The Hotel for the Homeless

A bold experiment at an old Lincoln Square motel represents a pioneering approach to housing the unhoused.

October 15, 2024, 6:00 am

The Diplomat Motel is a relic of the golden age of travel. Nestled between freshly built apartments and across from Tony’s Fresh Market on a stretch of U.S. Route 41 that runs on Lincoln Avenue, it’s a glimpse of what this North Side neighborhood of Lincoln Square was like before the Edens Expressway took travelers away from the old highway.

Combing through images online, I find a midcentury postcard of the Diplomat. Painted in peachy pinks and soft blues, the motel is delightful, with its neat lines of windows and a lovely little office. Clusters of sharp atomic diamonds evoke the architecture of the 1950s.

When I moved into the neighborhood in 2022, the Diplomat, still in operation at 5230 North Lincoln Avenue, no longer looked like the kind of building that could be on a novelty postcard. Instead, the motel was a muddy gray, its doors painted green with shocks of red trim. The windows along the sidewalk had been plastered over, a slab of nondescript brown that would press itself into your periphery when you walked past it. You didn’t know, but also you knew, what went on inside the Diplomat, why people would warn in a whisper to never let visitors stay there. When you idled in front, in traffic, the building felt like a bruise on the streetscape.

A few months later, Chicago artist Sick Fisher was hired to paint one of his signature trompe l’oeil murals onto the bare brown wall. In bubbly purples and greens, he added cartoonish columns, windows with flower boxes, a balcony rail. A placard on the ground-floor door reads “Presidential Suite”; the door above it opens to nowhere.

That was before the city announced, in 2023, that it was going to buy the motel. That it was going to turn the Diplomat into a transitional housing facility called the Haven on Lincoln, a chance to try something new that could maybe, just maybe, address this city’s struggles with homelessness.

Before then, the mural seemed like an inside joke — who could ever imagine a motel, this motel, with lush plants and a fresh coat of paint? But now, knowing what we know — knowing what will happen to the Diplomat in a few short months — the mural is a game. Turn your head a bit. Blur out the stained curtains, remove the dingy corners. Imagine what this place could be.

It was an early-September Sunday. Summer still had its grip on the city. My husband and I were stuck in traffic on Peterson Avenue and saw, right in front of an abandoned medical tower, a man lying on his back across the sidewalk, his arms and legs outstretched.

“Is he OK?”

“Should we call … ?”

In the seconds that followed, as we waited at the red light, we talked over each other, trying to assess the right thing to do. I dialed 911.

“I — we don’t know if he’s OK,” I began to explain to the operator. “He’s not moving and we’re not sure if he’s … if he’s hurt.”

The light turned green, traffic started moving. We drove away.

By the time we arrived home, only a few blocks away, we could hear the sirens getting closer. Perhaps for that man, we hoped. Maybe it was only heat exhaustion. Or maybe we misread the entire situation and this was just a story of someone trying to catch a beat, trying to get some rest in the midafternoon sun. But it didn’t look that way. And in the split second of decision, when we questioned if we should do anything, I felt myself wonder if really we needed to do anything at all. We sat in traffic, cars chugging bumper to bumper. Surely someone else had called 911; surely someone else had stepped up. But we couldn’t seem to shake the question: What if no one else had?

I’m thinking about this — about the ways in which we show up for our neighbors, about resources, about who’s responsible for what and for whom — on a Monday morning later that month as I make my way south on Lincoln Avenue.

Alderperson Andre Vasquez pushed for the pilot program, now called the Haven on Lincoln, to be in his ward.

It’s been a few weeks since I’ve driven through this stretch, and I marvel at how quickly this city can change. The new builds have built up, their shadows casting new shapes onto the road’s asphalt. The Diplomat Motel, once a stalwart, strong and foreboding among a sea of single-story strip malls and parking lots, is newly dwarfed by the three-story condo building that’s nearly complete. I pull into one of the Diplomat’s two parking lots, where I meet the man in charge of overhauling the motel.

“Honestly, we were mostly concerned about the solar panels we’re installing on the roof,” Sean McGuire, a senior associate at the architecture firm Gensler, says with a laugh when I ask about the rapidly changing streetscape, now full of multistory buildings that block the sun at times. We’re standing below the motel’s sign, which still beckons potential guests with promises of HBO and Showtime. A city truck idles in the parking lot; a man begins to snake a hose into the drain. “We’re double-checking the sewer and storm line,” McGuire explains as we make our way past the construction fencing and toward the building.

It’s been about a year and a half since the neighborhood got wind that this old motel was going to be converted into something the city was calling “stabilization housing,” and while I’ve spent the better part of that time trying to understand exactly what that entails, until today, I’ve never actually been to the Diplomat. The motel’s transformation into the Haven on Lincoln is a pilot program that will provide housing to homeless people in the throes of addiction and mental illness, without any requirements like sobriety — what’s known as a “housing first” model. And unlike traditional shelters, everyone will get their own room.

“This project is the kind of project that makes people want to study architecture,” McGuire says.

He motions to the parking lot. “All this asphalt will get torn up.” In its place will go a park with trees and shrubs and seating for upward of 75 people. I feel the sun beating down on the blacktop and imagine how pleasing some green space would be. It feels like this strip of Lincoln has been consumed by the dull gray of construction dust for years.

McGuire tells me about a project he worked on in Ohio. It was a neuroscience wellness center, one where the design of the physical space catered to the mental and emotional needs of patients dealing with neurodegenerative diseases. This kind of consideration, which McGuire says is a growing trend in architecture, is also influencing how he, the city, and Volunteers of America Illinois, the nonprofit selected to run the facility, all conceptualize the Haven.

In addition to having private space, every resident will have access to onsite services for medical, mental health, and addiction support. It’s modeled on an earlier city initiative. From April to September 2020, during the height of the pandemic, more than 200 homeless people, all over the age of 50, were placed in rooms at Hotel One Sixty-Six (formerly Cambria Chicago Magnificent Mile) in Streeterville. The impetus was to prevent the spread of COVID, particularly among vulnerable people, so medical services were brought onsite. Residents were given primary care and also treated for psychiatric and substance abuse disorders. If they needed medication, it was delivered to them. Doctors were able to provide consistent care and, over time, build trust — a different path for a group of people whose access to health care is often through emergency services.

At the Diplomat, McGuire swipes open one of the ground-floor rooms with a keycard. The furniture has been removed. The carpet is stained. On the wall is a still life of a fruit bowl.

McGuire tells me that they’re tearing up the carpet in every room, that they’re replacing the drywall and the lighting. “We want to create moments of celebration,” he says, referring to building’s color scheme, which will be anchored by blues and neutrals in order to convey a feeling of fluidity and contemplation. The same is true of the murals planned for the exterior and of the interior lighting, which won’t be too warm, or too sterile, but just right to give the place a little life.

I think about all the times I drove past the Diplomat before it closed and what I saw. In the parking lot, empty cars. In the open-air hallways, abandoned cleaning trolleys and industrial-size laundry carts. Never any people. Never many signs of life. The things that happened at the Diplomat were simultaneously mysterious and overt.

It makes this new openness — the purported transparency of a government program — feel almost strange. When the Haven opens in the late spring or early summer of 2025, it will house 40 people, all of whom will be what the city considers “high utilizers” of the system: individuals with repeated interactions with emergency rooms, 911 services, or shelters. They’ll be referred by the crisis support systems they’ve cycled in and out of for years and given direct access to the services they need to, hopefully, get back on their feet for good.

The rooms, standard motel size at 12.5 by 20 feet, are small, but big enough to allow a bit of storage. There’s a shower, a sink. McGuire points out space for a mini fridge. It’s the kind of place that’s comfortable without being too comfortable, which isn’t a bad thing. Residents won’t be here for very long — only three to six months — before they transfer into something more permanent. At least that’s the plan.

The Diplomat is one of nine motels that remain on Lincoln Avenue. Their decline has been steady since the Edens opened in 1951, and all have devolved from quaint accommodations into something more suspect. Neighbors have only their suspicions about what happens behind the drawn curtains and peeling paint — hunches that are occasionally confirmed when a guest throws something through a window in a fit of rage or the news reports that someone else got shot in the parking lot. But these motels have also evolved to fill gaps in the city’s housing landscape. At around $60 a night (often far less if you’re paying by the month), they’re not necessarily cheaper than a market-rate apartment, but you don’t need a deposit or a credit check. The only thing you need to qualify for a room is cash.

“It’s no way to live, the motels,” Glenn Hamilton tells me over the phone. We’ve never met in person, but he’s active on the neighborhood Facebook group. He was one of the first people to respond when I posted about wanting to talk with neighbors about the Diplomat.

“I live 3 blocks away and I’d be interested,” he wrote. “I own two similar type hotels near Chinatown so I know the pros and cons.”

That motels are already functioning as semipermanent housing seems to be an open secret. “We had to relocate a lot of folks that were living there,” Nancy Hughes Moyer, CEO of VOA Illinois, says of the Diplomat. “I think we were a little surprised by how many.”

There have been five overdoses at Hamilton’s buildings; he’s had to evict seven people. In one of his motels, there’s a lady on the first floor who’s addicted to crack and keeps everyone up at night, screaming. His other motel, though, he’s been able to turn around. It’s inhabited mostly by seniors living on Social Security. He charges them $500 a month for a room and shared bathroom. Hamilton installed cameras to keep an eye on the place.

That motels like these are functioning as semipermanent housing seems to be the city’s open secret. Hamilton says he knew when he bought them that they were more an investment in low-income housing than anything else.

A few weeks earlier, Nancy Hughes Moyer, CEO of VOA Illinois, had alluded to the same thing when I asked whether the Haven would open by December 2024, as originally planned. “The acquisition [of the Diplomat] took a little longer than expected,” she told me. “We had to relocate a lot of folks that were living there. I think we were a little surprised by how many.”

For those who wanted it, relocation meant being placed in another VOA facility or qualifying for rental assistance. But, according to Hughes Moyer, some residents of the motel opted to simply move to another motel: “They preferred to keep their commitments rather loose.”

Michael is tall and has a firm handshake. He doesn’t say, but I’d guess he’s in his late 40s or early 50s. The day I meet him, he’s wearing a long black sweat-wicking shirt and black nylon shorts. He lifts up his baseball cap to wipe his brow, then sets it on the back of his head.

“I’ve been raking for three hours,” he tells me, taking a drag of a cigarette. “I’m exhausted. Let’s go sit down.”

I follow him to the edge of Gompers Park in North Mayfair, where a line of around 20 or so tents runs parallel to a chainlink fence. A few cluster together, but most stretch out along the concrete path near the park’s perimeter.

Michael, who declined to give his last name, walks toward a little patch of dirt that he’s raked clean of leaves and trash. Under a series of pop-up nylon canopies sitting close to the ground is a collection of small grills. I follow Michael into a blue-and-gray tent, the one closest to the fence. Even though I have to duck my head as I enter, it’s bigger than I thought from the outside. There are three futons, arranged in a U, and a wooden side table. It feels more like a living room than a tent.

Michael at the Gompers Park encampment

Michael motions for me to sit wherever before taking a seat himself. He leans back. “Contrary to popular belief,” he begins before being interrupted by a younger guy asking if he’s got water.

“I do not. Brian or Andy over there, they should be able to get you some liquid.” The guy gives a half wave in thanks as he walks in the direction Michael is pointing.

“Contrary to popular belief,” Michael continues, his voice measured, almost melodic. He doesn’t speak slowly, but he’s not rushed. I’m in his house, on his time. “Contrary to popular belief, we’re not slobs living in squalor.”

Michael shakes his head. Holds his phone out to me. “Channel 9. Play the thing. The lady in charge of the …” His voice trails off. He’s referring to a WGN-TV news report from a week earlier. The Restore Gompers Park Coalition is upset about the encampment and has petitioned Mayor Brandon Johnson to move out the people living there. In the clip, the coalition’s spokesperson, Gail Beitz, a woman with short gray hair, says: “They need to get housing. They need to get shelter. They also are living in squalor, as well as unsanitary conditions.”

“Whatever,” Michael says. “People have come — people bring us food directly to our tents. Residents come visit. Bring their dogs, bring their kids.”

Michael, who lives in an encampment in Gompers Park, is skeptical about the Haven on Lincoln’s model. “It’s going to cause more confusion,” he says. “Too many egos. Rules and structure getting in the way.”

As we’re talking, I hear people laughing. Someone starts to play music. The weather is nice, the sun is shining. It’s still early in the day, but from where I sit in Michael’s tent, I don’t see squalor. That’s not to say Michael doesn’t want more permanent housing. He points to a wooden table that’s leaning against the fence. He and his partner found the table and matching chairs in an alley — they’ve been collecting things here and there, storing them in a small silver tent next to this one. “It’s my garage,” Michael laughs. I can’t help but smile: His brand of tidiness, this careful storage and organization of stuff, reminds me of my dad.

“The idea is, once we get our own place, at least we’ll have furniture to start with,” Michael continues. But the table is broken. So are two of the chairs. One of the men in the camp who has severe mental issues attacked some people during a recent episode, including Michael’s partner. They called 911, and the man happened to be sitting at the table when the police arrived. Michael says an officer kicked the chairs and knocked over the table, shattering its glass top.

“And then they didn’t even take him away,” Michael tells me. “He said, ‘Eh, I don’t think you’ll have any problems with him tonight.’ ” The officer asked if he wanted to sign a report, but Michael didn’t. He preferred that the man get psychiatric help. “I want you to see that he’s having issues here,” Michael told the officer. “Can you send someone, please?”

But the officer didn’t. While we talk, the man passes by the tent and asks Michael about something. It looks like he’s having a good morning. If Michael hadn’t told me, I would never have guessed the man has a history of attacking people.

I ask Michael about the Haven. He’s familiar with the old motel, a couple of miles east of here. “Drug use, prostitution, et cetera,” he responds.

Michael could potentially qualify for the Haven — he shared with me that he struggles with addiction. The man who attacked his partner certainly would. In general, people in this community are interested in what the program could offer. On the North Side, there are no other noncongregant facilities — that is, no other shelters where everyone gets a private space. (Such a shelter for men is slated to open this fall in Rogers Park.) Most of the city-contracted shelters are downtown or farther south, but most of the residents of the Gompers Park encampment have roots in this part of town. Michael’s kids live in Irving Park, and he doesn’t have a car. He’s not interested in moving farther away from what tenuous support systems he has.

I ask Michael if he’s ever stayed at a traditional congregant shelter. “Not necessarily,” he says. “Not entirely clean, there’s drug use, crime, and scandal.” The curfews make it so that he couldn’t get night shifts. Even if that weren’t an issue, the dorms are closed during the day, so he wouldn’t be able to get good sleep before work.

That would make a place like the Haven ideal for him. Still, he is skeptical about the model. “It’s going to cause more confusion,” he says, holding his cigarette up to his mouth. “Too many egos. Rules and structure getting in the way.”

He tells me that a year ago, he was at the top of the list for permanent housing with one of the area’s providers. But when representatives came to the encampment for his intake appointment, he was out looking for work, he says. His phone was broken, and he didn’t have the money to replace it, so he never received their calls.

They could have left a note, he says. “We hang notes on trees here.” It’s also how city workers let residents know when they’re coming to clean out the encampment.

I ask another encampment resident, who introduces himself as Candy Andy (“ ’Cause I’m sweet,” he tells me with a wink), about the Haven. He had an apartment for a year, after he got out of prison, but he lost it. He bounces around, does some couch surfing. “I’ve got three to six months to spare,” he says. “Give me transitional housing, it’ll work.” He’s wearing a T-shirt with a cartoon drawing of cheese.

“When they do bundle services [such as medical care and therapy], it’s great,” he continues. “The only question is in the aftermath, the fallout. What I mean is, after it’s done and moving on, where next?”

Candy Andy crosses his arms, flicks a homemade cigarette. “An overwhelming majority, painfully overwhelming majority, of the people who are out here are not only addicted to drugs but are, like, party animals. I’m saying there’s a time and place, you know?” He leans in close, with a wry smile. “And they don’t have that sense of time and place.”

I see people wandering around the encampment. One guy is filling a box with trash to take to the dumpster. A few of the guys don’t speak English, but Candy Andy helps them out: “I talk to and translate for other people. It’s what I do.” He’s fluent in three languages — English, Spanish, and Polish — and we spend a few minutes talking about Polish phrasal verbs.

“Look, I wouldn’t mind being in a cohort on a committee,” Michael tells me back in his tent. “I wouldn’t mind someone saying, ‘We’re writing a check, and we’re going to put you in a hotel right now.’ ” He leans back. “Occupancy rates are low — I’m sure we can give some kind of deal. We can give them a cut back on the taxes they’re paying right now.”

I hear a woman walk into the park. She’s asking if anyone is around — telling the residents that she’s figured out a way to help them make foundations for their tents using chicken wire and plaster. She saw the WGN report and wants to help. “I can run to the store right now to get supplies,” she tells them. As I walk toward the parking lot to leave, I hear Michael asking her questions. I can tell he’s used to this. Used to well-meaning people wanting to help.

At Gompers Park I got the sense that for some, encampments are preferable to shelters. The city’s system seems chaotic, at best. My friend Peter Rak, who worked at one of Chicago’s largest shelters (he prefers not to say which), echoes that sentiment: “Shelters are not great places to live.” Rak worked with only that one organization, but, combined with what Michael and Candy Andy shared, his experience seems to speak more generally. Rak’s shelter was frequently and severely understaffed. At night, in the dorms, drug use and violence were pervasive. Residents were sometimes robbed right outside the premises; those with mental illnesses were often targeted.

If someone was caught with drugs or alcohol, they were permanently banned. If someone became physical in any way, that also led to a permanent ban. Which meant residents might be one mental health episode away from getting kicked out and not having a place to stay. Meanwhile, the staff was dealing with upward of 200 people a night; there weren’t the resources to give individualized care to the people who needed it.

Then there’s the issue of personal property. Where Rak worked, there were too many people to not have strict parameters on storage; everyone who got a bed also got a small locker. But lockers abandoned for more than seven days were emptied out, and unclaimed belongings were ultimately disposed of. “If someone got hit by a car and had to spend a month in the hospital, or went to jail — really important documents would sometimes get thrown out,” Rak says. Documents that would be needed to apply for a job or to get housing.

There’s a fend-for-yourself mentality that pervades the shelter system. The promise of the Haven, if it works the way the city hopes, is that it will allow people to feel safe and secure. Once they have stability, the thinking goes, they can then address their health conditions in a meaningful way.

Green space and seating for 75 people will replace one of the old motel’s parking lots.Rendering: © Gensler

It’s why Hughes Moyer, the CEO of VOA Illinois, says the Haven will be what’s known as “low threshold, low demand.” To qualify for a room, residents need only to come as they are. That is where providers will meet them in their treatment. A person won’t need to do anything to qualify for a room, and there won’t be requirements for compliance or behavior. And whoever lives at the Haven will be able to come and go as they please.

But does this kind of agency really offer the safest environment? “Sometimes what you perceive as helping individuals feel safe can make them feel like you’re treating them like somebody that everybody else has to be protected from,” says Hughes Moyer. “You don’t want them to feel like they’re being surveilled.”

Watching the video of a community meeting from May 2023, I can feel the room crackle, the energy swell as people flow into the auditorium at Swedish Hospital. As things get started, 40th Ward alderperson Andre Vasquez stands behind the lectern onstage. Representatives from Chicago’s Department of Public Health and Department of Housing are there, too. Within minutes, it’s clear that this is not so much a community meeting as a pitch and plea: We want to do this. We should do this.

Vasquez was an early champion of the pilot project, having advocated for bringing it to the site of the Diplomat, which is in his ward. Now he’s downright giddy when I talk to him in July. “I think the city saw that I was more than willing to help quarterback to get this completed in a way that they probably didn’t see in other places,” he tells me, smiling. “The competitive part of me wanted to be the first to do it. No risk, no reward. We can get this thing done and show it’s successful.”

The line between bullish and brazen is razor thin, about as thin as the margin for error for a project like the Haven — but it’s where Vasquez seems to thrive, bringing unbridled optimism and progressive policies to a ward that is home to both multimillion-dollar mansions and clusters of tent communities. There’s a somewhat general consensus that this brand of idealism is what this quiet, residential corner of Chicago wants. (In 2023, Vasquez was reelected with nearly 80 percent of the vote.) But there are those who are vocal in their opposition. They identify as liberal, but they don’t trust the alderperson’s politics. They characterize Vasquez as naive and opportunistic, trying to make nice with the city’s new progressive leadership, even if it means making the neighborhood more susceptible to crime. “I think for most aldermen, it would be unusual to voluntarily pursue, or want something like this, in your ward,” says John Sugrue, a decades-long resident of the 40th Ward and president of the Arcadia Terrace Neighborhood Association.

The divide is on full display in the video of that May 2023 community meeting, which followed weeks of raucous debate in our neighborhood Facebook group. The comments, both on Facebook and at the meeting, range from supportive to vehemently disapproving. At one point, a woman shouts that the migrants don’t deserve to be here, incorrectly assuming the Haven would be for them.

By the time a woman named Maureen Carroll approaches the microphone, toward the end of the hourlong meeting, the energy is high. People start anticipating what will be said next, primed to applaud or boo. Carroll begins by stating that she has lived in the neighborhood since 1967 and that she worked decades earlier for Pat O’Connor, the longtime City Council member Vasquez defeated in a 2019 runoff. Even in the video recording, you can feel the room brace itself.

“We have people in our ward already,” Carroll says, “who live here, who grew up here, were born here, who, through no fault of their own, now have problems that their families, myself included, cannot solve.” The room, for the first time, is completely silent. “I’m 81 years old,” she continues, “and I love these people. But I cannot help them. This sort of program, if it is feasible and if it works, is something we need.”

I find myself walking toward the river one late-August afternoon. I promised my daughter a trip to the playground, but as we get close to the park, I remember what a neighborhood resident told me about the homeless encampment underneath the Bryn Mawr Bridge, which had been cleared out a few weeks earlier. “They’re back,” said Irena, who requested her last name not be used. She also lives in the 40th Ward, and her exasperation was palpable. “I heard there’s a family.”

Sure enough, I see a flash of neon webbing as the sun hits the reflective fabric that had been sewn on top of a bright blue tent. A biker whizzes by, unaware or uninterested.

“Earlier this summer, there were six or seven fires under the bridges,” Irena said. “No one wants to take responsibility for this.” I’d called to ask her about the Haven, if she thought it could be successful, but first she wanted to tell me about the bridge encampment. According to Irena, it had everything to do with the empty promises the city makes: “There was supposed to be a major cleanup on July 30. The city was going to get them placement. Most of those people came back.”

On this day, I see only one tent, but I get what she’s saying. Is the Haven, like the bridge cleanups, a solution, or is it lip service? Weeks after we talked, both the city and the CTA came under pressure to reform something, anything, after four people — at least two of them confirmed to be homeless — were shot in the early-morning hours on the Blue Line. It’s hard not to feel like the kind of solution that the Haven promises is merely a Band-Aid on a gushing, gaping wound.

I share this sentiment with Sendy Soto, the city’s first chief homelessness officer, appointed by Mayor Johnson in April, six months after he signed an executive order creating the position. Johnson is serious about combating homelessness, but voters rejected his signature proposal: the Bring Chicago Home ballot initiative, which promised to earmark $100 million a year for permanent housing and additional homeless services. Some consolation for the mayor: The City Council later approved his $1.25 billion housing and economic development bond, which included $20 million to $30 million for supportive housing through 2028.

Hughes Moyer of VOA Illinois, which will run the Haven

“There’s not enough funding — not only for the built environment, but also for the social services,” Soto says. “Bring Chicago Home would have directed that toward direct services. Despite the bond ordinance, we still need dollars for the organizations that are going into these facilities.” Additional money will be tough to come by, considering the city is facing a $982 million budget gap for 2025.

To get it up and running, the Haven received a patchwork of funding from the state and federal governments. Approximately $9.5 million has come from President Joe Biden’s American Rescue Plan, all of which will go toward onsite services and other needs and is to be spent by the end of 2026. The city itself is contributing around $10 million — $6 million from the Chicago Recovery Plan and $4 million in TIF funding to purchase and renovate the motel. Although it represents a relatively high percentage of the $58 million the city spent on addressing homelessness in 2023, it’s the bare minimum needed to start a program like this. Once residents move in, the city will seek additional funding sources, such as Medicaid reimbursement and grants, to sustain the program. If it works, the aspiration is to have something like the Haven in every ward.

“I really hope this program works,” says my friend who previously worked at a shelter. “But if it does, it’s going to be messy. It might not be the idyllic thing people have in their minds right now.”

Of course not everyone is convinced that throwing money at the problem will help all that much, that the Haven will be anything but a temporary fix. It’s something Irena brought up as we discussed what happens after residents leave the facility. “What do we know about the long-term success rate?” she said. “Are those people just going to go back to being homeless? What are the support services?”

The official explanation — and expectation — is that most of the residents, upon leaving the program, will qualify for certified community behavioral health clinics. These are nonprofits that provide, among other things, 24/7 crisis services and access to the same kind of services residents will have received at the Haven — though not typically shelter. “VOA will work with residents to ensure that they exit the Haven into housing that they feel will meet their needs,” Ryann Billitteri of the Department of Public Health said in an email. But without many comparable facilities around town, it’s hard to predict the long-term impact. A study released in December 2021 found that more than half of the residents from the Hotel One Sixty-Six project had been placed in some sort of permanent housing, ranging from specialized mental health facilities to Chicago Housing Authority units. But that’s as far as the data goes.

“Does the city have the resources? They have the folks that I trust.” I’m talking to the Reverend Lindsey Joyce, a pastor at three churches, in Rogers Park, Portage Park, and Logan Square, and the copresident of ONE Northside, a social justice coalition of over 100 community organizations and residents from seven North Side neighborhoods.

During the May 2023 community meeting, Joyce made one of the more impassioned statements. The audio crackles on the video recording when she begins to speak, nearly shouting: “We have been asking for something like this forever!” A year later, I ask what she thought of the pilot’s progress — if the information that’s been rolling out about the Haven gives her continued confidence in what the program can do.

“I wish we could provide stabilization housing for anyone who needed it, forever. But I know that’s not politically possible to do.” I hear the same fervor from the meeting echoing in her voice now. “We know what to do. It’s a matter of having the courage and will to do it.”

This courage is rooted in a kind of hope — a hope shared by Vasquez and Hughes Moyer and McGuire and countless others — that casts a vision for a future where people experiencing homelessness can actually work toward autonomy and freedom. The promise of a new approach can’t help but fuel an abundance of optimism.

There is also still much skepticism in the neighborhood that something like this could work, that future residents of the Haven will actually get the long-term support they need in a neighborhood with skyrocketing housing costs. Some neighbors worry that the Haven will only succeed in attracting more crime. But a few have come around. Hamilton, the owner of the motels in Chinatown, was one of the program’s loudest opponents early on. Now he tells me that he’s on board. He has talked with Vasquez. He’s met with the developers. His daughter works at Tony’s and has seen the shoplifting and petty crime subside with the closure of the Diplomat.

Perhaps it’s more than a change of heart for Hamilton. Perhaps it’s because he has his own motels and now understands what the city has been saying for months: that the things everyone is afraid of — the drugs, the violence, the crime — have existed in the neighborhood’s motels for years, so why not try to do something about it?

“I really hope this program works,” my friend Rak says. He left the shelter after a year, more disillusioned and confused about how to combat homelessness. “But if it does work, it’s going to be messy. It might not be the idyllic thing people have in their minds right now.”

I think about the kinetic energy of a word like “might.” The momentum that’s held in the breath before taking a leap into the unknown. There’s research, there are plans, there’s some precedent that suggests what the Haven could provide for the city. In 2016, Denver launched the Denver Supportive Housing Social Impact Bond Initiative, which provided transitional housing and onsite services to unhoused people. After two years, 81 percent of those who then moved into permanent housing remained housed. But there’s undoubtedly a dearth of long-term data, fueling anxiety and pointing to a simple truth: We won’t know if the Haven will work until we try.

“People who experience homelessness are the housing experts,” Joyce says toward the end of our conversation. “And they’ve told us, time and time again, that what they need is housing and wraparound support.”

In the parking lot of the old motel, McGuire tells me that he’s seen the vintage postcard of the Diplomat and that his team is going to try to bring it back to the way it was. They’re tearing down the faux stucco façade to showcase the midcentury modern design elements. Once the renovations have been completed, Sick Fisher has been commissioned to paint a new mural, this time with the peachy pinks and blues from the motel’s heyday. But we can’t really go back to the way things were, can we? We can only march forward and hope that whatever we’re doing, it’s our very best.