: Five Decades of Resistance in Chicago’s Uptown Community. Haymarket Books, 11/2022

Following those elections, which drew the deadlocked council into a draw between its dueling factions, Washington called upon Shiller to run for office. Their twin victories in 1987 heralded a new opportunity to advance the issues that mattered to them both. Many of those issues had been what drove Shiller to move to Chicago in the first place.

But the electoral victories of Washington and his allies did not come out of thin air. It took more than a decade’s worth of patient, often violent struggle to create the necessary conditions for these victories, rooted in the Sisyphean challenge of overcoming Chicago’s existing political machinery.

When Shiller first landed in Chicago with the ISC, Uptown was home to an eclectic mix of residents. The neighborhood was a site of deep trauma worsened by unscrupulous landlords who were prone to torch occupied apartments after years of leaving them neglected. Fires raged through the community during the 1970s, with one occurring an average of every three days, leaving residents to sudden, violent dispossession of homes that already threatened their well-being. 

Among the neighborhood’s downtrodden residents, the interrelated consequences of poverty and other kinds of marginalization resulted in poor health outcomes. This reality hit Shiller in the mid-70s. While she was selling copies of the BPP’s newspaper, she happened upon a woman who she’d attended college with in the 1960s. Released from a nursing home for the mentally ill, the woman was wandering the neighborhood streets, lacking any of the critical support she needed.

“There were so many people in Uptown that needed services that were just being completely denied, and they were all mixed up together,” Shiller says. “People treated them all the same way regardless, so that nobody was having their needs met, and everybody was being manipulated by the machine.”

Intercommunal Survival Committee members sell the Black Panther Party newspaper in Uptown in the 1970s. Courtesy Helen Shiller

Progressives launched their first major salvo against the 46th Ward machine in 1975, when José “Cha Cha” Jiménez, who had transformed the Young Lords from a street gang to a political organization, ran for alderman. With much of the Puerto Rican community pushed out of Lincoln Park into Lakeview and Uptown, Jiménez sought to unseat Chris Cohen. Jiménez garnered 27 percent of the vote, with his strongest support in Uptown. Despite the loss, his campaign laid the groundwork for the next few years, as a whirlwind of political activity shook up the City Council.

After winning his sixth election in 1975, Mayor Richard J. Daley passed away in December 1976. His replacement, Michael Bilandic, went on to defeat then-state senator Harold Washington in a 1977 special election. Then, just a year later, the 46th Ward would have its own special election, Shiller’s first, in which she took 35 percent of the vote, losing to ward secretary Ralph Axelrod. Both campaigns drew support from the Heart of Uptown Coalition, a block club coalition that served as the key uniting force in organizing a 12-block radius around Truman College.

Finally, in 1979, Shiller came within a hair of defeating the machine. Building on the 1978 effort, Shiller’s campaign message, “Independent Is Not Enough,” served as a critique of mayoral candidate Jane Byrne, who positioned herself as an outsider despite years of service under Daley. The campaign was marred by brutal opposition: Shiller’s volunteers were beaten up, racist graffiti defaced her campaign ads, and a Molotov cocktail destroyed her campaign office. Despite the violence, Shiller made it to a runoff, and appeared to have victory in hand in the election’s waning moments.

In the closing moments of election night, however, spurious word-of-mouth attacks suggesting that Shiller supported the Palestinian Liberation Organization made their way to Imperial Towers, two high-rise lakefront buildings with significant numbers of elderly Jewish residents. Shiller, whose Jewish ancestors had emigrated to Palestine in the 1920s, saw her victory disappear overnight, undone by powerful machine forces that barely kept her at bay, ultimately losing the runoff by 247 votes. 

“Don’t give me a label and then decide what I think, unless you’re actually able to understand where I’m coming from,” Shiller says, regarding the smear. “It wasn’t like I didn’t expect it, but it was what I always hated about politics.”

The next eight years were politically momentous, both locally and beyond. While Washington’s 1983 election suggested a wave of political progressivism within the city, the wider context looked quite different: with the 1980 election of Ronald Reagan, federal assistance to cities dwindled drastically, and by the time Washington died in 1987, Chicago had lost $100 million in annual Community Development Block Grant funding. These right-wing forces continued to dominate the larger context for Shiller’s work in office, and following Washington’s death in 1987, the fledgling coalition that put Washington into office would also dissolve amid the ascendancy of another Mayor Daley.

Then-alderman Dorothy Tillman and Helen Shiller file ballot petitions in the 1987 campaign.

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