Q&A: Author Tracy Kidder and Dr. Jim O’Connell on the new book ‘Rough Sleepers’

The Pulitzer Prize-winning author followed the Boston doctor and founder of Boston Health Care for the Homeless on and off over five years as he provided medical care to the city’s chronically homeless residents.

From left: Author Tracy Kidder poses for a portrait with Dr. Jim O'Connell who founded Boston Health Care for the Homeless. Jessica Rinaldi/Boston Globe

When author Tracy Kidder initially approached Dr. Jim O’Connell, founder Boston Health Care for the Homeless, saying he wanted to write about his work providing medical care to Boston’s chronically homeless residents, the doctor had mixed feelings. 

A fan of Kidder’s, he said he’d read all his work, including 2003’s “Mountains Beyond Mountains,” in which the Pulitzer Prize-winning author delved into the work of O’Connell’s old friend and fellow Harvard Medical School graduate, the late Dr. Paul Farmer

“I could not believe someone like Tracy Kidder would even be interested in our little part of the world,” O’Connell said. 


After all, he considered the work that he and his colleagues were doing on the Street Team at Boston Health Care for the Homeless as being “a very narrow lens.” But, as he noted in a recent interview with Kidder and, that lens and world he’s been dedicated to since 1985 is one that “opens up to show us a lot about who we are as a people.” 

Kidder, who lives in Western Massachusetts, ended up following O’Connell and the Street Team on and off over the course of five years, capturing the work of the doctor and his colleagues as they served the city’s “rough sleepers” — a sub-group of Boston’s homeless residents who often have been living on the streets for years, enduring extreme weather, violence, and trauma, and typically are reluctant to access services or go to shelters. (The average age of the Street Team’s patients is 53, and it is estimated they die at about 10 times the rate of the state’s general adult population.)


The result of that time spent with O’Connell is Kidder’s newest book, “Rough Sleepers,” which published Tuesday. In it, Kidder offers readers a glimpse of the work being performed by O’Connell and his colleagues providing medical care and succor to their patients, and capturing, not just the care provided by the team in clinics, on the street, and overnight through the Pine Street Inn’s outreach van, but the relationships between the health care workers and their patients. 


He also, through O’Connell’s experience and his own research, delves into the complexities of the broader crisis of homelessness and what continues to be needed to solve it. 

To tackle the current situation in Boston, O’Connell estimates 1,000 units scattered across the city would be needed immediately. And with people falling into homelessness every day, an additional 400 to 500 units would be needed each year to help keep up with the demand. 

Addressing the homeless crisis begins with housing, but much more work is needed to address the broad range of societal factors and failings — ranging from education to mental health — that result in people living on the street.

And more immediately, once people get into housing, some continue to need assistance and care in order to stay in it, O’Connell said — something there is not currently much support for at the federal level. 

“When you start to concentrate on the very chronically homeless, those who are living for long periods in the shelter and long periods on the street, the rough sleepers, the furies that pursued them into the streets and shelters don’t go away just because you get into housing,” O’Connell said. “Our experience has been that when they get into housing, they lose all the survival skills they honed so wonderfully on the street and now need the skills to be alone in an apartment, in a neighborhood they don’t know, without a community and a support system.”


In the face of what can seem like a crisis of overwhelming complexity, O’Connell acknowledged that for members of the public, it may seem that the problem is so big that anything an individual can do is futile. 

But he recalled the words of Barbara McInnis, a nurse who early on in his career providing care to the homeless told him “how to do [the] job” and for whom the medical respite program at Boston Health Care for the Homeless is named

“She would say that the best thing we could do is not pass by people without looking at them,” he said. “And that you should just acknowledge their presence. That alone would change the lives of many many people. Now that feels like you’re not doing much, but I think that is wisdom beyond wisdom.”

Kidder agreed, pointing out that the simple act has a corollary effect that the more people start to really look, to acknowledge the individuals who they would otherwise pass by without a thought, they may find themselves coming up with more actions they can take. 

“They go out and hand out sleeping bags, they give them money,” he said. “By the way, I just have to say this, that’s an individual choice, you choose not to give homeless people money, fine. But you shouldn’t flatter yourself into thinking you’re doing a good deed by having done nothing.”


Below, Kidder and O’Connell share more with about what they hope people take away from “Rough Sleepers,” what needs to be part of the conversation in tackling the crisis, and the importance of listening when providing medical care to those who are living unsheltered on the city’s streets.

The interview has been edited for clarity and length. Tracy, can you talk about when and why you realized you wanted to write about ‘rough sleepers’ and follow Jim’s work in Boston?

Tracy Kidder: I’m always looking for a good story, and I was accompanying a guy I was writing about who got a ride on [Pine Street Inn’s] outreach van. And I was fascinated by this world that was suddenly revealed to me, really, in plain sight. But, like many of us do, I performed that slight of mind where you manage not to see these people. 

Jim’s relationship to these people who were really strangers to me struck me as being quite remarkable. It would even be remarkable if they hadn’t been homeless, if they had just been regular doctor’s patients. Because as Jim told me, he was taught at Mass. General “you can be friendly, but not a friend.” But these were clearly warm relationships. … I wasn’t looking to write about homelessness. In fact, if that had been presented to me as a possible topic, I probably would have said no, no one’s going to want to read about homelessness. But this was different. 

I had been with Paul Farmer [writing “Mountains Beyond Mountains”] and … that stuck with me. I had seen a part of the world that I hadn’t really known existed, hadn’t seen. And now I was seeing it in Boston. So I felt it was an important subject, but also a really interesting story.

Do you feel you’ve been impacted or changed by what you observed and getting to know some of the patients that were served by the Street Team at Boston Health Care for the Homeless?

Kidder: I hesitate to say I’ve been changed. I mean, in some superficial, not very important ways. Suddenly what had been a muffin shop was now the place across the street from where this couple would sleep with all their bags and their witchcraft equipment. A colorful couple. And a storm at sea makes you think in the winter about the people you’ve gotten to know. When you see someone sloshing down a doorway on Bromfield Street, you think, I wonder who was sleeping there last night. 


But I hesitate to say it’s changed me. Because that would imply that I’d gone out and given up all my worldly possessions and gone to work — I haven’t done that. And to be really honest, I just wanted to tell a good story. … But of course I got fascinated with the project. That’s what happens. I concentrate on an individual — my dear departed editor once called them my “victims” — and then I get obsessed or really preoccupied with the same things that preoccupy them. 

The main thing I would want to say is that I had done this slight of mind, like so many Americans, [of not really seeing homeless people] … I hadn’t perfected it, but I was pretty good at it. And what that does is it makes you not realize that these are human beings, these people who are in such terrible straits are actually human beings. Because you actually don’t really want to realize that, right? Otherwise you might feel you have to do something. 

Dr. Jim O’Connell writes a prescription for Gypsy, a homeless woman, who has a bad infection on her arm in March 2002. Gypsy’s boyfriend, Walter, sleeps next to her. – Tara Bricking

The act of listening, and Jim’s skill as a listener, comes up frequently in the book. Jim, could you speak to why listening is such an important part of what you do on the Street Team?

Jim O’Connell: When I was training to be a doctor and then working as a doctor inside Mass. General, we did a lot of talking. I had gotten used to the fact that we were supposed to be the experts and tell everyone what to do and move on to the next person. And your comeuppance when you get to the shelters or the streets is that nobody cares that you’re a doctor. They don’t know who you are and don’t really care. And it takes time for you to be around, for them to get to know you and realize you’re not there for any other reason [than] to see if they need any help. And listening is how you did it. 


The best training I had for the job was years of being a bartender … if you don’t learn to listen, it becomes an incredibly long evening and no fun. I really learned to listen and take time. … So on the streets, we just learned that valuable lesson — people don’t trust you. But once they trust you, they want to tell their story. And then their stories unfold in just amazing complexity and you start to see a whole other side of someone you had initially just seen there as sitting there on the street corner. 

The invisible world that opens up as you listen. … That’s why I’m so grateful to Tracy, because I think he experienced that and was able to articulate it in a way that none of us can do. It’s one of the most important lessons all of us on our team has learned, that listening to people and letting them tell their story is really the foundation for then taking care of them. 

There remains a lot of stigma and misconceptions around homelessness, and when there is opposition to projects that are proposing either housing or additional support services for the population, the term “public safety” is often raised by people who are in opposition to those services or projects. Can you speak to that? How would you like to see the broader community pitch in to combat the stigma and the dehumanization of people who are living on the streets?

O’Connell: I think it’s totally understandable why people are afraid to open their neighborhood to what they don’t know. On the other hand, these are people who deserve homes, deserve lives, and have been pretty much structurally pushed into that situation most of the time by no fault of their own. 

So we’ve got to do something. … I think if we’re collectively, as a society really [going to] address this problem, and addressing it begins with housing, if you don’t have the housing, you can’t really address it. … That housing has to be, in fairness, distributed equally around. We all can’t say not in my backyard, because then there’s no backyard for these people to be. But it shouldn’t be that one neighborhood gets everything. That’s been the problem that I’ve seen pretty much throughout; most of the programs end up in the most impoverished areas and you don’t see them in the more gentrified or wealthy areas. 

In Boston, the issues around the area known as Mass. and Cass have gotten the most media and public attention in recent years when it comes to talking about homelessness. Can you speak to how people who are chronically homeless are not necessarily represented in that population, or not represented with the outsize focus on Mass. and Cass? What do you think that means for how the public, and officials, act on addressing homelessness in the city if there is just this focus and thinking that Mass. and Cass represents the entire issue across the city?

O’Connell: It’s a horrendously complicated problem that belies any simple solution. It’s absorbed all the oxygen about homelessness in the city for the last several years when, in fact, that’s 200 or 300 people out of the 6 or 8,000 that are homeless each year in Boston. 


So what’s happening with all the rest of the problem always worries me a lot … I would go out in the van at night time [that is] run by Pine Street Inn … for two nights a week up until the pandemic. And I got to know everybody who was on the street. We knew everybody. And over time, I knew many people who had been out on the street for 20 and 25 years. 

But when I went to Mass. and Cass, I didn’t know anybody. It was only a handful of people. So it was very clear to me that something new was driving that [and] new solutions had to be looked at. I don’t think any of us were ready for what that solution needed to be. 

We know we have to come up with better substance use services. All the services you could argue for — safe injection facilities, we have a spot that one of our docs, Dr. Jessie Gaeta, set up for making sure people don’t die after they’ve taken something — all of those things I think are really necessary. 

Then I think what [Mayor Michelle Wu] has done has been pretty darn creative at finding places for all those folks to go. But it’s a new population of primarily younger people with the burden of lots and lots of co-occurring medical, psychiatric, and substance use disorders. … It’s complicated, and I think everybody has to put up the white flag and say we’ve got to get together and come up with a mosaic of solutions. It’s not going to be one solution. And we have to say this is a citywide if not a statewide if not a national problem, not a Mass. and Cass problem. 

Am I right in hearing you say that you’re concerned that the thousands of other members of the homeless population are going to get left out of this push for solutions specifically around Mass. and Cass?

O’Connell: No, I think it’s something different I’m concerned about. 


What’s been going on all this time is some phenomenal work on the part of the shelters and housing programs. … All that good work, [which] is really something Boston should be proud of and the mayor should be proud of, gets swallowed up by all the attention to Mass. and Cass. It makes everybody say, “Oh, this homeless problem is so much worse.” We don’t get a chance to celebrate what has been successful. And I say that only because we’ll lose — the sympathy of the public is rapidly going.

I’ll never forget on Labor Day of 1991, there was an above-the-fold article on the top of the New York Times talking about compassion fatigue among homeless providers. Because during the AIDS epidemic and everything that they’d been doing, nothing seemed to work. And I worry that we’re going to get that same attitude if you just concentrate on Mass. and Cass, instead of seeing that there are ways to solve that. 

Kidder: This number stuff drives me crazy, as Jim knows. Because I really spent a lot of time trying to figure out how many people are homeless. And the conclusion I came to is that almost no big jurisdiction has that number clear. Within homelessness itself, you have people who are homeless for one day a year or intermittently homeless, you have people who are invisibly homeless, and by definition, you don’t know how many of those people there are. … One has to sympathize with the mayors who have really tried. … Every single mayor since [Raymond Flynn] has really had a good heart for homeless people, and probably almost all the governors. And yet, in spite of that, and in spite of all the progress that’s been made, it’s still not good enough, of course. 

O’Connell does rounds with colleagues from Boston Healthcare for the Homeless in April 2006. – Provided

Given the scale and complex nature of this crisis, how do you stay hopeful doing this work, Jim? How do you measure success? Or, Tracy, how did you observe Jim measuring success?

O’Connell: I’ve been doing [this] for most of, in fact, all of my medical career. And what have we accomplished? What are the outcomes that we can be really proud of? And we realized that we have been talking about a population that has a huge premature mortality rate. It hasn’t changed much over the years, doesn’t even change much once they go into housing. So we know that we still have a lot more to do to change that outcome. 


But when we step back and think about it, we’ve been privileged to be invited into the lives of these people who I would never have known anything about, who have lived lives of incredible courage after being handed the worst adversities in childhood and everything. So you get to really appreciate who these folks are. And most importantly, I think all of our nurses and doctors would say, they are incredibly grateful for the care we would give to them. And as you get to know them over time, you really become part of their lives and they become part of our lives. 

This is a job that I thought was going to be really hard, and it is really hard. But it gives us a huge opportunity to care for people, even if we can’t cure, we can really care. And even when people are going to die, being there when they die and helping minimize their suffering when they’re dying brings a huge amount of satisfaction to us, despite the overall horror of the tragedy of homelessness on the larger scale. 

Kidder: I was talking to a friend and I used the word success in this context, and he said that’s a capitalist word, why would you measure things by that standard? And I do think that it is wrong to measure things solely by that standard. After all, life itself is not sustainable, not infinitely, and to ameliorate suffering, I think, has always got to be worth it. I don’t know if this is right or not, but [here’s] what I, in my arrogant way, decided Jim’s story is: Here’s a guy who was so good at so many things, had a hard time picking one for a profession. When he did, when he was 30, he found he really loved it and he had a great time studying it. And when you’ve gone and really gotten good at something and now you have an opportunity to practice it among people who desperately need you and who are really grateful for what you’re doing, that’s a pretty good job.

What do each of you hope that government officials might take away from reading the book? How would you hope this informs public policy or action to address homelessness?

O’Connell: My hope is that as many people as possible will read this because what comes through in the book so magnificently from Tracy is who these folks are. That they’re just us, brokenness, all of that, they’re really just us. And if that just brings us all together to say, let’s figure out solutions to this, I think that would be a huge first step. 


I truly believe that the job we have [is] to take care of those people who for whatever circumstances have ended up chronically in the shelter. We have to take care of them. But then  … what are the policies and what are the things we need to change to make sure this same thing doesn’t happen to our 5- and 6- and 7-year-olds right now? And I think that calls us out. 

If government officials read this … we need to have good housing policies, better health care, better public health. We have to also fix the schools, because I really, truly believe almost every person we see has had awful experiences in school. … We have to go back and fix those things if we’re going to stem the tide. 

Kidder: I don’t mean this ironically or anything, I just never would try to dare to calculate the effect of something I’ve written on public officials, honestly. I know they have so many other pressures on them. And I think I should be sympathetic or at least try to be … because what we’re seeing here is a symptom. A really big and scattered symptom. 

I love Jim’s analogy of the prism, that what we see refracted are all these problems, which do begin with housing. … [Also on my list] are, do something about child abuse. One of the great psychiatrists [at Boston Health Care for the Homeless] who retired during my time there, a guy named Jim Bonner, he told me once that he thought 90 percent of his street patients had severe alcohol or drug abuse problems or both, and that somewhere up in 75 percent or so had really, not just bad childhoods, but really horrifying ones. And Jim, when I told him that statistic, he thought it might even be higher. … And then I really wish someone would really get on to the business of mental health. … We don’t have facilities for the people who are really severely mentally ill. … And it seems to me that’s a problem we really have to address and we better start addressing. … But I’m with Jim on this, let’s hope for a better future. Because if you solved this problem, you would really be improving this country enormously.


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