For a Bright Orange Tent: How one practical survival item caused the rise and fall of Chicago’s Tent City

By Sydney Boles

The first time Sean Brown slept in a puddle of water, he was a 15-year-old gay boy hiding in a ravine to escape a conservative family. The second time, he was a 44-year-old man in a bright orange tent, homeless for the second time in his life, evicted from the safety of a viaduct he called home.

Before it was disbanded, Uptown Tent City was a ramshackle but orderly community of uniform orange tents clustered beneath two bridges under a major thoroughfare. Some people came and went; others stayed for months or even years. The Lawrence viaduct had a reputation for rowdy, drunken fights in the middle of the night, whereas the Wilson viaduct was quieter.

People began sleeping under the viaducts around 2011 to skirt a city ordinance that kept people out of the park after 11 p.m. As word spread that the viaducts were a safe place to sleep, it became a permanent fixture in Uptown.

A woman known simply as “the soup lady” came by each night with dinner; caseworkers and outreach coordinators from local nonprofits stopped by to check on residents. Faith leaders led prayers on Sundays. Residents took turns standing watch and keeping the area clean. The community even had its own leadership structure, headed by 59-year-old opera aficionado Tom Gordon. Gordon loved music. Led Zeppelin and Pink Floyd were at the top of the list, with country and opera a close second. His favorite food was liver. And he was such a fixture of Tent City that in March 2017 the community voted to make him their unofficial mayor. (At least that’s what Gordon recounts. While no one disputes Gordon’s leadership, others dispute his claim that he was voted in. It’s entirely possible that Gordon declared himself mayor.)

Gordon took this responsibility seriously. “I was in charge of all supplies that came in, all the donations, made sure everybody got whatever came in. Nobody went without.”

Tent City offered some semblance of stability in the uncertainty of homelessness. And now it was gone.

September 18, 2017, when I met Gordon and Brown, was the morning construction crews blocked off the viaducts they both called home. No one knew what was going on. “Where you you going?” they asked each other. “I don’t know; where are you going?”

Gordon was delegating teams of residents and activists as they moved their belongings under the watchful eye of the police, but Brown did not participate in the kerfuffle. He sat in a lawn chair on the sidewalk, spectating as groups of residents and locals hauled belongings to and fro, sharing a box of crackers with a friend. He was remarkably relaxed, all things considered. Maybe it was because he was going apartment hunting.

When Brown left the Wilson Viaduct to go scope out a new place, he had a community, a tent, a home. When he returned at 2:30 p.m., his friends had moved on, and his tent had been left in a heap by the road.

In those few chaotic hours, the Chicago Department of Transportation began enacting its plan to construct bike lanes along the viaducts under Lakeshore Drive at Lawrence and Wilson Avenues in Uptown. The first step was fencing off the viaducts, effectively evicting some 45 homeless people, many of them elderly or disabled, from their encampment beneath the bridges.

From the night before the construction to the Wednesday after it, the bedraggled community was forced to move six times, under threat of arrest each time. There were rumors of medical emergencies and panic attacks due to the stress of moving; there was one arrest. Activists, advocates and city workers worked hard to help Tent City residents adapt after the eviction, but the end result was clear: they had nowhere to go, or at least, nowhere they could be a community again.

A Symbol of Resistance

From its earliest days as a group of men sleeping on cardboard beneath the viaduct to an established encampment fighting for its right to exist, Tent City came to stand in for a much larger – and often invisible – problem.

The Chicago Coalition for the Homeless estimates that 82,212 homeless people live in Chicago, but the city’s official count shows only 5,657. That’s because, according to guidelines from the federal Department of Housing and Urban Development, the city only tracks those who live on the streets or in shelters, despite the fact that that 82 percent of the homeless live “doubled up,” that is, relying on the couches, spare rooms and living room floors of friends rather than facing the street.

Tent City residents had two things that made them different: They had bright orange tents, and they knew their rights. Those two things became their undoing.

Homelessness is tricky to quantify precisely because homelessness is so unstable. Someone crashing with a friend one night might be in a shelter the next night; someone experiencing homelessness might find an apartment one month, fail to pay rent and wind up back on the street the next. But Tent City was permanent.

Tent City residents had two things that made them different: They had bright orange tents, and they knew their rights. Those two things became their undoing.

The tents were the product of a fundraiser by the Uptown Tent City Organizers, a group of formerly homeless folks and concerned citizens who took an interest in Tent City.

Andy Thayer was one of those organizers. He began the fundraiser to protect the homeless from the elements, but there was always another motive as well.  “The tents drew attention to an ongoing problem that had been ignored by the city,” said Thayer. “A lot of folks just go about their business, and [homelessness] became much more of a visible problem to people.”

On August 27, Thayer and the Uptown Tent City Organizers, represented by the Uptown People’s Law Center, filed an injunction in federal court as part of a pending lawsuit against the city. The lawsuit made a rather creative First Amendment argument: The lawyers asserted that Tent City, a group of people assembling in a public space, constituted an ongoing protest against the lack of affordable housing in Chicago, and that the displacement was a violation of their right to protest.

“It’s about having assembly as well as actually having your message reach an audience,” said Thayer. He pointed to a recent WBEZ report, which aired nationally, as an example of the power of the image of the tent to call attention to the lack of affordable housing. “This is an issue that’s affecting 50-75 people, yet it’s making national news. Fifty to 75 people out of 82,000. That shows how effective people’s First Amendment messages have been. And of course the city’s whole approach is, ‘We refuse to give people a place to set up tents anywhere in the city.’”

Several of those who lived in tents provided by the Uptown Tent City Organizers, and people like Tom Gordon, who distributed them, disliked Thayer and his organizers. They felt that people who weren’t homeless were robbing of them of their agency by using them as pawns in their political game. Still, the tents kept them warm and gave them some privacy. They may have disagreed with Thayer’s tactics, but by living in his tents, they participated in them.

Another lawsuit, this one filed by the Chicago Coalition for the Homeless, argued that Tent City residents were being discriminated against because they were homeless, which was in violation the 2013 Illinois Bill of Rights for the Homeless Act.

Diane O’Connell, the lead attorney on that case, said, “Any sane, rational person would argue that they have a right to be somewhere.”  But the city is — wrongfully, in her view — acting like “they don’t have any right to be any specific place.” 

Roughing It

Sean Brown always considered his homelessness temporary. When he lost his job as a production designer at a fashion house in October 2016, he figured he would find other work before he ran down his savings. But he hadn’t found another job by the time his lease was up. So he moved in with a friend for as long as he could, and when that hospitality ran dry, he started sleeping on beaches and construction sites.

This wasn’t the first time Brown had adjusted to life outdoors. He had emancipated himself at 15 and spent some time living in the ravine behind the home he grew up in. Now, he told himself his new homelessness was a retreat, a chance to unplug and go urban camping. But what was an adventure at 15 took a toll on his body at 44. Besides, he was HIV-positive now. “I have full-blown AIDS at this point,” he said.

The chaos of homelessness – and a general doubt in the efficacy of HIV treatment – made him lose track of his pill regimen. He developed pneumonia. Unable to practice proper hygiene, he contracted trench foot, a medical condition that is caused by prolonged exposure to cold, damp conditions. It was common among trench soldiers in World War I.

He got a job by lying about his health and his housing situation. Now that he had income, he stepped up his apartment search, but one room after another fell through at the last minute. His desperation deepened.

Brown came to Tent City in April 2017. “I went up to somebody and asked, ‘Who do I talk to about getting a tent here?’” He was directed to Gordon, and a week later, Brown had a bright orange tent to call his own.

Having shelter was good, but having neighbors was better. Brown could leave his belongings at the viaduct during the day instead of carrying everything he owned to work. He could borrow bandages and lend out his lighter. He had people to gripe with, people who understood, people who cared.

Because Brown had a job, he could do things his compatriots could not. “In my tent I had a tablet and phones that work and Bluetooth speakers and lights and clothes and… I could be just kind of a regular person that lives in a tent. I think people can kind of resent you for that.”

Being gay didn’t help. He had to project a brashness that didn’t come naturally to him. Early in his tenure at Tent City, Brown made his sexuality clear. “You don’t like fags?” he told his new neighbors. “Come over here and get your ass kicked by a fag in front of all of your friends and see how you like it.”

The Morning After

It rained the night after the eviction. Brown, gangly and approachable with a devil-may-care swagger, slept in his tent on the other side of Marine Drive along with the majority of his fellow Tent City residents. “I didn’t know that there was water in my tent until I needed something in the corner, and I picked it up and it was dripping.”

As soon as he popped his head out on Tuesday morning, he knew it was time to go. “There were these people there,” he said, “These legal people, and they were hashing around for a while, but I was like, it’s not gonna do any good. If they want us out, they want us out.” He grabbed whatever he could and said to himself, ‘I’ll take what I can carry and go and put this in storage and come back and get the rest.’ As he headed to his storage unit, he ran into none other than Tom Gordon.

Tom Gordon, 59, unofficial mayor of Tent City. Photo credit: Sydney Boles

In the crisis of the eviction, Gordon leapt into action. He intercepted Brown on the way to his storage unit, wrangled as many residents as he could, and dragged dozens of people’s’ belongings to a water treatment facility a few blocks away. But the police contacted the facility’s owners, and they kicked the bedraggled group out once again.

Over the next few days, the group splintered more and more. Breaking off alone or in groups of two or three, Tent City residents spread out across Uptown. Some went to homeless shelters; others went back to sleeping in the park, exposed to the elements and unable to erect tents.

Brown took off alone.

The Town’s a-Changin’

Uptown, long one of the North Side’s most affordable neighborhoods and possessing one of its highest rates of homelessness, is ripe for gentrification. Just north of Lake View, which is experiencing rapid development following the historic 2016 Cubs World Series win, Uptown’s housing value is predicted to rise 1.9 percent by September 2018.

46th Ward Ald. James Cappleman, whose jurisdiction includes Uptown, is a polarizing figure in the housing debate. Although he supports efforts to find affordable housing for residents in his ward, his tenure has seen the closure of roughly 1,000 affordable housing units and the large-scale development of luxury apartment buildings.

A social worker before he entered politics, Ald. Cappleman received the subtle rebuff of his former profession for his involvement in removing Tent City. The National Association of Social Workers said in a statement that it “expresses concern over the recent developments and movement of homeless individuals,” saying that “The social work profession supports the right of all individuals and families to have affordable housing in their community, as well as feeling the inclusivity that a community should bring to each member.”

Ald. Cappleman’s office did not return multiple requests for comment, but in a September 25 statement, the alderman said, “Alderman Cappleman and the city’s Department of Family and Support Services have been taking action to help those who had been living beneath the Wilson and Lawrence viaducts access food, shelter, mental health services, addiction treatment and medical care.” Among those successes was finding permanent housing for 53 people, short-term bridge housing for 21, and beds in homeless shelters for five Uptown residents in 18 months.

Housing Tent City residents was particularly challenging. Many had substance abuse issues, mental health challenges or criminal backgrounds that took most apartments off the table. But many also turned down what housing was offered to them because it was too far away or it wouldn’t allow their pets.

Perhaps because it may undercount the homeless population, Chicago’s initiatives to tackle homelessness mostly come in the form of one-off pilot programs. One such 2016 program, which promised to house 75 Tent City residents, ran months over its deadline and left many of those involved feeling angry and mistrustful of those involved, including Mayor Rahm Emanuel and 46th Ward Ald. James Cappleman.

Housing Tent City residents was particularly challenging. Many had substance abuse issues, mental health challenges or criminal backgrounds that took most apartments off the table. But many also turned down what housing was offered to them because it was too far away or it wouldn’t allow their pets.

Shelters were equally unsuitable: residents complained of bed bugs, there weren’t beds for heterosexual couples without children, and sleeping there meant having to lug everything they owned with them during the day. Jeremy Nicholls, an outreach worker at Cornerstone Community Center who helped connect Tent City residents with housing resources, blamed the stall on opaque bureaucracy that even experts struggled to navigate.

H Kapp-Klote is the communications coordinator at ONE North Side, an organization that is heavily involved in affordable housing issues in Uptown. Kapp-Klote said, “A ton of the people who live there are long-term residents of Uptown. They’ve lived in Uptown for 10 years or 15 years or 20 years. And they’re living there because the city isn’t finding them housing, but also because this is where their family is.”


Gordon spent the chaotic 48 hours after the eviction consoling people who were distraught by the eviction. Two people with no history of anxiety had panic attacks in those early post-eviction days; one woman, a diabetic, went into a seizure. Gordon’s mind was a running tally of where his people were and what resources they needed.

Gordon didn’t see Sean Brown for days after the eviction. Brown wanted to meet up with the group – if only to assure them he was alive – but he was just too busy surviving.

Hours stretched into days. Tuesday, Sept. 26, about a week after the eviction, was unseasonably hot. The whole city moved sluggishly and dripped sweat.  Brown texted me in the morning. He was dehydrated, he said. Could I bring him some Gatorade?

I met him in the McDonald’s parking lot at the corner of Wilson and Sheridan avenues. He looked unwell; he’d spent the hot afternoon sorting through his storage unit in preparation for his move. He’d finally found an apartment.

I asked him if he felt excited. He shook his head. It didn’t feel real, he said. “One reason you always see homeless people pushing shopping carts of all their things around,” he said, “is it always seems like housing is just about to come through, but for most people it never does.”

A few days later, Brown told me it was official. He was moving in within the week. He said he’d give me a tour of his new place, but then he stopped returning my calls. I called him over and over, but the phone went right to voicemail. I worried his housing fell through and he was in some kind of trouble. Finally, a mutual acquaintance assured me he had moved into his new apartment. He was fine, just busy moving in.

For his part, Gordon spent his post-eviction days walking the streets of Uptown, visiting each of his former constituents. Many were sleeping in the park near the former Tent City site under varying degrees of scrutiny by the Chicago Police Department and Parks Department officials. No one had a firm grasp on how firmly various ordinances, including one regarding erecting structures in public parks, would be enforced.

Gordon was worried about coats and blankets as colder weather loomed, but he was also tracking down a long-term spot to reestablish Tent City. “I want to lead them out of the area so they’re safe. So we’re looking at Edgewater and Rogers Park.” He hoped to find a private property, an abandoned school or an empty lot, and get written permission from the owners to camp there.

And for himself? Gordon was not looking for an apartment. “I probably will eventually. But I can’t leave these people. I can’t leave. People don’t have tents. They have no place to go. At least if I’m here, they have a chance.”

Following the closure of Tent City, those who still had their tents carried them around from place to place, unable to set them up but unwilling to part with them. The tent was no longer a symbol of resistance. It was just a crumpled heap of bright orange fabric.

Featured photo: Tent City residents and volunteers move tents on Sept. 18, 2017. Photo credit: Sydney Boles

This post has been updated to correct the name of attorney Diane O’Connell and clarify her quote.