Daring to win

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. Mark PoKempner, courtesy Helen Shiller

Shiller’s work didn’t simply ensure that her ward residents received effective government services. Her stubborn refusal to go along with the budget process is case in point: as a lone dissenting vote against many of Daley’s yearly budgets, she demonstrated through practical action just how little democracy Chicago residents could expect. A 1996 Tribune profile of Shiller described her as the Council’s “nag, its irritant, its prophet,” and one of Daley’s housing advisors, Marilyn Katz, described Shiller as someone “unbending in a city where people bend.”

Year after year, the city’s budget was a central battleground for Shiller’s approach. And her stubbornness worked: by presenting detailed questions about city resources and expenditures to each department, and working closely with lower-level staffers who weren’t subject to dictates from the mayor’s office to shun her, Shiller wrung resources from the city that might not have otherwise flowed into the community.

“The last thing they wanted was me to say anything about them and use their name, either positively or negatively, in front of the City Council,” Shiller says. “That wasn’t the point. The point was to get it done, and to figure out the best way to get the attention of a policy maker who could implement what we wanted.”

Shiller described the work as “bureaucracy busting,” demystifying the political machinery for the disenfranchised and otherwise ensuring that all service requests were addressed within 48 hours, even those made by constituents who did not support her politically. Her office consistently posted resources such as affordable housing waitlists and food drives, continuing the survival-program approach she first embraced when she came to the neighborhood. In this work, she circumvented Mayor Daley’s opposition, even as she knew it could ultimately reflect positively on the city’s executive branch.

“‘I am going to provide services in my ward that otherwise people wouldn’t get,’” she remembers thinking. “‘Guess what: [Daley’s] gonna get as much acknowledgment for having done that as I am, but we’re gonna provide the best service office in the city, in spite of [him].’”

After years of persistent opposition, Shiller endorsed Daley during the 2003 campaign. That political calculus was multifaceted, driven in large part by the mayor offering significant concessions to Shiller in the 1999 and 2000 budgets. As she writes in the book, “Once I endorsed Daley in 2003, the administration treated me just as they treated all of the other aldermen by allowing for aldermanic prerogative, which is essentially local democracy at work.”

Having the mayor’s support proved critical with the development of Wilson Yard, Shiller’s final major project and to this day an emblem of her approach to “development without displacement.” Constructed at the site of a former CTA repair station just south of the Wilson Red Line station that burned down in 1996, the five-acre plot became a fertile source of democratic planning within the neighborhood, initiating a decade-plus process to reimagine the site.

Planning began in July 1998 with a gathering of 250 ward residents at Truman College. It set the model for all future meetings, ensuring that residents of different backgrounds would have to talk with neighbors about competing visions for the project, building up different options that were detailed through hundreds of interviews and thousands of completed surveys. A referendum in the 1999 city elections in 11 neighborhood precincts asked voters if local, state, and federal resources should protect affordable housing in the ward. With 76.5 percent in favor, it suggested the community was ready for an ambitious undertaking.

Wilson Yard is impressive: the project built 178 units of affordable senior and family-sized housing, available to residents making 15 to 60 percent of area median income. With many in the ward opposed to an all-housing approach, the project also included the creation of a multi-floor property with a Target and other ground-floor retail, as well as the opening of an Aldi across the street. Developed using a Tax Increment Financing (TIF) district, a tool that Shiller had previously criticized for funneling resources to well-heeled developers, the project also included new parks for nearby Stewart School and Arai Middle School. Taken together, it reflected the contradictions and hopeful outcomes of working within a broken system, extracting the greatest possible benefit for the most people despite its many flaws.

“Without aldermanic prerogative, we never would have gotten Wilson Yards or any of the affordable housing that I was able to preserve and create in the 46th Ward,” Shiller says. “You can be sure that everything else would have kept going and the market would have taken over.”

Shiller and Harold, 1987With Tim Evans in the 1989 Gay Pride ParadeMeeting Nelson Mandela in 1994

Wilson Yard was a high-water mark for Shiller’s time in office, a parting gift for a community that had changed dramatically since she was first elected. By 2007, Shiller saw the finish line in sight: two decades in office had taken its toll, and she resolved to run one final race before she retired.

“If you don’t eat and breathe this work, you can’t do a good job,” Shiller says. “The ward had changed, and there were still many of the people that were part of my base, but too much of my time was spent on things that were not that important to me.”

The 2007 race saw a challenger who in many ways was Shiller’s antithesis: James Cappleman. By the time he ran for office, he had already served as president of the Uptown Chicago Commission, founded in 1955 to enact urban renewal projects in the neighborhood, including the Truman College redevelopment. Already a vocal opponent of Wilson Yard, which he compared unfavorably to Cabrini-Green, Cappleman revealed a deep frustration with Shiller’s insistent support for the ward’s destitute. As one Chicagoist journalist wrote after a debate between the candidates, “Cappleman makes much of his credentials as a social worker, yet the human component of managing a population that is coping with both mental illness and poverty is strikingly missing from his proposals.”

Cappleman, who declined to be interviewed for this article, could not unseat Shiller in her final campaign for office, taking 47 percent of the vote as her sole challenger. But after defeating tax attorney and fellow Shiller critic Mary Anne “Molly” Phelan in a runoff in 2011, he began to push back against his predecessor’s legacy, encouraging a new approach to development in the ward. After 12 years, a working-class toehold in the community has slipped, driven by increasing rental prices and a surge of high-end development that took its most dramatic form with the creation of the Stewart School Lofts, which transformed a long-standing elementary school into luxury apartments, reflecting the sharp decline in families living nearby. 

Much of this speculation has targeted one of the community’s most common sources of housing affordability: single-room occupancies, or SROs. Uptown has long had some of the greatest concentrations of these properties in the city, allowing long-term residents to stay in place for just a few hundred dollars a month. But it lost more than half of its SROs from 2008 to 2018, according to the Tribune, and has lost even more since then, with the 160-unit Lorali and the Darlington Hotel among the latest conversions. 

As alderperson, Cappleman has had a testy relationship with affordable housing advocates and the precariously housed in his ward. To Marianne Lalonde, a climate scientist and current 46th Ward candidate who came within 25 votes of unseating Cappleman in the 2019 election, his attitude has coarsened neighborly relationships within the community, bolstering the white, upwardly mobile people being drawn to the neighborhood through luxury development that has targeted the area for decades.

“When you set that example from the top down, you’re giving other people permission to act that way,” Lalonde says. “You’re saying that it’s OK for you to be disrespectful to your neighbors, and to me, that’s completely inappropriate. Your neighbors are your neighbors, regardless of income level.”

Lalonde has firsthand experience with the toll of rising rents in the area: when new owners acquired the six-flat she called home in 2020, they spiked her rent by $625 a month, a 35 percent increase. While she had the resources to put a down payment on a condo a few blocks away, she said other neighbors were not so lucky, including a single mom forced to accept an $800 increase so that her daughter could finish her last year of elementary school.

“I wrote to the new management company, and I said, ‘Do you know what you’ve done? Do you know the level of impact they’ve had on our building?’” Lalonde says. 

Gentrification takes place block by block, with the market steadily placing increasing pressure on residents. But it also comes in high-profile actions that signal imagined future changes. These were most recently on display when protestors occupied a parking lot at Weiss Hospital that was slated to have a luxury apartment complex built on the site. While the ward’s zoning advisory committee briefly blocked the project from moving forward, Cappleman’s influence reversed their decision. In August, protesters staged an 11-day occupation of the soon-to-be-redeveloped parking lot, with existing unhoused Uptown residents joined by community organizers. Dubbed Rise Uptown, it joins a long lineage of battles to promote community stability, public health, and affordability in the neighborhood.

At the same time, evidence suggests that gentrification forces are inexorably transforming the core fabric of the area. The 2019 sale of the Bridgeview Bank building, which had offered low-cost office space to nonprofits that served neighborhood residents, to Cedar Street, responsible for numerous SRO conversions in the area, exemplified these trends. Service providers openly discussed moving their bases elsewhere, in recognition that many of the residents they’d served no longer lived in the surrounding area. Paul Siegel, who has organized in the neighborhood over the past half-century, says that it’s been “death by a thousand cuts, and the cuts are getting bigger,” provoking the fighting spirit that remains grounded within the community.

“The two most recent cases are particularly bad and kill two birds with one stone, not only further undermining residential imbalance but threatening a needed community hospital and likely driving human service organizations from the area,” Siegel says. “However, we are not passive victims of this protracted assault, and as a result of our many struggles, Uptown’s multiracial fighting community still exists.”

Regardless of next year’s election outcomes, Uptown will continue to be shaped by the competing forces of gentrification and community resistance. Even as decades of transformation have resulted in the displacement of thousands of working-class residents, the bonds that countless people have formed to one of Chicago’s most inclusive communities are not easily broken, even as their physical presence is often lost.

That’s one of the animating themes of Dis/Placements, an ongoing research project led by UIC professors Anna Guevarra and Gayatri Reddy. Serving as a people’s history of Uptown, the project encompasses reading lists, guided walking tours, timelines, photography, and more, showing the unique imprint that these few square miles have had on the lives of countless people. Guevarra says that she felt the spirit of Uptown captured in Dis/Placements permeated the Rise Uptown occupations, creating a fleeting space beyond ordinary possibilities.

“People gathered to tell stories, share histories, and their dreams and visions for a just world,” Guevarra said. “Uptown has always been a gathering place, a port of entry for displaced communities, immigrants, the working class, and Rise Uptown reminded us of that history.”

As Shiller’s legacy and Cappleman’s tenure have demonstrated, albeit in disparate ways, resident involvement in day-to-day political activity is critical, regardless of political leadership. For Marc Kaplan, who began organizing with Shiller in the 1970s and most recently worked on the Weiss Hospital campaign with Northside Action for Justice, it’s this dedicated cadre of organized residents that is most critical to Uptown’s sustained political identity, not the politics of its officeholders.

“As we learned with 24 years of Helen as alderperson, no matter who’s in office, if you don’t have strong organizations that are pushing people’s power outside of the electoral structure, there are real limitations, even in the best of circumstances, as to what you can get done,” Kaplan says.

The problems that the neighborhood still faces are hardly unique, as Shiller first grasped decades ago. Their continued presence in the daily fabric of the political battles that define our city and many others is a testament to the long-term vision required for deep social change. Mayor Washington warned others that the necessary transformations would not come quickly, saying, “It will take 20 years to have an impact on institutional racism and institutional corruption.” Though Washington was only able to hold power for a fraction of the time he wanted to make these long-lasting changes, that mindset nevertheless stayed with Shiller.

More than a decade after leaving office, Shiller is just as dedicated to the issues that animated her decades of organizing and public service (while also picking up welding as a hobby). Much of her effort after leaving office has been dedicated to supporting the Westside Justice Center, an umbrella group that has housed nonprofit organizations and social justice-oriented legal aid attorneys, founded by Shiller’s son, Brendan. To celebrate the 50th anniversary of the founding of the Illinois chapter of the Black Panther Party in 2017, Shiller opened up her archives to the Center, helping curate an exhibit that’s still up at the Center’s headquarters at California and Harrison. 

For a moment, it also appeared that Shiller would return to City Hall, this time as the City Council’s first-ever independent financial analyst. With years spent poring over the city budget every fall, she considered herself a natural fit for the position, which first appeared in Rahm Emanuel’s 2014 budget recommendations. But by April 2015, Shiller withdrew from consideration, after her appointment became a lightning rod within the Council. 

Ironically, while her role as alderman elevated Shiller to a uniquely powerful position within Uptown’s organizing milieu, it’s the behind-the-scenes work of tending to archives, now stored in several hundred boxes in a multiunit home she shares with her granddaughter, that has allowed the many stories of Uptown as an organized community to endure. Guevarra and Reddy both credit Shiller for the dedication required to keep these materials intact, and are working with Shiller to digitize issues of Keep Strong, a magazine the ISC published from 1975 to 1980. Shiller, in turn, credits the Dis/Placements projects for ensuring Uptown’s history lives on, allowing people to see the ongoing impact within the fabric of the community.

While many have criticized Chicago’s ward model for entrenching the power of localized machine leaders over city resources, Shiller argues that Chicago’s democratic structure is worth salvaging. Its problems, she insists, are driven by Democratic Party power brokers using its spoils to help their friends instead of the everyday residents of Chicago’s 50 wards. Rather than have a chief of staff, her chief of survival set the tone for how her ward office treated its responsibilities: recognizing the ward office’s unique ability to connect government to people’s needs, and getting resources into the hands of residents.

“What came first was making sure that people had some place that they could communicate their needs, which then also informed the things that I needed to impact on the floor of City Council,” Shiller says. “That was an example of taking a structure, which can be good or bad, and putting in revolutionary content.”

In an election season with a near-unprecedented number of vacant seats, and a loss of more than 200 years of legislative experience, concentrated among alderpeople who happily followed this model, Shiller hopes those running will find ways to serve their constituents on an intimate level. While in office, the work was known as “bureaucracy busting,” an outlook that still resonates as Chicago’s government struggles to serve large swathes of its residents. Another approach is rooted in her years as a community organizer, drawn from the Black Panthers: survival pending revolution, borne from an awareness that people’s lives hang in the balance.

A quote from some of her own writing that hangs in a simple frame in Shiller’s home says it all. “We could live respecting our own potential as human beings and work for ‘power to the people,’” it reads, “or we could live and die with the haunting knowledge that we were afraid to respect and believe in ourselves and each other.” 

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