Thelia Stennis didn’t live in the worst of Gary Carlson’s 83 buildings.

Sewage wasn’t backing up into her tub, and there was no black mold or lead paint in her home — as far as she knew. But a wall in the living room looked to be buckling, the building’s hallway carpets stank when it rained, and the back gate to the building was missing a handle.

What really got to her were the roaches. “They were brown,” she said, “and some of them were the flying kind.”

A native Chicagoan in her 60s, Stennis describes herself as a “germaphobe” and “a little bit OCD.” She adheres mostly to a plant-based diet, enjoying homemade meals with herbs she grows herself. Because of the roaches, she said she stopped cooking and wound up “spending the rest of my little Social Security check on eating out.”

Stennis said the roaches invaded her fridge, squeezing past the aging rubber seal. She tried to keep leftovers in the microwave but discovered them there, too. She watched as her cat tried to protect her unfinished food from the insects by folding her feeding mat over her bowl with her paw. The roaches were undeterred.

“They’d come out in the daylight and act like they were paying rent, and I was the guest,” she said.

She said Carlson would send an exterminator to spray, but the treatment was ineffective and the roaches just came back. She said Carlson did not respond to her request to address the root cause of the infestation, which was somewhere in the building’s walls.

She said she battled them on her own. “I bought a gallon of roach spray and made myself sick.”

At night, Stennis said she had nightmares about the roaches, and her doctor told her the marks on her body were cockroach bites.

By the time a couple of community organizers from the Albany Park Organizing Committee knocked on her door in early winter 2023, she had been living in Carlson’s buildings for almost a decade. She said the main reason she hadn’t moved elsewhere was because of the Housing Choice Voucher — also known as Section 8 — subsidizing her rent.

“It’s very difficult to find people to rent to you with a voucher,” she said. And she wanted to stay in Albany Park, where she found convenient amenities, easy access to public transit, and a diverse community that reminded her of her early childhood in Hyde Park.

The organizers persuaded her to join a few other voucher-holder tenants at a meeting in which they strategized about how they could get city agencies to do something about Carlson. Some of them, including Stennis, had tried calling the city’s 311 complaint hotline before, which didn’t seem to do much. Others had tried to complain to the Chicago Housing Authority, which administers the voucher program.

In the case of Stennis’ building, the CHA had sent some of them letters saying they had to move out because of the poor conditions — but the timeline and financial assistance the agency gave them was unrealistic, the tenants said. Stennis and her neighbors decided it was time to raise some hell with a multipronged approach: They wanted to pressure the CHA to give them more time and money to relocate and the city to crack down on Carlson.

The group named itself the Fair Tenants Union. Unlike other tenant associations around Chicago, theirs was made up of voucher holders who couldn’t attempt a rent strike without the risk of losing their subsidy. But their vouchers — a few hundred of the 42,500 in the city — also gave them a pressure point to use against Carlson most other tenants don’t have. And they soon learned the city was already two years deep into investigating tenants’ complaints and leveraging every legal mechanism available against their landlord.

Each year, the city gets roughly 40,000 calls about building problems, and the city’s 168 inspectors write up violations in more than 15,000 inspections. Many building owners do what it takes to fall into line and make their properties safe, but city officials and tenants are often frustrated by landlords who refuse. It requires the motivation of many officials working together to keep pushing even to get a building into housing court — which happens about 2,000 times every year. Targeting a landlord more systematically happens so rarely it tends to make the news.

The city, which ultimately took the vast majority of Carlson’s buildings to housing court, was spurred to take action not just by his tenants’ calls but by a confluence of other factors: neighborhood outrage about how things that went on inside Carlson’s buildings impacted the community and the left-leaning culture of Albany Park, which has led to the election of two Democratic socialist alders highly sympathetic to tenants’ struggles.

The rare pressure on Carlson cost him millions of dollars and negatively impacted his reputation. But it didn’t cost him his business or his buildings, most of which are fully occupied today by new tenants paying market rents.

“#1 PAY YOUR RENT!”

Carlson, 72, mustachioed, with curly gray hair and a booming voice, conducts his business perched in a leather chair a few steps away from his bedroom on the second floor of a humble clapboard three-flat near the corner of Montrose and Lawndale avenues. It’s next door to a small brick warehouse, where all his businesses are registered.

A white-haired man with glasses and a mustache sits in a desk chair surrounded by filing cabinets looking through a three-ring binder.
Gary Carlson in his office in July. Credit: Abel Uribe for Injustice Watch

To see Carlson at his Bosch painting of an office is to witness a man so comfortable with himself he goes shirtless for visitors as window fans purr past walls of bookshelves and file cabinets crammed with tenant and building records. Family photos of his workers and tchotchkes from Romania brought back by a contractor pepper the space. One wall is upholstered with plastic drawers filled with pens, keychains, and mini calendars printed with messages, such as: “I love you Gary R. Carlson” and “#1 PAY YOUR RENT!”

Six desks for Carlson and his two office workers cram the floor of the space that was originally the unit’s living room. There’s barely any room to maneuver for the three other employees who pop in throughout the day. Between the computer monitors, there are phones and police scanners, printers and tools, cleaning sprays, barbells, a magnet strip with knives, candy, and plastic clamshells of muffins. There are even blue-and-white envelopes with records on past tenants, some who long ago died, just in case, Carlson said, a reporter comes asking questions. “Nobody believes anything that I say,” he said, his voice rising to a roar. “I have to prove everything.”

He says he’s been described as a “slumlord,” a label he resents and calls “vocational hate” tantamount to racial slurs.

Carlson grew up in Albany Park and graduated from Roosevelt High School. He began buying buildings in the area in 1982. Over the course of two wide-ranging interviews with Injustice Watch Carlson described accumulating investment capital as a teenager: He worked delivering papers for the Chicago Tribune, used the money to pay for training as an auto mechanic, and began fixing cars in the alley behind his parents’ garage — which brought more money.

Carlson bought his first building, a six-flat at 3745 W, Agatite Ave., from his landlady, who allowed him to make payments over time. It took him a decade to pay off the $100,000 loan and nearly $96,000 in interest.

Carlson’s business is mostly analog. Tenants pay their rent by dropping money orders into a slot in his door and communicate with him by phone or in person. Each time he mentioned a new address, he called one of his workers to bring him a new red vinyl binder. He welcomed Injustice Watch to photograph the documents and notes on the building inside. One included a yellowed newspaper clipping about landlords’ rights to seize tenant belongings over unpaid rent.

“I have no secrets, and I don’t lie,” Carlson said, as he recounted amassing buildings through the 1980s and ’90s, when Albany Park was “full of all type of bullshit … graffiti, undesirable people on the street.” He said he didn’t have any goal in mind as he first began acquiring properties other than to “have fun.” He bought one building “just for the pleasure of giving all them tenants a new address.”

As his empire began to grow, Carlson self-financed some of the buildings by liquidating government savings bonds he’d gotten from relatives. Other buildings were seller financed. He used the insurance payout from one building that burned down to buy another. He wanted to have bank mortgages, “but they wanted me to do too much shit, take a little blood out of my veins, and sign all the documents in blood. That’s what it seemed like to me.”

Eventually, the lure of bank money proved stronger than Carlson’s distaste for paperwork, and today, he said disdainfully, he makes more than $100,000 per month in mortgage payments. Carlson said he bought the last three buildings in his portfolio sight unseen in late 2020, while he was in the hospital. “What feels good about buying the buildings? I own more than the next guy.”

In the early 2000s, Carlson stopped running his auto mechanic business to focus exclusively on landlording. By then, he’d had enough business experience to know “you never, ever lose money in real estate, you just don’t make as much.”

Carlson had been renting to Section 8 voucher holders since 1990. He recalled in vivid detail the first tenant who asked him to take her voucher. Eventually, Carlson became one of the largest vendors receiving voucher payments from the CHA, collecting nearly $5 million in rent subsidies in 2020. He estimates at one point, about 400 households with vouchers lived in his buildings — the majority of his tenants.

“There’s three things that give you the feeling of invincibility when you’re a landlord,” Carlson said. “You’ve collected all your rent, you have no vacancies, and you have no building code violations.”

Carlson’s reputation wasn’t always as negative as it is today. Former tenants and city officials told Injustice Watch he had a history of responsiveness to tenants and a cooperative attitude toward the city despite his eccentricities.

But tenants also told Injustice Watch it was frustrating Carlson could only be reached by phone at his office between 8 and 8:30 a.m. Monday through Thursday; getting issues addressed required persistence. Carlson’s buildings were frequently cited for building code violations, but he also tended to resolve them quickly. Nineteen of Carlson’s properties were among the buildings with a history of serious code violations identified by Injustice Watch. Before 2021, Carlson had paid at least $20,000 in fines for code violations at those buildings.

Ald. Carlos Ramirez-Rosa, 35th Ward, recalled Carlson welcoming a “positive loitering” event after a neighborhood shooting around 2016, firing up grills, and contributing food to a cookout at one of his properties. He said Carlson also set up trash cans around the area and put his staff in charge of the pickups.

“I saw the efforts he was making to keep the neighborhood clean,” Ramirez-Rosa said. “Any time there was a report of fly dumping, he’d have his team clean it up right away. My ward superintendent at the time was happy with him.”

A modest two-story wood-framed house with peeling paint on the door.
Gary Carlson conducts business out of a second-story unit in a three-flat on Montrose Avenue. Credit: Abel Uribe for Injustice Watch

Ramirez-Rosa said in 2019 “things really took a turn for the worse” at Carlson’s properties — a claim Carlson disputes but tenants supported. They said maintenance requests started to go unanswered, cockroaches and bedbugs began to proliferate, and mold grew on walls and ceilings damaged by leaking roofs. The 33rd Ward and 35th Ward office staff told Injustice Watch they began to hear more complaints from Carlson’s tenants.

Broken gates and chronically unlocked lobbies were a major concern for tenants and neighbors alike. People who didn’t live in the buildings could easily gain access. Criminal activity in some buildings escalated to the point that in early 2020, a firefighter was shot in the leg while working to extinguish a car fire in front of one of Carlson’s nine-unit buildings at the corner of Wilson Avenue and Kimball Avenue.

Guns were found in a first-floor apartment, along with cocaine, heroin, ecstasy, and methadone — all packaged for individual sale, according to city records. Less than a month later, a 27-year-old mother of three was shot and killed in another one of Carlson’s buildings a mile away, and guns were found at a third property. The following month, police reported an attempted break-in at another building. The month after that, police responded to a shooting at a fifth property.

Throughout summer and fall 2020, reports of break-ins, armed intimidation, robberies, assaults, and shootings at or near Carlson’s buildings continued to pour into the 17th police district, where many of his properties are concentrated.

Tenants and aldermen raised questions about Carlson’s leasing agent, Erik Rodriguez, who had a prior felony conviction for selling drugs.

In late 2017, the Chicago Police Department began an undercover operation targeting Rodriguez, who has worked for Carlson for nearly 20 years. Police reported buying crack cocaine from Rodriguez on six occasions before raiding his office at 3716 W. Montrose Ave., a commercial building owned by Carlson just west of his headquarters. They arrested Rodriguez and found more than 9 grams of “suspected cocaine” at the office packaged for individual sale.

He ultimately pleaded guilty and was sentenced to 24 months of probation. Carlson said he didn’t recall the incident. Rodriguez, who sat in on Injustice Watch’s interviews with Carlson and frequently chimed in, said he was selling drugs in an attempt to “cut a corner and make a few dollars,” around Christmastime. “I shouldn’t have done it. I was very forthcoming with Gary.”

He said Carlson had been understanding and treated him like a family member who had gone astray. Rodriguez denied being involved in any of the crimes at Carlson’s properties in more recent years.

Carlson said he tried to solicit help from police to remove the unauthorized people from his buildings but was told he had to file eviction cases. This infuriated him, as in years past, he had found police willing to remove squatters.

Life got complicated for Carlson in 2020. The city sued him over the criminal activity in one building and electrical code violations in another; a tenant filed a lawsuit over injuries from a ceiling collapse in her unit — all cases would eventually settle. Carlson also said he had a prolonged hospital stay that year.

But Carlson rejected the idea that the Covid-19 pandemic had any effect on his property management or revenue. Instead, he contended, any downturn in rent collection was because of “the conspiracy between the city of Chicago and the Chicago Law Department.”

City brings the heat

In early 2021, after yet another police response to a shooting at one of Carlson’s buildings, Ramirez-Rosa requested a meeting with the local police district commander, the CHA, and the Department of Law, the Department of Housing, and the Department of Family and Support Services, according to emails obtained by Injustice Watch.

At the time, the CHA reported 320 voucher-holder households were living in Carlson’s buildings. Ramirez-Rosa wanted to brainstorm ideas for holding Carlson accountable for the crime and code violations at his properties while protecting the “working poor and working class” tenants.

“I do not want to see his tenants displaced,” Ramirez-Rosa wrote in the email to top officials at the city agencies. “I want his tenants and his neighbors to feel safe and secure in their homes.”

Soon, the Law Department sent Carlson a letter saying he had 30 days to address safety issues at six of his buildings or face suits for violating the city’s “drug and gang house” ordinance. Under the ordinance, the city can take landlords to housing court for lax management of building security regardless of whether there are building code violations at the property. In practice, getting a landlord into court over violations of the drug and gang house ordinance can be leveraged to conduct more inspections and hold the landlord accountable for dangerous and hazardous conditions in a building.

One of the buildings specified in the letter was already the subject of a pending housing court case for building code violations. In the letter, assistant corporation counsel Meira Ryan laid out a 17-point list of fixes, all specifically aimed to reduce criminal activity and address tenant safety at the six properties: changing exterior locks, so each building had unique keys; installing security cameras; banning and evicting certain people thought to be involved in the ongoing crime; and putting up “no trespassing” signs.

Carlson called the letter “a nasty gram.” To him, it was just another example of “the city of Chicago acting normally, like a bunch of fucking assholes.”

Meanwhile, the 33rd Ward and 35th Ward offices convened government stakeholders to begin deploying the “Strategic Task Force” — a coalition of the Department of Law, the Department of Buildings, the Department of Housing, and the police — against Carlson. The task force acts as a specialized investigative unit, performing inspections for the purpose of collecting evidence to strengthen the city’s case in court.

Carlson likened the inspection blitz to military assault. “The city is stomping through my buildings like Nazis,” he said. “The violations, some of them are founded, a lot of them are unfounded.”

The task force gave Carlson a 90-day period to make repairs. Unlike the prior 30-day notice, these didn’t focus only on securing buildings but also on fixing conditions issues such as mold, lead paint, and plumbing.

Days later, the CHA informed Carlson he was suspended as a vendor in the voucher program.

Shortly after the expiration of that 90-day period, the police raided Carlson’s building on the corner of Montrose and Lawndale avenues. They seized heroin, cocaine, and $2,000 in a safe and arrested two men long-associated with the rash of crime in Carlson’s properties. Carlson told Block Club Chicago after the raid the police had refused to remove the two men despite his multiple requests for them to do so, “But everybody’s still blaming me.”

According to Illinois law, police cannot remove even unauthorized people from a building unless they are making an arrest — which does not prevent the person from returning once out on bond. The only legal means for removing any tenant or occupant is for the landlord to file an eviction case.

Three days after the raid, the Department of Law signaled it had had enough. In an email to all the city stakeholders, Ryan acknowledged Carlson had made progress on some of their directives but failed on others. She reported how Carlson had “removed problem tenants” in two units and filed an eviction case against a third. He had changed locks on 10 buildings, but those on 66 others remained unchanged.

“We have not received any updates regarding changes to the way management secures vacant units or conducts routine visits to his properties to ensure they remain safe,” Ryan wrote. “To our knowledge, not a single camera has been installed.”

“Law is of the opinion that Mr. Carlson has failed to make a good faith effort to implement the necessary and reasonable abatement measures” Ryan concluded. “Therefore, we respectfully request that the Department of Buildings continue conducting inspections on each of Mr. Carlson’s buildings with three or more units, so that we may move forward in housing court.”

An older white man with grey hair sits in a leather office chair with his button down shirt half open, looking at open filing cabinets. NExt to him sits a younger man in a t-shirt and jean shorts.
Gary Carlson, left, and his leasing agent Erik Rodriguez in Carlson’s Albany Park office in May. The filing cabinet in front of Rodriguez is filled with paperwork related to the city of Chicago’s 73 housing court cases against Carlson. Credit: Abel Uribe for Injustice Watch

In a rare move, the city decided to target the landlord’s entire portfolio. Between July and November 2021, the city filed housing court cases against 48 of Carlson’s buildings. Then the CHA began to suspend payments to Carlson for the voucher holders’ units because of failed inspections. Tenants received notices they would have to move if Carlson didn’t comply with the building code, which left people confused about how much time they had to find new homes and prompted calls to the ward offices. In an email exchange with 33rd Ward and 35th Ward staff at the end of 2021, Daniel Cruz, the CHA’s senior director of government and external affairs, clarified tenants would not have to move immediately if Carlson fixed the building code violations by a certain date.

“I will flag for you that we notice a pattern of brinksmanship with this landlord,” Cruz wrote. “As deadlines approach, he will respond to the city’s Buildings Department and CHA.”

Month after month, the city kept inspecting buildings and filing cases. By mid-February 2022, the city had taken 23 more of Carlson’s buildings to court, and in a rare exercise of the Buildings commissioner’s power to shut down hazardous buildings, ordered one to be cleared and kept vacant. A week after the last of the city’s 73 cases against Carlson was filed, a massive fire ripped through the corner of Richmond and Montrose avenues, destroying a brewery and gym, as well as Carlson’s 21-unit apartment building next door. Fire officials initially posted on social media the blaze appeared to have started below the wooden back stairs of Carlson’s property. However, a Chicago Fire Department spokesman told Injustice Watch investigators were not able to determine an ultimate cause.

One landlord, one judge, 73 cases

Throughout 2022, the cases against Carlson moved quietly through housing court. When the city takes a landlord to court over municipal code violations, the tenants have no formal role in the case, unless they file a motion to intervene and the judge grants it.

In contrast to criminal prosecutions, where victims and witnesses of crimes play a central role in proceedings, tenants aren’t typically called to court to testify about the conditions of their home. In housing court, the city’s lawyers serve as the prosecutors, and the city’s inspectors present the evidence. The only other parties who typically have a formal voice in these cases are the banks that hold the mortgages.

When the government prosecutes people for violations of criminal statutes, the goal of the criminal court is to establish whether a defendant is guilty and disperse appropriate punishment. But when the government prosecutes landlords for violations of the building code, the goal is essentially restorative justice — not so much to punish the wrongdoer but to repair the root cause of the harm, bringing the building into compliance with the code.

“Compliance — that’s the first goal,” said Judge Leonard Murray, the supervisor of the housing court section as he described why city lawyers file building code enforcement cases in the courtrooms he oversees.

“No property in the city of Chicago meets the code 100%, believe me, no such thing,” he said.

Still, once the government files its case, it must present evidence, and property owners are entitled to a trial to defend against the allegations their buildings aren’t up to code. “There aren’t many cases that go to trial,” Murray said.

Instead, city lawyers use the threat of a trial — and the heavy fines that losing one could bring — to pressure building owners to make repairs. Most cases, Murray said, end in a settlement when the city inspectors report substantial compliance and the city drops its case.

In the United States, the Bill of Rights prohibits government agencies from seizing private property without compensating the owners. With limited exceptions, the government also cannot prevent anyone from owning real estate, no matter how bad their history as a landlord. Unlike some municipalities (including many local suburbs and unincorporated Cook County), Chicago does not license landlords, limiting the legal means for intervening in their business.

But housing court does offer a few tools besides the threat of fines to use against landlords who are unwilling or unable to fix their buildings.

If the building is abandoned, the court can transfer title of the property to the city, which can then sell it; the court can order a building to be kept vacant until the code violations are fixed; the court can order a building to be demolished if the unaddressed violations are putting the public at risk; and the court can appoint a receiver — a third-party company charged with handling anything from small repairs to major structural overhauls. Receivers submit bids for work to the court, hire approved contractors, and pay them up front. They are made whole through priority liens on the property, which put them ahead of delinquent mortgages when the property is eventually sold. In the case of heat-related repairs, receivers are reimbursed by the city.

It is technically possible to punish landlords criminally. Property owners can be jailed for up to six months under the building code or the state “criminal housing management” statute, but these charges are all but unheard of. The last report of a Chicago landlord being sentenced to jail over code violations was 22 years ago.

As the city attorneys shepherded Carlson’s buildings through court, they asked for receivers to be appointed for some of the properties. Ramirez-Rosa and 33rd Ward Ald. Rossana Rodriguez sent an enthusiastic letter to the Law Department “in full support of the petition for receivership for Gary Carlson properties,” because, they wrote, “Gary Calson is not a capable landlord. … We believe a receivership is the only way to compel Gary to manage his buildings responsibly.”

But all of the 73 cases against Carlson landed before Murray, who told Injustice Watch he weighs the decision to appoint receivers carefully.

“It’s fee shifting,” he said. “I don’t take it lightly.”

Murray said he perceives the city to sometimes ask for receivers “because it’s the easy way out. I think it’s important to give the owner the opportunity to try to fix it themselves.”

Murray never appointed any receivers for Carlson’s buildings. For months, the cases were repeatedly continued, while Carlson’s lawyer reported to the city’s attorneys his client was working on things. Carlson was given new timelines to complete repairs, but tenants said they weren’t seeing much change. Meanwhile, they continued to receive letters from the CHA telling them they had to move out or lose their vouchers. After ward offices contacted the CHA, the agency said tenants would only have to move if Carlson failed to fix the building code violations.

The people v. Gary Carlson

The CHA’s notices left tenants confused and anxious, they said, and helped mobilize Stennis and her neighbors to form the Fair Tenants Union in early 2023, a year and a half since the city began filing its cascade of cases against Carlson. Some of the union members had lived in Carlson’s buildings for decades, some were older adults, or taking care of family members with disabilities. Many were afraid to be displaced from Albany Park.

“I thought, ‘We gotta do something,’” Stennis said. After meeting with the community organizers and other voucher holders in Carlson’s buildings, the fledgling tenant union asked the 33rd Ward and 35th Ward offices to advocate on their behalf with the CHA. The city council members didn’t get much of a response.

And so in May, the Fair Tenants Union had a press conference shaming the CHA in front of the agency’s headquarters in the Loop. They held signs accusing the agency of “knowingly placing tenants in the hands of a slumlord, for years” and demanded two things: more time to move and more funds for relocation assistance than the $500 initially offered.

“It’s hard to find an apartment, and you’re asking us to move on the spot? These are people who are marginalized or retired,” Stennis said. “You can’t move for $2,000 in Albany Park.”

They continued the pressure on the CHA throughout the early summer, speaking up at board meetings and demanding responses to their grievances. Eventually, the agency gave in, removing deadlines for moves out of Carlson’s buildings and granting tenants up to $1,500 in relocation aid. The CHA announced this policy change would also apply to voucher holders in other troubled buildings.

At the same time, the Fair Tenants Union was getting off the sidelines in court, too.

With the help of the Law Center for Better Housing, they filed a petition to intervene in one of the cases against Carlson. They attached pages of pictures from their apartments in a 13-unit building on Harding Avenue, taken 20 months since the city had filed its case against the building, showing swaths of black mold on walls; ceiling paint bubbling from moisture; electrical outlets blackened by sparking wires; and massive, black cockroaches. They asked the court to free them from the obligation of paying Carlson rent until issues were fixed and to be awarded damages for Carlson’s alleged violation of Illinois’ “implied warranty of habitability” — the obligation for landlords to provide code-compliant housing in exchange for rent. For months, Murray set continuances for the tenants’ request without a ruling on whether they could play a formal role in the case.

Outside court, the alders’ offices continued to be in touch with the city lawyers prosecuting Carlson. At one meeting, the city lawyers told them “that the judge was not amenable to many of the requests of the counsel and was apt to provide many extensions to Carlson,” according to meeting notes obtained by Injustice Watch. “They expressed openness to the motion introduced by the tenants’ lawyers, though they seemed pessimistic about the judge’s reaction.” When the alders asked how the judge might be persuaded, the city lawyers “seemed pessimistic that the judge was movable,” according to the notes.

Murray told Injustice Watch he doesn’t think state law allows tenants to intervene in housing court cases against their landlords, and the right to intervene is reserved for neighboring property owners.

The law, he said, “is not talking about folks in the building; it’s talking about the surrounding neighbors to the extent that their property rights and valuations are affected by what’s going on in that building.”

Murray refused to discuss one of the earliest appellate court decisions to the contrary with Injustice Watch and said another housing court judge’s decision allowing tenants to intervene did not obligate him to rule the same way.

Silhouettes of tenants standing around a projector showing a Zoom housing court hearing.
When Gary Carlson’s tenants showed up to a hearing on the city’s lawsuit against their landlord, they were disappointed they weren’t given the opportunity to speak up. Credit: Illustration by Verónica Martinez

In September, members of the FTU gathered around a projector at the Albany Park Organizing Committee’s tiny storefront half a mile away from Carlson’s office and tuned into a Zoom hearing before Murray. They hoped to tell the judge about the conditions they continued to endure, but Murray, joining the hearing by phone, never turned on his camera or asked them to speak. He hung up shortly after confirming that closed-door settlement talks between Carlson and the city were continuing. By then, the Law Department had added 52 of Carlson’s buildings, including the one on Harding Avenue, to its public scofflaw list.

“That’s it?” one confused tenant asked.

“That was a total letdown,” another one added.

The tenants had expected a formal court hearing, with a judge in robes. But this was more typical of a day in housing court, where many of the scheduled dates on a case consist of brief updates to the judge about agreements between building owners and the city.

For the next two months, court dates continued in a similar manner, with the tenants and their lawyer logging on to Zoom in the hopes of a hearing on their motion to intervene and logging out minutes later with no clear understanding about where things stood.

Stennis and others couldn’t make sense of Murray’s demeanor in court — or at home or in his car, where he sometimes conducted hearings. They said the court process was nothing like they expected it to be. This fostered a conspiratorial skepticism among some, and a sense of hopelessness about ever getting a fair shake.

So indignant were the tenant union members about not being able to get their day in court they had a mock hearing at an Albany Park church in late November: The people v. Gary Carlson

They invited neighbors and the press and put up a 14-minute slideshow with images of the problematic conditions in their homes overlaid with quotes of dismissive and belittling things they had heard from Carlson. They printed a zine explaining their experiences and demands.

“We were hopeful for positive change when the city finally sued him last year,” read the text in the zine. “However, the city’s housing court is not designed to account for tenant experiences.” The text went on to excoriate Murray, accusing him of unprofessionalism and incompetence.

“We have no choice but to hold our own hearing to share publicly how one man, [Gary Carlson], with the support of many systems, has caused great harm to us and our community.”

Stennis and others, some of whom had already managed to move out of Carlson’s buildings, said they spent years living with mold and bugs, as well as thousands out of their pockets on abatement. They told stories of being threatened with eviction for reporting issues with their apartments, and claimed Carlson treated them rudely and shouted at them. Carlson was also invited to participate but canceled at the last minute on the advice of his lawyer. 

Carlson told Injustice Watch tenants’ complaints are always answered and if they aren’t it’s because the tenants haven’t called. One of his employees attended the event and said the accusations against Carlson were unfair.

Stennis took to the mic in front of the gathered crowd after two other union members shared their experiences. She said she tried to warn Carlson about a possible fire from a sparking light switch in her unit, to no avail.

“I was so nervous I stopped using the switch,” she said.

She described using hammers and chisels to break ice on the outdoor stairs of her building in the winter and personally paying for salt.

“I had to cover all the costs out of my own pocket,” she said. “If I wanted to be safe, I had to take care of the dangerous conditions myself.”

“Yes, I’m a strong Black woman, but damn, I be tired sometimes,” she said. “It’s exhausting having to argue with somebody every day.”

Stennis said she was grateful to be living in a new apartment where she felt safe. “But people are still suffering in Gary’s buildings,” she said. “The city, Judge Leonard Murray — no one is taking accountability for this shit. And it’s high time someone did.”

The tenants were worried the city would settle its cases against Carlson, and nothing would change. Despite losing most of his voucher-tenant base, Carlson continued to populate his buildings with new residents — many of them were recently arrived migrant families.

‘Nothing beats a failure but a try’

In February, two and a half years after it began filing its cases, the city reached a settlement with Carlson: He accepted liability for all the code violations at all the properties and agreed to pay $35,400 in fines for violations at 59 buildings.

Carlson also agreed to hire a professional management company to oversee 13 of his buildings, install cameras and have an after-hours call service at 11 others, and keep vacant two buildings that were too unsafe to inhabit.

He also agreed to “provide notice to all current and future tenants of normal business hours (8:00-5:00) and contact name/info for person managing the property,” according to an overview of the settlement agreement provided by the city. Carlson was given a year to bring all properties into compliance with the building code or face daily fines of $500 per violation.

Ramirez-Rosa and Rodriguez released statements praising the city’s efforts and celebrating a win over Carlson. The tenants and organizers were cautiously optimistic. Who would be enforcing the terms of the settlement and monitoring Carlson’s compliance? It was never made clear, but tenants and organizers soon understood it would be on them to continue policing Carlson.

Less than four months after the settlement, the city was back in front of Murray with an emergency petition to hold Carlson in contempt of court for not following through with the agreement, particularly not hiring the promised management company.

But Murray made no rulings and issued no fines after Carlson’s attorney told the city Carlson was imminently entering into a contract with a different management company. The cases were continued again.

Despite promising the city he would start to accept calls from tenants throughout the day, the half-hour, four-day-per-week complaint line was still the protocol for tenants in buildings managed directly by Carlson as of mid-July.

During the interview with Injustice Watch, he was indignant at the notion he should keep different hours. “Why are they telling me something that they’re not telling anybody else? Including my peer group of landlords, why?”

Having an open-door policy means “anybody that comes in, you have to stop and talk to them, now you’ve got a nasty, rag-a-nag tenant that’s gonna bully their way into your space and demand that you send a man over to their apartment right now to kill the roaches — at 10 minutes to five, on a Friday!” Carlson was on a roll, his voice rising. “I decided that I don’t take any calls on Friday — to send a message to my miserable tenants that I don’t take this type of complaint on Friday.”

Close up of a doorknob, two bones and a pad of Post-It notes on top of a filing cabinet.
Gary Carlson says he likes to show prospective tenants items he and his staff have pulled out of clogged toilets over the years — which include this doorknob and bones. Credit: Abel Uribe for Injustice Watch

In addition to paying the fines, Carlson said he’s spent at least $2 million so far fixing violations stemming from the city’s cases. The insurance payout from the building on Richmond Avenue burning down has helped offset those costs, he said. Carlson isn’t worried Murray will impose more fines, or that there would be other penalties for noncompliance with the terms of the settlement. It seemed the whole experience of being taken to court hasn’t been more than a temporary, if expensive, nuisance.

“They would love to see some type of reporting that Gary is suffering,” Erik Rodriguez told Injustice Watch at the end of the interview.

“Oh, that would make their day,” Carlson agreed, speaking of the Law and Buildings Departments staff, to whom he repeatedly referred to as “the black hand,” shadily colluding against him.

Asked whether they had anything to say to city officials, they responded enthusiastically.

“Fly a fucking kite,” Rodriguez said, flipping up the middle fingers of both hands. “You got a brother? Fuck him, too.” 

Carlson said today, his business is better than ever. Most of his tenants are recent immigrants who pay market rents: from $750 for a studio to $2,000 for a four-bedroom unit. As he described his current tenants, Carlson’s eyes suddenly welled with tears.

“These immigrants work,” he said, his voice catching in his throat. “They get up every day, the husband is gonna work, the wife is gonna work, the kids are gonna work.” He said his former Section 8 tenant base “feels like they’re entitled to you. Your immigrants have got a high level of appreciation.”

Carlson’s defiance came as no surprise to Stennis, her former neighbors, and the organizers who had helped them mobilize the Fair Tenants Union. Staff from the 33rd Ward, where most of Carlson’s buildings are now located, said they continue to receive complaints from residents about conditions at Carlson’s properties.

“I think that Gary is just a symbol of what it looks like for housing to be commodified and for it to be OK that housing is commodified,” said Evelyn Vargas, an organizer with the Autonomous Tenants Union who had assisted Carlson’s tenants.

“You put in all of these systems to get the worst of the worst of the landlords, and they don’t work. This story is a good example of what doesn’t work. And it has cost people their homes, their lives, their peace.”

Stennis says since moving out of Carlson’s building, her health has improved, and she attributes that to decreased anxiety over her housing conditions. “Having a landlord that causes your stress will affect your entire life,” she says.

A black woman in a headwrap and flowy shirt smiles in front of a large green plant.
Thelia Stennis at her new apartment in Albany Park on July 13. Credit: Abel Uribe for Injustice Watch

She and her cat now live in a newly constructed building where her airy two-bedroom unit has sweeping views from the sixth-story windows. On a recent walk past her last Carlson residence, just a few blocks away, she noticed the back gate of the building was still as broken as it was years ago. Gray paint peeled in clumps and a hole gaped in a porch step next to her old back door.

Despite the letdowns in housing court, she has no regrets about organizing against her landlord, and she credits that work with the fact that she was able to get the time she needed from the CHA to move and to find a new place to live in Albany Park. As she likes to put it, “Nothing beats a failure but a try.”

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Alejandra Cancino reports on housing and the court system. Before joining Injustice Watch in 2023, she was an editor training emerging journalists and an investigative reporter whose award-winning work focused on the intersection between government and business. She has worked at City Bureau, the Better Government Association (now the Illinois Answers Project), the Chicago Tribune, and the Palm Beach Post. Alejandra grew up in Latin America and Miami and enjoys traveling the world in search of good hikes.

Maya Dukmasova reports on judges, prisons, and the courts. Before joining Injustice Watch in 2021, Maya was a senior writer at the Chicago Reader, where she produced award-winning long-form features and investigative stories, as well as profiles, film reviews, and essays on a wide range of topics. Maya was born in St. Petersburg, Russia, and spent much of her childhood in Appalachia. She moved to Chicago after completing a master’s degree in art history at the University of Cambridge and now lives on the Far North Side.