48 pages 1-hour read

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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Part 6Chapter Summaries & Analyses

Part 6: “A System of Friends”

Part 6, Chapter 1 Summary

Kidder describes the trials and experiences of BJ, John Cotrone, and Tony as they support each other, support Jim, and build community together. Tony tries to care for BJ as best he can, particularly since the state refuses BJ a chronically unhoused status. Many of Tony’s friends die. Often, his response is to disappear when this happens. John Cotrone sits with a woman named Angie. She shares with Kidder and John her experience of finding housing, which she eventually gets kicked out of so that the unit can be demolished and turned into condominiums.

Part 6, Chapter 2 Summary

Kidder describes Tony’s life living on the streets. He describes the immense lengths to which Tony must go to survive on the street, including sharing his nights with women companions for warmth and company. As Kidder and Jim follow Tony through trains and tunnels, Tony shows them how he navigates the city and shares Boston’s history with them.

Part 6, Chapter 3 Summary

Members of the Street Team, like Eileen and Julie, explain to Kidder the importance of community in the face of what they, through their patients, face. The team members tell Kidder it’s important to be dedicated to the job and remain flexible. Angie gets evicted, though the team works to find her new housing. Kidder describes Arnold, an elderly man who struggles to find somewhere to shower, stay, and be taken care of. He’s been kicked out of nursing homes, hospitals, and shelters. Tony takes care of him, eventually taking him to the hospital.

Part 6, Chapter 4 Summary

Kidder describes the chaos of Tony’s life and the many times he leaves against medical advice. Kidder tracks Tony’s pattern—he goes through moments of illness and disappears, but when he can rest, he is calm and lucid. Tony joins Kidder and his wife for a visit to the Museum of Fine Arts. Tony shares his insights and perspectives, which Kidder details as astute. Kidder also describes his initial embarrassment at walking around the museum with an unhoused man.

Part 6, Chapter 5 Summary

Kidder writes first about the annual memorial service held in 2018. Jim feels that developing relationships with the new generation of rough sleepers will take more time than he has left to give. Kidder details a conference held by Jim where Jim shares the importance of boundaries and a willingness to accept the Sisyphean nature of the work.

Part 6, Chapter 6 Summary

At a gala event, Jim shares a slideshow and stories about various patients the Health Care for the Homeless Program has treated over time. Jim focuses on one woman, Beckie, who’d received housing and built a life free from drugs off the streets. Because Beckie no longer needs the voucher to maintain the apartment in which she has lived for over nine years, she is being forcibly evicted so that the building can be converted into condominiums. She is now being removed from the home she’d worked for.

Part 6, Chapter 7 Summary

Jim uses Beckie’s narrative to share the larger realities of houselessness. He tells the gala that the problem is like a “prism,” reflecting the fissures in American educational, health care, and corrective systems. Kidder details statistics about nationwide figures of houselessness in areas like Los Angeles and Colorado. Jim provides examples of community-based programs that are working to solve it.

Part 6 Analysis

Kidder continues to examine Systemic Failures as a Catalyst for Houselessness. He includes bits of speeches from Jim and testimonies from his patients to reveal how the system fails unhoused people. The educational system lets students who are experiencing poverty and abuse at home slip through the cracks. This sets up these students for higher instances of incarceration. Following incarceration, legal ramifications and stigma prevent previously incarcerated people from obtaining housing or work easily. People who struggle with mental illness are turned away due to lack of insurance or because facilities are overburdened. A variety of institutional failures culminate in houselessness.


Kidder shows these circumstances for unhoused people to be in the overwhelming majority. This runs in direct opposition to the Reagan administration’s efforts to blame houselessness on the individual. Kidder refutes this using multiple statistics, personal narratives, and his own observations.


The criminal justice system and its role in houselessness figure heavily into Tony’s story. Tony first experiences houselessness because of incarceration; many people who leave prison do not have the resources to find (and rent) an apartment, get clothes to interview in, or find transportation. Unless previously incarcerated people go through programs that help with re-entry, they must figure out how to do so on their own. Kidder hints at how isolating this can be, such as when Tony realizes that pay phones aren’t a common device any longer after leaving prison.


Re-entry is complicated by stigma. Being a felon can create barriers to housing, employment, and interpersonal relationships. In Tony’s case, these barriers are even more severe because of his status as a level-three sex offender. Kidder illustrates the ramifications of being labeled as a felon throughout the narrative. Tony’s status prevents him from getting housing. He must consistently register through complicated processes. Kidder demonstrates how the criminal justice system impedes people from moving forward with their lives.

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