The Battle for Boston: Race, Class, and the Future of Progressive Cities

MHS Event

This is a hybrid event. FREE for MHS Members. $10 per person fee (in person). No charge for virtual attendees or Card to Culture participants (EBT, WIC, and ConnectorCare). The in-person reception starts at 5:30 and the program will begin at 6:00.

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Lessons from Ray Flynn’s Mayoralty Ahead of the 2026 Midterms

As the nation heads into the 2026 midterm elections, questions about race, class, and the future of America’s cities are once again at the center of public debate. This conversation explores what Ray Flynn’s Boston—its neighborhood politics, its struggles over inequality, and its experiments in progressive urban governance—can teach us about those challenges today. Drawing on The Battle for Boston, author Don Gillis joins former Mayor Raymond L. Flynn and longtime policy advisor Neil Sullivan to examine how the city confronted housing segregation, tenant rights, and neighborhood development in an era of deep social division. Their conversation offers a historically grounded look at how cities navigate conflict, build coalitions, and shape democratic life—insights newly resonant as voters prepare to head to the polls.

Panelists

Raymond L. Flynn is a lifelong resident of South Boston; he served as the 52nd Mayor of Boston from 1984 to 1993 and was appointed by President Bill Clinton as United States Ambassador to the Holy See from 1993 to 1997. Before entering politics, Flynn was a standout basketball player at Providence College, earning All American honors and the 1963 NIT Most Valuable Player award. He served in the Massachusetts House of Representatives (1971–1978) and on the Boston City Council (1978–1984). As mayor, Flynn’s tenure was marked by efforts to desegregate public housing, strengthen tenant rights, expand neighborhood affordable housing development, and support the homeless.

Don Gillis is a community organizer, educator, and longtime activist in Boston, and the author of The Battle for Boston. He served as Mayor Ray Flynn’s Director of Neighborhood Services and Executive Director of Economic Development from 1984 to 1993. He has advised mayors in several Massachusetts cities and has led major economic and workforce development agencies. Gillis holds a PhD in urban sociology and the sociology of education and an MA in community sociology from Boston University. He has taught courses on Boston’s neighborhoods, race and ethnicity, workplace inequality, and the sociology of HBO’s The Wire, with a focus on how race and class shape urban life and public policy.

Neil Sullivan recently completed 33 years as executive director of the Boston Private Industry Council (PIC), the city’s workforce development board, and now serves as senior advisor for youth employment and work based learning at the Massachusetts Workforce Association. From 1984 to 1992, Sullivan was policy director for Mayor Ray Flynn, shaping initiatives in education, employment, and neighborhood development. Earlier in his career, he worked as a community organizer and campaign strategist for Massachusetts Fair Share (1978–1982) and taught high school in the Chicago area (1974–1977).