FreeportSpeech: A Frank Conversation About Homelessness

Cullen Ryan, Executive Director Community Housing of Maine, Deborah Desantis, CEO of CSH, a national organization on homelessness, Dr. Jim O’Connell, President of Boston Health Care for the Homeless Program and subject of renowned author Tracy Kidder’s book Rough Sleepers about his work with Boston’s homeless community, and Tracy Kidder himself will join this conversation about the homelessness crisis nationally and in Greater Portland and proposed alternatives to how we currently manage this issue.

Maine Public is very pleased to be a media sponsor of this experience. Click here to order tickets or go to FreeportSpeech.org for additional information. Maine Public Members do receive a special ticket discount. Use the code MP2025 at checkout.

About the speakers:  
 
Dr. Jim O’Connell serves as the President of Boston Health Care for the Homeless Program and is an Assistant Professor of Medicine at Harvard Medical School. Dr. O’Connell received his medical degree from Harvard University in 1982 and completed residency in Internal Medicine at Massachusetts General Hospital. In 1985, he began full-time clinical work with homeless individuals as the founding physician of the program. He established the nation’s first medical respite program in 1985. Working with the MGH Laboratory of Computer Science, Dr. O’Connell designed and implemented the nation’s first computerized medical record for a homeless program.

Tracy Kidder is an American author and has been described as the “master of the nonfiction narrative.” In 2023, he published Rough Sleepers in which he tells the story of Dr. Jim O’Connell and the founding and growth of the Boston Health Care for the Homeless Program, following O’Connell and his colleagues for five years as they served the Boston homeless community. Kidder’s book, The Soul of a New Machine, about the creation of a new computer at Data General Corporation, received the Pulitzer Prize and a National Book Award in 1982.

Cullen Ryan has served homeless and special needs populations for 38 years. A formerly licensed clinician with a BA from the University of Vermont and an MA in Counseling and Psychological Services from St. Mary’s University, Cullen has provided case management, family therapy, and individual/group psychotherapy to homeless adults, families, and adolescents in a variety of clinical and non-clinical settings in three states. Since 2004, Cullen has served as Executive Director of Community Housing of Maine, the largest supportive housing provider for homeless and special needs populations in the state.

Deborah Desantis is President and CEO of the Corporation for Supportive Housing (CSH), the largest Community Development Financial Institution in the United States devoted to housing solutions for those at risk of homelessness. She has led the organization since 2007, tripling its lending and support toward the creation of over 300,000 permanent stable homes for individuals and families struggling through multiple challenges, including homelessness, lack of healthcare, and intergenerational poverty. DeSantis has spearheaded the reorganization of CSH to deepen its focus on data-driven results, innovative funding models such as Pay-For-Success, and expansion into high-need communities.

Lead Sponsors for this event are Amy Woodhouse and Tobey Scott. Net proceeds from this event to benefit Tedford Housing.