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‘If you want to solve homelessness in Boston, you’ve got to take a look at the real estate market’

A conversation with Tracy Kidder, author of the upcoming “Rough Sleepers,” and Dr. Jim O’Connell, a trailblazer in caring for the city’s homeless people.

Dr. Jim O’Connell checks on a homeless person on the grounds of the Old West Church in 2017.Bill Brett

Stories of exceptional Bostonians have kept author Tracy Kidder busy. His last three books have delved into their life’s work: Mountains Beyond Mountains tells the story of Dr. Paul Farmer, the Harvard-trained physician who set out to heal people in the poorest countries, from Haiti to Rwanda, through his nonprofit. In A Truck Full of Money, Kidder traces the journey of tech entrepreneur Paul English from the early days of the Internet through his work as a philanthropist. Now comes Rough Sleepers, set to be released on January 17, which chronicles the urgent mission of Dr. Jim O’Connell, another Harvard-trained physician who helped found Boston Health Care for the Homeless Program more than 35 years ago.

O’Connell, who has long served as the nonprofit’s president, still goes on van rides at night, organized by Pine Street Inn, to offer help to so-called rough sleepers, a 19th-century British term for homeless people. These are the people who live on the streets for years and are reluctant to seek medical care or stay in a shelter. Instead O’Connell and his team come to them, dispensing blankets, soup, and sandwiches with the hope that outreach might persuade some rough sleepers to come in for a checkup. With a staff of about 400 across 30 clinics, Boston Health Care for the Homeless treats homeless and formerly homeless patients for conditions ranging from frostbite to heart disease.


Kidder, a Pulitzer Prize winner for nonfiction who lives in Western Massachusetts, shadowed O’Connell on and off for five years on van rides, into clinics, and at Mousey Park, an informal gathering place for homeless people that was next to Massachusetts General Hospital until its expansion grew into the space.

O’Connell’s work began in the 1980s, a period that marks the modern era of homelessness when the Reagan administration began deeply cutting subsidized housing, mental health programs, and services for the poor. The doctor focused on the chronically homeless because they are the most medically vulnerable. As Kidder explains in his book, people who live mostly in shelters in Massachusetts suffer a death rate about four times higher than that of the state’s overall adult population. People who stay on the streets year-round die at about ten times the normal rate.


Kidder and O’Connell recently met up with me in Boston to talk about the forthcoming book and what it would take to end homelessness. This conversation has been edited and condensed.

Tracy, this is your second book about a Harvard Medical School doctor. What drew you to Jim’s story?

Kidder: I was writing a book about Paul English, and he had a lot of money for philanthropy burning holes in his pockets. He’d always been very interested in homelessness, and went around talking to people in town, and they said, “If you want to know about homelessness, you’ve got to go see Jim O’Connell in Boston.” He did, and in due course, I was invited to take a ride on the outreach van.

I was struck by a world that was sitting there in plain sight, but that we choose not to see, well, most of the time. I was also struck by the relationship between the doctor and these people. It seemed like friendship.


That was how it began, and I became more and more interested.

Jim, you first met Paul Farmer when he was a medical student, before he started Partners in Health. He visited Pine Street Inn in 1985, your first year working as a doctor there. Even back then, Paul (who died in 2022) believed that Harvard doctors needed to do more to serve their communities.

O’Connell: We got to be very good friends. We would be on a panel and he would always introduce me as this poor Harvard-trained doctor who never got more than a mile from his medical school. I would listen to what’s going on in Peru and all over the world, and then at the end, he would always bring it back, and say, “But isn’t it interesting, within a mile of our medical school, we’re finding the same health disparities that I’m finding in Rwanda.”

Tracy, you described how the van rides offer “a glimpse of a world hidden in plain sight.” Has writing this book affected how you see Boston?

Kidder: It’s pretty hard on a cold winter’s night to discover that behind Brooks Brothers is this warm vent, and you find there’s a bunch of humanity huddled there.

I’d never heard of the term “rough sleepers.” What’s the origin?

O’Connell: I went over to England one time because they wanted to learn what was going on in Boston. There is, in the British system, the [term] “rough sleepers.” Over here, we’ve always tried to ask people what’s the right word to call somebody who’s homeless. Is it a person experiencing homelessness? Most of the people we know like the idea of being a “rough sleeper.” They don’t want to be an “unsheltered person.”


Kidder (right) with O’Connell, cofounder of the Boston Health Care for the Homeless Program and the subject of Kidder’s latest book.Jessica Rinaldi

Tracy, while you set out to write a book about Jim, it’s almost as much about the homeless patients he treats — Tony, Joanne, Rebecca, and many more. Too often we look the other way when we encounter people living on the street.

Kidder: Before the book, I was really guilty of that myself. Jim has always liked to tell the story of the actor Richard Gere, doing some movie in a park down in Greenwich Village, where he lived and knew everybody. He dressed up like a homeless guy and sat on the bench, and nobody even looked at him.

O’Connell: He testified before Congress when we needed to get some money, and it was striking to me, too. It was a movie called Time Out of Mind. He was playing a homeless man, and what he realized, in his own neighborhood, no one even looked at him during eight hours of filming. And he said that was the hardest part of being homeless.

Much of the book takes place before the encampment arrived in 2021 at Massachusetts Avenue and Melnea Cass Boulevard — the region’s epicenter of the opioid and homelessness crises. What do you make of Mass. and Cass?


Kidder: I suspect people will equate that with all the people who are homeless in the city, and that’s not fair. That is not what that’s largely about.

O’Connell: I think about that all the time. It’s a huge problem, but when you think of the attention to homelessness over the last five or ten years in Boston, it has been largely Mass. and Cass. That’s 200 to 300 people. It’s a small percentage of the 11,000 people we see every year within our program. What’s happening to all the others is the other question I always want to ask.

In the book, Jim routinely checks on a mentally ill patient, but never hospitalizes her. Then she had a psychotic episode, was arrested, and committed to a hospital. Some years later, Jim runs into her and she looks great, and she says: “You left me there for ten years and you did nothing.” So is involuntary treatment good or bad policy?

O’Connell: This just emphasizes how complicated this is. At nighttime, she was polite to us, and when we finally broke through, she was taking sandwiches and talking to us. We considered that real success. But she got sent to a hospital, put on medication, and got real good treatment. When that’s available, that’s not a bad way to go. As she would say, just give me a chance — don’t leave me out there.

But too often now, we send people to the emergency room involuntarily, but where they go from there is really upside down. Tracy came with me to visit one guy who got committed to a hospital. It was just horrible.

Kidder: There are so many important distinctions here. It’s really complicated. We don’t have proper mental health services... . How can we do this without due process of law? I don’t think it is a solution.

Jim, you’ve been doing this work since 1985. Has homelessness in Boston gotten worse or better?

O’Connell: Fundamentally, I have to say it’s gotten better. People who were homeless for a long time on the streets and in shelters now can get housing. The street folks, in particular, had the hardest time getting housing because they needed to be on medications, they needed to go through a whole process, they have criminal records. They really were the ones who almost never got housing. It wasn’t until 2004 when all of a sudden those are the people that went to the top of the list.

That’s when a report came out on a “Housing First” model to help the chronically homeless. But when we look at Los Angeles, where there are significant resources devoted to creating housing, homelessness seems unsolvable. What about in Boston?

O’Connell: We’ve been out to LA, and it’s the place I would go to work if I were starting my career now. It’s 40,000 to 50,000 people on the streets. It is approaching an unsolvable problem without some major housing scaled to trillion-dollar levels. In LA, the latest statistic is that for every 200 people who get housed in a year, there are about 260 new people who come along. So you’re always behind. To catch up, it’s going to have to be like the war in Afghanistan — you’re just going to have to put a ton of money into it.

Kidder: If you want to solve homelessness in Boston, you’ve got to take a look at the real estate market. I’m thinking about a patient I wrote about who had found her own apartment, had supported herself, wouldn’t ask for any public assistance. Her apartment was being put on the market, she tried to raise a quarter of a million of dollars to buy it. She was dying of lung cancer, and died frantic because she was going to be homeless again.

Jim, you’ve said to end homelessness in Boston, we would need 1,000 units right away, and then 400 to 500 new units every year to keep up with the growth of homelessness.

O’Connell: That’s doable. But with the caveat we recognize that for some percentage of those people, they need a huge amount of support. A lot of times we’re putting into housing somebody who’s been on the streets 25 years. They suffered unbelievable trauma, they’re not capable of working. What do they do with their lives? Their whole community is back on the streets. If you put them in a basement apartment in Mattapan, it’s probably not going to go so well, even with a case manager looking in once a week.

I’m always going to put a footnote saying, there’s a difference between solving homelessness and keeping it solved. Part of the solution would be making sure we learn what permanent supportive housing is, and who needs that, and what does that support mean.

Housing doesn’t address the root causes of homelessness. What would?

O’Connell: The ultimate solution to homelessness is going to be learning how to prevent it in the first place. And the way you prevent it in the first place is you fix the schools. If I had all the money in the world, I’d fix the schools. And then you’ve got to make sure blighted neighborhoods are fixed up, and crime is addressed. Then you’ll stop the flow coming in.

Kidder: Homelessness is a symptom of a huge number of ills in American society. There is a terrible lack of truly affordable housing and decent affordable housing because that covers all the problems that can lead to homelessness, combined with the long-term effects of child abuse, educational deficiencies, lack of treatment for mental illness, foster care — you could go on and on. It’s not one little thing.

I just don’t know how we ever can resolve this without just saying as a society, “Dammit, this is wrong.”

Jim, you were supposed to treat homeless patients for one year, and then go off to a prestigious oncology fellowship. You never went. What changed?

O’Connell: I lucked into this. I’m the quintessential accidental tourist. I just love being a doctor. And even though I thought I would be doing this briefly, there was something about taking care of a bunch of people who really appreciated having you there and who were really sick. What has changed me is that this work let me understand what being a doctor is all about.

Tracy, has writing this book changed you?

Kidder: It’s such a simple thing — it sounds stupid — but to know these people as people ... I’ve seen a part of the world that I didn’t really know existed with Paul Farmer in Haiti. Then to see it right here in Boston, it was kind of amazing. As Jim once said, misery and unnecessary deaths happen in the citadel of medicine — in the very shadow, literally, of a great medical institution. It’s important to know the truth about what’s surrounding us. And I’m very grateful to Jim for showing me that.


LEARN MORE: Author Tracy Kidder and Dr. Jim O’Connell will speak about Rough Sleepers at the Cambridge Public Library on January 17 at 6pm. The Harvard Book Store event is free but RSVP is required. Learn more at

Shirley Leung is a Business columnist. She can be reached at