Rough Sleepers

Dr. Jim O'Connell's urgent mission to bring healing to homeless people


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January 17, 2023 | ISBN 9780593677469

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About the Book

NEW YORK TIMES BESTSELLER • The powerful story of an inspiring doctor who made a difference, by helping to create a program to care for Boston’s homeless community—by the Pulitzer Prize–winning, New York Times bestselling author of Mountains Beyond Mountains

“I couldn’t put Rough Sleepers down. I am left in awe of the human spirit and inspired to do better.”—Abraham Verghese, author of Cutting for Stone

A BEST BOOK OF THE YEAR: NPR, BookPage, Chicago Public Library

Tracy Kidder has been described by The Baltimore Sun as “a master of the nonfiction narrative.” In Rough Sleepers, Kidder tells the story of Dr. Jim O’Connell, a gifted man who invented a community of care for a city’s unhoused population, including those who sleep on the streets—the “rough sleepers.”

After Jim O’Connell graduated from Harvard Medical School and was nearing the end of his residency at Massachusetts General, the hospital’s chief of medicine made a proposal: Would he defer a prestigious fellowship and spend a year helping to create an organization to bring health care to homeless citizens? That year turned into O’Connell’s life’s calling. Tracy Kidder spent five years following Dr. O’Connell and his colleagues as they work with thousands of homeless patients, some of whom we meet in this illuminating book. We travel with O’Connell as he navigates the city streets at night, offering medical care, socks, soup, empathy, humor, and friendship to some of the city’s most endangered citizens. He emphasizes a style of medicine in which patients come first, joined with their providers in what he calls “a system of friends.”

Much as he did with Paul Farmer in Mountains Beyond Mountains, Kidder explores how Jim O’Connell and a dedicated group of people have improved countless lives by facing and addressing one of American society’s most difficult problems, instead of looking away.
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Praise for Rough Sleepers

“Excellent . . . a detailed portrait of the lives of homeless Americans . . . [Kidder] asks us—correctly, I think—to consider that in a world of far too much cruelty, the compassionate person standing at the bottom of the cliff is part of the story too.”The Washington Post

“Excellent and immersive . . . sure-handed.”The Wall Street Journal

“To read Rough Sleepers is to confront not only the consequences of homelessness, but to wrestle with knowing that, as terrible as the problem is now, it would so be much worse if not for the sacrifices of people like O’Connell.”Los Angeles Times

“Wrenching.”The New York Times

“O’Connell is a fascinating protagonist . . . not only one of the good guys but a good guy who is vigorous, self-critical and even funny.”—Minneapolis StarTribune

“[An] uneasy portrait of the United States . . . Kidder turns his meticulous but generous eye on Jim O’Connell.”Harper’s Magazine

“A book that celebrates the great good that one man and his program have done in the face of grueling, unimaginable odds. Kidder has humanized a sprawling, thorny subject by focusing on people, not policy.”Portland Press Herald

 “Tracy Kidder has reported the hell out of important stories before, but never more finely and relentlessly. It’s a story full of hard questions, a story with many heroes.”—William Finnegan, author of Barbarian Days

“The estimable Tracy Kidder has found another unsung saint—this time not in the backcountry of Haiti or in genocide-ravaged Burundi but on the streets of a major American city. And once again, he has crafted a story that sheds light on a larger landscape of injustice.”—Adam Hochschild, author of American Midnight

Rough Sleepers is yet another enlightening reminder from Kidder that we should, and can, do better.”The Christian Science Monitor

“A searching, troubling look at the terrible actualities of homelessness.”Kirkus Reviews (starred review)

“With a straightforward scrutiny that reveals without judging, Pulitzer Prize winner Tracy Kidder offers a long, hard look at the lives of homeless people. . . . Intensely immersive.”BookPage (starred review)

“Keenly observed and fluidly written, this is a compassionate report from the front lines of one of America’s most intractable social problems.”Publishers Weekly
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Rough Sleepers


The Van

Around ten on a warm September night, the outreach van stopped in the kind of South Boston neighborhood said to be “in transition.” On one side of the street was a new apartment building, its windows glowing, its sidewalk lit by artful imitations of old-fashioned streetlamps. On the other side, in murky light, stood an abandoned loading dock. A heap of blankets lay on the concrete platform. Someone passing by wouldn’t have known they were anything but discarded blankets. But when the driver of the van walked up the steps and spoke to them, saying he was doing a wellness check, a muffled voice came back from underneath: “F*** you. Get the f*** outa here.”

The driver turned away and shrugged to Dr. Jim O’Connell, who was standing at the bottom of the steps. “Let me try,” the doctor said, and he climbed up to the platform and knelt by the gray mound. “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.”

An earthquake in the blankets, then an eruption: Tangled hair and a bright red face and a loud voice, saying in a Boston accent, “Doctah Jim! How the f*** are ya!”

For the next half hour, Johnny reminisced—about the alcohol-fueled adventures of his past, about mutual old friends, mostly dead. The doctor listened, laughing now and then. He reminded Johnny that the Street Clinic was still open on Thursdays at Mass General. Johnny should come. That is, if he wanted to come.

Dr. Jim—James Joseph O’Connell—had been riding on the outreach van for three decades. During those years he had built, with many friends and colleagues, a large medical organization, which he called “the Program,” short for the Boston Health Care for the Homeless Program. It now had four hundred employees and looked after about eleven thousand homeless people a year. Jim was its president, and also captain of the Street Team, a small piece of the Program, with eight members serving several hundred homeless people who shunned the city’s many shelters and lived mainly outside or in makeshift quarters. About half of Jim’s administrative work now lay in managing the Street Team, and all of his clinical work went to doctoring its patients, Boston’s “rough sleepers,” as Jim liked to call them, borrowing the British term from the nineteenth century.

The van was a crucial tool for reaching those patients. It was financed by the state and managed by the Pine Street Inn—Boston’s largest homeless shelter. Nowadays two vans went out from the Inn each night. They had become an institution, which Jim had helped to foster in the late 1980s. Back then he used to ride three nights a week, usually until dawn. Now he went out only on Monday nights and got off around midnight.

When Jim had begun these tours on the van through Boston’s nighttime streets, he had imagined the world of rough sleepers as a chaos. But it turned out that most of them had territories where they hung around and panhandled during the day—“stemming” was the street term, its etymology obscure. For sleeping, they had favorite doorways, park benches, alleys, understories of bridges, ATM parlors. Rough sleepers were like homebodies without homes. At the start of a ride, Jim and the driver and the driver’s assistant would trade the names of people they were worried about, and they could usually find each of them within an hour or two. Jim was like a 1950s doctor making house calls, though the van rarely dispensed more than minor medicine. Rather, it was meant for bringing food and blankets and socks and underwear to rough sleepers, and, more urgently, for finding people in distress and bringing them in, if they would come—to hospital emergency rooms or the city’s homeless shelters. The van was also a tool for keeping in touch with patients and their ailments and collecting the unpublished news of the streets.

Like all members of his Street Team, Jim carried a small knapsack, his doctor’s bag, its contents refined and miniaturized over the years. It consisted mostly of basic first aid gear and diagnostic equipment—a blood pressure cuff that wrapped around the wrist, a little pulse oximeter, an ear thermometer, a simple blood glucose meter, a stethoscope. Among the losses he regretted was the pint bottle of whiskey he once carried for the times when a patient was in alcohol withdrawal and on the verge of seizure. “You couldn’t do that now. It’s become a moral issue.”

He wore his cellphone in a holster on his hip, and he carried a small flashlight, thin enough to hold in his teeth if he needed both hands to examine a patient. A flashlight remained one of the Street Team’s essential tools for checking on rough sleepers. Some years back, one patient had asked how Dr. Jim would feel if his doctor came to his bedroom in the middle of the night and woke him up by shining a flashlight in his face. Jim took the issue to the Program’s board of directors, a group of about sixteen, which included experts in health and medicine and finance, and several formerly homeless people. The board convened a meeting of about thirty rough sleepers who issued this advice, long since become policy: The wellness checks should continue, but when they woke people up late at night, Jim and his Street Team should first shine their flashlights on their own faces so as not to startle the patients.


The van stops under streetlights on Bromfield Street not far from Boston Common. It’s like a small bus, with several rows of seats, mostly occupied by boxes of blankets, underwear, and socks. In the rear there’s a small canteen, with boxes of sandwiches and condiments, vats of hot chocolate, coffee, and soup. Jim gets out, opens the back doors, and looks around for customers. He has a ruddy face and silver hair that falls almost to his collar and over the tops of his ears. He wears light-colored corduroy pants, a collared shirt, and clogs. He’s six feet tall and trim and moves with an athlete’s self-assurance that makes a task look easy, and his voice is full of energy and cheer as he waits on the customers at the back of the van.

A thin Black man comes wandering into the light, out of an alley.

“You got soup?” he asks.

“Yes!” says Jim, grabbing a Styrofoam cup and filling it from one of the vats.

“You got crackers to go with it?”


“Isn’t there a doctor who goes with you guys?”

“I’m a doctor,” says Jim. Then he introduces himself, offering his hand.

“I want to change my doctor,” says the man. “I hear good things about you.”

“We’d be happy to take care of you. We’d be thrilled.” The man should come to Street Clinic this Thursday, Jim says, adding that it’s held at “Mass General”—the gigantic Massachusetts General Hospital, not far away, near the banks of the Charles River.

The van makes many stops. It encounters a mixture of people. There seem to be about half as many women as men, and lone women are rare, almost certainly because the streets at night are especially dangerous for them. There are many Black faces, but far fewer than white ones, and this is surprising. Homelessness afflicts Black and Latino people disproportionately both in the United States and in Boston, and one might expect that the same would be true of the city’s rough sleepers. Jim has long worried that the van and other outreach efforts have consistently missed rough sleepers of color, and yet most of the van’s drivers and their helpers are themselves Black and Latino. Over the years they have often searched for their own in the nighttime city. Maybe, Jim thinks, the Black and Latino communities are more willing than Boston’s white world to harbor their homeless. In any case, once people have fallen to living on the streets, they have reached a certain horrible equality.

A young-looking white woman comes into the light on Washington Street, hopping on one foot and then the other, running her hands through matted, strawberry blond hair, all the while feverishly scratching her arms and neck and face. “That’s what people will do on K2,” Jim says softly, as the woman approaches. K2 is synthetic marijuana, which has notoriously unpredictable effects.

Her voice is loud and high: “Holy shit! I got lice! I was exposed to lice and I’m freaking out. I already got all the treatment and somebody stole it.”

“Where did you get the treatment?” Jim asks.

“I bought the shit at CVS, and somebody stole a hundred dollars’ worth of frigging lice removal shit, I got court tomorrow, my mother’s sick in the hospital, dying, and I need to go see her but I’m not gonna go there and expose people. A lot of chicks have ’em and don’t tell.”

About the Author

Tracy Kidder
Tracy Kidder graduated from Harvard and studied at the University of Iowa. He has won the Pulitzer Prize, the National Book Award, the Robert F. Kennedy Award, and many other literary prizes. The author of Strength in What Remains, My Detachment, Mountains Beyond Mountains, Home Town, Old Friends, Among Schoolchildren, House, and The Soul of a New Machine, Kidder lives in Massachusetts and Maine. More by Tracy Kidder
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