Raymond Flynn

Flynn grew up in South Boston, where he has spent most of his life living.[3][4] Flynn is Irish-American.[5] His father was a union longshoreman, and his mother was a cleaning lady.[5] Flynn's father was an immigrant to the United States.[6] Flynn grew up a member of the Gate of Heaven Parish in South Boston.[3]

Flynn was a three-sport star athlete at South Boston High School.[3]

Flynn attended Providence College on a basketball sports scholarship.[3] 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).[3][7]

Later in life, while a Boston city councilor, Flynn would receive a master’s degree in education from Harvard University.[3]

In April 1963, he was selected by the Syracuse Nationals in the fourth round of the NBA draft.[8] 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.[9] Philadelphia traded his NBA rights to the Boston Celtics in September 1964,[10] and in October he was the last player cut from the Celtics roster.[11]

Before his political career, Flynn worked as a youth worker, high school teacher, a probation officer,[3] and a longshoreman.[12][13]

Flynn as a member of the Massachusetts House of Representatives

Capitalizing on his local sports hero celebrity,[3] Flynn won election to the Massachusetts House of Representatives in November 1970.[14] 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."[3]

Flynn was an opponent of court ordered desegregation busing.[3][15] 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.[16] 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 join 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 through telephone calls.[3]

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.[16]

In March 1975, he announced himself as a candidate for the 1975 Boston mayoral election.[16] 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,[16] falling a mere 1,467 votes shy of election.[17]

Flynn co-authored a bill to end government funding of abortions covered by Medicaid. The bill, co-authored with State Representative Charles R. Doyle. This was passed by the state legislature, but successfully vetoed by Governor Michael Dukakis.[18][19] 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. This was again vetoed by Dukakis.[19] The "Flynn-Doyle amendment" would be successfully passed over Dukakis' veto in 1978, after Flynn had already left the legislature to serve on the Boston City Council.[16][20]

Flynn was elected to the Boston City Council in November 1977.[16] Flynn would be reelected in 1979 and 1981. In 1981, Flynn was the top vote-getter by a large margin.[3]

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."[21] 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.[3] South Boston, which Flynn represented, was regarded to be relatively politically conservative.[22]

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 ordinances 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.[3][21] 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.[15]

In October 1979, Flynn, together with Joseph F. Timilty, rescued a Black man from an encounter with a White mob on the Boston Common.[16]

Flynn, with his wife Kathy, at his 1983 election night celebration

In April 1983, Flynn announced his candidacy for mayor of Boston.[16] In the October nonpartisan primary election, Flynn and State Representative Mel King placed atop the results, advancing to the general election.[16] King was the first African American to be a candidate in a Boston mayoral general election.[22] Both Flynn and King had originally been viewed as underdogs in the primary election.[3] Flynn defeated King in the general election.[16][3] Flynn and King had known each other since childhood, meeting through both playing basketball, and had both served as state representatives at the same time and worked together there on legislation. They would ultimately have a lifelong friendship, despite having run against each other for mayor.[23]

Flynn's campaign received no real financial support from major sectors of the city's business community.[3] Flynn outright refused to accept campaign donations from developers with projects pending before city agencies, or lawyers of such developers.[3] 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 spent roughly $400,000, while King's spent less than $350,000.[22]

Dudley 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.[22]

While Flynn had earlier in his political career opposed gay rights issues,[6] by the time of his mayoral campaign he was making an active effort to court the gay vote at a time when gay communities across the United States were becoming more politically organized.[24]

Flynn, second from left, next to Boston City Council members Dapper O'Neil and James M. Kelly (circa 1984–1987)

Flynn served as mayor from his inauguration on January 2, 1984[26] until his resignation on July 12, 1993.[27] During his tenure, Flynn was regarded to be a popular mayor, which was reflected in high approval ratings.[3] As mayor, Flynn maintained a prominent public profile.[28] In 1984, journalist Colman McCarthy described Flynn as having a "blazonry of political zeal that makes him one of the nation's most attractive Democrats."[29]

In 1998, Jack W. Germond and Jules Witcover of The Baltimore Sun wrote that, as mayor, Flynn had, "built a national reputation as an advocate for the homeless and a local reputation as a hands-on politician who showed up at every fire or police emergency."[30]

At the time that Flynn was preparing to leave office, in an article published in The Christian Science Monitor, George B. Merry described Flynn as a mayor whose "hands-on" approach had made him, "one of the most visible mayors in Boston history," and whose leadership had delivered mixed results. Merry described Flynn's leadership as having been heavily focused on neighborhood-level quality of life issues,[31] writing,

NO Boston mayor in the past half-century has been more neighborhood-oriented than Raymond Flynn. In his 9-1/2 years at City Hall he has directed his attention and the city's resources toward improving life for its citizens. Unlike predecessors John Hynes, John Collins, and Kevin White, who concentrated on changing the physical face of Boston with new buildings, Mayor Flynn has focused on improving municipal services and on people things like street lighting and playgrounds.[31]

State, national, and international politics

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.[34]

Flynn considered running in the 1990 Massachusetts gubernatorial election, but, due to police controversies, his struggling relationship with the minority community, and his anti-abortion stance, he ruled out a run.[16]

Flynn became a national leader on urban matters.[35] 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.[36] Flynn served as president of the United States Conference of Mayors during 1991–92.[37][38] 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."[3]

Flynn visited South Africa several times to see anti-apartheid figure Nelson Mandela when he was in prison.[39] In June 1990, four months after Mandela's release from prison, Flynn welcomed him to Boston on a trip Mandela took visiting many cities in the United States.[40]

Ahead of the 1992 United States presidential election, there was some talk about whether Flynn could be a prospective vice presidential running mate on a Democratic ticket.[33] In February 1992, Flynn unsuccessfully urged New York Governor Mario Cuomo to run in the presidential election.[16] It took Flynn a while to grow warm to the Democratic Party's ultimate presidential nominee, Bill Clinton.[35] He endorsed Clinton in late June 1992.[41] Flynn, a lifelong anti-abortion activist, played a role in drawing the anti-abortion ("pro-life") Catholic vote to pro-abortion rights Bill Clinton in the general election.[42] Flynn physically campaigned on Clinton’s behalf in roughly half of the nation’s states.[16]

Despite opposition to gun control measures earlier in his political career,[6] as mayor Flynn supported such policy, heavily campaigning in support of the passage of the Brady Bill.[3]

Revenue package

Flynn, with Massachusetts Senate President William Bulger (circa 1984–1987)

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.[3] The state, at the time, viewed the city government as wasteful and inefficient.[3] 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.[3] 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.[3] Flynn heeded the advice of this advisory committee, and "opened the books" on the city's fiscal situation, something that his immediate predecessor, Kevin White, had refused to do himself.[3] Ultimately, the Municipal Research Bureau gave its approval to Flynn's revenue package and lobbied for it.[3]

Flynn also met across the state with individuals and groups such as local officials, business groups, and trade unions in order to persuade them to lobby their own legislators to support the state legislation he was seeking.[3] 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.[3]

In 1984, the initial revenue package that Flynn championed was defeated in the state legislature.[3][43] In 1985, Flynn proposed and lobbied for a revised revenue package.[43][44] This revenue package passed, and was signed into law by Governor Dukakis.[3][45]

Education and childcare

Flynn speaks to children in a classroom (circa 1984–1987)

In 1989, Flynn spearheaded the creation of a policy which requires that new commercial developments in the city's downtown provide childcare services on-site or otherwise fund resources for off-site childcare spaces. However, the policy would, for decades, prove difficult to enforce due to the fact that the policy did not provide a clear definition of the amounts that developers needed to pay for off-site childcare spaces. This was addressed in 2022, when Mayor Michelle Wu signed an executive order outlining a formula to determine the amount of these payments.[46]

In 1993, George B. Merry wrote that while Flynn had "vastly upgraded" the city's public school system as mayor, at the time of Flynn's departure from the mayoralty, the school district, "appear[ed] to be facing an uncertain future."[31]

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.[33][47] Before this change, the elected school board had come to be regarded as fractious.[48] 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.[49] 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.[49]

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.[49]

In 1993, Flynn wrote an open letter to those seeking to run in the 1993 Boston mayoral election to succeed him which pronounced his regret for having changed the city's school board to an appointed board, and which expressed his preference for reverting it back to an elected one. This was to no avail, and Boston remains the only municipality in Massachusetts without an elected school board.[49]

Public safety and law enforcement

Flynn swearing-in Francis Roache as police commissioner in 1985

In 1985, Flynn appointed Francis Roache as the city's police commissioner.[50] Roache was a childhood friend of Flynn, and would be one of his closet associates during his mayoralty.[51]

Flynn's administration funded neighborhood watch groups.[3]

In 1990, Flynn received 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.[16]

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.[51] 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.[51] Flynn appointed William Bratton the city’s new police commissioner.[16]

In 1993, George B. Merry observed that crime in the city remained "a continuing problem" at the end of Flynn's tenure.[31]

Urban development

Flynn working at the mayor's office in Boston City Hall (circa 1984–1987)

Flynn at the Boston waterfront (circa 1984–1987)

Flynn took office amid a period of urban flight by the city's middle class.[54] 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.[21] When Flynn took office, downtown real estate developers were highly worried by his populist agenda. Flynn opted not to socialize with real estate developers, and refused to take political contributions from developers that had projects being considered by the city government.[55]

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.[3][21] Flynn was successful in his fight to implement rent control laws in the city.[3]

During Flynn's mayoralty, the city had a strong development market.[3]

During Flynn's mayoralty, major projects included the new Boston City Hospital complex.[3] 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.[3] The city also significantly improved its parks and recreation centers.[3]

Flynn focused on addressing the quality of life in neighborhoods, as well as on addressing gentrification.[3]

The city built what was an unprecedented number of new units of affordable housing during Flynn's mayoralty.[3] 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.[3][21]

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.[3] 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.[3]

Flynn successful fights to enact rent control laws and strong tenants' rights laws put him at odds with the landlord lobby. The Flynn administration also funded tenant groups, who organized against bad landlords.[3] 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.[21]

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.[21]

Boston's development director Steve Coyle oversaw the institution of controversial "downzoning" growth management safeguards aimed at combatting the "Manhattanization" of the city's historic downtown and neighborhoods.[3]

Flynn's administration collaborated on development with nonprofit organizations. 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.[3] They worked with community development corporations to undertake the rehabilitation of thousands of housing units in the city.[21] 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.[3][56]

Resignation and succession

Flynn and his wife, Kathy, attending 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).[42] 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.[16] The Senate unanimously confirmed his nomination that month,[36] and he resigned as mayor on July 12, 1993.[42][57]

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.[58] 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.[59] 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.[60]

When Flynn resigned on July 12, 1993, Menino became acting mayor.[60] Menino would go on to win the 1993 Boston mayoral election, becoming mayor.[61]

Flynn served as Ambassador Extraordinary and Plenipotentiary to the Holy See from September 2, 1993, through September 20, 1997.[62] He was the first member of the Democratic Party to hold this post.[36] He was appointed on July 1, 1993, and presented his credentials on September 2, 1993.[62]

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.[36] Flynn's tenure was somewhat shaky, however.[63][28] In 1998, Jack W. Germond and Jules Witcover of The Baltimore Sun described his tenure as, "unorthodox and controversial."[30] Flynn twice received reprimands from the United States Department of State: in one instance for publicly discussing domestic American policy, and in the other instance for having an employee of the embassy manage Flynn's family's finances.[63]

At the time he accepted the position of ambassador, Flynn made it known that he intended to eventually return to politics, likely running for another public office.[31] While ambassador, Flynn considered running for governor of Massachusetts in 1994 to unseat incumbent Republican Bill Weld. However, Flynn announced in April 1994 that he would not run in the 1994 gubernatorial election.[64]

During his time as ambassador, the campaign committee for Flynn's mayoral candidacies was subject to federal and state investigation.[65][66] In February 1996, Flynn plead to having misused campaign funds during his tenure as mayor and agreed on repaying $12,500 in funds to his campaign committee. The state of Massachusetts' attorney general was considering bringing a civil lawsuit against Flynn regarding these funds.[66] Douglas deRusha, the former bookkeeper for Flynn's mayoral campaign committee, went to prison for embezzlement.[65] Coincidentally, the same month that Flynn plead to having misused campaign funds, an unrelated investigation resulted in Flynn's former top-aide during his mayoralty, Joseph Fisher, pleading guilty for having failed to report more than $51,000 that he had received as bribes and illegal favors during his seven years serving special assistant to Flynn during Flynn's mayoralty.[66] Both investigations generated negative publicity for Flynn.[65]

In early 1997, eying leaving his post, Flynn made an effort to become a university athletic director, reaching out to Boston-area universities such as Northeastern University. His mayoral successor, Thomas Menino, attempted to help persuade Boston-area universities to hire Flynn for such a position. This effort was to no avail, however. Shortly after, Massachusetts Governor Bill Weld, who had already expressed interest in appointing Flynn to an unpaid position on a state commission, expressed interest in potentially offering Flynn a paid position in his gubernatorial administration.[67] In early September 1997, Flynn shared his intent to run for governor of Massachusetts in 1998. Two weeks later, Flynn announced his intent to resign his post as ambassador.[65] Flynn left his post on September 20, 1997.[62]

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.[63] The article included a reporter's claim to have, firsthand, witnessed Flynn walking around Boston while seemingly drunk while visiting the city on break from his ambassadorial duties on August 6, 1997.[68] Flynn attributed the article to the paper's opposition to his planned 1998 gubernatorial campaign and also to contempt for his "class, religion and ethnic background."[63] This article was seen as hurting Flynn's public image.[28] Flynn defended himself in an interviewed aired by 60 Minutes in April 1998.[68]

Following his service as ambassador, Flynn considered running for governor of Massachusetts in 1998.[28] Flynn made public in January 1998 his intent to later that year launch his candidacy.[68] However, obstacles, such as a lack of financial campaign reserves and the political challenge of running for governor in the state of Massachusetts with a strong anti-abortion stance like his, dissuaded him.[28] Another factor that made his candidacy challenging was the perceived difficulty of winning statewide with a political identity so strongly tied to the city. Flynn's ambition of being elected governor was regarded as being a longshot.[30]

Instead of running for governor, after Joseph P. Kennedy II announced his intent not to seek an additional congressional term, Flynn decided to run in the 1998 election for Massachusetts's 8th congressional district seat that Kennedy would be vacating. Flynn formally announced his candidacy in June 1998,[30][69] and in September lost in the Democratic primary election, the real contest in the heavily Democratic district, to Somerville Mayor Mike Capuano, who went on to win the general election.[70] Flynn placed second with roughly 18% of the vote.[71]

Flynn was the only anti-abortion candidate of the ten running in the primary, and his campaign advertising utilized photos of him with Pope John Paul II and Mother Teresa.[71] Flynn had run a quiet grassroots campaign operation.[71] Flynn was endorsed by the local chapters of the International Longshoremen's Association and Iron Workers unions.[30] Flynn had been regarded as an early front-runner in the primary,[30][71] and private and public opinion polls had showed him to be leading.[30] However, polls show that Capuano enjoyed a last-minute rise in support that resulted in his victory over Flynn.[71]

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.[28]

Flynn endorsing Michael Flaherty in the 2009 Boston mayoral election (with Flaherty's "runningmate" Sam Yoon visible behind Flynn)

L–R: Kathy Flynn, Raymond Flynn, State Senator Linda Dorcena Forry, and U.S. Senator Ed Markey at the 2016 State of the Union Address

Flynn (center) during Boston's 2023 Saint Patrick's Day celebrations with Governor Maura Healey (left) and Congressman Stephen Lynch (right)

In 2001, for several weeks Flynn openly explored a possible run in that year's special election to succeed Joe Moakley as the congressman from Massachusetts's 9th congressional district. However, in mid-June 2001, Flynn ruled out such a run and threw his support behind a potential candidacy by State Senator Stephen Lynch,[72] who ultimately ran and won the election.[73]

While he has not run for office again himself, Flynn subsequently maintained some involvement in politics and related matters. In 2004, Flynn unsuccessfully pursued litigation to reverse the Massachusetts Supreme Judicial Court ruling that had, earlier that year, legalized same-sex marriage in Massachusetts.[74] 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.[75] In the 2000 presidential election, Flynn and the Catholic Alliance organization that he headed endorsed the Republican of George W. Bush and Dick Cheney.[76] In 2010, Flynn again crossed party lines to vote for the successful candidacy of Republican nominee Scott Brown for the United States Senate.[77] In 2012, Flynn appeared in television ads supporting Brown for reelection.[78] Flynn also voiced support for Mitt Romney, that year's Republican nominee for president.[79] Flynn has also continued to comment on United States relations with the Holy See. In 2009, Flynn responded critically to rumors that President Barack Obama might be considering Caroline Kennedy for Flynn's former post, opining that her pro-choice abortion stance would make her unbefitting to serve as ambassador to the Holy See.[80] In 2013, Flynn criticized plans to relocated the Embassy of the United States to the Holy See to a building that would be adjacent to the Embassy of the United States to Italy.[81]

Flynn involved himself in media after concluding his career in public office. In 1998, Flynn had a role as a radio host on WRKO in Boston.[82] In September 2014, Flynn became a regular contributor to The Pilot, the official newspaper of the Roman Catholic Archdiocese of Boston.[83] In February 2017, Flynn became a columnist for the Boston Herald.[84]

In 1999, Flynn became president of Catholic Alliance, a nonpartisan Catholic advocacy group.[85] In this role, while remaining a Democrat, he and the Catholic Alliance endorsed George W. Bush in the 2000 presidential election.[76] Flynn also became president of another Catholic political advocacy organization, Your Catholic Voice.[86] He later started Catholic Citizenship,[87] serving as its national chairman. He cited the organization as arising from conversations he had with a figure in national Catholic activism that affirmed in Flynn the importance of his message relating to adhering to Catholic teachings above partisan political concerns.[88] Beginning in 2004, Flynn also served on the advisory board of Catholics for the Common Good, a lay apostolate for evangelization of culture.[89]

Flynn and his son Raymond Flynn Jr. with priests and Cardinal Bernard Francis Law (circa 1984–1987)

Flynn with Pope John Paul II during his mayoralty (circa 1984–1993)

Flynn and his wife, Kathy, during his mayoralty (circa 1984–1987)

Flynn running in the 1984 Boston Marathon

Flynn is married to Catherine (née Coyne), who often goes by "Kathy". They have six children: Ray Jr., Eddie, Julie, Nancy, Katie, and Maureen.[1] In November 2017, son Edward M. Flynn was elected to the Boston City Council.[90] Flynn has continued residing in South Boston.[54]

While serving as mayor, Flynn played himself in the 1989 Cheers episode "The Stork Brings A Crane".[91] In the episode, Flynn has his entourage take away Cliff Clavin, who writes to Flynn once a week.[92]

Flynn was an avid runner who made headlines in 1984 when he ran in the Boston Marathon (with a finishing time of 4:23:54[93]) and the New York City Marathon (finishing in 3:59:46[94]).[95]

In March 2007, Flynn was grand marshal of the 246th New York St. Patrick's Day Parade.[96]

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.[97]

In September 2008, Flynn was hospitalized after he collapsed at a Boston-area speaking engagement.[98] 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.[99] In April 2021, Flynn was hospitalized and received a hip replacement surgery after suffering a fall.[100] In December 2021, Flynn was hospitalized after again falling, this time having broken a bone in his neck.[57]

During his political career, Flynn was regarded to be an "economic liberal" and "cultural conservative."[101] Over the course of his political career, Flynn's positions on some matters remained consistent, while others evolved. Flynn has often endorsed Republican candidates in closely contested elections, including George W. Bush in the 2000 president election, Scott Brown in 2010 and 2012 senate elections, and Mitt Romney in the 2012 presidential election.[102]

In his early political career, Flynn prominently opposed court-ordered school desegregation busing.[3][15] Over the course of his political career, Flynn consistently opposed abortion.[42] Opposing gun control policies in his early political career[6] as mayor Flynn supported gun control policies.[3] Opposing gay rights issues in his early political career,[6] by the time of his first mayoral campaign made an active effort to ingratiate himself to the gay community.[24] However, due to his own opposition of same-sex marriage,[103] shortly after the Massachusetts Supreme Judicial Court ruled that same-sex marriage was a protected right in Massachusetts, Flynn attempted litigation to see their ruling overturned.[74] Flynn opposed decreases initiated during the Reagan presidency to federal revenue sharing with cities. [31][34] Elected mayor on a populist platform, Flynn supported wealth redistribution.[55]

Flynn (left) sits alongside Governor Charlie Baker on February 11, 2016, as Baker signs into law legislation renaming the Black Falcon Cruise Terminal the "Flynn Cruiseport Boston".

In February 2016, the Boston Marine Industrial Park was renamed the Raymond L. Flynn Marine Park.[104] A nearby bridge was also renamed in Flynn's honor.[105] In May 2017, Governor of Massachusetts Charlie Baker dedicated Flynn Cruiseport Boston, located in the Port of Boston.[106][107]

Flynn has received a number of civic awards.[108] 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".[36] 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 that 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."[54]

Flynn is the co-author of two books:

• Flynn, Ray; Moore, Robin (2000). The Accidental Pope: A Novel. St. Martin's Press. ISBN 0312268017.
• Flynn, Ray; Moore, Robin; Vrabel, James (2001). John Paul II: A Personal Portrait of the Pope and the Man. St. Martin's Griffin. ISBN 0312266812.

• 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

Wikimedia Commons has media related to Raymond Flynn.

• Appearances on C-SPAN
• Guide to the Mayor Raymond L. Flynn records at cityofboston.gov
• Ray Flynn biography at the Dominican School of Philosophy and Theology