Former Gang Leader Faces Tough Choices as City Clears Chicago’s Largest Tent Encampment

With winter approaching, James Rios stands defiant in refusal to accept shelter life, as City pushes for solutions

Photo byScreen Capture/Youtube Video [Creator]

CHICAGO - As the bitter cold of Chicago’s winter inches closer, the city’s largest tent encampment in Humboldt Park is being dismantled, and most of its residents are being offered rent-free apartments. But for James Rios, a former gang leader turned homeless, and his fiancée, the prospect of moving into a homeless shelter feels like anything but a solution.

City officials have declared that everyone living in the park must leave by December 1st, with promises of either a housing unit or a shelter bed. Yet, Rios, 44, remains determined to avoid shelters, clinging to what little autonomy and safety he believes he has left.

After spending several months in a flimsy summer tent, Rios and his girlfriend have recently moved into a battered orange ice-fishing tent just feet away from their previous setup. Hoping for a bit more warmth, Rios has been patching up the tent’s tears with duct tape, trying to prepare it for the harsh winter. However, even with these makeshift repairs, he admits it’s far from ideal.

“I’m stuffing this hole with this steel sponge so that the rats — penetrating through it, when they nibble on that — they will stop because it doesn’t agree with their teeth,” said Rios, once a prominent figure in a street gang near the park.

Rios’ neighbors in the Humboldt Park encampment have slowly disappeared as they accepted the city's offer of housing in different neighborhoods across Chicago. He gestures to the tents once occupied by people like Angel Torres, a man who moved into a rent-free apartment in the South Side’s Chatham neighborhood.

“There’s another guy that disappeared here we call Cuba,” Rios said, pointing to a now-vacant orange tent. “I’m sure he got housing.”

According to city officials, around 100 unhoused people have been living in Humboldt Park, and the majority will be offered apartments. For those left out of the housing offer, shelter beds are the fallback plan.

“The park is being cleared because people are moving into housing,” explained Sendy Soto, Chief Homelessness Officer under Mayor Brandon Johnson.

Still, Rios and his fiancée fall into the group who might not receive a housing unit, and he’s adamant about not accepting a shelter.

For Rios, a shelter isn't just an undesirable option—it’s a non-starter. “It wouldn’t work out because of my fiancée,” he said. “They would split us up, meaning she would have to be somewhere else.”

On top of that, Rios fears the strict rules in shelters—such as curfews and smoking bans—and worries about his personal safety and freedom. “I’ve seen what happens in shelters,” Rios says. “There’s too much control, too many rules. I need my own space.”

The sense of community that once existed around the campfire near his tent is also slipping away. In recent weeks, a group of about a dozen people would regularly gather to share food, stories, and camaraderie. Now, that sense of support has faded, and those who remain are growing more desperate.

On a recent afternoon, Rios was trying to wake his hungover girlfriend when a shirtless young man appeared, wielding a hatchet and mumbling about a debt. “He just came up swinging,” Rios said. “I told him to come back later.”

This dangerous encounter is just one example of the escalating tension and instability that has accompanied the dismantling of the Humboldt Park encampment. The community, once filled with a mix of mutual support and moments of peace, is unraveling.

Rios, who has lived through more than his share of hard times, now faces a new kind of crisis—whether to stay in the park or move into a shelter that feels like the wrong choice.

Rios’ journey to this point is marked by hardship and poor choices. Raised in a struggling single-parent household in Lincoln Park, a neighborhood that was once more low-income, Rios watched as his mother turned to dealing drugs to feed her three children. When she was caught and sent to jail, Rios and his siblings were separated.

At just 11 years old, Rios began his involvement with gangs. He was drawn in after bringing some marijuana to a local park and gaining the attention of older gang members. “I thought I could fit in,” he said.

By 13, his own father introduced him to cocaine, pulling him further into a world of crime. What followed were years of gang involvement, felony convictions, and time behind bars. It wasn’t until his late twenties that he began to question the life he had committed to.

“When I got in my late 20s and I started noticing that I ain’t getting no pension, no retirement funds, and I’m paying for lawyers and I’m ... doing time in jail for trying to protect this neighborhood and having a gun on me. And I devoted my life to this gang that only caused me so much harm,” Rios reflected.

Though he made attempts to settle down—marrying, divorcing, and raising five children—he could never completely sever ties with his gang. Even as he tried to learn trades like carpentry and barbering, his life continued to spiral. Alcohol became his coping mechanism, and his criminal record continued to grow.

In 2021, a domestic violence incident led to yet another prison stint. When he was released, he had nowhere to go, finding himself homeless and sleeping in his car until it was towed for unpaid tickets.

It wasn’t long before Rios found his way to the Humboldt Park encampment. But life on the streets brought new challenges, and the death of his son last year was a devastating blow that led him further into drinking.

“It was so heartbreaking and it just hurt me so bad, and it just led to drinking. And actually [it] put my life in danger plenty of times, because I cared less about my life,” Rios said.

After losing his son, Rios’ downward spiral accelerated. Though he was temporarily housed in an apartment at the beginning of this year, he didn’t maintain contact with his social worker, ultimately losing the apartment by the summer.

Now, he shares an ice-fishing tent with his new girlfriend, both battling their own demons as they face a bleak and uncertain future.

City’s Efforts Fall Short Amidst Growing Homelessness

Chicago’s homeless crisis has become increasingly dire, with organizations like All Chicago Making Homelessness History working tirelessly to place as many people as possible into housing. Yet, the resources available simply aren’t enough.

“We are assessing almost 10 times as many people as we have the capacity to house,” said Beth Horwitz, Vice President of the organization.

Mayor Johnson’s push for a “mansion tax” earlier this year aimed to address the city’s growing homelessness issue by raising funds for affordable housing, but the measure was rejected by voters. As a result, the financial support for housing those in need is still in short supply.

For the estimated 85 households living in Humboldt Park’s encampment, the city has only secured funding for 63 rent-free apartments. For people like Rios, who haven’t been offered housing and refuse shelter beds, the future looks uncertain.

Alderman Jessie Fuentes of the 26th Ward acknowledges that dealing with those who refuse both housing and shelter will be a difficult task. “We may have a few that sort of refuse to leave,” Fuentes said. “Those are going to be very tough conversations and realities. We may need to find an alternative placement for them.”

Fuentes emphasized that clearing the encampment is crucial for both the safety of those living in the park and the surrounding community. “The goal is to be able to clear the encampment so that the park rules can be enforced both for the safety of our unhoused neighbors and for the safety of residents across the district.”

For Rios, the situation is becoming more desperate by the day. On his first night in the new orange tent, the wind knocked down the center support, and rain began to seep in. His girlfriend left in frustration, leaving him to face the cold and the uncertainty alone.

“I was getting rained on inside the tent,” Rios admitted. “I cried for about an hour, all balled up under the blanket.”

As the city’s efforts to clear Humboldt Park ramp up, Rios is left with few options. Though he remains reluctant to accept a shelter bed, he is beginning to reconsider his stance. “I might have to take a shelter bed after all,” he admitted.

As the deadline looms and temperatures continue to drop, the future for James Rios and many others in Chicago’s homeless population remains uncertain.