The last time Raymond L. Flynn held elected office was 1993, his final year as mayor of Boston. But as US Senator Scott Brown and Democratic challenger Elizabeth Warren fight out one of the country’s most hotly contested races, Flynn, improbably, has entered the conversation.
It started over the summer, when Flynn, a registered Democrat, appeared in a campaign ad in which he endorsed Brown, a Republican, and continued this month when former governor Michael S. Dukakis lashed out at Flynn at the Democratic National Convention.
In a Senate race that has turned on issues of class and authenticity, Flynn, a figure inextricably linked with blue-collar South Boston, personifies an important, if arguably dwindling, bloc of voters that Brown needs to capture. On Saturday, Flynn joined Brown as the senator shook hands at Castle Island.
The hope among GOP strategists is that the backing of the former mayor, who identifies himself on the phone as “Ray Flynn from South Boston,” opens the gates for others like him to part ways with Warren, a Harvard law professor who lives in Cambridge.
“His endorsement gives conservative, white Democrats permission to vote for Scott Brown,” said Rob Gray, a Republican political strategist. “They may be saying to themselves, ‘I like Brown, but I’m a Democrat and I can’t vote for a Republican. But wait a sec, Ray Flynn is a Democrat, so I guess its OK.’ ”
Not so, say leading Democrats, who have dismissed Flynn as nothing short of a turncoat, pointing out that the former mayor also supported George W. Bush over Al Gore and endorsed Brown over Democrat Martha Coakley in the 2010 special election. Flynn, who was the US ambassador to the Vatican from 1993 to 1997, was one of six former envoys who wrote a letter in support of Republican presidential candidate Mitt Romney in July.
Dukakis went so far as to suggest that Flynn was betraying the ideals that he championed as mayor.
“The Ray Flynn that I worked with then, and I knew and respected, wouldn’t have given Scott Brown the time of day,” Dukakis thundered at the convention. “Tax cuts for the rich? Repealing Obamacare? Are you kidding me? Flynn? I don’t know what’s happened to him.”
Flynn says nothing has happened to him. In a recent interview, he pointed out that most of the politicians he supports — including state Representative Nick Collins, state Senator Jack Hart, and US Representative Stephen F. Lynch — are Democrats.
Flynn said that he has always stood for candidates who stand for “people I grew up with, people who work for a living, they have kids, they pay tuitions, they are struggling, they lost their jobs, they have a kid that is sick, they have a parent that needs to get in a nursing home.”
Flynn said he came to his conclusions about Brown based on “what I knew about his personal life growing up.”
“It’s really a nonpolitical message about the man, rather than it is about politics or ideology,” he said. “I didn’t go through his congressional record or roll call. I don’t have time for that. People don’t have time for that. I am interested if the guy is honest, that he has personal integrity.”
In the ad, Flynn describes Brown as “a regular guy, honest” and never brings up the senator’s stance on issues, particularly the one that people who know Flynn well say is the most important to him.
An ardent Catholic, Flynn is a vehement opponent of abortion.
Although Brown has repeatedly said he favors abortion rights, Flynn cited Brown’s endorsement by Massachusetts Citizens for Life, the state’s leading anti-abortion group. In the US Senate, he cosponsored the Blunt Amendment, which would allow health plans and employers to refuse to provide or pay for services such as abortion that they oppose on religious or moral grounds.
“He was endorsed by Massachusetts Citizens for Life,” Flynn said. “That’s an organization I believe in. That means there must be something there, that he has a lot of respect for life and the needy.”
Neil Sullivan, who was chief policy adviser to the former mayor, described Flynn’s backing of the Republican as “a single-issue endorsement.”
“I view his endorsement of Scott Brown as Ray Flynn, citizen for life,” Sullivan said.
Flynn’s endorsement could be a useful piece in a strategy to cast Brown as a Republican whom Massachusetts Democrats can vote for.
The incumbent has also secured the endorsement of Democrats of regional renown such as Konnie Lukes, former mayor and current city councilor in Worcester, and Paul Walsh, former Bristol district attorney, A Scott Brown flier featuring Flynn, Lukes, and Walsh and the headline “Democrats agree . . . ” showed up in mailboxes last week.
The question is how many voters Flynn’s appeal will carry. Gray, who was campaign manager for Paul Cellucci’s successful run for Massachusetts governor in 1998, said that for a Republican to win a statewide election, the candidate needs to win two of 10 votes by registered Democrats.
Gray and other observers agree that Flynn’s endorsement carries nowhere near the heft of that by Mayor Thomas M. Menino, who announced his backing of Warren on Friday.
In the last mayoral election, Flynn threw his support behind Michael F. Flaherty, who lost to Menino by 15 percentage points.
“From Menino’s own perspective, it reminds people that he, and not Ray Flynn, potentially controls a significant number of votes in the city,” said Peter Ubertaccio, director of the Martin Institute at Stonehill College.
But Wards 6 and 7 in Boston, which include Flynn’s erstwhile stronghold, South Boston, were the only ones in the city where Brown won the majority of votes in the 2010 special election.
“I would say that at least 30 percent of Democrats in this state are more conservative, more traditional, and would relate to what Scott Brown said about being bipartisan,” said Todd Domke, a Republican political analyst.
“Flynn saying Scott Brown is a regular guy sends an implicit message that Elizabeth Warren is more of an elitist,” Domke said.
As for Warren, Flynn said it’s not personal.
“I never met her,” he said. “I never said hello, not that I wouldn’t. I never met her, I never saw her, I don’t know the first thing about her.”Andrew Ryan, Michael Levenson, and Glen Johnson of the Globe staff contributed to this report. David Filipov can be reached at email@example.com. Follow him on Twitter @davidfilipov.