Credit: Maya Dukmasova

Depending on who you talk to, 46th Ward alderman James Cappleman is either a cold, deceitful hater of the poor who’s destroyed much of Uptown’s affordable housing stock or a friendly, responsive neighborhood booster who’s made Uptown a better place to live.

Since Cappleman, 66, was elected in 2011, the 46th Ward has seen massive transformations. High-rise luxury towers have been erected, the Wilson Red Line stop has been revamped; homeless encampments have been cleared, single room occupancy (SRO) buildings—which provided cheap studio living—have been closed. The benches have disappeared from many CTA bus stops, as have the hoops from many public basketball courts. It hasn’t all been the alderman’s doing. Developers and gentrifiers have for decades eyed Uptown, a prime swath of lakefront real estate that has long been one of the north side’s low- to mixed-income neighborhoods with a level of racial integration unheard of in most parts of the city.

For almost a quarter century before Cappleman’s election, the ward was led by Helen Shiller, whose persona was as polarizing as his. She was slammed for being antidevelopment and not tough enough on crime, and lionized for her track record of preserving the neighborhood as a home for the poor. In 2007, after Shiller’s last election, in which she beat Cappleman without a runoff, the Reader‘s Ben Joravsky wrote: “The ward . . . is more or less divided between wealthier lakefront high-rise voters who are alarmed by Shiller’s rhetoric and poorer blacks, whites, and Latinos who rally to it.”

But a curious thing happened in 2015. Though he received kudos for his pigeon deportations and promotion of broken­-windows policing strategies, Cappleman was vulnerable enough to find himself in a runoff after just one term. And the challenge came from the right. Sure, he’d pushed to close SROs and tried to get the Salvation Army to stop serving meals to the homeless, but these moves to “clean up the neighborhood” were apparently not enough. His opponent, corporate lawyer Amy Crawford, ran on basically the same tough-on-crime platform that had helped get him elected after Shiller quit politics. Crawford’s candidacy put anti-Cappleman “Shilleristas” in the tough position of choosing the lesser of two evils. But this time around, all five of Cappleman’s challengers are coming from the left.

Far from being a firebrand retail politician, Cappleman has a soft-spoken manner. He grew up on the Gulf of Mexico, near Houston, and has a silky voice with the slightest twinge of a southern accent. He came to Chicago in the 80s as a friar with the Franciscans—the mendicant Catholic order dedicated to serving the poor. He eventually left monastic life, came out of the closet, forged a career in social work, and opened a homeless shelter for men dying of AIDS. He described himself at the time as a “pretty far-left-wing feminist,” and came to know Uptown first as a case manager with what is now Heartland Alliance. In 1999, Cappleman and his husband, Richard Thale, a court advocate for the 19th police district, settled in the neighborhood.

James Cappleman
James CapplemanCredit: Maya Dukmasova

Cappleman’s critics scoff at the frequent invocation of his monk-turned-social worker biography, but he seemed earnest enough as he spoke to the Reader about the formative years of his life. Cappleman says he was galvanized to get more involved in the community in 2001 after witnessing street violence and mismanagement at a Chicago Housing Authority-subsidized building in his neighborhood. One day he showed up to a neighborhood peace walk and put public pressure on Shiller and the CHA to evict a gang leader illegally living in one of the units. He got results.

“That was my first moment where it clicked on me that this works,” he said. “Negotiations, going back and forth. And I liked it.” The experience got him thinking about running for office. He became increasingly critical of Shiller and Uptown’s social service agencies, some of which, he says, weren’t using “evidence-based best practices” to help the neighborhood’s struggling residents “become stabilized.”

When asked about past positions—like why, in 2004, he opposed the residential portion of Wilson Yards being entirely affordable housing—Capplemen says he sides with what experts recommend. Later, he leaned on the same argument when pressed by the Reader on his removal of basketball hoops at an Uptown park a few months into his term. He touted it as a crime-fighting measure: “If you can show me research showing a benefit from basketball in an unsupervised setting where gang recruitment is going on, I’ll reconsider,” he told us.

As we got deeper into a discussion of his record, Cappleman’s warm, reflective demeanor disappeared and something hardened in his eyes. He leaned forward in his chair and became increasingly defensive about his history of supporting Uptown’s poor.

“There was a lawsuit filed about the viaduct, that people had to leave,” he said, referring to the last big showdown between the city and Uptown’s homeless, when the Lawrence and Wilson viaducts needed to be repaired and the sidewalks narrowed to make way for new bike paths. “There was a federal judge that ordered them to leave. And they criticized me because I wouldn’t tell the police to ignore a federal court order.”

But there’s another version of that story going around. After our interview ended I shuffled two blocks south on Sheridan to the Uptown People’s Law Center, which had filed the lawsuit against the city that ended with that court order. There I found attorney Alan Mills, Uptown resident and homeless advocate since the late 1970s, who was on his way to lunch in a black “Outlaw poverty, not prostitution” hoodie. “The only reason we went to federal court is because [the city was] forcing them to move,” he told me, rolling his eyes. In his recollection, Cappleman wasn’t trying to stop the displacement.

Other claims the alderman made were equally suspect. Like that he’d mounted a serious effort to try to keep Lawrence House—a crumbling SRO that was tied up in bankruptcy court and was eventually bought and redeveloped by the Flats real estate group into a hip microapartment building with a coffee shop and a bar on the ground floor—as affordable housing. Kate Walz, an attorney from the Sargent Shriver National Center on Poverty Law who represented Lawrence House tenants in their fight against imminent building closure without a relocation plan, burst out laughing when I relayed Cappleman’s version of events. “He was fully supportive of Flats coming in. He was coming to court and speaking to the need for the property to be vacated,” she said. “He appeared, from statements he made in court, intent on having the building closed, and largely unsympathetic to [tenants’] needs and concerns.”

Cappleman had told me he’d brought nearly two dozen Low Income Housing Trust Fund units into the community, voted to protect SROs in 2014, and that, despite the fact that there’s more subsidized housing in Uptown than anywhere else in the city, he wants more. The ONE People’s Campaign however, a political 501(c)(4) offshoot of the nonprofit ONE Northside community organization, couldn’t corroborate. Staff, whose sympathies lie with the ward’s have-nots, eagerly showed me spreadsheets tracking the number of SRO units lost (803, with 200 more on the chopping block) and upscale rental units created (1,265, including 64 at the shuttered Stewart Elementary) on Cappleman’s watch. They’d also found that “interested parties” connected to these developments had donated more than $56,000 to Cappleman in his second term alone.

None of this has been lost on Cappleman’s challengers, who’ve all been accusing the alderman of hypocrisy and running on a promise to make Uptown something other than a developer’s playground. If you think that an anti-gentrification platform will alienate the ward’s “wealthier lakefront high-rise voters,” perhaps not in 2019: a majority of every precinct in the ward voted in favor of lifting the state ban on rent control last November.

Just a couple of doors down from Cappleman’s campaign office, Erika Wozniak Francis, 36, is organizing a run lubricated by union support and her minor celebrity as a cohost of The Girl Talk live show at the Hideout. A fifth-grade teacher at a northwest-
side elementary school and a frequent critic of the city’s TIF deals, Wozniak Francis has out-fundraised the other challengers and is supported by Congressman Jesus “Chuy” Garcia, David Orr, and other progressives.

Erika Wozniak Francis
Erika Wozniak FrancisCredit: Maya Dukmasova

She’s even earned the endorsement of the National Association of Social Workers’ Illinois chapter—which Cappleman once belonged to. The group is now distancing itself from the alderman. “We reject James Cappleman’s efforts to displace the economically disadvantaged under the ruse of social work best practices,” it wrote in a statement released last week.

Wozniak Francis, who speaks in a breathy tone punctuated by expressions of intense enthusiasm and wide-eyed empathy, was thrilled to have the support. If elected, she promises to require developers to keep 30 percent of units in new ward buildings affordable on-site. She also wants to improve neighborhood schools. “Uplift [Community High School] under CPS terms is considered underutilized, which drives me crazy,” she said. “Seventeen kids in a class is actually a really great class size.”

She (like all the other candidates running against Cappleman) also vows to join citywide efforts to create an elected school board, reopen mental health clinics, bring back community policing, lift the state ban on rent control, and pursue ethics reforms for the City Council.

A few blocks north on Sheridan Road, Marianne Lalonde, 32, has her campaign headquarters in the Institute of Cultural Affairs, where giant maps of proposed changes to the Wilson Avenue off-ramps to Lake Shore Drive hang on the walls. A sign in the window reads: “Science Against The Machine!”—Lalonde has a PhD in chemistry from Northwestern. She also worked as a legislative aide for Ohio Democratic senator Sherrod Brown. Her campaign, largely funded by a network of family and friends, has received an endorsement from mayoral candidate Lori Lightfoot.

Lalonde seems to have a hard time smiling, although she’s got an encyclopedic knowledge of granular issues in the ward. She’s involved in a long list of local organizations: a block club, a local park board, the women’s shelter Sarah’s Circle. “It was through my involvement that I started to understand that our alderman’s office wasn’t hearing everyone’s voice equally,” she said.

Marianne Lalonde
Marianne LalondeCredit: Maya Dukmasova

Lalonde slammed Cappleman for taking money from developers seeking zoning changes (his self-imposed rule—that he won’t take donations within a year of a developer receiving requested changes—doesn’t impress her) and from Ed Burke; for voting to divert $15.8 million in TIF funds toward a luxury high-rise when an aging community center needed renovations; for his support of a Lake Shore Drive project that would cut Weiss Memorial Hospital off from easy access to the thoroughfare. She wants to see a community benefits agreement created for the rehab of the Uptown Theatre. She also thinks the City Council needs a scientist. “Scientists are naturally objective,” she said coolly. “They’re detail oriented in their decision­-making, they look at data critically, and they’re BS filters.”

The two men in the race display less local expertise and have far less money in their campaign funds than Wozniak Francis and Lalonde. But they’re equally frustrated with Cappleman and want to make the 46th Ward a kinder and gentler place.

Justin Kreindler, 38, lives in the East Lakeview part of the ward. He’s the only candidate with kids, and his campaign platform comes down to “housing, education, and a peaceful community,” he said. He wants to push developers to build more three-bedroom apartments to accommodate families, to launch a PR campaign to make local schools more attractive, and to stop throwing armed cops at every problem rooted in poverty.

Kreindler says he was inspired to run by watching Cappleman “bash” the community during his 2015 campaign. “It baffled me why someone who disliked their community so much would want to run to be alderman.”

Kreindler, who works with the youth leadership nonprofit Public Allies, is measured—and honest if he doesn’t know the answer to a question. He has the soothing manner of a guy who probably doesn’t mind changing diapers and likely wears Tevas in the summer. He’s also campaigning to make sure East Lakeview—where a third of the ward’s residents live—isn’t an afterthought.

Meanwhile, Buena Park-based Jon-Robert McDowell, 37, is deeply concerned about the city’s pension debt ruining any chances the 46th Ward might have to remain affordable. “You have to deal with financial mismanagement we have in the city to get resources to people in Uptown,” he says.

A few years back McDowell had to drop out of a graduate program to work and help pay for the medical care of a brother who’d been diagnosed with Crohn’s disease and was dropped by his insurance. He packed up his mom and the rest of their siblings and moved from New York to Chicago, where they could afford to all live together. McDowell traded dreams of writing political commentary for working on campaigns, and now holds a job at a digital marketing firm. He’s confident enough to crack jokes when talking to voters, but of all the candidates he seems the least sure about his prospects of winning. He says it’s tough to compete with Cappleman, who sent him six mailers in three days just last week—clearly something the alderman can afford due to his connections to big money. “I can’t see any reason why I wouldn’t vote for whoever that other person was in a runoff,” McDowell says.

If he’s subconsciously pessimistic about his chances at the ballot box, he’s got good reason to be. The 46th Ward has a history of electoral skepticism toward newcomers, and all of these challengers have lived in the ward for less than than five years. Perhaps the person best poised to recapture the energy and votes that propelled Shiller is 27-year-old Angela Clay.

With a warm manner and familiar style that means hugs on the second meeting, Clay makes you feel like you’re the only one in the room when you’re talking. She’s the only black candidate, and would be the ward’s first black alderman. Though she’s lost friends to gun violence and knows about the grinding poverty some of her neighbors experience, she doesn’t talk about the Uptown of the past as the bad old days, like Cappleman does. Instead, she waxes lovingly about the neighborliness that helped people thrive.

Angela Clay
Angela ClayCredit: Maya Dukmasova

Clay’s family has an 80-year history in Uptown, and she grew up in a subsidized housing building on the corner of Hazel and Sunnyside, where she lived with her mother and grandmother. She attended all the neighborhood schools. She remembers the neighborhood as “buzzing” during her childhood. “All of us are interconnected because we were a part of the same struggles.”

Clay has served as the president of Voice of the People in Uptown, the nonprofit affordable housing developer behind the building she grew up in, but currently works in HR at a bank. Watching the neighborhood get less affordable and youth resources dry up, and not seeing Cappleman fight like Shiller used to, motivated Clay to run. She says the alderman too often claims problems are out of his hands. She doesn’t blame Cappleman for gentrification, however, but for not doing enough to ease its blow on lower-income residents. She says that just because drug dealing isn’t as prevalent on the streets doesn’t mean it’s not happening—or that its root causes aren’t still there.

Her campaign has almost no money, and she organizes her volunteers out of Everybody’s Coffee on Wilson, a cafe that touts itself as the place that filters “coffee, not people.” But, she says, she’s built a coalition she’s confident will turn out to vote when they see a candidate they can relate to.

If Clay or any one of the other challengers manages to get to a runoff, it seems likely the bases of the others will fall in line to help that candidate oust the incumbent. And between the five of them, they collected 2,000 more signatures on their nominating petitions than Cappleman.

The alderman, meanwhile, is still leaning on his tough-on-crime message and insisting he’s been the champion that both the ward’s business leaders and its poor need. When I asked if he’d thought about what he’ll do if he loses, Cappleman seemed baffled. He enumerated all the new improvements in the ward, and listed more to come, what with the Baton and Double Door moving in, and the long-awaited renovation of the Uptown Theatre looming at last.

“What do you think the odds are of me losing right now?” he asked. “I’ve been in tough elections. In 2011 there were 11 of us in this race. 2015 was a tough race. And 2019—I would not want to run against me.”  v