This content is made possible through TCR’s partnership with Medill Investigative Lab-Chicago at Northwestern University
Beneath the shadow of the bustling overpass on Chicago’s Near West Side, where Desplaines Street meets Hubbard, is an informal encampment residents call the “Chocolate Factory.”
Jeremy Holomshek, better known as Elmo, is a 43-year veteran of the streets who has faced a lifetime of displacement. “Foster care, boys’ homes… I got tired. Took to the road.”
As a long-term resident, he reflected on the years he has spent at the site. “I have a tent over there. Been here around three years. I feel like I’m stuck here though.”
He came to Chicago in search of family. He found his father, only for the man to commit suicide just a few days later. “I didn’t know him all my life, so it wasn’t too bad. I talked to him one day, then he was gone.”
While battling homelessness, Elmo has also faced drug addiction and violence. “There’s help here, but it depends on what you want to do,” he said. “Shelters ain’t the greatest unless you want to get bed bugs and your stuff stolen.”
After years of heroin, Elmo is one of the few to detox without medical care. “I just didn’t want to be that guy anymore.”
However, he is still very aware of the mental health struggles that affect his neighbors. “Schizophrenia, bipolar, you name it,” he said. “But nobody wants to deal with it.”
Elmo lives amidst a patch of tents, tarps, and found materials that have become home to a rotating population of unhoused Chicagoans, many of whom battle with addiction, mental illness, and cycles of incarceration and abandonment. The Chocolate Factory has become a tightly knit community fighting to survive on the city’s margins, where access to resources prioritizes short-term aid over long-term recovery.
The Chocolate Factory did not simply appear overnight. It is the product of a cycle of forced relocation and systemic neglect. Many of its current residents were displaced from a larger, more visible encampment that once stood beneath the viaducts in the West Loop near Clinton Street and Lake Street. That site became a target for removal after neighbors raised complaints about open drug use, violence, and discarded needles, with some claiming the area had devolved into an open-air drug market. Under pressure from residents and city officials, the encampment was cleared but not resolved.
In December 2023, tension over the encampment increased after 34th Ward Alderman Bill Conway and others insisted the camp be cleared in the middle of winter. Crews removed tents, power-washed sidewalks, and placed Department of Family and Support Services workers on the scene to offer shelter and clean-up services. According to CBS News, the local aldermen said drug arrests and a fatal shooting occurred in the encampment in the following weeks. However, unhoused people filled the area again, drawing concerns that the city was incapable of keeping the site cleared out.
What followed was predictable. Without stable housing alternatives, many of those individuals simply moved a few blocks away to the Chocolate Factory, which lies beneath Des Plaines and Hubbard. This pattern underscores a hard truth: sweeping an encampment doesn’t eliminate homelessness. It merely shifts it elsewhere.
Ali Simmons, a senior case and street outreach worker at the Chicago coalition to end homelessness, argues that these displacements are not only ineffective but harmful. “We definitely believe that encampments shouldn’t be displaced,” Simmons said. “If there is not enough affordable housing and you can’t offer anybody who’s unsheltered or experiencing homelessness with housing, then you shouldn’t be forcing them to move.”
There are many reasons people stay in encampments: they’re afraid of unfamiliar or unsafe shelter placements, they don’t trust institutions and many suffer mental health challenges and substance use. But in every case, displacing people without offering housing only perpetuates homelessness across different corners of the city.
Ultimately, the real solution is not more enforcement. It’s more affordable housing and policies that meet people where they are, not where the city wants them to disappear.
There is something deeply unsettling about the Chocolate Factory compared to other camps scattered across the city. At many other sites, most people leave during the day, hustling for food, money, or supplies through panhandling, scripting, or boosting. But at the Chocolate Factory, many residents stay put.
The stillness hints at an unseen economy, deeper trauma, or a level of stagnation born of long-term entrenchment and limited options. It underscores the complexity of encampments and the dangers of applying simplistic assumptions to the people within them.
The sites that were so easily discarded by the city served as home to others. The consistent cycle of homelessness leaves many questioning how these individuals found themselves homeless in Chicago. Each person has their own story.
For many, the journey to the Chocolate Factory started a long time ago. After becoming homeless in the nineties, Charles Ramsey now has a roof over his head. He once lived at the Chocolate Factory, but with recent housing support programs, he was finally able to move into permanent housing and leave the encampment behind.
Even with five children and a grandson, he feels removed from the life he could have had. “I don’t want to see [my grandson] like this. Not when I’m still using. It’d tear me up.”
He speaks candidly about the weight of addiction and regret as he is on heroin, which causes him to feel “depressed a lot because [he is] not accomplishing what [he] needs to accomplish.”
Ramsey’s current stability is born of support services. He claims that receiving his own place through housing services helped him prioritize his mental health. “I really think I’m gonna become sober this year. I’m really gonna do it.”
Another Chocolate Factory camp resident, 44-year-old Robert Besterfeldt, emphasized how critical stable housing is to his recovery. He became homeless after struggling with addiction and sees a clear link between shelter and sobriety. “If I get housing somewhere, I’m immediately putting myself in the methadone program,” he said. “I was clean for over five years, but I have to have stability to be able to do that. You can’t have stability out here.”
Life at the Chocolate Factory is hardly secure. Residents deal with the daily realities of exposure to the elements, limited access to hygiene, and living under the constant threat of displacement. Violence is common. Theft is routine. Trust is hard-earned.
Residents report that shelters are overcrowded or unsafe, while housing waitlists can take years. For many, living outside feels like the only viable option despite the dangers.
The psychological impact is profound. Without consistent mental health care and addiction treatment, many fall through the cracks. But small victories can bring hope even in the most dismal circumstances. The opportunity to detox, reconnect with family, or secure stable housing can truly make a difference.
It’s a familiar cycle for many individuals at the Chocolate Factory: emergency care, discharge, and relapse. Jenanne Luse, a nurse practitioner with the Night Ministry, said, “They detox people for a few days, and then discharge them back onto the streets. If there was a way to connect emergency care to case management, that could change lives.”
Luse is witness to just how difficult it is to secure stability without support. “Right now, we patch wounds. We can’t treat the root causes. The emergency room is a revolving door.”
She is convinced that better continuity of care could help by “utilizing the emergency room and having case management services [to] meaningfully connect people to primary care.”
Nearly all who were interviewed expressed the same frustrations: long waitlists for housing, under-resourced shelters, and a mental health system that is unequipped for chronic trauma and addiction.
“They help you immediately, but then long term you’re on your own,” Besterfeldt said. “If they helped more in setting you up with a program leaving the hospital…where you could continue staying sober, [then you would] be able to get up on your feet and start doing something in your life.”
The closing of encampments in the West Loop demonstrates a clear lesson: without longer-term alternatives, people don’t vanish–they resettle. They pitch tents elsewhere, in less visible, more precarious locations. Displacement is a surface-level solution to a structural problem.
Encampment sweeps give the illusion of progress, but they often worsen trauma. Possessions are lost. Medical treatments are interrupted. Social networks that provide informal support dissolve overnight. And most importantly, the underlying issues, such as lack of housing, untreated mental illness, and addiction, remain unresolved.
“I have tried my best to make [the Chocolate Factory] home,” Elmo said. “Everyone here does their best to get by and help each other.”
Despite everything, the Chocolate Factory remains as a community stitched together by resilience and necessity. The name carries a hint of irony but has a defiant ring. It’s not sweet, but it’s their home. Even among broken systems and broken dreams, hope persists. And it demands to be heard.
Falling through the cracks is so lame. These people die.