The Battle for Boston

How Mayor Ray Flynn and Community Organizers Fought Racism and Downtown Power Brokers

Don Gillis

Polis: Fordham Series in Urban Studies

Pages: 432

Illustrations: 39 b/w illustrations and 15 charts

Fordham University Press
Fordham University Press

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ISBN: 9781531509835
Published: 06 May 2025
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How Mayor Ray Flynn’s leadership and a coalition of activists transformed Boston, challenging established powers and setting new precedents for urban governance

The Battle for Boston captures the remarkable era under Mayor Ray Flynn, whose election in 1983 marked the beginning of a profound shift in the city’s political and social landscape. Don Gillis, a Flynn senior advisor, chronicles the inspiring journey of a city that dared to challenge the entrenched power brokers—including developers, landlords, and banking industry leaders—through powerful grassroots campaigns.

Gillis provides a vivid portrayal of the political dynamics and the coalition of community organiz­ers, neighborhood leaders, and residents that played a pivotal role in rejecting the business-backed growth machine and the city’s historically divisive racial politics. This book charts the strategic battles fought within the corridors of power and on the streets and highlights the substantial impact these movements had on the city’s governance and power dynamics.

In a historic turn, in 2021, Michelle Wu became the first woman, person of color, and Asian- American elected Mayor of Boston. Wu’s victory on a similarly progressive platform as Flynn underscores the enduring relevance of his legacy, signaling a hopeful future for more inclusive and effectively governed cities.

The Battle for Boston poses a critical inquiry: Can cities truly embrace progressivism and gov­ern effectively in the twenty-first century? This qualitative narrative study is a testament to the possibility of such governance, driven by the indomitable spirit of those who strive for a fair and equitable society.

After taking office during a time of financial crisis and deep division, Mayor Flynn helped bring people together to solve problems and advance the common good across the city’s neighborhoods. From historic housing reforms and the creation of thousands of good jobs, to compassionately addressing homelessness and the AIDS epidemic, to improving parks and recreation facilities, to balancing the budget, Mayor Flynn’s administration made Boston better, fairer, and stronger.---President Bill Clinton

This book uncovers the complex challenges of how Mayor Ray Flynn advanced racial unity in Boston and shared the benefits of growth. The social revolution in the city that established a more progressive politics resulted in the election of Mayor Michelle Wu. It is a must-read for community organizers and civic leaders.---Hubie Jones, Dean Emeritus Boston University School of Social Work and Black civic activist

The Battle for Boston reveals Boston’s periods of growth and change, reckoning and reconciliation, and how Flynn, who led at the national and international level, always knew where he came from and who he was elected to serve. He is a true champion of everyday working men and women, kids, and seniors, people with disabilities, the poor, the needy, and the homeless. Gillis’s book captures their stories and the battle to make Boston a more equitable city.---Marty Walsh, former Mayor of Boston and US Secretary of Labor

Ray Flynn doesn’t get enough credit for what he did around racial inequities This book speaks to the challenges he faced. There is no doubt he moved the city forward.---Joyce Ferriabough, Boston media and political strategist, former president of Black Political Task Force

Ray Flynn is a wealth of wisdom; I’ve learned so much and appreciate how his dedication to people in our neighborhoods still shines through.---Michelle Wu, the first woman, person of color, and Asian-American elected Mayor of Boston

The Battle for Boston helps us understand the challenges in urban America today and the role of progressive leadership in city politics. It is a must-read for students of urban politics and lovers of cities. It proves that progressives can win and put their vision into action. I want to honor all Ray Flynn contributed to Boston and, therefore, to the racial healing of America.---Bill de Blasio, former Mayor of New York City

In The Battle for Boston, Don Gillis makes an important contribution to our understanding of city politics. Using Boston as a case study, he elevates important urban issues of politics, power, and inequality. This book is a must-read for scholars, policymakers, and others interested in charting pathways toward increased equality in contemporary cities. Gillis helps promote and inform public debate about deepening inequalities and sharpens understanding of the promise of progressive cities.---Japonica Brown-Saracino, Professor of Sociology, Boston University, author of A Neighborhood That Never Changes: Gentrification, Social Preservation, and the Search for Authenticity and How Places Make Us: Novel LBQ Identities in Four Small Cities

Don Gillis, PhD, is a community organizer and longtime activist in Boston. He has advised mayors of several cities and led economic and workforce development agencies. He holds a PhD in urban sociology and the sociology of education and an MA in community sociology from Boston University. He has taught sociology courses such as Boston’s People and Neighborhoods, Race and Ethnicity, Occupations and the Workplace, Racial and Social Inequality in Schools, and the Sociology of HBO’s The Wire.

Boston Neighborhoods Map | ix

List of Charts and Tables | xi

Foreword by Mayor Bill de Blasio | xiii

Preface: A City in the Twenty-First Century | xvii

Introduction: Can Cities Be Economically and Socially Progressive? | 1

1 City Limits and Opportunities | 14

2 Political, Social, and Economic History of Boston | 32

3 The New Boston and the 1983 Race for Mayor | 46

4 Community Organizing as Political Governance | 78

5 Confronting the Housing Crisis and Landlords | 91

6 Redlining, Blockbusting, and Fighting Bank Discrimination | 110

7 Challenging the Growth Machine: A New “Social Contract” | 125

8 Boston’s Racial Politics: Ending Racial Violence | 149

9 Civil Rights and Wrongs: The Search for Racial Justice | 169

10 “Death at an Early Age”: Public Education Debates | 196

11 Rebuilding the City: Urban Finances and Infrastructure | 226

12 Confronting Poverty and Homelessness | 234

13 The 2013 and 2021 Mayoral Elections: New Directions for Boston | 245

14 How Does Urban Progressivism Succeed? | 272

Acknowledgments | 311

Appendix 1: Cities Defined as Progressive | 315

Appendix 2: Urban Theories Used in Boston Analysis | 327

Interviews by Author | 331

Notes | 333

Bibliography | 365

Index | 379

Photos follow page 206