48 pages 1 hour read

Tracy Kidder

Rough Sleepers: Dr. Jim O'Connell’s Urgent Mission to Bring Healing to Homeless People

Nonfiction | Biography | Adult | Published in 2023

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Summary and Study Guide


Rough Sleepers: Dr. Jim O’Connell’s Urgent Mission to Bring Healing to Homeless People (2023) is by journalist Tracy Kidder. The book profiles Dr. Jim O’Connell’s work with the unhoused population of Boston through the Boston Health Care for the Homeless Program. Kidder is known for his literary style and thorough research methods. In Rough Sleepers, Kidder accompanies Dr. O’Connell on vans through the streets of Boston as he treats patients and offers them food, clothing, and transport to shelters or hospitals. This nonfiction book explores how health care contributes to and is permeated by class and houselessness in the Northeastern United States.

Kidder received the Pulitzer Prize for The Soul of a New Machine (1981), the story of a team of computer engineers with an obsessive work ethic who developed a 32-bit minicomputer in a year.

This study guide refers to the hardcover first edition of the book published by Random House.

Content Warning: This study guide mentions instances of extreme violence such as rape, domestic violence, and childhood sexual assault, as well as depictions of grievous injury, illness, and substance abuse. It also mentions extreme injustices like racism, classism, and anti-gay bias.


Rough Sleepers: Dr. Jim O’Connell’s Urgent Mission to Bring Healing to Homeless People details the life of Dr. Jim O’Connell and his instrumental role in Boston’s Health Care for the Homeless Program. Dr. Jim O’Connell, called Jim throughout the text, was first a philosophy student and then a bartender. He agreed to participate in a year-long grant program after his residency at Massachusetts General. What began as a year of service turned into a lifelong mission to serve the people of Boston who live on the streets and in shelters. Through his early tenure in the program, Jim realizes that unhoused people die at 10 times the normal rate. Prior to Boston’s Health Care for the Homeless Program involvement, they experienced illnesses and injuries not usually seen inside the walls of Massachusetts General Hospital.

Over the years, Jim and his team build strategies to best support their patients, including unconventional methods not otherwise practiced in standardized medicine. Jim learns from nurses (like Barbara McInnis) who originally founded the clinic through grassroots donations and their own efforts that compassion, patience, and community are the surest ways to heal the people they treat. Many of the patients Jim and his team help have histories of severe trauma, substance abuse, and mental health disorders, and they have been greatly impacted by systemic failures across the United States.

Kidder summarizes and analyzes these failings, revealing the many complex layers that contribute to houselessness including stigmatization, racism, a lack of resources, gentrification, and the criminal justice system. As Kidder charts the successes and struggles of the program, he tells the story of the rise of houselessness in the United States and the many people and institutions directly impacted by it.

Tony (Anthony) Columbo becomes a key character through whom Kidder reveals the realities of houselessness. Tony is a patient of Jim’s and a “rough sleeper,” a person who sleeps exclusively outdoors and not in shelters. Tony becomes central to both the program and the narrative—his wisdom, generosity, and experience provide key insights into the trauma, adversity, and strength that unhoused people experience daily. Through Tony and Jim, Kidder explores the realities, failures, and victories of health care for unhoused individuals and how practices of compassion and care can model for the rest of the world how to better help humanity.