A Journey from Homelessness to a Room of One’s Own

At a supportive-housing facility, chronically unhoused New Yorkers get a new lease on life, with a gym, a computer room—and on-site mental-health and medical services.

A person wearing a sweatshirt is seen from behind looking out a window.
Jessica tours her new apartment at 90 Sands, February 15, 2023: “I slept on Thirty-fourth Street between Madison and Fifth for, like, a year and a half, the same spot,” she said.Photographs by José A. Alvarado Jr. for The New Yorker

Jessica moved into 90 Sands Street, a vast new supportive-housing facility in Brooklyn, on February 15th: a bleak, cloudy morning. The move came not a moment too soon; there had been much upheaval in her life in the previous few weeks, including an assault by her ex-boyfriend and two of his friends that had left her with facial bruises, and an overdose caused by the presence of the animal tranquillizer xylazine in her heroin—an honest error, it seemed, on the part of her trusted dealer—for which the forty-two-year-old was rushed to Mount Sinai from the transitional-housing facility where she’d been living for nine months. “I was dead,” she told me with characteristic flair, in her strong Southern accent. “When I left in the ambulance, I was dead. They gave me CPR, they took me to the best hospital in Manhattan, and they shocked me in the hospital six times.”

Her hospital discharge paper flapped in the breeze on top of one of the many plastic tubs that Jessica, her friend Bill, and her case manager, Carley Medley, hauled from Jessica’s transitional-housing room to the van that Medley was driving. (Jessica’s name and those of her friends and family have been changed.) Given that Jessica had spent most of the previous seven years living outdoors (with two interludes in jail for probation violations on old drug-related charges), she had amassed a remarkable number of possessions: Barbies and LOL Surprise! Balls, craft kits, scented candles, and an array of cosmetics. Jessica is savvy and resourceful, which is partly how she managed to survive, alone, on New York’s streets. In addition to panhandling, which usually brought in a hundred dollars a day, she ran an online business with a friend, selling merchandise they’d bought at a discount from “boosters,” who often had stolen it from large stores. Hence the random assortment of brand-new items in her bins.

Medley and Jessica met in 2019, when Medley, who is now twenty-nine, moved to New York with the goal of working in homeless outreach, an interest that was sparked by research on unhoused mothers that she did as a student at Ohio State. She got a job with the nonprofit Breaking Ground, working on a team that seeks out homeless people in and around Macy’s flagship Thirty-fourth Street store. Breaking Ground’s goal is to coax these clients, as they are known, into transitional and ultimately permanent housing without requiring that they first accept treatment for the drug, alcohol, and mental-health issues that are widespread among New Yorkers who live outdoors. This strategy, known as “housing first,” was pioneered in New York, in the early nineteen-nineties, by Sam Tsemberis, a psychologist whose organization, Pathways to Housing, began renting apartments for homeless people with mental-health diagnoses and delivering medical and psychiatric services to them at their new residences—debunking the prevailing belief that people could not remain stably housed without having first undergone treatment. Study after study showed Tsemberis’s approach to be far more successful than requiring treatment in advance. Housing first became a federal policy in the United States with passage of the Hearth Act, in 2009, though advocates say that its implementation is spotty.

Outreach of the kind that Medley was doing at Macy’s is the first step, but even identifying an unhoused person in a bustling department store can be a challenge. “Being in Macy’s is kind of like hiding in plain sight,” Medley told me. “It’s like, Oh, I think I’ve seen that woman sitting here every day this week, and she was here last week. Maybe we can go introduce ourselves, let her know what we’re here for.” This stage of the process, which is known as engagement, is uncertain and often protracted; mistrust leaves many unhoused people reluctant to interact, and, when you’ve managed to survive outdoors in New York City, you might be excused for thinking that you don’t need anyone’s help.

“I just have to finish reading them first.”
Cartoon by P. C. Vey

Jessica is slight, with rounded shoulders, thanks perhaps to years of pushing the small shopping trolley she often has with her. She’s white, with hazel eyes and thick dark hair that reaches to her waist, although she keeps it tied back. While living on the street, she used the oversized sink in Macy’s wheelchair-accessible restroom to clean herself. “I’d strip down naked, sit in the sink, and take a bath,” she told me. “Wash my hair and everything. I would be in there for, like, three hours. . . . They knew it was me in the bathroom, ’cause I would go, like, twice a week.”

Medley first encountered Jessica panhandling outside Macy’s with a sign that identified her as pregnant and fleeing an abusive marriage. Alarmed, Medley alerted her fellow outreach workers. “And they were, like, ‘Carley, that’s so cute. It’s your first day, you don’t know anything yet.’ Her belly looked so real. And they’re, like, ‘Yeah, she’s been pregnant for like a year. It’s a big baby.’ ”

Jessica cheerfully acknowledges the fabrication: “I wouldn’t make any money without that sign!” She is garrulous and unabashed about her drug use and her troubled history, which has included both pregnancy (a daughter and a son, whom she ceded to their father when they were pre-teens, are now healthy young adults) and abusive relationships (her last boyfriend, the one who assaulted her in January, also knocked out many of her teeth and slashed her with a knife, leaving a broad scar). She says that she was introduced to heroin in her mid-thirties by her third husband, who relapsed shortly after their wedding into an addiction that Jessica had been unaware of. “He held me down and shot me up,” she told me. “I had never used drugs in my life, not even smoked weed.” Her husband then persuaded her to leave the Southern state where they were living and come with him to New York. “I said, ‘You promise you’re not going to leave me by myself?’ And he did.” Within a year, she found herself alone in a new city, loosely connected to a group of about fifty drug users, she said, all of them living on the street in midtown Manhattan.

90 Sands, which started taking supportive-housing residents in September, 2022.
Jessica holds the keys to her new apartment at 90 Sands on her move-in day.

Situated in Dumbo, near the Brooklyn waterfront, 90 Sands is thirty stories high and has Richard Scarry-esque views of New York Harbor. Jessica’s newly renovated studio apartment looked pristine, and its triple-paned windows replaced the din of the Manhattan Bridge subway traffic with suctioning silence. Like all the supportive-housing apartments in the building, it was furnished with a full-sized bed, a small table, and two chairs. There were built-in shelves and drawers in an enormous closet, and a “welcome box,” containing bedding, kitchen and cleaning supplies, and toiletries. The building has a gym, a computer room, a laundry room, a bike room, and an outdoor plaza, as well as a team of service providers that includes psychiatrists, a doctor, a nurse practitioner, and an employment specialist.

“There are a hundred types of people who are homeless, but there are basically two patterns: people who are homeless for short periods of time and people who are homeless for very long periods of time,” I was told by Dennis Culhane, a social-science researcher at the University of Pennsylvania, who has spent decades studying modern homelessness and has worked on the problem under the Bush and Obama Administrations. Short-term homelessness is best addressed with what is known as “rapid rehousing”: granting emergency cash and rent money for up to two years. Permanent supportive housing like 90 Sands is the most effective solution for those in the chronically homeless category: generally people with disabilities—usually mental illness or substance-use disorders, often both—who need long-term rent subsidies and support services to keep them stably housed. A recent study showed that about ninety per cent of homeless people who enter supportive housing remain housed after two years.

Supportive housing has evolved since it was introduced in New York, in the early nineteen-eighties, and exists in various forms, from “scattered site” arrangements, in which tenants occupy ordinary apartments (singly or with a roommate), to entire buildings like 90 Sands. What the different arrangements have in common is that case management comes to the tenants with the goal of helping them remain housed. According to an estimate provided by the Supportive Housing Network of New York, there are now thirty-seven thousand units of supportive housing in New York City, about ninety per cent of which are for single adults, and about thirty-eight hundred more are under construction. Still, the quantity is woefully inadequate to the current need. (A Department of Social Services spokesperson said that the city is working to “aggressively expand” its supportive-housing capacity.)

90 Sands was originally a residential hotel for Jehovah’s Witnesses, and it has some unusual features, including a panoramic observation deck on the top floor and a gargantuan underground kitchen that will be rented out to a commercial tenant. Snagging such valuable real estate for a supportive-housing development required some creative financing from Breaking Ground, which then brought in the Center for Urban Community Services (CUCS) to provide on-site social services and medical care. The two organizations have been collaborating on such projects in New York since 1991. By late spring, 90 Sands, which started accepting residents in September of 2022, had filled all of its three hundred and five supportive units, sixty per cent of the building’s apartments. (The supportive residents’ rent is paid by New York City’s Department of Housing Preservation and Development, in combination with either a public-assistance housing allowance or a third of the resident’s income or disability payments.) The remaining hundred and eighty-five apartments are designated “affordable” units to be rented by low- and middle-income New Yorkers through a separate bureaucracy that has proceeded more slowly (as of this writing, about forty-five per cent of the affordable units had been leased), for sums ranging from $537 to $2,132. Mixing supportive and affordable units is a standard industry practice, and the two types of tenants are co-mingled throughout the building. Sixty-one thousand applicants entered the city’s lottery for 90 Sands’s affordable units, a testament to New York’s ongoing crisis of affordable housing.

Eligible individuals are usually referred into specific units by New York City’s Department of Social Services. However, 90 Sands served as a test case for direct referrals, in which Breaking Ground and CUCS, both major players in the city’s street-outreach work and transitional-housing programs, were able to refer qualified clients (Jessica being one) into two-thirds of 90 Sands’s supportive units. This made for an expedited process that proved timely when busloads of asylum seekers began filling the city’s shelters last fall; housing-approved tenants were able to move out quickly to make room.

To qualify for supportive housing at 90 Sands, a homeless person must have received a diagnosis of either a substance-use disorder or a serious mental illness, such as bipolar disorder or schizophrenia. Jessica’s heroin addiction made her eligible, but she insisted, in January, as I sat beside her on a freezing Upper West Side pavement outside Bed Bath & Beyond while she panhandled, that she had no need for that kind of support. “I’ll stay for, like, a year, and hopefully they can find me an apartment without supportive housing. I don’t want to take something from somebody that really needs it,” she said. By the time she moved in, a few weeks later, she had reduced her daily heroin intake from two grams—or twenty-plus bags (“My tolerance is out of this world”)—to a quarter of a gram, which she divided into morning and evening injections. When Jessica was in jail in 2018, she went on methadone, which allowed her to stay heroin-free for several months, but she now regarded methadone as another form of addiction and believed that it was harder on her body than heroin. Years of homelessness and drug use had taken their toll on her physically: she needed oral surgery to remove all her teeth; the veins in her arms were “shot,” meaning damaged from years of injecting; and, in January, a deep new wound appeared where she had injected heroin into her calf—a by-product of that animal tranquillizer that nearly killed her.

“That is a lot of paper . . . my God,” Jessica said at the start of her lease signing, which took place in 90 Sands’s brightly lit conference room at a table decorated with silk flowers. As her emergency contact, Jessica listed Mary, her aunt, whom she lived with as a young child in the Midwest and often referred to as her mother. Her biological parents, whom she called her sperm and egg donors, both had drug addictions and were absent from her early life. Her mother reappeared when Jessica was six and drove her from her aunt’s home to the South. “I didn’t even know her,” Jessica said. She remembers looking out the back window of the car and screaming for her aunt and her grandmother as she was driven away. Her mother had a new husband who abused Jessica, and she left home at fifteen. She finished high school and a year of community college while sharing a small, rented trailer with a female friend. She had her children at nineteen and twenty-two with her first husband and recounts having thrived professionally in young adulthood as a deli bakery manager for a supermarket chain, with more than a dozen bakeries under her supervision. “I had a new car every other year, a house. My kids were spoiled rotten. We went on vacation twice a year,” she told me. But a violent rupture with her second husband brought an end to this stability, and the children went to live with their father. She spoke of wanting to go back to school for culinary arts. “I can decorate wedding cakes, all kinds of cakes. I can do anything in a grocery store,” she said. She and her aunt remained in frequent contact and shared a passion for reading—thrillers especially. When I visited Jessica while she was panhandling on the Upper West Side, she’d come straight from the public library and had in her trolley a backpack crammed with fiction by Michael Connelly, Nora Roberts, Nicholas Sparks, and others. While panhandling, she usually reads a book a day.

After the lease signing, Jessica unpacked her library books and a few other items, including a tiny green cactus in a ceramic vase, which she placed on her new windowsill. Medley handed over Jessica’s birth certificate and New York State I.D.: two hard-won “vital docs,” whose retrieval had been essential to qualifying her for supportive housing. Jessica had lost virtually everything while living outside—most people do, which is why it’s nearly impossible to apply for housing while chronically homeless, and why street outreach and case management are crucial to the process.

It was time for Medley to head back to Manhattan, and Jessica walked out to catch a ride with her. 90 Sands occupies a gap between the Manhattan Bridge, the Brooklyn Bridge, and the B.Q.E.; at times, the roar of overhead trains can halt conversation. “I know nothing about Brooklyn—at all,” she reflected, eying her new surroundings. Her heroin dealer, her panhandling spots, her friends—all of that was still in Manhattan. She climbed into the van with Medley and rode back.

The ongoing influx of asylum seekers caused the number of people being sheltered in New York City to balloon from around sixty-seven thousand last December to a hundred and eleven thousand in August, according to city data. (Counting the homeless is an imperfect science, and the data from D.H.S. and from the Department of Housing and Urban Development don’t always align.) But homelessness had already been rising for nearly a decade in New York and a number of other American cities—Los Angeles, Seattle, Portland, San Francisco, and Washington, D.C., to name a few—where median rents had begun to exceed an average person’s (or family’s) ability to pay. New York State has the second-highest number of homeless people in the nation (largely living in New York City) after California, but whereas almost seventy per cent of California’s homeless live on the street (a sizable portion in vehicles), fewer than six per cent of New York’s do, making homelessness far less visible here. Many factors account for this disparity, chief among them the fact that New York City is the only municipality in America to guarantee a legal right to shelter for individuals and families—the result of court-approved agreements between advocates and the city that date back to the nineteen-eighties. (Massachusetts has a right to shelter for families.) Research disproves the notion that homeless people migrate to the West Coast for the weather; rather, a comparative paucity of shelter beds likely explains the more overt presence of homelessness there.

The six per cent or so of New Yorkers who choose to remain outdoors despite the city’s right to shelter are almost all single adults who tend to be chronically homeless and predominantly male. Often, they sleep on the street because they’re unwilling to enter the city’s huge, centralized shelter system, which separates men and women into large congregate settings, sometimes dozens to a space. (Family shelter is handled through a different centralized system.) Drugs and alcohol are forbidden in city shelters; there are metal detectors and bag searches and a ten-o’clock curfew if one is not to lose one’s bed. Many shelters require that residents vacate the dorms during the day.

“Have you ever thought that maybe I don’t do anything all day because you won’t let me do anything all day?”
Cartoon by Ngozi Ukazu

Thousands of New Yorkers do successfully avail themselves of the city’s shelters. One example is Kenneth Roberson, who moved into 90 Sands last September and was a lively source of knowledge and street smarts for me throughout my research. Roberson, who is sixty-four and Black, with bright-blue eyes, is an avuncular presence; he often covers his shaved head with a do-rag, maintains a tightly manicured mustache and goatee, and has a love of flashy sneakers. As a youth living in the Bronx, he ran with the Wild Cowboys, a notorious drug gang. He doesn’t discuss his crimes, except to say that they went along with what he calls “the life style” of drugs and easy money, which always ends—he likes to quiz me on this—in either jail or death. (“Jenny on the block!” he’ll crow, when I get it right.) Roberson logged more than twenty years behind bars through a combination of state and county bids, the last of which he completed fifteen years ago, at nearly fifty. During his criminal era, he spent two years on the run from police over parole violations, sleeping in abandoned buildings in Harlem to keep the law from breaking down the doors of the two women he adored—his long-term partner, a corrections officer who passed away in 2017, and his mother, whom he cared for in her NYCHA apartment until she died the following year, leaving him homeless because his name wasn’t on her lease. (“God bless you, baby,” Roberson sings out at the mention of either woman.)

Recalling those desperate years of sleeping in derelict spaces can still move Roberson to tears (particularly when he’s drinking vodka), and he had no intention of doing it again after his mother’s death. He reported to the city’s shelter system, where his history may have protected him from what many describe as a predatory atmosphere. “They know who’s who,” Roberson told me. “ ‘Oh, yeah, that’s the drug dealer. Don’t fuck with him. Oh, this guy, yo, he’s been upstate before, he did a lot of time. . . .’ ” Roberson advocated for himself with the shelters’ often overloaded case managers. “You gotta stay on top of those people,” he explained. His vigilance paid off in the form of a city housing voucher.

For those who lack Roberson’s institutional experience, particularly people with fragile mental health, drug addiction, or both, congregate city shelters can be frightening and dangerous. A thirty-four-year-old woman who lives at 90 Sands experienced a psychotic break while doing graduate work in literature at Columbia University. Her erratic behavior got her expelled from the program and cost her her apartment. She spent three years in city shelters, where she says that she was a target of violence from other women. “It’s like prison,” she told me. “But there’s no bars to protect you from people in shelters.” She is working on a memoir about those experiences.

Jessica never entered the shelter system; she’d heard stories of how violent it was, and her husband, who was fleeing arrest warrants when they came to New York, didn’t want to be tracked through official records. The two spent their first winter sleeping in a dog park near Wall Street. “And then we came to midtown and I slept on Thirty-fourth Street between Madison and Fifth for, like, a year and a half, the same spot,” she told me. “I was comfortable. I’ve had mattresses, I’ve had couch cushions I’ve slept on, I’ve had the foam things you can buy that go on your bed: I would put one down on the cardboard and get underneath my thousand blankets.” She carried a knife, but said she’d never had to use it.

The enclaves that people make for themselves outdoors in New York—temporary, vulnerable, subject to vandalism, confiscation, and theft—are proof of how primal the nesting instinct is for nearly all of us. Many formerly unhoused people speak almost tenderly of “my spot” or “my place”: under scaffolding; on church steps; on roofs or in stairwells; in abandoned cars. While accompanying an outreach team in Brooklyn, I saw a frail Black woman using bleach and a broom to scour not just the sidewalk around her makeshift home—constructed of bright-colored beach umbrellas, under elevated subway tracks—but the street itself. John Wood, a white man in his fifties who moved to 90 Sands in March, told me that he’d come to the city from upstate eight years ago with his wife, “my soulmate,” with whom he shared a heroin addiction. The pair refused to be separated into shelters, and Wood instead constructed a series of insulated cave-homes, gouging them into hillsides in Riverside and Morningside Parks. At night, the couple lit their caves with dozens of candles whose eerie flickering beauty Wood captured in videos on his cell phone. That phone was long gone, as were the homes, each eventually discovered and destroyed; as was Wood’s soulmate, who died of blood poisoning resulting from her drug use. But the memory was clearly a vivid one.

Kenneth Roberson, who moved into 90 Sands in 2022, after years in city shelters.

Many people describe acts of kindness from strangers who came to know them over time in their chosen spots. A young woman I spoke with, who immigrated from South Asia with her family when she was eleven, became homeless in her twenties after refusing an arranged marriage. Her parents banished her from their apartment, and she lived in and around parks in Queens for several years, hardly speaking to anyone, often weeping, but cared for by locals who left her plates of hot food, blankets, towels, and money when they passed by on their way to work.

Outreach workers are also a presence in the lives of most people who live outdoors in New York. A handful of nonprofits—Breaking Ground, CUCS, Goddard Riverside, BronxWorks, Project Hospitality, and the Bowery Residents’ Committee (B.R.C.)—contract with the city to coördinate the systematic canvassing of all five boroughs, including the subways, in round-the-clock shifts, seven days a week. Outreach teams must also respond within two hours to 311 calls reporting a problem that involves a homeless individual. (Homeless people may report themselves as a way of requesting help.) These teams of at least two hand out supplies—bottled water and sunscreen in summer, socks and hand warmers in winter—and perform wellness checks, particularly during Code Blue and Code Red periods when temperatures are extreme. A psychiatrist and a physician or nurse practitioner accompany each outreach team once a week to treat patients at their street locations. At the end of each shift, outreach teams enter notes into a central database: listing which clients they saw where, and what interactions took place. Breaking Ground’s corporate partnerships, like the one with Macy’s, operate in addition to this structure.

The goal of all street outreach is to invite homeless individuals first “onto caseload”—meaning that they agree to share their story in detail and to work with a case manager—and then into transitional housing. For those who are averse to city shelters, transitional housing can take the form of “safe havens” or “stabilization beds”—together referred to as “low-barrier units”—newer models that are smaller and more flexible and forgiving than most city shelters. These facilities are often co-ed, though sleeping spaces are divided by gender, and they usually offer more private units, with dividers that extend partway to the ceiling. Like shelters, they serve meals, but there are no curfews, and residents are required to check in only once every seventy-two hours in order to insure that their beds are held for them—an easier standard to meet for those whose lives are disregulated by active addiction or mental-health crises. With a higher concentration of case managers and housing specialists on-site, low-barrier units have become desirable alternatives to city shelters, albeit on a lesser scale. (There are about thirty-five hundred such beds in the city.)

Even with elaborate coördination and information-sharing, though, the process of transitioning someone from the street into housing is patchy and precarious at best. Clients move around and rarely have phones; case managers—a position that generally requires no higher education, license, or specialized training—are poorly paid and often overburdened, though the good ones are heroic and save lives.

Last December, I joined a morning shift in Manhattan with Ramata Touré, a thirty-year-old assistant director at Breaking Ground’s Connect to Care program, which is funded by a consortium of more than sixty companies through the Partnership for NYC. Touré oversees four supervisors and twenty outreach case managers, but, she says, she still likes to do outreach herself “once in a blue moon, just to keep up with my skills.” In a subway entrance on West Forty-sixth Street, she engaged a stocky, strident forty-five-year-old Black man, who was leaning on a pair of crutches and opening a Slim Jim with his teeth. He identified himself as Paul Cameron, and immediately began to complain about not having been placed in transitional housing. Touré offered to arrange transportation for him that afternoon to Olivieri’s, a drop-in center on West Thirtieth Street (drop-in centers have reclining chairs where clients can stay overnight), while she looked for a safe-haven bed for him. Cameron was brashly skeptical. “Everything you say has been said to me,” he challenged Touré. “You sound enthusiastic, but I heard that before.”

Touré had long braided hair, and wore a bright-green Partnership for NYC jacket. “I can’t speak for others,” she rejoined amiably. “I can only say what I can do from our engagement today and on.” She gave Cameron a woollen hat, gloves, and granola bars, and took his photograph so that afternoon outreach workers driving the promised van would recognize him. But I later learned that, when the van arrived at the appointed time, Cameron wasn’t there. It was a cold day, and he may have gone into the subway, where outreach is handled exclusively by the B.R.C. “That’s sometimes where the disconnect can happen, with the up and down,” Touré told me. “When it’s cold, clients will go down.”

A native New Yorker, Touré was studying forensic psychology at John Jay College when she volunteered to join D.H.S.’s PIT count in East Harlem—a “point-in-time” tally of every American municipality’s total homeless population is required every two years. She liked the work and applied to Breaking Ground as a case manager soon afterward. (She completed her master’s degree in social work last fall.) In the Times Square pedestrian plaza, Touré approached the Recharge Station, an outdoor booth operated by Fountain House, a mental-health organization. A small group of people—some tourists, it appeared—were partaking of coffee and snacks while charging their phones. “Identifying who may or may not be homeless can be the tricky part here,” Touré said, scanning the crowd. “People expect clients to look a particular way, and here you will not find that; clients are dressed appropriately, keep up with their hygiene, and blend in. You have to look for a tell: sometimes they’ll have dirty fingernails, certain little markings, and the footwear kind of gives off a little bit.”

A hesitant, bearded older Black man approached Touré; he had been on Breaking Ground’s caseload but had fallen off—something that often happens when people are hospitalized, jailed, or leave the city for a time. Touré arranged for him to go back on and noted his preference for a safe-haven bed. Later, she spotted an elderly white woman hunched over a suitcase under a scaffold, wearing a red Christmas sweater and a red face mask. The woman’s tiny hands were exposed to the bitter chill. Touré approached respectfully. “My name is Ramata. I’m from Breaking Ground. Are you O.K.?” she asked. “Do you want a hand warmer or anything?” The woman started, then recoiled, shrieking incoherently. Touré backed off with an apology. “Some clients resist the engagements,” she explained.

About a month later, in January, I joined James Martin, a CUCS supervisor for street outreach, for a 5:30 a.m. shift in upper Manhattan. Martin is fair and open-faced, and moves at times with the awkwardness of a very tall person. It was a Code Blue day, and we looked for three individuals who required wellness checks but weren’t visible that morning; likely, they’d gone underground to avoid a deluge of rain the previous night. Martin was also searching for a fourth person, a Black woman named Iishea Stone, a wheelchair-bound amputee who had discharged herself from Harlem Hospital—she’d been admitted with Covid—but hadn’t returned to the Kelly, a CUCS safe haven on West 127th Street, where she’d been living for several months. Martin drove past a corner bodega in West Harlem that was Iishea’s usual street spot, but she wasn’t there.

Cartoon by Ken Levine

In upper Harlem and Morningside Heights, Martin canvassed several areas where homeless individuals often encamp, including one under the Henry Hudson Parkway, accessible by a short hike through underbrush. Martin, who fell into outreach work years ago and also completed his master’s degree in social work last fall, spent two years in the Peace Corps in Ecuador; he led the way, calling “Buenos días! ” I followed him into a breathtaking debris field of single-use plastics and kaleidoscopic trash. Though devoid of human beings, the place intimated a breadth of recent activity: soiled mattresses, lighters, brooms and brushes, cigarette butts, a sequinned blue dress, rain-sodden socks, plastic cutlery, lipsticks, curlers, a spool of thread, a hurricane lamp, a crushed baby stroller, and a ubiquitous sprinkling of orange syringe caps. It was a reminder that life doesn’t stop for people who live outdoors, invisible though they often may be to the rest of us. Iishea Stone, the woman Martin had been looking for, articulated this point for me a couple of weeks later, after outreach workers had located her by the bodega and she’d cheerfully accepted a ride back to the Kelly.

“I had a life before this,” Iishea said once she’d rolled her wheelchair into a small office off the Kelly’s bustling hallway. “When I was homeless, I used to roll around the streets at night. I like being outside; I’m like a butterfly. There’s a peace of solitude. I was able to talk to God. If God spoke back, I was able to hear him—either a thought or an emotion, I was able to connect it to God. I roll the streets, like ‘Wheeeeeeee!’ I own the streets—there are no cars.”

The wheelchair was a relatively new addition to Iishea’s life; in 2020, she was run over by a subway train that severed her left foot and half of her left hand. (She had a prosthetic leg, but it hurt to wear it.) At fifty-one, she was a riveting presence, radiant, athletic, and a mesmerizing narrator of a dizzying life story: sexually abused from age five by her stepfather and three older brothers; dismissed by her mother even after the abuse was corroborated by another family member; introduced to crack cocaine at thirteen by family friends who had driven her to an after-school swimming practice. Iishea left home—Far Rockaway—that year and survived on the streets thereafter, mostly around Times Square, where she sold drugs and sought out the company of people who would protect her. She served multiple prison sentences for drug dealing. “The last time was four and a half to nine, and I did every bit of nine years, because I did four state bids already. So I became a ‘persistent predicate,’ which means you keep doing the same goddam thing and you’re gonna get it. But I’m not mad at that.” In prison, she added, “I became a welder, I became a metal fabricator, a cook, I got my G.E.D., and then I got with the older women and I listened. I knew they didn’t want nothing from me. I could sit down and actually be O.K. with listening, you know? And I learned. So when I came home I was a woman. And every bit of a phenomenal woman. And everything I had was enhanced. Everybody will say you become pessimistic from being in prison. Nope. N-O. I found refuge.”

When Iishea completed that sentence, she was in her late thirties. She returned to New York and reconnected with an old acquaintance who became her husband. What followed was a golden interlude: the owner of the Brooklyn halfway house where Iishea stayed after prison agreed to rent her a house in Prospect Lefferts Gardens, and she and her husband lived there with their nine cats. Both stopped using and went on methadone. Iishea’s husband had maintenance jobs at two churches, and Iishea worked at a deli and went to T.C.I. College. Every other Thursday, they took the train to Harlem for a comedy show. Then their housing fell apart: they were supposed to move into a rental apartment in a Brooklyn brownstone, but the building was sold to new owners who rescinded the agreement—a development that seems to have crushed them.

“We got a monkey wrench thrown in our plans . . . it felt like all our hard work just went down the drain,” Iishea told me. They went to a family shelter and were placed in a boarding house on Park Avenue, in Harlem, that was vermin-infested. Both went back to drugs and began drinking heavily. “We used to sit there and watch the mice playing tag on our table. . . . Everything just . . . it went downhill. Everything you built—you watch it disappear just like that.”

Her husband found maintenance work in Harlem, but Iishea had returned to dealing by the time she fell onto the subway tracks, in the winter of 2020. “The state shut me down,” she said. “The government shut me down This happened maybe thirty-five days before the panic of the Covid. Bang! I couldn’t get into these places. They didn’t want to answer their phones.” In August of that year, her husband died from cirrhosis of the liver. “He was the only ray of sunshine in my entire life. Him. Him,” she told me, weeping. “And when he died the only refuge I got is God, and sometimes I don’t feel like I got him.”

Iishea’s account of what happened next was a textbook case of how street outreach is supposed to work. For months at a time, she slept in front of a bodega at the corner of Frederick Douglass Boulevard and West 116th Street. “I’m never shy of working. I used to sweep up, or help them with the boxes and the fruit. They have a flower shop in front—they used to teach me about the flowers and stuff.” She suffered from asthma and congestive heart disease and had been told that she might need a pacemaker. (At one point, she told me, a heart-monitoring vest she’d been prescribed was stolen from her at a city shelter.) Then she was approached by a representative of the cucs-led Manhattan Outreach Consortium. “They was, like, ‘Someone really, really, really cares about you. They called us and asked us could we help you. Iishea, what is it that you want?’ And I told them, ‘I don’t know what I want right now.’ So they kept coming, and they kept seeing me in that same spot or the immediate vicinity. And then one day I was, like, ‘O.K. I’m ready.’ ”

The Kelly, which has sixty beds and caters to chronically homeless clients with serious mental-health diagnoses (eighty per cent of whom also use drugs), is a friendly place, and Iishea raved about her three roommates and the Kelly’s director, Aimee Poulin. Her case manager was another story: according to Iishea, she had been absent for several weeks and left her in limbo. Iishea had yet to be approved for disability benefits or even for public assistance. “I don’t understand why they won’t give me no type of income at all,” she fumed, looking down at the stump of her left shin. “Inquiring minds want to know: What the fuck?”

Iishea still used crack cocaine, she told me (“Please don’t ask me to deal with this shit sober!”), but her use had diminished since she’d moved into the Kelly. “When I was on the street, every day, every minute of my life, was idle time. I didn’t want to feel anything, so I used. I haven’t stopped, but I sure cut the hell down. At this point, it’s when I want to do it, not when I need to anymore.” She had a new suitor who was not a drug user—a Dominican man who’d begun courting her when she was sleeping outside the bodega. “Whenever I feel like I want to indulge, I can, and he feels no way about it. He don’t judge me,” she said. The keys to his apartment—on the ground floor, luckily, a city bus ride away—hung around her neck. She visited him overnight sometimes, but since her January disappearance she’d always returned to the Kelly within the required seventy-two hours, in the hope of eventually getting her own apartment. “Don’t get the fuck-its!” she told me, acknowledging her tendency to give up impulsively out of frustration and impatience. “These people allot you a lot of room. I don’t want no rope to hang myself. I just want that room so I can get my place, that’s it. Ooh, that’s it.”

The cactus on Jessica’s windowsill was soon joined by sprouting bamboo stalks in a glass vase, and an aroma dispenser that suffused the air with a puff of floral sweetness every few minutes, masking the smell of the Newport 100s she smokes. Her books were carefully arranged, along with her collection of tiny Ty Beanies. I was startled to find that a miniature set of wheeled plastic shelves I’d handed down to her contained orange-capped syringes from a needle exchange, plastic baggies full of miniature cotton balls, and the small squat cylinders that her heroin came in (at one point, her dealer would refund her two dollars and fifty cents for each one she returned to him).

Before I arrived to visit, Jessica had been touching up her walls with a Magic Eraser to remove fingerprints left by Bill, the friend who’d helped her move, and whom she’d allowed to stay in her apartment for several days. That morning she’d demanded that he leave. Bill’s fiancée had died recently from an overdose (he does not use drugs), and he’d fallen hard for Jessica on the rebound, even accompanying her while she was panhandling. “Ever since Bill started following me around, I stopped making money,” she vented. “He’s trying to hug and kiss me. And I’m, like, ‘Dude, my sign says “Pregnant with an Abusive Husband”—they think that’s you and I’m still with you! Get away from me!’ ”

She’d made a new friend at 90 Sands, Troy, who she’d correctly sensed was a fellow heroin user. Although he was on methadone, he’d shot up with her several times and made tacos for her in her apartment. Bill was jealous of the new friendship, and Jessica had heard him grumbling under his breath when Troy came over the previous night. As she was telling me this, Bill called her cell phone. “O.K., I have company,” Jessica told him testily. “I’m allowed to have company, Bill, and I’m allowed to have friends. And it’s not Troy. . . . Don’t get an attitude with me and say it like you just said it.” She listened for a while, then protested, “You’ve gotta stop this jealousy shit. I told you I would be the most loyal best friend you ever had in your life, but I’m not interested in you that way.” Bill’s shouted reply prompted her to explode: “It ain’t got nothing to do with getting high! Because you don’t get high? You think I want you to be a fucking heroin addict? Are you, like, crazy?” More bellowing from Bill. “I have company, so I have to go,” she said, cutting him off. “I love you, too. Bye.” After hanging up, she continued to rail as though Bill were in the room: “Are you an idiot? Do you think I want you to be a heroin addict? I wouldn’t wish that on my worst enemy. Do you think I want to live like this?”

“Sorry, kid, Daddy doesn’t have any records called ‘Catch with Me’—why not request some Ethiopian jazz?”
Cartoon by Gingle Pingle

What the housing-first policy has meant at 90 Sands, practically speaking, is that three hundred and five people whose mental-health issues or drug use—or both—were severe enough to keep them on the street for an average of eight years all moved into one building within the span of eight months. Supportive tenants’ former case managers are supposed to remain actively involved for the first three months after their clients move into 90 Sands, in order to soften the handoff to an unfamiliar case-management team, but a number of tenants told me that this “after-care” hadn’t happened for them—one of many ways in which the case-manager position, with its low pay and high turnover, can constitute an unreliable link in the structure of homeless outreach and supportive housing, even as its low barriers to entry also encourage serendipitous vocations like Touré’s and Martin’s. Nearly all the people I spoke with described a trail of failed or abandoned case-manager relationships preceding the successful one—like Jessica’s with Medley—that finally helped get them off the street and into housing.

The vibe among tenants, in those early months at 90 Sands, was an uneasy mixture of wariness and need. Roberson’s good will, for instance, stopped short at the prospect of neighborly visits. “Don’t knock on my door about nothing” was how he summarized his position. “Once you start giving, people take advantage of that. I’m not trying to break bread. You stay your distance, I stay mine.” He considers that, of his fellow-tenants, “sixty per cent is whack, and forty per cent is good.” When I asked him to clarify which group he was part of, he said, with a chuckle, “I came from the sixty per cent, but I’m down with the forty per cent.”

Within a few weeks of meeting Troy, her new neighbor-friend, Jessica called security to have him removed from her apartment after he hit her in the face. Later, they patched things up; then she swore off him again, saying he was using her for drugs. Then he agreed to take care of her new cat . . . and so on. Relations with neighbors are complicated, as any city dweller knows, but the nature of supportive housing can compound those complications. One tenant who moved into 90 Sands last fall confided to me that the people in the next apartment had installed cameras inside his unit and were firing commentary at him through the walls. Understandably, he wanted to escape this invasion by changing apartments. But, to his frustration, Matthew Minogue, 90 Sands’s building director, wouldn’t grant his request.

Russell Reavesbey, with his cat, Roxy, in his apartment at 90 Sands, in May.

Russell Reavesbey, a fifty-six-year-old Black Muslim who wears shiny, bright-colored jilbabs, has a tendency to close his eyes while speaking, as if to tame his thoughts. When agitated, he paces. In both states, he often revisits a litany of losses: his mother, in 1998; his father, in 2000; a brother, who died of AIDS; another brother who was killed in a car accident; a sister who was murdered. “There’s not one moment I don’t miss my mother and my father,” he told me. “Ain’t nobody around, nobody I can talk to.”

Reavesbey had been homeless virtually his entire adult life until he moved into 90 Sands, having cycled for decades among shelters, safe havens, jails, and psychiatric hospitals. He became a father at forty-three; that daughter is now thirteen, living with her mother, and their second daughter is a year old. He wants to get his G.E.D. and become a veterinary assistant—he adores animals—but says that his Social Security card was stolen by terrorists during 9/11. There is one loss that always sends Reavesbey into pacing mode: when he was living on the street in Brooklyn and was picked up by police, he asked his then girlfriend to watch his bag, which contained a precious family photo album he’d somehow managed to hold on to through the chaotic years. When Reavesbey was released the next day, bag and treasure had been lost. “It was all I had, because Mother and Father were dead and gone,” he fumed, stalking his apartment in stocking feet as he recalled the discovery. “Those pictures to me was, like, sentimental, you understand? And that hurted me! I want to kill her, man.”

He was also furious at whichever of his neighbors had found the apartment key he thought he’d lost somewhere in the building and failed to return it. “Somebody has my key, and if I find out who has that key I bet you this: they won’t be staying in here,” he muttered. “Won’t be staying in here, because Imma—oh, Miss Jenny, I didn’t mean to say it like that.” He fell into pained silence until I assured him that all was well between us. “I just didn’t want you to see the other side of me, that’s all,” he said. “I figured you’d be disappointed or something.”

Reavesbey was one of 90 Sands’s first tenants. He moved in on September 15th, the same day as Donald Malloy, who is known as Speedy. Speedy, who is Black, wears square glasses, fashionably torn jeans, and has a large tattoo of a microphone on one forearm. He’s restless and fit and loves to work delivering food and packages. He’s open about having bipolar disorder and P.T.S.D., which were diagnosed during his teen-age years. He grew up in his grandmother’s home in Queens Village, but when she passed away and the bank foreclosed on her house he and his mother, with whom he has a volatile relationship, moved into a new apartment. After a physical fight with her when he was twenty-three, Speedy began sleeping in stairwells and on public-housing roofs, with spells in jail, psychiatric hospitals, and ten different shelters before outreach workers found him sleeping on the subway and referred him to a safe haven. He’d had relationships with women simply to have a place to sleep, he told me. “I lost my home, my family’s broken down. It make me cry a lot,” he said.

When I visited Speedy last February, a pan of stewed oxtails he’d recently cooked was sitting on the stove. “I grew up in a household where everybody fight,” he told me. “Everything was broken. My family broke the house, they broke the window, they broke the thermostat. When I was young, I used to punch walls and everything. My brother used to do the same. I don’t destroy nothing up in here. I make sure I clean everything. I do not like pests!” His windowsill was strewn with medication bottles; loose tobacco and weed covered the kitchen table. He rolled the mixture into cigarettes and smoked them in succession.

Within a few weeks of moving into 90 Sands, Speedy began clashing with the security guards who are stationed at the building’s entrance around the clock. A government-issued I.D. is required for nonresidents to enter, and Speedy was incensed when a guard refused to allow his female guest into the building. “I’m, like, ‘You’re security but you ain’t gonna tell me how to live, ’cause I pay my rent here.’ I flashed my Taser. They called the ambulance and police; you can’t have weapons up in here. I’m, like, ‘I just want to go to the hospital. I don’t know what y’all talking about. . . .’ But if I hit them I’m gonna get kicked out. I’m gonna lose my privileges of living here.” Speedy was taken by ambulance to the hospital, where he was asked a series of mental-health questions and released later that night.

“I threw it in the river,” he said of the Taser. “I don’t want to go back to sleeping on trains or sleeping on rooftops or sleeping with three hundred people in shelters. No. I can’t do it no more. I just can’t.” He mentioned often that he had turned thirty and wanted to complete his education. “There’s a lady that was eighty-six that went back to school, and she got her diploma,” he told me. “It’s never too late. Never.”

In March, I received a text at 4:01 a.m. from a man named Victor Lopez, whom I’d interviewed at his safe haven and again at 90 Sands, where he’d moved earlier that month after decades of homelessness: “I need to talk to you something happened yesterday that was dangerous to my life in the building it needs to be addressed or it may be one day someone’s life may be taken like mine almost was yesterday please call me today later.”

That afternoon, I accompanied Lopez to basement level C1 at 90 Sands, where Breaking Ground and CUCS have their offices. Lopez, a slight, courtly sixty-one-year-old who wears a porkpie hat and walks with a cane, relayed his story to Minogue. He’d been visiting a friend on another floor the previous afternoon and was waiting for the elevator in order to return to his own apartment. “All of a sudden I hear, ‘Open the fucking door.’ Elevator opens, she comes out with a big kitchen knife, chasing after me. As I was going backwards, I said, ‘But I didn’t do anything to you.’ She stopped, and my friend opened her door when I ring her bell. I stood inside her apartment for hours.”

Minogue, a cheery man with a red beard who worked for years in the forensic ward at Bellevue Hospital, has the air of someone who would be difficult to shock. “I’m aware of this tenant. I know who we’re talking about,” he assured Lopez, and urged him to file an incident report with building security. He also mentioned that Lopez had the option of pressing formal charges. (The son of a police officer, Minogue works to maintain good relations with the local precinct, which he said was aware of 90 Sands as a “hot spot.”) “Our building is very well covered in cameras,” Minogue said to Lopez. “We can’t provide footage to police unless they provide us with a subpoena. That could happen if you press charges. I’m not encouraging you to. . . . You have a right to feel safe in the place where you live.” He did encourage Lopez to share his experience at the monthly tenant meeting that took place the following day.

Speedy, in his apartment, in May. “I don’t want to go back to sleeping on trains or sleeping on rooftops or sleeping with three hundred people in shelters,” he said.

I caught up with Minogue before that meeting and asked him about the policy on threatening behavior at 90 Sands. “There are things that people do here, and behaviors that they engage in, that would very likely not be tolerated in other buildings,” he told me. “We try not to leap too readily to evictions for behavior stuff. But some are just blowing that tolerance—or one in particular is blowing it—way out of the water.” The difficulty for Minogue and his staff lies in balancing the conflicting needs of many fragile and unstable tenants. “There’s an erosion of feeling that you’re in a place you can call home if you feel like you’re under assault,” he told me. “And when there’s a lot of stuff happening, fights or threats and things like that, that erosion happens more quickly.” Lopez didn’t attend that tenant meeting, but I heard other complaints about his assailant.

After the meeting, as I was entering the F-train station, I paused to give a dollar to a gaunt, forlorn figure wearing a face mask, huddled on the pavement wrapped in a soiled gray blanket. As I leaned down, the man lowered his mask and grinned at me. “Hi, Jenny!” It was Lopez. I was stupefied; I had sat at his kitchen table the previous day but had failed to recognize him without his porkpie hat—hadn’t really looked at him, perhaps.

People who used to cohabit in safe havens may cease to feel an affinity once they’re sharing an apartment building—evidence of the wide array of backgrounds and histories that converge under the generic rubric “homeless,” a category I’ve come to feel is no more descriptive than that of “voter” or “employee.” A man I’ll call Danny, a member of the International Union of Operating Engineers, is licensed to drive bulldozers, backhoes, and small cranes. When I first met him at the Kelly safe haven, Danny, a trim and voluble forty-six, told me, “If I never became homeless, I wouldn’t even talk to these types of people. But because I’ve ridden the trains, them same people have given to me food, given to me a dollar, given to me things when I didn’t have anything, so I’m not going to shun them. These are my people.”

Danny grew up outside Philadelphia, the son of a white mother and a Black father. A self-described “Neanderthal type of guy” who admires Donald Trump, he was living in a house in Westchester with his wife, a nurse, and their three children when, in 2018, he began to suspect that his oldest son might be gay and confronted him disapprovingly. Enraged, Danny’s son retaliated a few weeks later by stabbing him in the abdomen. The internal injuries caused hernias that have made it impossible for Danny to return to work, and the violent rift with his son broke up the family. Danny began living in his C-Class Mercedes, eventually downgrading to a Toyota. Four years passed as he moved in and out of shelters and slept on subways, unable to get the abdominal surgery he needed without a place in which to recover. He fell apart mentally and physically before finally connecting with outreach workers at the Salvation Army and moving into the Kelly.

Yet Danny has family and a social fabric that many at 90 Sands lack. His new apartment is full of gifts from his mother. He and his wife have divorced, but he sees his children regularly and says that he’s working to repair relations with the son who injured him. His case manager is helping him plan for his surgery, after which he intends to resume full-time work. Shortly after moving into 90 Sands, he paid a social call to a fellow Kelly resident’s new apartment and found himself among people smoking crack and K2, a form of synthetic marijuana. He quickly distanced himself from that crowd and has focussed instead on discovering Dumbo’s upscale social offerings. A few weeks after moving in, he texted me, “I had to tell you Jennifer that this place gives so much more than inspiration and desire. A lust for life. 90 sands gave me that ☺.”

Marvell Calloway, in his apartment, in May. “I go about my business of that day and come home to peace and quiet, everything done, decent and in order,” he said.

Marvell Calloway, a forty-five-year-old commercial driver from Florida, furnished his 90 Sands studio immediately upon moving in: a rug, an enormous TV, two counter stools, and a multi-panelled poster of a golden-eyed panther, all coördinated in black and gray with red accents. With its astonishing view of the Brooklyn Bridge, the apartment looks like a real-estate ad. Calloway, who is Black, has a gold grill on his upper front teeth and a manner that combines elaborate Southern politeness (“Yes, Ma’am”) with occasional deadpan irreverence. “That just me, you know,” he said of his décor. “I had a vision in how I like to organize things. I go about my business of that day and come home to peace and quiet, everything done, decent and in order.” He is wary of his fellow-tenants, some of whom he knew from two years of living at a safe haven, where, he said, “common sense is not common, especially when it comes to hygiene. You gotta give ’em a extra push: ‘Get in the shower, the water free! Ain’t got no alligators, no sharks, and such.’ I guess they just stuck in that salvage life.”

Calloway has always worked, yet homelessness has nipped at his heels for much of his adult life, in large part because of alcoholism. (While at the safe haven, he joined A.A. and has been sober for more than a year, attending A.A. meetings daily by Zoom on his phone.) He was drawn to New York in 2019 by the higher minimum wage, and for months slept in shelters and parks while working at a bakery in Grand Central Terminal to pay for the transfer of documents he needed in order to drive commercial vehicles here. Like Roberson, Calloway resists easy friendships at 90 Sands. “Let me see your place, man! No, I don’t do that. I tell him, ‘It look just like yours. You know when you walk in your door with your key? Imagine that, just with me in it.’ ” Like Danny, Calloway has a professional network and good income prospects—things that are beyond the reach of many at 90 Sands. “All my friends are employed,” he told me. “So when I talk about work, it won’t be unfamiliar. It’s different than a person that ain’t never had a job. I’m, like, ‘You ain’t got no type of hustle in you? How in the world?’ I got cans in my closet. When it fill up, I’m taking them to the recycling shop. It’s not much money, but it’s money: five cents a can.”

Moving is disruptive for everyone. But the first weeks in a new home can be particularly volatile for people with serious mental-health or addiction issues—especially if they haven’t experienced stable housing in years or decades. Sarah Lipsky, the program director at 90 Sands, supervises the “supportive” part of the housing. (She was recently promoted and will soon oversee a portfolio of CUCS buildings, including 90 Sands.) A playful presence, with close-cropped blond hair and a palpable affection for her tenants, Lipsky told me, “One of the most reparative things, to me, in what we do is having the opportunity to build that relationship with people. There’s so much healing that can happen just by being there and being a person who leads with that love and care and concern and respect that so many people haven’t had. It doesn’t solve everything, but it does a lot for people who have been collectively disenfranchised.”

But the breakneck pace of move-ins and a shortage of staff in the early months at 90 Sands sometimes made it challenging to form the necessary case manager-tenant bonds. Jessica’s case manager was brand-new when they met at her lease signing, and she left the job three weeks later. Jessica, who is still in frequent contact with Medley, had little interest in engaging with a successor. Nor was she required to; while it is a condition of cucs’s government funding that the organization provide a quarterly service plan for every supportive tenant, which includes goals and challenges, in addition to an annual psychosocial assessment, the tenant is not obliged even to speak to a case manager, much less partake of CUCS’s on-site services. This can lead to an awkward dance of case-manager pursuit and tenant avoidance that requires skill and ingenuity on the case manager’s part to break through. “We try to focus on creative engagement, not just sitting there trying to call somebody all the time,” Lipsky told me. “Are you visiting them at their apartment? Are we exhausting our options for how to engage with this person? And then we just keep going. We can be very annoying. Persistence doesn’t always beat resistance, but when you offer consistency I do think eventually people feel that, and it pays off.”

When the case manager-tenant bond gels successfully, the results can be immediately striking. Johannah Rippe, a white thirty-three-year-old from upstate New York, arrived at 90 Sands after a decade of homelessness that began in the company of her parents, both of whom used heroin and moved with Johannah and her six siblings to New York City when she was twenty-two. (Her father, Curtis Rippe, was stabbed to death last year, a story that made the news.) Rippe began tasting her parents’ heroin at age nine. Later, when she was pregnant with the first of the two children she’s had with her long-term partner, Ivan, a doctor insisted that she go off her bipolar medication. She tried using heroin to dull the mental and physical pain, and quickly became addicted. Both of her children were removed from her care in infancy by the Administration for Children’s Services.

While Rippe and I waited for her lease signing at 90 Sands in February, she showed me a cell-phone picture of herself at twenty-three, bare-armed and fresh-faced, cradling her first newborn. I was stunned by how different she looked ten years later. That day, she was dressed exactly as she had been when I met her at the safe haven where she and Ivan had spent the past two years (because Ivan is Mexican and undocumented, he can’t join Rippe at 90 Sands, or apply for supportive housing, until they’re legally married): both times, she was cocooned inside hoodies with grime-encrusted cuffs, bowed under a thick parka that fell to her knees, a blue Narcan pouch dangling from her neck on a lanyard. It was hard to conjure up the physical person underneath all those layers, and her posture was so radically hunched that she could barely make eye contact. (She has severe back pain, she told me.) Yet three weeks after Rippe’s move, I caught a glimpse of her running through the 90 Sands lobby in black tights, a clingy dress, and platform shoes—a lithe young woman again. When I visited her apartment, she was pressed for time; her new case manager, with whom she was in close and frequent contact, had arranged for her to have a physical exam in the medical suite downstairs. When I commented on her change of attire, she said, “I’m in my house now. I’m not outside 24/7. Of course I don’t need three, four, five coats. I’m in eighty-degree weather—I got my own thermometer!”

There was another change in Rippe that struck me as we stood together at her front door: her posture had straightened a little. “You can tell, right?” she said, with evident pleasure. “Everybody told me, ‘You look different now, Johannah.’ ’Cause I’m not outside all day like this.” She resumed the more exaggerated stoop, which I recognized suddenly as the stance of someone perpetually seated at ground level and looking up at passersby, as Rippe had done for years. The next time I saw her, she and her case manager had arranged for her to enter a methadone program the following day. She is still enrolled there.

Likewise, Iishea saw immediate results after the Kelly paired her with a new case manager, Mariah Jones. Within six weeks of my first visit, she’d begun receiving public assistance and had had an interview for Supplemental Security Income. Under Jones’s management, her housing packet was moving forward. She was also relying on Jones’s help to get her prosthetic leg refitted; the suction part had been lost during a hospital stay, along with her dentures—she’d had no upper teeth for months. When I next saw Iishea, her hair was elaborately curled; her boyfriend had been treating her to a hair-stylist appointment every two weeks. “I’m sure now,” she said of the relationship. “He’s sixty-seven years old, and it’s not like he’s involved in shenanigans and bullshit. He’s more seasoned. He don’t speak a lot of English. English is predominant here, so I help where I can. And then I clean and I cook and I cook and I clean. . . . He’s just so sloppy. Just like a man, I swear. Ooh, girl, it’s the truth.”

Iishea was eager to be photographed for this article. She’d lost her phone and was awaiting a replacement, so I made a date through Jones. We chose April 7th, a Friday when good weather was predicted. I arrived at the Kelly with the photographer and dozens of Krispy Kreme doughnuts and hazelnut coffee, Iishea’s favorites. But she wasn’t there and didn’t show. Everyone at the Kelly was surprised; she’d had her hair done especially for the photo shoot, they told me.

Jones assumed that Iishea was at her boyfriend’s, but Iishea was not seen or heard from in the weeks that followed. Outreach workers visited the corner by her usual bodega repeatedly, without luck. Jones completed the housing packet, making Iishea eligible for a supportive-housing placement through the city’s centralized system (likely not at 90 Sands, which was nearly full and far from Iishea’s beloved Harlem). Cucs undertook what is known as a diligent search: contacting hospitals, jails, and the morgue. The Kelly reluctantly released Iishea’s bed. I went uptown in May and found the small group of buildings where, I was convinced, based on Iishea’s description, her boyfriend lived. I wrote her several identical letters and taped one to every front door, urging her to call me. I visited her bodega, but the man at the counter said that he didn’t know whom I was talking about. The woman at the flower stand recalled someone posting a picture of a missing woman outside the store, but it had come down after a while.

My shock at Iishea’s disappearance was a testament to how little time I’d spent among people whose lives have been riven, for decades, by violent instability. At 90 Sands, ten people died in the first four months of 2023, eight of them from suspected overdoses. (One of the non-overdoses was a man I’d interviewed in December, David Hoeltzel, a mechanical engineer who taught at Columbia in the nineteen-eighties and nineties and told me that he’d first begun to unravel when he failed to get tenure.) Nearly everyone I knew at 90 Sands had seen a body bag leaving the building. On my way to Russell Reavesbey’s apartment, I passed the door to a unit where a suspected overdose had occurred; it was secured with a neon-green N.Y.P.D. “Seal for Door of D.O.A. Premises.” Messages had been scrawled onto the seal: “Luv u Sis,” and “Jus know your time spent on this earth was great,” and “A100 u will always be remembered.”

Taped just inside Reavesbey’s door was a small xeroxed photograph of a Black man wearing a bandanna: another tenant who had recently overdosed. Given Reavesbey’s tendency to brood over deaths that occurred decades ago, these reminders of mortality were keenly distressing. His mood that day was fiery and changeable; at one point he paused in his pacing and slammed the kitchen counter repeatedly for emphasis: “People died in this building. If the next two people that I know is gonna die of this fentanyl, then I need to be transferred, ’cause I can’t stay in this type of situation. I can’t!”

A small tiger cat with yellow-green eyes lay curled on a folded blanket on the floor, observing Reavesbey’s outburst. He’d adopted her a few weeks earlier from a woman on another floor and was calling her Roxy. Early on, he’d complained to me that Roxy was “unmotivated,” but things had improved between them. “She done got so used to me,” Reavesbey said, his mood softening suddenly when he focussed on his pet. “The more I feed her, the more she got attached to me. She’ll come towards me, and I rub her belly.” He picked up Roxy and cradled her gently. “She’s a one-in-a-million cat,” he said, smiling for the first time that day. “She’s the queen of this apartment.”

Signs went up all over the building warning of the risks of fentanyl and xylazine and urging people not to use any drugs while alone. (Fentanyl, a powerful synthetic opioid, can be found in most street drugs, including cocaine products.) Medically prescribed Narcan kits were dispensed door to door and installed in every hallway. “Obviously, people die of overdoses in many contexts,” Eve Goodman, who has worked with CUCS for seventeen years and teaches a training session on death and dying for CUCS employees, told me. “I think that sometimes people move into apartments and feel lonely. And one of the things that help with loneliness is to get high. But when someone moves into a housing program they’re more likely to be using by themselves. When you overdose, that’s that; you can’t give Narcan to yourself.”

At about this time, I ran into Jessica returning to 90 Sands from the post office, where she’d been mailing out online orders. I accompanied her to her apartment, assuming that she was just dropping off her trolley before heading back out for an ophthalmology appointment. As we chatted, she began to prepare a shot of heroin, finally flicking the syringe a couple of times and rising to her feet. “I’ve gotta go in the bathroom for a minute, sweetie,” she said.

A silence fell on the room in her absence. Her cat whined outside the bathroom door and then shoved it open with his head. I heard Jessica tell him faintly, “Stop.”

More silence, broken only by voices from the hallway and occasional chugs from her aroma dispenser. The cat mewed. I felt rising anxiety. After five minutes I called, “Are you O.K.?”

She laughed softly. “Yeah.”

I spent the next five minutes reminding myself of where the Narcan kit was and trying to recall how to administer it.

“Still doing O.K.?” I finally asked. To her inaudible answer, I pressed, “What was that?”

“The more I try to rush, the longer it takes.”

Twelve minutes after Jessica left the room, the toilet flushed and she reappeared, relaxed but unchanged. “All right,” she said. “I’ve gotta go. Already gonna be late for my appointment.”

Mercifully, the overdoses at 90 Sands slowed; of the six fatalities in the building since the end of April, four were from natural causes and the causes of the other two are, as of this writing, undetermined. (One of the latter deaths was that of John Wood, the builder of cave homes.) Spring arrived, the weather warmed, and the mood in the building felt lighter. More people could be found sitting outside on the curved wooden benches that intersperse landscaped flowerbeds in 90 Sands’s public plaza.

When I visited Reavesbey in May, another tenant had given him a carpeted blue-and-gray house for Roxy, and the cat watched him serenely from her cushy new bower. Reavesbey told me that he wants to train her to dance. He wants her to become a mother. “I have a philosophy about Roxy: Roxy is coming into her own,” he said. So, it would seem, is Reavesbey. “I’m doing good for myself,” he told me. “I pay my rent, food-shop for myself, food-shop for this cat, clean up, sleep, mop, wash the clothes.” His daughters have come with their mother to visit. For a man in his fifties setting up a home for the first time, these are immense accomplishments. In August, both Reavesbey and Speedy signed new two-year leases.

With all of 90 Sands’s supportive units filled, the gruelling transition is over, leaving Lipsky and her staff with more time to focus on creating community events in the building, all of which are open to every tenant. There have been buffet lunches and board-game sessions and book deliveries from a nearby branch of the Brooklyn Public Library. There are hopes for group haircuts and foot soaks and self-defense classes. Meanwhile, the affordable units are slowly filling up, reducing the over-all proportion of tenants with acute needs. I spoke with the tenants of two affordable units, a young woman and a middle-aged man, both of whom have found living at 90 Sands challenging in the same ways that supportive tenants have. Both plan to stay—in part because of the vigilance of the management and the cleaning staff, and in part because, without an affordable apartment, they would have to leave New York altogether. “In the grand scheme of things,” the woman told me, “you have your own apartment that you can keep clean, that’s near transit. . . . Those moments of stress can feel like they trump all the good, but they don’t.”

When I interviewed Minogue and Lipsky together, in July, they were energized and optimistic. Minogue likened the ongoing evolution of a building like 90 Sands to a stockpot: “You never use up all the stock, you’re constantly re-adding stuff to it, it has a fire underneath it all the time, and you can never leave it alone a hundred per cent. Things are better, they’re just not done.” Lipsky agreed, adding, “We’re still in that settle phase, and probably will be for at least the next two, three years.”

Even in a newly renovated building with panoramic views of New York Harbor, affordable tenants will likely need to embrace the vision and mission of supportive housing embodied in 90 Sands: some three hundred individuals who, for years, slept on stoops, steps, roofs, in stairwells, under scaffolding and under bridges, in abandoned buildings, outside Starbucks, inside Macy’s, freezing through subzero New York winters and sweating on the sidewalk through broiling summers are presently housed. (No unit has been surrendered, although legal proceedings that could lead to eviction are under way for Lopez’s assailant.) Many still live in poverty, often without having finished high school, and are hobbled by disabilities and criminal records that make panhandling a more lucrative job than any other they might conceivably obtain (and getting a full-time job would terminate their benefits and thus their guarantee of housing). Some have problems that can’t easily be solved, particularly after decades of turmoil have erased any memory of a stable baseline, if they ever had one. But it would seem inarguable that they have a better chance of meeting these challenges now, while housed, than they did while they were living on the streets.

“We can end every person’s homelessness. We know how to do it,” Dennis Culhane, the sociologist, told me. For select populations—homeless AIDS patients and homeless veterans—this has already to some extent been done. Culhane helped design the Obama Administration’s veteran homelessness initiative, which, starting in 2009, used a combination of rapid rehousing and supportive housing to achieve, by 2016, an over-all reduction of homelessness among veterans by nearly fifty per cent. “We showed that you could move at scale and dramatically impact the number of people who were homeless in a particular population,” Culhane told me. The budget agreement, which was bipartisan, required an increase in the federal budget for veteran homelessness from some four hundred million to more than a billion dollars in 2016. Those systems, established more than a decade ago, continue to work, according to HUD: the number of homeless veterans dropped by another eleven per cent between 2020 and 2022.

The forces underlying modern homelessness are many and complex, but they boil down to a withdrawal of the federal government’s commitment to providing either affordable housing or a functional safety net for its vulnerable citizens. S.S.I. benefits for disabled Americans are burdensome to apply for and frequently denied, and they often exclude addiction, or addiction-related disabilities like cirrhosis, as qualifying conditions. Even when granted, S.S.I. pays a maximum of about a thousand dollars per month, depending on the region—which, even in its entirety, is only half the median market rent for a studio apartment in New York City. Medicaid under managed care is failing catastrophically to meet Americans’ mental-health needs—including those of people suffering from opioid-use disorder who would benefit from medication-assisted treatment, fewer than twenty per cent of whom have received it. Despite measurable progress since the early two-thousands, the number of Americans who fall into homelessness each year exceeds the number who exit from it. Subsidized housing is the answer, nearly everyone seems to agree, though what form it should take is debated. Culhane believes that the pace of building and renovation is too slow to address the problem, and favors rental assistance that individuals could use for apartment shares, or even to stay with family or friends. But states are reluctant to spend this money.

Still, lawmakers and citizens who recoil from the expense of ending modern homelessness would do well to ponder the cost of maintaining it: eight and a half billion dollars a year on emergency shelter alone, according to Culhane’s research (based on 2015 data), or about twenty-seven thousand dollars per bed per year—eleven billion and thirty-six thousand in today’s dollars. That eleven-billion-dollar expense doesn’t include, as Culhane reminded me, “the excess use of health care, emergency rooms, E.M.T.s, longer hospitalizations. It’s not counting the impacts on parks, sanitation, police, libraries, education. . . . There is hardly a public-sector system out there that is not impacted by homelessness.” In a landmark study from 2002, Culhane calculated the cost of chronic street homelessness for a single mentally ill person to be forty thousand dollars a year—about seventy thousand dollars in today’s money. That’s a lot of money to spend on a horrific status quo.

“Nobody wants to be confronted with a spectacle of human suffering every time you walk out your door with your kids,” David Giffen, the executive director of New York’s Coalition for the Homeless, told me. “I hate to put it in terms of enlightened self-interest, but if you don’t want somebody sleeping in your subway then let’s put a system in place that provides four walls, a roof, and a bed for that person.” In a country with skyrocketing housing costs and insufficient mental-health care, virtually anyone could end up in that position of need. “It’s not a question of these people,” Giffen said. “These people are us.”

In late July, Iishea’s case manager e-mailed to say that there seemed to have been some activity on her E.B.T. card, or food-stamps account. I returned to West Harlem on a sweltering afternoon to look for Iishea again, and this time I managed to find a hair salon on West 116th Street that I thought might be the one where she’d been getting her hair done. Sure enough, a woman who was braiding a customer’s hair inside the salon knew whom I meant. “Ah, Iishea. Wheelchair,” she said in strongly accented English. Then she added, sadly, “She pass away. Long time ago. Overdose.” The news had come from Iishea’s boyfriend, she said, the one who had been paying for her appointments.

Still not satisfied, I proceeded to the buildings where I’d left letters for Iishea two months earlier. I rang all the ground-floor apartment buzzers and managed to find one tenant who identified himself as a former crack user and said that he knew of Iishea’s overdose death “through the grapevine.” He told me which apartment her boyfriend lived in, and I left a letter in Spanish asking him to call me, so that I could find out exactly what had happened. I never heard from him. The Kelly was finally able to confirm with the morgue that Iishea had died on April 6th, the day before our scheduled photo session.

In a broader sense, I know what happened to Iishea Stone: a luminous and extraordinary woman was failed repeatedly—by her family’s pathologies, by poverty, and by a social safety net that couldn’t seem to catch her. Had Iishea grown up with the advantages I had, she might have accomplished anything. Instead, she suffered acutely and slipped away so invisibly that, thus far, the Kelly does not know what was done with her body. How many Americans are we losing this way? How can we—the wealthiest nation in human history—tolerate those losses? The fact that we can, and do, despite knowing that it’s wrong, is what is meant by the moral cost of homelessness.

For Jessica, April brought the unthinkable: her aunt Mary, the woman she called her mother and listed as next of kin on her 90 Sands lease, died unexpectedly on the operating table during a lung biopsy. When I visited Jessica a couple of days later, she hadn’t stopped shaking. She had spoken to Mary the night before the biopsy, trying to calm her fears about the procedure. “I woke up at four o’clock, wide awake, and I had a horrible feeling,” she said. “I waited, because I knew she wouldn’t be up at four. I messaged her at seven-thirty, and I was, like, I love you so much. I knew she wasn’t coming home, I knew it.” She sobbed openly as she spoke.

Jessica’s aunt never knew that she had relapsed into heroin after going on methadone a few years ago. “She’s the only person I’ve ever lied to about it in my life,” Jessica told me. “I couldn’t break her heart like that.” But Mary had known about Jessica’s homelessness and was hugely relieved when she moved into 90 Sands. “My cousin said, ‘She told me she’s so proud of you.’ I was, like, I don’t know what for.”

Jessica’s cousin had advanced her money for a plane ticket to get to the funeral, which was the following afternoon. She planned to leave before dawn to take the subway to LaGuardia, but was grappling with a logistical problem: she didn’t want to carry heroin on the plane and needed some way to keep from going into withdrawal while she was away. The obvious answer was to carry a sealed dose of methadone, but Troy, her sometime friend at 90 Sands, was demanding sixty dollars for one of his take-home doses. “I’m, like, ‘Are you fucking for real right now? I’ve given you money all the fucking time, I’ve given you dope, I’ve given you cigarettes, and you’re trying to charge me for methadone. Really?’ When I get back here, shit’s gonna change,” she resolved. “I’m not talking to none of them no more. I’ll change my number if I have to.” She left without the methadone, and returned, dope-sick, within twenty-four hours.

Changing her life was not as immediate or neat as Jessica had promised herself it would be. After a fight with her dealer’s girlfriend escalated into a fight with the dealer himself, she stopped buying heroin. Her withdrawal was manageable at first; she had tapered down enough that the sickness was bearable. But then illness seized her again; she vomited for days, and developed areas of infection in her legs that opened up into deep wounds. When those began to heal, she was too exhausted to leave her apartment. In mid-June she stopped answering texts, which was so uncharacteristic of her that I grew alarmed and went to 90 Sands, where I asked security to call upstairs on the internal phone to her apartment. She was there; her cell-phone service had been turned off because she was too drained to panhandle and hadn’t paid the bill.

I found her lying on her bed beside the small set of plastic shelves, from which all the drug paraphernalia had been removed. She was noticeably thinner. I asked whether she thought her recovery from heroin would stick this time, when it hadn’t before. She reminded me that, when she’d left jail on methadone, she’d returned to New York with no place to go: “It was wintertime, I didn’t have blankets, I didn’t have anything.” Medley wasn’t her case manager yet, and no organization she contacted could find her a bed. Inevitably, she had rejoined the safety of the homeless drug users she knew and, after holding out briefly, returned to heroin. Now, in her own apartment, the situation was different: “I’m not around nobody.” She had talked to her dealer on the phone a couple of times. “He asked me, ‘You coming again, Jessica?’ ” She demurred, “Uh-uh, I’m sorry, I love you, but I can’t do it. Can’t be around that right now.”

Unfortunately, she was still around heroin, and the rash of solitary overdose deaths had encouraged communal use. By the time I saw Jessica two months later, in August, she was using again (albeit on a smaller scale) and had new wounds caused by xylazine-adulterated doses that she said she’d purchased from a dealer living in the building. Still, in the halting realm of opioid recovery a spell of sobriety is an accomplishment—even if, as she’d insisted back in June, it was due less to grit than to sheer exhaustion, even depression, in the wake of her loss. “I just did not have the will power to get out of bed and go outside to try and make money—that’s what it boils down to,” she said. It struck me that what Jessica was describing was grief. Here, inside her clean, quiet, aromatic apartment, she had the luxury of indulging it. “My cousins are, like, ‘You need to get up and go do something.’ No, I don’t. You don’t understand. I was homeless on the streets. They can’t grasp how hard it is. I was always outside. I walked ten miles a day, probably. Like, I don’t need to get up.”

Jessica is hoping to enroll in a culinary-arts program next semester, and is trying to get bone grafts so that her teeth can be replaced. She has started working with her 90 Sands case manager, and is receiving medical care for her wounds from the on-site doctor. She still intends to get off heroin.

“The wins can be really small at times,” Lipsky reminded me at our last meeting, when I expressed distress over Jessica’s perilous health, without naming her. “You meet people and you see where they are at that current stage, and where they could be. It does take time. And it takes investment, and it takes consistency. It takes trust and belief in that person to get to that point when five, ten years down the line you look back and think, Wow! Look where that person came from.” ♦