When a blizzard hit Washington, D.C., one evening three decades ago, I grabbed a notepad and walked down K Street to see how the homeless were faring. I was, with no special originality, looking for a metaphor, a snapshot of the nation’s fallen state. K Street is the city’s power corridor, a downtown canyon where lobbyists eat expensive lunches and lay expansive plans while the homeless panhandle and sleep in doorways. On the street with solutions to every problem sprawled a problem that defied solutions. “It’s not that we don’t care about the homeless,” explained an international consultant, hurrying past the slumped figures to get home. “But because we have something to do, we walk around them.”

As the snow fell, the scene grew bleak. “Joke! Joke! I ain’t no joke!” a disturbed man howled. Another had buried himself beneath a pile of cardboard boxes and blankets that a well-wisher had topped with a sandwich. An astonished tourist from Albania snapped pictures of the public destitution to show friends that “this is America.” I filed a dark story for The New York Times and wondered if in a half-century Americans would look back on the era with disbelief, “the way schoolchildren react to Dickens’s London.”

Thirty years on, that doesn’t seem likely. The Dickensian plight of the homeless continues, and the public may be less sympathetic. When a former marine named Daniel Penny was arrested for killing a mentally ill homeless man, Jordan Neely, on a New York City subway last May, he attracted a conservative cheering squad and nearly $3 million in crowdfunded aid for his legal defense. After nearly a decade of decline, homelessness began rising in 2016 and last year leapt by 12 percent to the highest level since the federal government started its count in 2007. The growth was especially sharp among chronically homeless people sleeping outside of shelters, whose numbers have risen three quarters over the past seven years. These rough sleepers are the focus of Rough Sleepers, Tracy Kidder’s latest and important book.

Kidder is an accomplished writer of narrative nonfiction whose books are generally built around characters with special passion for their work. In The Soul of a New Machine, for which he won a Pulitzer Prize in 1982, the protagonists were computer engineers. Among those chronicled in subsequent books were a group of Massachusetts house builders; Paul Farmer, an American doctor and anthropologist who worked in Haiti and other countries; and Paul English, a Boston tech entrepreneur and philanthropist who cofounded the travel website Kayak, among other companies. The star of Rough Sleepers is Dr. Jim O’Connell, the founder of the Boston Health Care for the Homeless Program.

The book has two great virtues. Most important, it offers personhood to people many Americans have trained themselves not to see, or to see only through the lens of fear. Kidder captures the mental illness and addiction that bring many rough sleepers to the streets, but also their resilience, generosity, and genius for survival. It is not easy to write with both empathy and candor about people whose demons leave them complicit in their suffering. Kidder does so masterfully.

The book is also a meditation on a life of service. O’Connell was the founding physician of the program in the 1980s and built it into a national model. The work is gratifying but taxing and filled with frustrations. Workweeks that can stretch to a hundred hours harm his personal life, and patients ignore his advice. The more he sees, the less certain he becomes of solutions. Kidder casts O’Connell as a hero, but he’s a hero without answers, which is part of his appeal. He perseveres by savoring small victories and because it is the decent thing to do. With public discourse so marred by angry certitudes, O’Connell’s modest steadfastness is an example to commend.

Kidder met O’Connell through Paul English, who is a supporter of the Boston homelessness program. The program operates an outreach van, and a ride-along got Kidder hooked. He was especially intrigued by the relationships O’Connell had built with his marginalized patients.

The book opens on the streets of South Boston with the van’s driver approaching a man under a pile of blankets whose response to a wellness check is “Get the fuck outa here.” O’Connell tries next, kneeling next to the would-be patient and greeting him by name: “Hey, Johnny. It’s Jim O’Connell. I haven’t seen you in a long time. I just want to make sure you’re all right.” A face pops through the blankets: “Doctah Jim! How the fuck are ya!” A half-hour of banter ends with O’Connell’s gentle invitation to visit the clinic at Mass General.


O’Connell didn’t set out to save the world. As a flashback early in the book explains, he was a working-class kid from Newport, Rhode Island, whose childhood was colored by his mother’s episodes of severe mental illness. Following his graduation (as salutatorian) from Notre Dame, he studied philosophy at Cambridge, taught school in Hawaii, tended bar in Rhode Island, and laid plans to become a Vermont country lawyer.

Then, while on vacation on the Isle of Man, he witnessed a motorcycle accident. Sitting with the injured biker while others summoned help, he felt an “intimate contact with life,” a kind of communion, and realized it was what he’d been seeking. He attended Harvard Medical School and was finishing his residency at Mass General when he was awarded an oncology fellowship at Memorial Sloan Kettering. A golden future was assured. Then leaders at Mass General asked a favor. The mayor of Boston was starting a health care program for the homeless; would O’Connell defer the fellowship for a year to run it? He couldn’t think of a way to say no.

A hazing followed. On July 1, 1985, O’Connell reported for duty at the Pine Street Inn, a shelter with a clinic run by nurses unimpressed by his résumé. “You’ve been trained all wrong,” said Barbara McInnis, the lay Franciscan who became his mentor. To treat the homeless, she warned, doctors needed to talk less and listen more. She made him stash his stethoscope and soak patients’ feet. With listening skills honed by tending bar, O’Connell proved a quick study. His patients included a schizophrenic man whom O’Connell recognized from Mass General, where he’d been famously noncompliant; after several weeks of footbaths the patient took his meds. To ensure that alcoholics took their tuberculosis pills, O’Connell got a bartender to dispense them before the first beer. As TB and AIDS washed over the clinic, O’Connell’s sense of mission deepened. He deferred Sloan Kettering for a second year and then said he wasn’t coming, sacrificing considerable pay and prestige.

O’Connell doesn’t expect gratitude, which is good, since, as Kidder makes clear, he rarely gets it. Surrounded by difficult patients, he shows a gift for what a colleague calls “pre-admiration”: he assumes that the patients’ virtues will eventually appear. When one clogs the toilet by flushing her clothes, he embraces her as “complicated.” O’Connell takes pains to find a nursing home for a man dying of cancer, only to discover him back in the alley with his buddies, pouring vodka down his feeding tube. Rather than judge, O’Connell salutes the man’s agency in choosing to die among friends. The program rarely tries to forcibly hospitalize the mentally ill, arguing that doing so earns their spite. But not hospitalizing them can earn spite, too, as O’Connell tells colleagues. “Fuck you,” says a woman who had rejected his help when living on the streets but got well after the police arrested her and took her to a mental hospital. “You left me out there for ten years and did nothing.”

Other thorns lodge in his side. The job pays so little at the start that he is forced to moonlight as medical director of a detox center, and the long hours help destroy a marriage and another relationship. Over four decades, the program grows to employ four hundred people (with help from Medicaid, a crucial part of the story), but O’Connell chafes at the financial pressure to practice efficient medicine, which he considers an oxymoron. Unlike most of the staff, O’Connell gives cash to patients, on the theory that they need it and that it incentivizes compliance with follow-up care. The crisp bills—fives, tens, and twenties—cost him a few thousand dollars a year. But another member of the staff complains that the practice creates a hostile workplace, since patients favor O’Connell. The board asks him to stop, and he does, more or less.

Despite the frustrations, O’Connell connects with those he treats and occasionally helps transform their lives. He receives near-weekly visits at the clinic from a middle-aged man who held the record for drunken trips to the emergency room (216 in eighteen months) but got sober, housed, and employed. Four members of the board were once patients. One of them, Joanne Guarino, gives an annual lecture to first-year students at Harvard Medical School, recounting her recovery from thirty years on the street, where she survived rape and AIDS. Her pluck, grace, and affection for O’Connell draw an ovation.

Service to the poor is often sustained by faith, but O’Connell has little to say about God. He finds a model in Sisyphus—or Sisyphus as imagined by Camus, who converted the tale of futility into a parable of purposeful striving. Although Sisyphus is condemned forever to watch the rock he pushes uphill tumble back down, “the struggle itself toward the heights is enough to fill a man’s heart,” Camus insisted. “One must imagine Sisyphus happy.”


Ameliorative work has its critics—on the right, some say it rewards indolence; on the left, some warn it masks injustice. O’Connell, the former philosophy student, just carries on. “This is what we do while we’re waiting for the world to change,” he says.

About a quarter of the way into the book, a second major character appears. O’Connell is preparing to leave the clinic at Mass General one day in September 2016 when a new patient arrives. He is larger than life in every way: six foot four, loud and muscular, with an “odor of sweat and slightly rotten fruit.” Tony Columbo (a pseudonym) has spent two decades in prison. He is living on the street and needs Suboxone to quiet his craving for heroin. He is agitated and digressive. “When he said ‘Make a long story shawt,’ he tended to do the opposite,” Kidder notes.

At this point in his career, O’Connell is sixty-eight and on his second marriage. He has an infant daughter and has told his wife he’ll be home early, knowing she would need relief from childcare. He doesn’t have time to see Tony but sees him anyway. O’Connell hesitates to prescribe Suboxone without a urine test, but after a tense back-and-forth he bows to Tony’s desperation and issues the script.

Complications ensue. Tony has discarded his ID so can’t fill the prescription. O’Connell accompanies him to the CVS and vouches for his identity, but Medicaid refuses to pay. The drug costs $120. O’Connell pulls out his credit card, and Tony raises a protest of uncertain sincerity. The pharmacist resubmits the request, and this time Medicaid approves. O’Connell leaves the store, then realizes that Tony hasn’t eaten all day. He returns, buys him a sandwich, and puts a twenty-dollar bill in the bag. He is only three hours late getting home.

Tony’s journey provides the narrative arc for the rest of the book, and his literary purpose is clear: he is there to humanize the dispossessed, which he does unforgettably. If Kidder had license to invent a character, he couldn’t have conjured one more captivating. In Kidder’s resonant phrase, Tony lingers in the mind like “an unfinished chord.”

At forty-four, Tony has spent most of his adulthood in prison. Though he was convicted of “assault with intent to commit rape,” Tony denies any sexual crime—he was just robbing a drug dealer, he says. His array of previous diagnoses include bipolar disorder and possibly schizophrenia, and he has been using cocaine along with heroin, partly to numb knee and back pain. He didn’t finish high school, has no apparent work experience, and is a street fighter capable of great violence.

He is also charming, insightful, energetic, resilient, and bearing the weight of a victimized childhood in the Italian North End, where his father was a low-level gangster who bloodied the apartment by beating his wife and kids (though, Tony says, not him, as the youngest and favorite). Among the childhood experiences Tony casually mentions is being kidnapped and raped—when he was twelve, or maybe fourteen, he says with odd vagueness.

Rough Sleepers doesn’t dwell on it, but Tony’s victimization may be part of a larger pattern. Several of O’Connell’s patients allude to childhood sexual abuse, including Joanne, the board member who draws the students’ applause. “I was sexually abused as a child, and that went on for years and years,” she says, explaining how her journey to the streets began.

In my own reporting on people in chronic poverty I’ve found that surprisingly large numbers volunteer that they were sexually abused, sometimes in casual asides meant to explain other problems, like depression or addiction. In Charleston, South Carolina, last year, I met a school bus driver who had been evicted and was living in her car; she said childhood molestation had left her unwilling to form relationships with her children’s fathers or seek their financial help—one of many reasons she cited, in addition to low wages and high rents, for her awful predicament. As a source of other destabilizing conditions, childhood sexual abuse may be more common and more damaging among the deeply disadvantaged than is generally understood.*

Tony can be extraordinarily kind. He is a protector of weaker people on the street, and watches over sleeping women to keep them safe. When he fights, it’s often to punish other homeless men he views as predators. One of the people he cares for is BJ, a fifty-year-old double amputee with the ability to consume startling amounts of vodka. Kidder writes:

Over the years, many rough sleepers had tried to take care of BJ, but none, Jim thought, as conscientiously as Tony. In the evenings as winter loomed, the pair would make their way down Cambridge Street, tall dark Tony striding along beside BJ in his motorized wheelchair, heading for one of the outdoor sleeping spots with an overhanging roof. Tony would lift BJ off his chair and lay him down in one of the sleeping bags he’d scrounged from some charity or Good Samaritan….

BJ would sometimes tip over onto the sidewalk, and Tony would set his chair upright and put him back in it. Tony kept an Allen wrench in one of his many pockets for making small repairs when the little red vehicle broke down. He cleaned BJ up when he soiled himself.

The program operates a medical shelter where ailing clients can stay for a few months. As an off-and-on resident, Tony becomes a self-appointed caretaker—part social worker, part triage nurse. He tells O’Connell who among the patients is lonely, who’s relapsing, and who’s getting ready to flee. Tony fantasizes about becoming a peer counselor, so that others might learn from his mistakes. He is sufficiently empathetic and gifted that O’Connell considers giving him a formal job. But his periods of stability alternate with abrupt returns to the street.

The story of doctor and patient has its symmetry, each an introspective man searching for purpose. What propels the rest of the book is whether O’Connell can save Tony—from addiction, mental illness, street enemies, and his status as a registered sex offender, which disqualifies him from most housing aid and makes it all but impossible to rent an apartment. Even when the program finds a subsidy, landlords won’t accept him. Though Tony has served his prison term, a life sentence of homelessness lingers on. He reappears from weeks on the streets filthy, strung out, and paranoid. “My fear is the call that says he’s dead,” O’Connell says.

Kidder is interested in character, not policy—Rough Sleepers has little new to say about why homelessness exists or how to reduce it. A brief history covers familiar ground: the destruction of cheap boardinghouses where men like Tony once slept and their replacement by luxury buildings; the emptying of mental hospitals without adequate community care; the weak safety net for the disabled. But there’s not much about the broader inequality from which homelessness springs and almost nothing about politics or the paucity of housing aid. To connect the policy dots, readers might consult Marybeth Shinn and Jill Khadduri’s In the Midst of Plenty: Homelessness and What to Do About It (2020), a clear-eyed journey through a rich academic literature.

Kidder makes clear that the homeless population is extremely diverse—it includes veterans, runaway teens, and survivors of domestic violence, among other groups—and that the problems of rough sleepers (chronically homeless people largely living outdoors) like Tony are extreme. What Kidder calls the “hardcore rough sleepers” account for only three hundred to four hundred of the eleven thousand patients O’Connell’s program serves. As Dennis Culhane of the University of Pennsylvania has shown, about 80 percent of the people who experience homelessness are quickly rehoused and stay housed for many years. Shadowing a school social worker in rural Texas not long ago, I met a homeless student who wrote her college applications from six addresses, including a shelter, and went to Harvard—that’s homelessness, too.

One debate that Rough Sleepers does inform is that over Housing First, an approach to helping the chronically homeless that is under conservative attack. Housing First programs provide subsidized apartments to homeless people and offer—but do not require—treatment for mental health and substance abuse. By contrast, previous programs required clients to meet benchmarks like sobriety to get housing, leaving many people back on the streets. Several studies found that Housing First programs raised the odds of keeping people housed, and federal grants favor the approach. Housing First’s supporters say the programs save lives. But critics see liberal permissiveness and would redirect the money to rescue missions and other groups that impose treatment mandates.

O’Connell agrees that housing is a human right, but he has found limits to what it can achieve for the especially troubled population he serves. In 2005, as part of a state experiment to test Housing First, his program acquired twenty-four vouchers that provided clients the ability to rent private apartments. Some could find units only in far-flung neighborhoods, where they felt uncomfortable. Some caroused and got evicted. One was so disoriented by indoor living that he pitched a tent in his living room. After a decade, the vouchers had been issued and reissued to seventy-three patients; of them, nearly half had died, and of those living just one in eight had housing.

One lesson seems to be that deeply disadvantaged people like Tony and BJ need more accompanying services than even a program as good as O’Connell’s can provide. After four decades of Sisyphean struggle O’Connell doesn’t sound like a man who thinks the end of homelessness is within reach. “Caution was one of Jim’s themes in these later days of his career,” Kidder writes. “He wanted to temper expectations.”

For much of the three years Kidder follows him, Tony’s trajectory is unclear. One day, he’s the social director, crisp and empathetic. The next, he’s sleeping outdoors, disheveled and despairing. What triggers his falls isn’t clear, but the ratio of good days to bad worsens. Tony deftly defuses a fight, potentially saving a life, then lands in the ER “in florid, thrashing paranoia.” He returns not long after with a knife wound and broken ribs, probably from a collision with a baseball bat. If the story teaches us anything, it’s that living on the streets is life-threatening, even to someone with Tony’s exceptional size and strength.

As Tony’s condition worsens, Kidder, who is drawn to him like everyone else, abandons his position as fly on the wall and tries to help. When Tony’s failure to register as a sex offender threatens to send him back to prison in 2019, Kidder accompanies him to a court hearing. The “mind-numbing, butt-numbing” waits and byzantine procedures strike Kidder as another injustice to the poor, and he snaps at a public defender who shows up hours late. The lawyer snaps back but persuades the judge to clean the slate. Kidder embraces the hope that Tony has found a new start.

For those trying to help Tony, a lingering puzzle is his nonchalance about his experience of childhood rape. Was he feigning indifference for emotional protection? Did he invent the tale? Distraught after another spell of rough sleeping, Tony takes O’Connell aside and pours out the real story: he was repeatedly raped by a priest. (Kidder confirms that the priest Tony names was a sex abuser.) The suffering from grief and shame has never ended, and Tony is convinced it never will. “I knew back then when I was a little kid, there’s no such thing as God.”

A strength of Kidder’s portrait is his respect for Tony’s intelligence, a trait that affluent, educated people often overlook in the poor. Armed with a prison library card, Tony has read Maslow, Freud, and Jung and admires the artist “Martisse.” Kidder arranges a visit to the Museum of Fine Arts and brings his wife, Fran, an artist and teacher. Tony is dirty and smells bad, and Kidder is “embarrassed for feeling embarrassed.” The unease spreads when Tony scoffs that an abstract painting looks like “the face of a dude I beat up.” But he gets drawn into a discussion of technique, and his curiosity blossoms. He compliments Maurice de Vlaminck’s use of color and compares the posture of an Egon Schiele nude to Michelangelo’s David, which delights the teacher in Fran. “I just can’t help thinking what he could have been,” says O’Connell, who joins the tour.

A few months later, Tony is dead. He dies on a sidewalk, with cocaine, alcohol, and fentanyl in his blood, beside a woman he often protected. O’Connell sees the death as a kind of suicide, a way to silence the hurt and shame. The program staff cry at the news, and a group of rough sleepers gathers in a park to praise him as a protector. “We call him the Night Watchman,” one says.

A mystery remains: the truth of the crime that had sent him to prison and branded him a sex offender. Tony had denied committing a sex crime, but Kidder tracks down the police report. It says that when Tony was twenty-six, he held a knife to a man’s throat, pulled down the man’s pants, and tried to rape him—the childhood victim, it seems, became a victimizer. Kidder is glad not to have known this while Tony was alive, because it might have changed how he saw him. But O’Connell has learned to ignore his patients’ pasts. The man he knew tried hard to overcome the traumas that had stalked him and did so while looking out for others. “There was nothing about Tony that I could ever dislike,” he tells Kidder.

O’Connell displays pictures of patients in a gallery outside his office. Tony’s is quickly framed. For a long time, O’Connell resisted the temptation to photograph patients, for fear of being intrusive. Then one asked him to, and many others followed. Accustomed to invisibility, they were grateful to be noticed. That’s what this impressive book achieves—it allows these overlooked people to be seen.