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The city’s top lawyer is also Walsh’s rock

Eugene O'Flaherty, an aide to Boston Mayor Marty Walsh, shook hands with Jacqui Krum, an official with Wynn Resorts, during a February meeting of the state’s Gaming Commission.John Tlumacki/Globe staff/file/Globe Staff

The first of three profiles of the advisers closest to Mayor Martin J. Walsh as he embarks on his bid for reelection.

Eugene O’Flaherty tried hard to kill this story.

I’m too boring to be profiled.
Haven’t you anything more important to do?
The former legislator known for blowups with the media argued his case all the way to the Globe’s editor, with whom O’Flaherty once had a spectacular run-in, which we’ll get to in a minute.

When he couldn’t stop the story, the attorney who heads the City of Boston’s law department sat for an interview that fairly well confirmed what many say: 1) Gene O’Flaherty is pretty intense, and 2) he’s passionately loyal to his longtime friend, Mayor Martin J. Walsh.

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Consider the nondescript nature photo on display in O’Flaherty’s City Hall office. It is actually a picture of the Garden of Gethsemane, a copse of olive trees in Jerusalem where the Gospels say Jesus Christ was betrayed.

“The picture reminds me of the travesty of betrayal,” said O’Flaherty, explaining why he keeps it. “It serves as a reminder to me to stay loyal so as to never feel the shame that Judas felt.”

City politics is arguably a notch or two less momentous than selling out the Messiah, but point taken. That attitude helped O’Flaherty get his job.

“You need someone who’s extremely loyal to you in that position,” said Walsh, speaking of the corporation counsel, the city’s top lawyer. “You need a lawyer you can have confidence in, who can be somewhat of a confidant.

“You’re dealing with complex issues; you’re dealing with issues like casinos that you don’t want somebody out there talking at a cocktail party, at a coffee shop, or whatever it is about what’s going on.” The media, Walsh said, are always trying to find information. “You’re not getting it out of Gene. He keeps it very close to the vest. That’s an important characteristic to have.”

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O’Flaherty, a Democrat who represented Charlestown and parts of Chelsea in the House, walked away from his own 17-year political career to take the job. He has been a trusted Walsh adviser during the administration’s most trying episode: an ongoing federal investigation that has led to the indictment of two Walsh staffers this year on extortion charges.

O’Flaherty was also at the center of Walsh’s controversial strategy to fight a Wynn Resorts casino project in Everett with a ferocious legal battle that cost close to $2 million. Then, when the legal fight failed, O’Flaherty played a key role in successful negotiations to make peace with Wynn.

He was one of a tight group of Walsh aides nicknamed “the fourfecta” inside City Hall, according to city e-mails from Walsh’s first year in office that were acquired by a public records request. The other three were Walsh chief of staff Dan Koh, chief of policy Joyce Linehan, and former director of operations Joe Rull, who left city government in 2015.

O’Flaherty is generally among a handful of senior Walsh staffers who meet most mornings to go over city issues, O’Flaherty said.

When Walsh made his triumphant 2014 visit to Ireland as the newly sworn mayor of Boston, he brought one City Hall employee: Gene O’Flaherty, accompanied by his wife. They traveled to Rome together in 2015, for a papal conference on human trafficking and climate change; O’Flaherty, as a legislator, oversaw passage of the state human trafficking law.

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“Gene is the person at City Hall the mayor relies on more than anybody,” said Jack Hart, who served in the Legislature with O’Flaherty and Walsh and is close to both. “It’s not about building a profile for himself in the newspaper. Everything he does is for the good of Marty Walsh. You can’t say that about everybody.”

The mayor’s allies say that O’Flaherty, a 48-year-old Gen Xer, brings perspective and political experience to an administration heavy with millennials. “Gene is probably the strongest and most thoughtful voice Marty Walsh has,” said former House speaker Thomas Finneran.

Walsh and O’Flaherty entered the Massachusetts House together in 1997. Both say they bonded immediately over their Irish roots.

“He was an immigrant, I was an immigrant,” O’Flaherty said.

Well, technically no. Both men were born in Boston, children of Irish-born parents, though O’Flaherty lived five years in Ireland as a boy. His verbal shorthand shows how deeply he identifies with Irish history and politics, his family’s part in it, and its immigrant experience. He lights up describing the first time he was a guest at the home of Walsh’s mother: “The minute I walked into the house I knew it was a traditional Irish household — not an Irish-American household. Because of the way she cooked the cabbage, the way she cooked the bacon; it was as if I was in my auntie’s house.”

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O’Flaherty’s parents and four brothers were born in County Kerry, Ireland. They moved to the United States in 1963. O’Flaherty, born in 1968, is the only member of his immediate family with a US birth certificate. His brothers called him The Yank. When he was 5, O’Flaherty moved to Ireland with his father, John, and lived on a farm. “I was raised in that very Irish republican environment in Kerry,” O’Flaherty recalled. “A very political environment.” An uncle served in Parliament. A grandfather had been jailed for his role in the 1916 Easter Rebellion against the British.

“We have been involved in politics in Ireland since the foundation of the state and even before that,” O’Flaherty said. He moved to the Irish enclave in Manhattan’s Hell’s Kitchen neighborhood in 1977, then to Medford and Chelsea, where his father for years ran a formal wear store.

O’Flaherty was a controversial pick for corporation counsel, coming from Beacon Hill with a reputation as an occasional hothead, full of scowls and glares, who practiced hard-nosed politics and combativeness with the press. He was not a glad-hander, not a schmoozer.

“He was impeccably polite even when I felt he was going to slug me,” said one former State House colleague. “If you watched his body language and expression, it was scary as (expletive).”

Friends say, yes, O’Flaherty’s public game face could be intense, but that personally he is warm, compassionate, and wickedly funny.

“I don’t have ambition to be liked by everybody,” O’Flaherty said.

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For 12 years on the hill, he reigned as chairman of the influential Judiciary Committee, ground zero for many of the Legislature’s most highly charged issues. “It’s nothing but a horrific set of migraines,” said Finneran, who first gave O’Flaherty the post. “There is a lot of emotion and high pressure and political tactics brought on that committee. You don’t want someone who caves in.”

Several former House colleagues describe O’Flaherty the legislator as very tough and serious about his politics.

“You didn’t see him smile much,” recalled former North Adams representative Daniel E. Bosley, who nonetheless said he likes O’Flaherty. “You always knew where you stood with him. There were times he prevented the membership from taking a bad vote. He would take the heat on things that weren’t politically popular but were probably the right thing to do.”

Representative Ellen Story, an Amherst Democrat, laughed when asked about O’Flaherty. “I’m not going to say anything,” she said. Was that a joke? Or did she really not want to say anything? “I really don’t.”

O’Flaherty was often in the cross-hairs of interest groups, which accused him of slow-walking hot-button legislation. It was nearly an annual event, O’Flaherty said, for some special interest to “pick out an issue, associate it with a tragedy, associate it with a name, and then use that to change fundamental principles.” During the 2008 fight over Jessica’s Law, calling for minimum mandatory sentences for child rapists, America saw O’Flaherty on national television testily telling an ambush interviewer from the Bill O’Reilly show to “go back to journalism school.” In the 2012 fight over eliminating the statute of limitations for child sex abuse, O’Flaherty got fed up and announced he was done as Judiciary chairman, after a critical column by the Globe’s Kevin Cullen. He later changed his mind.

Opponents accused him of stalling legislation because of a conservative bent, or because he worked as a defense lawyer. Neither was true, O’Flaherty says. He says he was excoriated for standing up for sound principles — prosecutorial discretion, for instance. Or because the law recognizes valid reasons for imposing statues of limitation: memories fade with the passing years, witnesses move away or die, exculpatory evidence can be lost.

He rarely bothered to explain his political stands to the media at the time, which is now “one of the greatest regrets” of his years in office, he said. “I knew [reporters] wouldn’t write what I said anyway. But just for my personal satisfaction,” he wishes he had engaged the media to “get the issues into the public sphere and force a conversation about constitutional principle and the like.”

Former representative Carl Sciortino said O’Flaherty’s reputation was not always fair. “He was chair of Judiciary when I was leading efforts on transgendered rights,” he said. “The public perception was he was a roadblock but he and I had productive conversations. He was always a very smart and serious guy.”

In one instance O’Flaherty did engage with the media, in 2005, he sent what he says was an ill-advised e-mail to then-Globe Metro columnist Brian McGrory, complaining about a piece critical of Finneran. O’Flaherty’s e-mail fantasized about giving the columnist “a black eye and a sore arse.”

McGrory, now editor of the Globe, quoted the e-mail in not one, but two biting columns. “The counterpunch far exceeded the initial assault,” O’Flaherty said recently, with a smile. They have since mended fences.

As Walsh’s top in-house lawyer, O’Flaherty has mostly served under the radar, even as City Hall was roiled by the indictment of two Walsh officials for allegedly withholding city permits until a music festival agreed to hire union stagehands.

The law department could be open to some second-guessing, such as around the mayor’s failed lawsuit to block the Everett casino. After the city accumulated nearly $2 million in outside legal fees, a Suffolk Superior Court judge dismissed Boston’s complaint, while scolding the city and its lawyers for spreading “spurious” claims and “hyperbole.”

O’Flaherty, who graduated from the Massachusetts School of Law, declined to talk about advice he gives the mayor — “I’m his lawyer.” But speaking in generalities, he defended his department, “given the issues we have been confronted with, the complexity of those issues.” He says he hasn’t thought about resuming his own political career, and intends to hold his job as long as Walsh wants him.

Near the end of a long interview, O’Flaherty reiterated he did not want to be profiled. He said the only attention — “if you could call it that” — that he ever wanted in politics was the approval of his district, which elected him nine times.

“I didn’t really care much about a larger constituency,” he said. “I don’t know if that’s good or bad. But I think it allowed others, including the media, to create almost a caricature of me. Obviously a part of me wants to correct that. But a bigger part of me doesn’t.”


Mark Arsenault can be reached at mark.arsenault@globe.com. Follow him on Twitter @bostonglobemark