Raymond Flynn

Raymond Leo Flynn (born July 22, 1939) is an American politician who served as 52nd Mayor of Boston, Massachusetts from 1984 until 1993. He also served as United States Ambassador to the Holy See from 1993–1997.

Flynn was an All-American college basketball player at Providence College. During his senior year, Flynn was selected the " Most Valuable Player" in the 1963 National Invitation Tournament. After a brief professional basketball career, Flynn worked in a several fields, including as a high school teacher and a probation officer, before entering politics. Flynn began his political career as a Democratic member of the Massachusetts House of Representatives from 1971 to 1979, representing the South Boston neighborhood during the turbulent Boston desegregation busing crisis of the early 1970s. Flynn opposed federally-mandated school busing. Throughout his political career, Flynn held a strong anti-abortion position. As a state legislator, Flynn co-authored the "Flynn–Doyle amendment" that would have banned government-funding of abortions covered by Medicaid. This was vetoed by Governor Michael Dukakis. Flynn later served on the Boston City Council from 1978 to 1984.

Flynn successfully ran for mayor of Boston in 1983 and took office in 1984. Flynn was reelected in 1987 and 1991. Polls showed Flynn to enjoy strong approval from Bostonians during his mayoralty. As mayor, Flynn balanced the city's budget, eliminating a large budget deficit. To address the deficit, Flynn lobbied heavily for the passage of a revenue package for the city in the Massachusetts Legislature to provide additional state aid to the city and the authorization for the city to raise new local taxes. In 1985, a revenue package was passed and signed into law by Governor Michael Duakakis. In response to discriminatory practices studies found banks to be practicing in Boston, Flynn took actions which persuaded banks to reach a $400 million community reinvestment agreement with the city. Flynn succeeded in getting legislation passed to replace the city's publicly-elected school board with the new Boston School Committee, members of which are appointed by the city's mayor. Flynn would quickly come to express his regret about this change. In 1990, Flynn saw strong criticism from Black leaders over the Boston Police Department's handling of the investigation into the murder of Carol Stuart. As mayor, Flynn advanced plans to desegregate the city's public housing. Flynn's administration gave neighborhood groups more of a voice in the use of the city's development and planning authorities in their neighborhoods. This included innovative move of granting the Dudley Street Neighborhood Initiative powers of eminent domain. Flynn successfully fought to enact rent control laws and strong tenants' rights laws. Flynn also served as president of the United States Conference of Mayors from 1991 to 1992.

Flynn resigned as mayor in 1993 in order to accept an appointment by President Bill Clinton as ambassador to the Holy See. He expanded the position's mission to involve participation in addressing problem areas around the world. During his tenure as ambassador, he also encountered some controversy. In 1998, Flynn unsuccessfully ran for the United States House of Representatives. Flynn later served as president of Catholic Alliance, a nonpartisan Catholic advocacy group.

Early life and education

Flynn grew up in South Boston, where he has spent most of his life living. Flynn is Irish-American. His father was a union longshoreman, and his mother was a cleaning lady. Flynn grew up a member of the Gate of Haven Parish in South Boston.

Flynn was a three-sport star athlete at South Boston High School.

Flynn attended Providence College on a basketball sports scholarship. Flynn was an All-American college basketball player at Providence College, and during his senior year was selected as the " Most Valuable Player" in the 1963 National Invitation Tournament (NIT).

Later in life, while a Boston city councilor, Flynn would receive a master’s degree in education from Harvard University.

Professional basketball career and early career

In April 1963, he was selected by the Syracuse Nationals in the fourth round of the NBA draft. The Nationals relocated to Philadelphia to become the 76ers, but Flynn did not play for them, as he spent part of the 1963–64 season with the Wilmington Blue Bombers of the Eastern Professional Basketball League. Philadelphia traded his NBA rights to the Boston Celtics in September 1964, and in October he was the last player cut from the Celtics roster.

Before his political career, Flynn worked as a youth worker, high school teacher, and a probation officer.

Massachusetts House of Representatives (1971–1978)

Monopolizing off of his local sports hero celebrity, Flynn won election to the Massachusetts House of Representatives in November 1970. As a state representative, Flynn was generally representative of the views of his South Boston district’s constituency., He was pro-trade unions, for affordable housing and tenants rights, opposed redlining, opposed expansion at Logan Airport, and opposed cutting welfare programs. He was also a supporter of providing more state funding to special needs students in schools. Peter Dreier would later describe his positions as a state representative as having, largely, been a, "parochial South Boston pol with progressive leanings."

Flynn was an opponent of court ordered desegregation busing. In 1973, he worked against implementing the city of Boston’s desegregation school busing plan even filing a lawsuit against the Massachusetts Board of Education over the matter. Flynn argued that desegregation busing would pit poor Black and poor White families against one another within a second-tier school system, all while wealthy suburbanites sent their students to well-funded schools. Flynn refused to the militant anti-busers, Louise Day Hicks and William Bulger when they released a statement of resistance that was seen as having racist overtones. Flynn urged against violent actions that were being taken by some in protest of busing. As a result of his refusal to join the more militant factions of resistance to busing, Flynn alienated himself from the more extremist factions of his community. His car was firebombed, and his family received death threats by telephone calls.

In 1974, Flynn filed legislation to repeal a state law which required that children attend school. He would claim this had been a mistake during his 1983 mayoral campaign.

In March 1975, he announced himself as a candidate for the 1975 Boston mayoral election. However, he withdrew in June after struggling to fundraise, and instead launched his candidacy for the Boston City Council. He would lose his race for city council that November, falling a mere 1,467 votes shy of election.

Flynn co-authored a bill to end government-funding of abortions covered by Medicaid. The "Flynn-Doyle amendment", co-authored with State Representative Charles R. Doyle, was passed by the state legislature, but successfully vetoed by Governor Michael Dukakis. Flynn and Doyle then, later that year, attached the bill as a rider to a state pay-raise bill, which was passed by the Massachusetts State Legislature, but this was again vetoed by Dukakis. The amendment would be successfully passed over Dukakis' veto in 1978, after Flynn had already left the leislature to serve on the Boston City Council.

Boston City Council (1978–1984)

Flynn was elected to the Boston City Council in November 1977. Flynn would be reelected in 1979 and 1981. In 1981, Flynn was the top vote-getter by a large margin.

Peter Dreier would later describe Flynn as having transitioned as a city councilor, "from a parochial neighborhood politician with progressive leanings to a crusader with citywide appeal." while on the Boston City Council. Drier would describe Flynn as having been an, "18-hour-a-day workaholic," and the, “hardest working City Councilor". He had a reputation for regularly attending public meetings. South Boston, which Flynn represented, was regarded to be relatively politically conservative.

As a city councilor, Flynn opposed rate increases by utility companies. He was viewed as an ally of trade unions, welfare recipients, and working women. Flynn regularly proposed tenants' rights bills on the Boston City Council, which were defeated. Flynn believed that his city council colleagues were influenced by sizable donations from the real estate lobby, especially faulting the Greater Boston Real Estate Board. In 1983, Dudley Clendinen of ''The New York Times'' wrote of Flynn’s politics,

In October 1979, Flynn, together with Joseph F. Timilty, rescued a Black man from an encounter with a White mob on the Boston Common.

1983 mayoral campaign

In April 1983, Flynn announced his candidacy for mayor of Boston. In the October nonpartisan primary election, Flynn and State Representative Mel King placed atop the results, advancing to the general election. King was the first African American to be a candidate in a Boston mayoral general election. Both Flynn and King had originally been viewed as underdogs in the primary election. Flynn defeated King in the general election.

Flynn's campaign received no real financial support from major sectors of the city's business community. Flynn outright refused to accept campaign donations from developers with projects pending before city agencies, or lawyers of such developers. Both the Flynn and King campaigns had low-expenditures compared to the nearly $2 million campaign that outgoing mayor Kevin White and the political machine supporting him had spent on his candidacies in the 1975 and 1979 mayoral elections. Flynn's campaign spend roughly $400,000, while King's spent less than $350,000.

Dudly Clendinen wrote that Flynn had worked to establish himself as a champion of the poor and elderly and to appeal across ethnic lines to ethnic minority voters.

Primary election

Flynn first announced his candidacy in front of a public housing project, pledging that he would be a "people's mayor". He was viewed as an underdog at the start of his campaign, due to a lack of funding, a political organization, or connections to the business or media establishments.

Flynn and King had both shaped the narrative of the debate during the hotly-contested primary, successfully creating a "downtown versus the neighborhoods" narrative, with Flynn and King taking the side of being in support of the city's neighborhoods. A major item of debate was linkage, a fee that would be placed on downtown developers to raise funds for affordable housing. Flynn and King placed in the primary above candidates who were perceived as more representative of "downtown" interests. Coinciding with the primary, voters also strongly approved non-binding referendums in favor of a linkage policy and the creation of neighborhood councils. Both referendums had been supported by the group Massachusetts Fair Share.

During the primary, the city's progressive activists were largely sharply divided between Flynn and King's candidacies. Flynn benefited from grassroots support.

General election

In the general election, Flynn received the political endorsement of "The Boston Globe" editorial board. Among the groups endorsing Flynn were low-income