ABSTRACT This dissertation examines the years 1980-2000 as a sociologically transformative period in Boston's history. The guiding research question is how organized politics and the policies that emerged responded to racial conflict, inequality and economic development, and wholesale change in the city's economic base during this period. The policies of the three governing regimes--the end of Kevin H. White's sixteen-year term, Raymond L. Flynn's nine years in office, and the beginning of Thomas M. Menino's twenty-year mayoralty--are analyzed in the content of these domains to identify the outcomes of several policy agendas that have helped shape life in Boston today. This analysis is in the context of urbanization and urbanism, viewed through the lenses of urban regime, growth machine coalition, progressive city, and government communalism theories. The study utilizes retrospective autoethnography linked with interviews and archival data research. The study found that during the end of the mayoral administration of Kevin White, Boston was in turmoil politically and racially. Political contests centered on growing poverty and inequality and racial unrest in the city. The election of 1983 was a "critical election" both because an African American was in the final runoff and because the two finalists repudiated the growth machine coalition and the racial politics of the past. Flynn's election began the populist transformation of economic policies in Boston to heal racial divisions. After he resigned to become Ambassador to the Vatican, the urban regime of Thomas Menino left intact many of the redistributive policies Flynn enacted; however, it also gradually returned to the growth machine coalition model of economic development, fueling the greatest class and income inequality in Boston's history. In the final analysis, both the policies of each urban regime and the activities of the religious, cultural, business, and neighborhood organizations that comprise city life changed the city in sociologically significant ways. This is the story of Boston 1980-2000, the role of its three mayors during that period, and how the city entered the twenty-first century with its physical decline in part reversed but with issues of race and class remaining significant touchstones.