Yesterday was International Overdose Awareness Day. In the afternoon, service providers, volunteers, and elected officials, along with family and friends of victims, all gathered on the New Haven Green to remember those we lost in the last year, most of whom had experienced homelessness at some point in their life.

The relationship between drug use and homelessness is complex. A simplistic assessment might be that the latter is sometimes the result of the former, though, given the trauma of homelessness itself, the former is just as likely (if not more likely) to be the result of the latter. It would be more cautiously accurate to characterize homelessness and drug use as simply parallel circumstances.

In any case, I made the mistake of reading the closing chapters of Tracy Kidder’s book on the community treated by the Boston Healthcare for the Homeless Program when I woke up this morning, with those names recited yesterday still ringing in my ears.

In ROUGH SLEEPERS, Kidder profiles Dr. Jim O’Connell and his journey from bartender to medical student to unwitting founder of a new, experimental pilot program in Boston to provide street medicine. For those who work with unhoused people, particularly in the Northeast, O’Connell is a bit of a folk hero. When I attended a talk he gave at a symposium in New Haven about five years ago (pre-pandemic), I was impressed by his work, but I wouldn’t say my mind was blown. New Haven, after all, has its own version of Dr. Jim and its own street medicine team; as it happened, the Director of the Homeless Health Care Department at New Haven’s Cornell Scott Hill Health Center, Phil Costello, is a disciple of Jim O’Connell’s, so the parallels between the Boston Healthcare for the Homeless Program and Hill Health’s Homeless Health Care Department are hardly surprising.

For me, Kidder’s work filled in the gaps in the history, describing how the program came to be, and following O’Connell over his 35+ year career, right up to the pandemic. But it also elaborated on how the team’s methodology and approach evolved over the years, illustrated through their interactions with a cast of recurring characters — their patients — most notable of whom is “Tony.”

Those who work in this field — i.e., those who work with the rough sleepers — will see streaks of Tony in the people they’ve known over the years. The themes of depression, despair, violence, unpredictable behavior, and gracious love will be all too familiar to frontline workers especially. For that reason alone, ROUGH SLEEPERS can be an incredibly painful read. For outreach workers, expect the last few chapters to be read through the watery haze of tears.

But truly, ROUGH SLEEPERS is worth pushing through. In fact, I would characterize it as “essential reading” for social workers, medical professionals, and (most importantly) anyone in a decision-making position regarding services for unhoused and, especially, unsheltered people. For the first two groups, not all social workers and medical professionals will find themselves primarily working with the homeless population, but the lessons and strategies that O’Connell and his team demonstrate are relevant to anyone who strives for the person-centered approach of “meeting people where they are.”

Moreover, the experienced reader will notice many of the same internal struggles that O’Connell and his team (as well as the author himself) deal with in navigating their relationships with the rough sleepers. In response to the discovery of one patient’s criminal record, O’Connell says, “There are some people on the street who do nasty things to other people, and then I just have a hard time liking them. … But I don’t think we judge — at least I haven’t — we don’t judge people on what led them here. It’s what they do once they’re here.” That’s an incredibly progressive and innovative take for O’Connell’s generation; younger practitioners and service providers, steeped in the values of harm reductionist strategies, would likely go one step further and say, “We simply don’t — or at least, try not to — judge anyone at any time. Period.”

For public officials and executive leadership in hospitals, clinics, shelters, and other services for unhoused people, Kidder offers a critical window into (or maybe for some readers, a reminder) of the seemingly intractable situations and impossible task of providing for people who seem so committed to self-destruction. But, as Kidder implies throughout the book, it is this very perspective — that it’s impossible to help those who won’t help themselves — that the work of the Boston Healthcare for the Homeless team rightly challenges. O’Connell doesn’t shy away from what even he sees as a Sisyphean task — pushing the boulder up the hill only to have it continually roll back down. For him and his team, the struggle is itself important and worthy of their efforts. In our data- and results-driven world, I doubt O’Connell’s bosses would completely agree, and I think, in any U.S. city, you’d have a hard time finding an executive of any kind of service provider for unhoused individuals (let alone an elected official) to consider “improved wellbeing” as an acceptable metric of success. But as Kidder’s interviewees remind the reader again and again, their job is simply to heal one person and one wound at a time — not save the world.

By the end of the book, every word becomes a painful testament to our society’s collective failure to ensure the health and welfare of everyone in our community. Kidder’s reporting implicitly argues that we leave those whom we deem unworthy of compassion out on the street, while praising people like Jim O’Connell as “saints” and “angels without wings.” That praise, laced with private donations, falls far short of the kind of humanity and compassion (backed by real, long-term investment) needed to provide for those who otherwise become the “rough sleepers.” We make excuses for our coldness — because they’re addicts, because they’re crazy, because they’re lazy, because they WANT to be out on the street — but the truth is that we turn our backs because, for all our progress in the last 150 years, we simply don’t want to see or understand those who are different or those who are in pain. Jim O’Connell and his team take the opposite approach. Not only do they strive to offer medical care to those who have been deserted by the broader community, but they open their hearts in every way imaginable so as to offer complete human care to their patients. And, in the end, if their patients become their friends, so be it. They’ll mourn their deaths accordingly.