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Raymond Flynn
Mayor Raymond L. Flynn portrait (9577542118) (1).jpg
Flynn in the mid-1980s
4th United States Ambassador to the Holy See
In office
September 2, 1993 – September 20, 1997
President Bill Clinton
Preceded by Thomas Patrick Melady
Succeeded by Lindy Boggs
52nd Mayor of Boston
In office
January 2, 1984 – July 12, 1993
Preceded by Kevin White
Succeeded by Thomas Menino
49th President of the United States Conference of Mayors
In office
Preceded by Robert M. Isaac
Succeeded by William Althaus
Boston City Councilor
In office
January 1978 – January 2, 1984
Preceded by Louise Day Hicks and John J. Kerrigan
Succeeded by N/A (number of at-large seats reduced)
Member of the Massachusetts House of Representatives
In office
January 1975 – January 1978
Preceded by Royal L. Bolling Sr. and Dorris Bunte
Succeeded by Dorris Bunte
Constituency 7th Suffolk
In office
January 1971 – January 1975
Serving with Michael F. Flaherty Sr.
Succeeded by Elaine Noble
Constituency 6th Suffolk
Personal details
Raymond Leo Flynn

(1939-07-22) July 22, 1939 (age 84)
South Boston, Massachusetts, U.S.
Political party Democratic
Spouse(s) Catherine Coyne
Children 6 (including Ed)
Parent(s) Stephen Flynn
Lillian Kirby Flynn
Alma mater Providence College (BA)
Harvard University (MA)

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. ..... 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 panning 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.

..... 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,

Councilman Flynn, a resident of South Boston, opposed busing in the early days of desegregation. But he has evolved through the years into more of a populist, concerned with problems of housing, police protection in the face of rising crime and other needs of the elderly and poor.

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

Raymond L. Flynn and Kathy Flynn at election night victory party (9614720739)
Flynn, with his wife Kathy, at his 1983 election night celebration

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 tenant organizations, elderly organizations, and a number of labor unions.

In the election, both Flynn and King worked to build progressive coalitions, and both pledge to dedicate themselves to working across ethnic divides in the city. In the five weeks leading up to the general election, the two candidates held more than fifty local neighborhood debates.

The campaign was peaceful, and only a handful of isolated racial violence incidents occurred during it.

Mayoralty (1984–1993)

Hon. Joseph F. Feeney, Mayor Raymond L. Flynn, Councilor Albert L. "Dapper" O'Neil, Councilor James M. Kelly (9617961524)
Flynn, second from left, next to Boston City Council members Dapper O'Neil and James M. Kelly

Flynn served as mayor from his inauguration on January 2, 1984 until his resignation on July 12, 1993. During his tenure, Flynn was regarded to be a popular mayor, which was reflected in high approval ratings As mayor, Flynn maintained a prominent public profile.

General politics

Reelection campaigns

Flynn was reelected mayor in 1987 and 1991, winning more than two-thirds of the vote each time. In his reelections, he won a higher vote share in Black and Hispanic areas of the city than he did in White areas.

In 1987, Flynn carried every ward of the city, except his native South Boston (perhaps due to his promise, weeks before the election, to desegregate all-white Boston Housing Authority developments in South Boston).

Flynn's 1991 campaign for a third term came despite of his 1981 campaign promise to only serve two terms. In his 1991 campaign, he ran a low-profile campaign that he touted as being "grassroots", and ran no television or radio advertisements. He centered his candidacy on ties to the city's neighborhoods and his successes in balancing the city's budget.

State and national politics

Flynn, Ferraro, and Dukakis
Flynn and Governor Michael Dukakis campaigning with Democratic vice presidential nominee Geraldine Ferraro before the 1984 presidential election

Flynn was an outspoken critic of the cuts that President Ronald Reagan championed making to federal revenue sharing, urban development grants, and housing and job assistance programs.


Flynn became a national leader on urban matters. In 1987, as chair of the United States Conference of Mayors’ Task Force on Hunger and Homelessness, Flynn advocated for the passage of the McKinney–Vento Homeless Assistance Act. Flynn served as president of the United States Conference of Mayors during 1991–92. In this role, Flynn challenged the theories of some pundits that cities were becoming economically obsolete due to the rise of "edge city" suburbanization, by arguing that, "as cities go, so goes America".

Ahead of the 1992 United States presidential election, there was some talk about whether Flynn could be a prospective vice presidential runningmate on a Democratic ticket. In February 1992, Flynn unsuccessfully urged New York Governor Mario Cuomo to run in the presidential election. It took Flynn a while to grow warm to the Democratic Party's ultimate presidential nominee, Bill Clinton. He endorsed Clinton in late June 1992. ..... Flynn physically campaigned on Clinton’s behalf in roughly half of the nation’s states.

Economic matters

Community reinvestment agreement with banks

In 1989, two studies (including one by the Boston Redevelopment Authority) found the city's major banks to be discriminating in their mortgage lending, hiring, and branch location practices. In collaboration with community activists, Flynn raised a more than year-long campaign to pressure banks to change their practices. He also announced a plan to issue a regular city-sponsored "report card" on bank practices, and a "linked deposit" policy to have the city then withdraw funds from banks that received poor track records on these "report card" and to expand its deposits in banks which instead worked to meet the needs of the city's neighborhoods. As a consequence, the banks reached a $400 million community reinvestment agreement with the city, in which the banks promised to open new branches, change lending and hiring practices, and to collaborate more closely with CDCs and community groups.

Fiscal matters

When Flynn took office, the city had a $40 million deficit. Flynn was able to balance the city's budget each year he was in office and improved the fiscal controls of the city. Flynn was able to improve the city's bond rating each year he was in office. When he left office, the city had its highest bond rating in its history.

In his first term as mayor, Flynn dealt with a drastic cut in federal funds allocated to Boston.

During his mayoralty, Boston divested from corporations that invested in Northern Ireland and Apartheid South Africa.

Revenue package
Boston Mayor Ray Flynn and Massachusetts Senate President William M. Bulger
Flynn, with Massachusetts Senate President William Bulger, in the 1980s

To address the city's deficit, upon taking office, Flynn worked to receive additional state aid and state legislature authorization to raise new local taxes. The state, at the time, viewed the city government as wasteful and inefficient. Flynn needed the help of the city's business community to convince the state. Particularly the business community's watchdog group, the Boston Municipal Research Bureau. In order to convince the business community that the Flynn administration was going to spend new revenues in a cost-effective manner, he recruited business community members to top positions in the municipal budget and treasury departments, and also created an advisory committee on management and budget operations that featured representatives from the business community. Flynn heeded the advise of this advisory committee, and "opened the books" on the city fiscal situation, something his predecessor, Kevin White, had refused to do himself. Ultimately, the Municipal Research Bureau gave its approval to Flynn's revenue package and lobbied for it.

Flynn also met across the state with individuals and groups such as local official's, business groups, and trade unions in order to persuade them to lobby their own legislators to support the state legislation he was seeking. Flynn made the argument that Boston's economic and fiscal health was critical to that of all of Massachusetts. He characterized Boston as being a generator of jobs and state sales tax revenue, as well as the home to institutions which benefited the entire state.

In 1984, the initial revenue package that Flynn championed was defeated in the state legislature. In 1985, Flynn proposed and lobbied for a revised revenue package. This revenue package passed, and was signed into law by Governor Dukakis.

Labor matters

Flynn created the "Boston jobs" program, requiring that developers that obtained city permits to hire Boston residents for half of all their construction jobs, minorities for one quarter of all their construction jobs, and women for one-tenth of all their construction jobs.

When Boston hotel owners and Hotel Employees and Restaurant Employees Union Local 26 were in conflict, and looked poised for a long and tense strike in 1985, Flynn had his police chief privately inform hotel owners that they could not count on the Boston Police Department to protect strikebreakers or preserve order outside and within hotel establishments. This private action of Flynn helped weaken the resolve of the hotel owners, who settled with Local 26, netting the union a significant victory.

When Flynn traveled to southwestern Virginia to support coal mining households during the Pittston Coal strike against the Pittston Coal Group, he learned from United Mine Workers President Richard Trumka that William Craig, a member of Pittston's board, was also vice chairman of Shawmut Bank, the city of Boston's second largest lender. Upon returning to the city, Flynn threaten that Boston would withdraw its deposits from the bank unless Craig resigned from the board of Pittston.

School board

Mayor Raymond L. Flynn speaking to class (9519683530)
Flynn speaks to children in a classroom

In July 1991, Flynn won a fight to turn Boston School Committee from an elected school board to one whose members are appointed by the mayor. This change took effect in January 1992. Before this change, the elected school board had come to be regarded as fractious.

As he approached his departure as mayor in 1993, Flynn questioned whether the change had been a good decision. He conceded that it had disenfranchised the input of voters in shaping the school board, and had upset many communities of color in the city. In 1993, little over a year since the appointed board had taken office, disorder had already arisen on the board, and Black organizers in the city were pushing to revert to an elected school board. In July 1993, Flynn remarked,

Let me acknowledge that taking the right to vote away from people is not a pleasant thing for me. It’s a big issue in the minority community. I know it. I still hear it...and it’s a very valid concern.

Flynn also conceded that the appointed school board had failed in terms of accountability, remarking in 1993,

When I argued for an appointed school board, I spoke about the power of accountability...Accountability was the critical element of change. That’s how it should work. But it hasn’t worked that way. It’s time to change that.

In 1993, Flynn wrote an open letter to those seeking to run in the 1993 Boston mayoral election to succeed him, pronouncing his regret in changing to an appointed board, and expressing preference in reverting back to an elected one. This was to no avail, and Boston remains the only municipality in Massachusetts without an elected school board.

Public safety and law enforcement

Mayor Raymond L. Flynn swearing in Police Commissioner Francis "Mickey" Roache (9519688286)
Flynn swearing-in Francis Roache as police commissioner in 1985

In 1985, Flynn appointed Francis Roache as the city's police commissioner. Roache was as childhood friend of Flynn, and would be one of his closet associates during his mayoralty.

Flynn's administration funded neighborhood watch groups.

In 1990, Flynn was placed under strong criticism from Black leaders over the police’s handling of the investigation into the murder of Carol Stuart, including the arrest and intensive search of William Bennett.

In response to concerns over the police department (including those stemming from the investigation into Carol Stuart's murder), in May 1991, Flynn empaneled the St. Clair Commission, headed by James D. St. Clair. In January 1992, the St. Clair Commission released its report, which was critical of the Boston Police Department for mismanagement, and urged against reappointing Commissioner Roache when his term expired that April. Flynn appointed William Bratton the city’s new police commissioner.

Urban development

Mayor Raymond L. Flynn working in office (9516904745) (a)
Flynn working at the mayor's office in Boston City Hall (circa 1984-1987)
Mayor Raymond L. Flynn at waterfront (9504745458) (1)
Flynn at the Boston waterfront

Flynn took office amid a period of urban flight by the city's middle class. Peter Dreier would describe Flynn as having been elected "with a populist mandate to 'share the prosperity' of Boston's downtown economic boom—particularly in terms of jobs and housing—with the city's poor and working-class residents. Flynn had campaigned for office in his initial election on a housing-focused platform.

When Flynn assumed office, the federal government was greatly decreasing federal funding for urban housing, job training, and economic development programs. Boston had been reliant on federal funding for these uses for the preceding quarter-century. Flynn looked to the private sector. He worked to use public-private partnerships as well as government regulatory tools of the private sector such as zoning and rent control. Flynn was successful in his fight to implement rent control laws in the city.

During Flynn's mayoralty, the city had a strong development market.

During Flynn's mayoralty, the City of Boston regained control over the Boston Housing Authority, which had previously been in court receivership. Weeks before the 1987 mayoral election, Flynn publicized a plan to desegregate all-white housing developments of the Boston Housing Authority located in South Boston. In 1988, the city of Boston reached a formal agreement with the federal government to integrate public housing in South Boston.

The Flynn administration provided neighborhood groups with a strong voice in planning and development, as well as other decisions, through neighborhood councils, zoning committees, and project-specific advisory groups.

During Flynn's mayoralty, major projects included the new Boston City Hospital complex. The city also created what was its first long-term capital plan for fixing its streets, infrastructure, school structures, and for creating new precinct stations and recreation centers. The city also significantly improved its parks and recreation centers.

Flynn focused on addressing the quality of life in neighborhoods, as well as on addressing gentrification.

The city built what was an unprecedented number of new units of affordable housing during Flynn's mayoralty. Flynn's administration successfully overcame the political forces of the city's real estate industry to put in place a policy that doubled the linkage fee funds that downtown developers were required to provide to neighborhood housing funds. Over the course of his mayoralty, this fund received over $70 million, and helped in the city's creation of over 8,000 units of affordable housing.

After a five-year campaign by Flynn and community activists, United States Secretary of Housing and Urban Development Samuel Pierce agreed to hand over to community-based non profits and tenant organizations a total of 2,000 HUD-subsidized apartments located in roughly 70 buildings that had been abandoned by their owners. Later on, Clinton HUD Secretary Henry Cisneros decided to change HUD policy to replicate the success Boston ultimately had in turning around troubled HUD projects.

Flynn successful fights to enact rent control laws and strong tenants' rights laws, which put him at odds with the landlord lobby. The Flynn administration also funded tenant groups, who organized against bad landlords. In 1986, Flynn worked successfully with tenant activists to get the Boston City Council to pass a ban on developers evicting tenants in order to clear apartment buildings for condominium conversions. In 1988, he worked to successfully get the City Council to empower the city's rent board with regulatory powers over condo conversions and lodging houses. Flynn also got the City Council to put in place rent control on projects in the city subsidized by United States Department of Housing and Urban Development if the owners exercised the option to prepay their federally subsidized mortgages. These movies potentially protected thousands of subsidized units in the city from conversion to market-rate housing.

Flynn also championed inclusionary housing policies that would require developers of market-rate housing to provide units for moderate and low-income residents. In July 1986, Flynn presented the Boston Redevelopment Authority with a potential policy to require private developers to designate 10% of their housing units in projects with at least ten units for moderate and low-income residents. This push faced strong opposition.

Boston's development director Steve Coyle oversaw the institution of controversial "downzoning" safeguards aimed at combatting the "Manhattanization" of the city's historic downtown and neighborhoods.

Flynn's administration collaborated on development with nonprofit organizations. They worked with community development corporations to undertake the rehabilitation of thousands of housing units in the city. A very notable example of collaboration saw the city government delegate its own urban renewal powers (including eminent domain authority) to the Dudley Street Neighborhood Initiative, a community group in the Roxbury neighborhood, who are allowed to use that authority in parts of the neighborhood.

Resignation and succession

Mayor Thomas M. and Angela Menino with Mayor Raymond and Kathy Flynn at swearing in ceremony as Acting Mayor in July of 1993 (15674913102) (1)
Flynn and his wife, Kathy, attend the ceremonial swearing-in of Thomas Menino as acting mayor

In 1993, Flynn resigned during his third term as mayor when he was appointed by Clinton to serve as United States Ambassador to the Holy See (the Vatican). Flynn was nominated in March 1993, and announced he would be resigning as mayor. However, in June, he reconsidered whether he would accept the role. He met with President Clinton and United States State Department officials to better define what his role would be as ambassador. The Senate unanimously confirmed his nomination that month, and he resigned as mayor on July 12, 1993.

Upon the announcement of Flynn's nomination, it became anticipated that then-Boston City Council President Thomas Menino was, per the city charter, going to assume the office of "acting mayor" upon Flynn's expected resignation. Flynn had had a longtime friendship with Menino. However, their relationship was noted to have become somewhat terser during the period in which Flynn was preparing to hand over the office to Menino. One cause for their rift was that, after Menino had promised he would appoint 100 new police officers when he took office, Flynn beat him to the chase and did so himself, which angered Menino.

When Flynn resigned on June 12, 1993, Menino became acting mayor. Menino would go on to win the 1993 Boston mayoral election, becoming mayor.

Ambassador to the Holy See (1993–1997)

Flynn served as Ambassador Extraordinary and Plenipotentiary to the Holy See from September 2, 1993, through September 20, 1997. He was the first member of the Democratic Party to hold this post.

Clinton had Flynn expand the role of the post's mission. Flynn not only represented the United States to the Holy See, but also represented the United States' in imperiled areas around the world on matters of social justice and economic justice. Flynn helped lead relief efforts related to an earthquake in India, and was involved in humanitarian aid efforts to nations such as Bosnia and Herzegovina, Haiti, Kenya, Somalia, Sudan, and Uganda. He was also involved in efforts to broker the Good Friday Agreement. He also collaborated with the Holy See on efforts to resolve problems in various areas of the world. He also played a key role in brokering an agreement to start a formal process to have Israel and the Holy See establish formal relations with each other. Flynn's tenure was somewhat shaky, however. He twice received reprimands from the United States Department of State. One instance was for emphatically discussing domestic American policy, the other instance was for having an employee of the embassy manage Flynn's family's finances.

Shortly after his resignation, on October 3, 1997, The Boston Globe published an article which both accused Flynn of having been a sub-par diplomat as ambassador and of having had a longtime drinking problem. Flynn accused the newspaper of attacking him both because, he alleged, the paper opposed his planned 1998 gubernatorial campaign. Flynn also he alleged that the newspaper held contempt for his "class, religion and ethnic background." This article was seen as hurting Flynn's public image.

1998 congressional campaign

Following his service as ambassador, Flynn considered running for governor of Massachusetts in 1998. ..... Instead, Flynn ran unsuccessfully for Massachusetts's 8th congressional district seat that was being vacated by Joseph P. Kennedy II in 1998. Flynn formally announced his candidacy in June, and in September lost in the Democratic primary election, the real contest in this heavily Democratic district, to Somerville mayor general election winner Mike Capuano, placing second with roughly 18% of the vote. Flynn had been an early front-runner in the primary. However, Capuano won, with polls showing Capuano to have enjoyed a last-minute rise in support.

..... Flynn had run a quiet grassroots campaign operation.

Ceci Connolly of The Washington Post observed during the campaign,

In this era of "third way," suburban, New Democrat politics, Flynn's New Deal, patronage-oriented, urban populism may have outgrown its welcome even here in the bosom of liberalism. The triple-decker houses once bulging with large ethnic families are now occupied by yuppies for whom the name Flynn is just a distant memory...While some candidates attempt to repackage themselves or tack with the political winds, Flynn is adamantly retro -- hoping the style and themes that worked so well nearly two decades ago can deliver one more victory.

Later politics

2009 RayFlynn mayor Boston Massachusetts
Flynn endorsing Michael Flaherty in the 2009 Boston mayoral election (with Flaherty's "runningmate" Sam Yoon visible behind Flynn)
Ed Markey 2016 SOTU CZS5IVZWkAAnbRS (1)
L–R: Kathy Flynn, Raymond Flynn, Linda Dorcena Forry, and Ed Markey at the 2016 State of the Union Address

During the general election campaign of the 2009 Boston mayoral election, Flynn and his one-time mayoral opponent Mel King both came together to endorse Michael Flaherty’s campaign against Thomas Menino.

In 2010, Flynn crossed party lines to vote for the successful candidacy of Republican nominee Scott Brown for the United States Senate. In 2012, Flynn appeared in television ads supporting Brown for reelection; Flynn also voiced support for Mitt Romney, the Republican nominee for president.

Media career

In 1998, Flynn had a role as a radio host on WRKO in Boston. In September 2014, Flynn became a regular contributor to The Pilot, the official newspaper of the Roman Catholic Archdiocese of Boston. In February 2017, Flynn became a columnist for the Boston Herald.

Religious advocacy

Unidentified priest, Mayor Raymond L. Flynn, unidentified priest, Ray Flynn, Jr., Bernard Cardinal Law (9519693564)
Flynn and his son Raymond Flynn Jr. with priests and Cardinal Bernard Francis Law (circa 1984-1987)

In 1999, Flynn became president of Catholic Alliance, a nonpartisan Catholic advocacy group. In this role, while remaining a Democrat, he and the Catholic Alliance endorsed George W. Bush in the 2000 presidential election. Flynn also became president of another Catholic political advocacy organization, Your Catholic Voice. He later started Catholic Citizenship, serving as its national chairman from 2004 until 2008. Since 2004, Flynn has also served on the advisory board of Catholics for the Common Good, a lay apostolate for evangelization of culture.

Personal life

Raymond and Kathy Flynn (9519689736) 1
Flynn and his wife, Kathy, during his mayoralty

Flynn is married to Catherine (née Coyne), who often goes by "Kathy" . They have six children: Ray Jr., Eddie, Julie, Nancy, Katie, and Maureen. In November 2017, son Edward M. Flynn was elected to the Boston City Council.

While serving as mayor, Flynn played himself in the 1989 Cheers episode "The Stork Brings A Crane". In the episode, Flynn has his entourage take away Cliff Clavin, who writes Flynn once a week.

Mayor Raymond L. Flynn at finish of Boston Marathon (9516895633) (1)
Flynn running in the 1984 Boston Marathon

Flynn was an avid runner who made headlines when he ran in the Boston Marathon and the New York City Marathon in 1984.

In March 2007, Flynn was grand marshal of the 246th New York St. Patrick's Day Parade.

In May 2007, Flynn joined the College of Fellows of the Dominican School of Philosophy and Theology in Berkeley, California, who also awarded him the honorary degree Doctor of Humane Letters.

In September 2008, Flynn was hospitalized after he collapsed at a Boston-area speaking engagement. In March 2011, Flynn's home was broken into; among the valuables taken were rosary beads blessed by Pope John Paul II and letters from influential world figures. In December 2022, Flynn broke was hospitalized after falling and breaking a bone in his neck.

Flynn has continued residing in South Boston.


In February 2016, the Boston Marine Industrial Park was renamed the Raymond L. Flynn Marine Park. A nearby bridge was also renamed in Flynn's honor. In May 2017, Governor of Massachusetts Charlie Baker dedicated Flynn Cruiseport Boston, located in the Port of Boston.

Flynn has received a number of civic awards. He has received the B'nai B'rith International Humanitarian Award, Martin Luther King Jr. Award, and Boys Club of America "Man of the Year Award". In 2019, the business interest organization A Better City awarded Flynn a "Lifetime Achievement" award. Then-mayor Marty Walsh presented the award to Flynn at an awards ceremony. Walsh praised Flynn, declaring tat Flynn had, "led at the national and international level, while always staying closely connected to the people in our working class neighborhoods. He’s always been a champion for everyday people: working men and women; kids and seniors; people with disabilities; and everyone who calls the city of Boston their home."

Electoral history

State Representative

1970 Massachusetts House of Representatives 6th Suffolk district Democratic primary
(2-member district)
Party Candidate Votes %
Democratic Michael F. Flaherty Sr. 5,083 26.4
Democratic Raymond L. Flynn 2,041 19.6
Democratic James F. Condon 3,104 16.1
Democratic Joseph F. Toomey 1,878 9.8
Democratic David J. Keefe 1,566 8.1
Democratic William J. Grant 1,167 6.1
Democratic John J. Driscoll Jr. 1,113 5.8
Democratic Thomas J. Sullivan 691 3.6
Democratic John J. O'Callaghan 333 1.7
Democratic Donald W. Mello 228 1.5
Democratic John V. Kazarian 259 1.3
Total votes 19,259 100
1970 Massachusetts House of Representatives 6th Suffolk district election
(2-member district)
Party Candidate Votes %
Democratic Michael F. Flaherty Sr. 10,834 52.4
Democratic Raymond L. Flynn 9,824 47.6
Total votes 100
1972 Massachusetts House of Representatives 6th Suffolk district Democratic primary
(2-member district)
Party Candidate Votes %
Democratic Raymond L. Flynn (incumbent) 4,710 33.4
Democratic Michael F. Flaherty Sr. (incumbent) 4,418 31.3
Democratic Robert M. O'Brein 3,310 23.5
Democratic Paul T. O'Leary 635 4.5
Democratic Ronald F. Bassil 576 4.1
Democratic Ali J. Fiumedoro 175 1.2
Democratic Pa J. L. Rosemond 144 1.0
Democratic Geoffirey P. Morris 128 0.9
Total votes 14,096 100
1972 Massachusetts House of Representatives 6th Suffolk district election
(2-member district)
Party Candidate Votes %
Democratic Michael F. Flaherty Sr. (incumbent) 10,660 48.3
Democratic Raymond L. Flynn (incumbent) 10,113 45.8
Republican Ernest A. Fragopulos 1,305 5.9
Total votes 22,078 100
1974 Massachusetts House of Representatives 7th Suffolk district Democratic primary
Party Candidate Votes %
Democratic Raymond L. Flynn (redistricted incumbent) 3,526 100
Total votes 3,526 100
1972 Massachusetts House of Representatives 7th Suffolk district election
Party Candidate Votes %
Democratic Raymond L. Flynn (incumbent) 5,761 100
Total votes 5,761 100
1976 Massachusetts House of Representatives 7th Suffolk district Democratic primary
Party Candidate Votes %
Democratic Raymond L. Flynn (incumbent) 3,988 75.9
Democratic Gerard F. Burke 1,265 24.1
Total votes 5,253 100
1972 Massachusetts House of Representatives 7th Suffolk district election
Party Candidate Votes %
Democratic Raymond L. Flynn (incumbent) 6,817 100
Total votes 6,817 100

City Council

1975 Boston City Council election
Candidates Preliminary Election General Election
Votes Votes
Louise Day Hicks (incumbent) 46,030 82,050
Christopher A. Iannella (incumbent) 35,793 71,484
James Michael Connolly (incumbent) 25,536 71,157
Albert L. O'Neil (incumbent) 38,203 66,583
Lawrence S. DiCara (incumbent) 32,119 62,247
John J. Kerrigan 35,117 60,581
Frederick C. Langone (incumbent) 27,579 60,238
Patrick F. McDonough (incumbent) 22,464 57,968
Joseph M. Tierney (incumbent) 33,700 57,003
Raymond L. Flynn 27,754 55,536
Gerald F. O'Leary (incumbent) 33,653 55,390
Jack Cole 22,542 53,176
Clarence E. Dilday 14,774 34,531
Franx X. Curley 14,661 32,339
Thomas M. Connelly Jr. 14,345 28,433
Thomas A. McDonough 14,775 24,847
Edward Brooks 10,719 22,959
William T. Donovan 8,557 18,106
Joseph A. McCarthy 8,127
Robert J. Feeney 8,047
Salvatore LaRosa 7,365
Reba Williams 5,356
Albert DiNicola 5,135
Ralph M. Cotellesso 5,121
Arthur Michael Pascal 4,409
Robert P. Kane 3,832
Jacqueline Y. LeBeau 3,387
Alfred Smith 3,320
Sean M. Harvey 3,182
Victor Naum Themo 2,084
John Hillson 1,713
All others 1 1
1977 Boston City Council election
Candidates Preliminary Election General Election
Votes Votes
James Michael Connolly (incumbent) 22,212 37,479
Raymond Flynn 19,248 35,757
Christopher A. Iannella (incumbent) 21,577 35,682
Dapper O'Neil (incumbent) 20,875 35,543
Lawrence DiCara (incumbent) 19,048 32,232
Joseph M. Tierney (incumbent) 17,500 31,913
Rosemarie Sansone 12,954 30,531
Frederick C. Langone (incumbent) 15,156 30,268
Patrick F. McDonough (incumbent) 15,868 30,205
Louise Day Hicks (incumbent) 19,862 30,058
Gerald O'Leary 14,979 23,868
Gerard P. McHale 12,753 20,610
John J. Kerrigan (incumbent) 11,810 20,045
Arnett L. Waters 10,589 18,109
Lawrence E. Blacke 9,801 16,899
Bruce Bolling 8,634 15,518
Stephen C. Farrell 8,505 13,980
Paul J. Ellison 7,919 11,542
William T. Donovan 7,198
Elizabeth Buckley 6,886
Robert Whitey McGrail 6,740
Harold L. O’Brien 5,869
James J. Tobin 4,907
Polly Jane Halfkenny 4,380
John T. Cuddy 4,288
Celia M. Sniffin 3,965
Diane Jacobs 3,827
Norma Walsh Gramer 3,559
Richard Hird 2,365
George R. Geller 1,675
1979 Boston City Council election
Candidates Preliminary Election General Election
Votes Votes
Lawrence DiCara (incumbent) 42,339 69,102
Christopher A. Iannella (incumbent) 45,184 69,069
Raymond Flynn (incumbent) 45,648 66,662
Frederick C. Langone (incumbent) 48,063 64,873
Dapper O'Neil (incumbent) 48,781 60,846
Joseph M. Tierney (incumbent) 43,759 58,674
John W. Sears 41,108 58,205
Rosmarie E. Sansone (incumbent) 46,391 57,552
Patrick F. McDonough (incumbent) 34,646 55,123
Louise Day Hicks (incumbent) 44,659 54,714
James T. Brett 34,941 51,767
Terence P. McDermott 30,124 39,882
Barbara A. Ware 19,519 33,951
Stephen C. Farrell 20,173 27,038
Charles Yancey 14,487 22,301
Edward Brooks 19,772 24,165
Richard M. Lane 17,424 17,771
David Joseph McKay 12,873 15,981
Jeannette L. Tracy 11,711
Phyllis Igoe 9,205
Stephen Michael Cidlevich 8,645
Eugene A. Cavicchi 6,626
Peter K. Hadley 5,187
1981 Boston City Council election
Candidates Preliminary election General election
Votes Votes
Raymond Flynn (incumbent) 31,898 53,136
Christopher A. Iannella (incumbent) 25,462 44,621
Dapper O'Neil (incumbent) 24,240 40,474
Frederick C. Langone (incumbent) 23,000 39,780
Joseph M. Tierney (incumbent) 17,649 35,185
Michael J. McCormack 14,178 33,861
Terence P. McDermott 11,981 31,707
Maura Hennigan 14,325 31,637
Bruce Bolling 15,273 30,672
James M. Kelly 14,941 30,079
Patrick F. McDonough (incumbent) 17,165 29,591
Edmund McNamara 12,007 29,301
David Scondras 11,616 28,571
Charles Yancey 12,378 27,007
Francis X. Coppinger 11,034 21,675
Craig Lankhorst 10,301 20,769
Pamela J. Gilman 10,070 14,776
Gerard P. McHale 10,407 14,173
Joseph W. Casper 9,906
Frederick T. Scopa 9,444
John F. Melia 8,788
Stephen G. Michaels 8,325
Brian Hickey 8,222
John P. Grady 7,855
Richard B. Hogan 7,794
Edward M. McCormack 7,610
William G. Broderick 7,134
Joseph E. Maher 6,269
Maureen Craven Slade 5,759
Althea Garrison 5,442
Joseph T. Fitzpatrick 3,947
David F. Burnes 3,784
David Alan Mittell Jr. 3,660
Francis X. Goode 3,227
Thomas P. Casserly 3,005
Warren I. Brown 3,001
John S. MacDonald 2,881
Edward J. DeSantis 2,688
John B’Smith III 1,936
John K. Rees 1,791


1983 Boston mayoral election
Candidates Preliminary election General election
Votes % Votes %
Raymond Flynn 48,118 28.86 128,578 65.07
Mel King 47,848 28.70 69,015 34.93
David Finnegan 41,657 24.99
Lawrence DiCara 15,148 9.09
Dennis J. Kearney 10,992 6.59
Frederick C. Langone 2,262 1.36
Bob Kiley 316 0.19
Michael Gelber 207 0.12
Eloise Linger 168 0.10
1987 Boston mayoral election
Candidates Preliminary election General election
Votes % Votes %
Raymond Flynn (incumbent) 42,366 70.39 63,714 67.47
Joseph M. Tierney 16,257 27.01 30,714 32.52
Joel San Juan 1,083 1.08
Richard A. Black 484 0.80
1991 Boston mayoral election
Candidates Preliminary election General election
Votes % Votes %
Raymond Flynn (incumbent) 43,123 67.29 63,582 74.58
Edward J. Doherty 12,281 19.16 21,659 25.41
Graylan Ellis-Hagler 8,682 13.55


1998 Massachusetts 8th Congressional District Democratic primary
Party Candidate Votes %
Democratic Michael E. Capuano 19,446 22.9
Democratic Raymond L. Flynn (incumbent) 14,839 17.5
Democratic George Bachrach 12,157 14.3
Democratic John T. Connor 11,092 13.1
Democratic Marjorie O'Neill Clapprood 10,446 12.3
Democratic Christopher F. Gabrieli 5,740 6.8
Democratic Charles Calvin Yancey 4,437 5.2
Democratic Susan M. Tracy 2,858 3.4
Democratic Thomas M. Keane, Jr. 2,150 2.5
Democratic Alex Rodriguez 1,802 2.1
Write-in All others 21 0.0
Total votes 84,988 100

See also

  • 1971–1972 Massachusetts legislature
  • 1973–1974 Massachusetts legislature
  • 1974–1975 Massachusetts legislature
  • 1975–1976 Massachusetts legislature
  • 1977–1978 Massachusetts legislature
  • Timeline of Boston, 1980s–1990s
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