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Defining Michael Flaherty07:46
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Michael Flaherty and fellow City Councilor Maureen Feeney during a hearing at City Hall in 2006. Flaherty's colleagues describe him as ambitious and a risk-taker with remarkable behind-the-scenes political skills. (AP)
Michael Flaherty and fellow City Councilor Maureen Feeney during a hearing at City Hall in 2006. Flaherty's colleagues describe him as ambitious and a risk-taker with remarkable behind-the-scenes political skills. (AP)

Michael Flaherty has spent the last 10 years on the Boston City Council. Now that he's running for mayor, some of his colleagues are surprised by who he has become: a candidate who calls himself inclusive, a progressive and different from Thomas Menino.

"It's almost like there's Michael Flaherty: Part One and Michael Flaherty: Part Two," said Maura Hennigan, who served with Flaherty for six years.

So, who is Michael Flaherty?

THERE'S NO DOUBT ABOUT WHERE HE CAME FROM: a political family in South Boston. His father was a state representative and later a judge. But his father urged him away from politics.

"I think that if his father had his way, he'd be doing anything but running for office," said Joe Hamilton, a friend of Flaherty's since grade school. Hamilton said the senior Flaherty gave this advice:

"You live your life. I've had my life. You've gone through school, go make your own trail. He advised all of us. There's other ways of making a living out there."

Flaherty learned how to talk to voters from his father. But it was his "Uncle Jimmy" who taught him how to be a political operative. Just talking about Uncle Jimmy makes Michael Flaherty's eyes well up.

"Jimmy would be the one who would give you the straight scoop of all the things that go into a campaign," he said, "whereas my dad was the front person."

In 1994, Jimmy was killed in Florida, where he was leading a double life.

"Unbeknownst to anyone in the family, he was straight while in Boston and he was gay while in Florida," Flaherty said. "To this day, I often wonder if the climate around LGBT issues were — that's something that I'll probably always struggle with."

His uncle's murder also influenced his politics, according to Flaherty. For years he spoke passionately about homophobia. Then, once he was on the council, Flaherty was the first city official to endorse gay marriage.

That impressed David Breen, a gay friend who worked with Flaherty as a prosecutor years before.

"Running from South Boston for City Council at-large and from a district where he has a strong base, there was no reason he needed to be so out front on gay marriage," Breen said. "Absolutely no political reason for him to do it. He did it because it was the right thing to do. He did it because he had friends and relatives who needed that help."

FLAHERTY WEARS HIS SUPPORT FOR GAY MARRIAGE as a liberal badge of honor. That and his early support for Barack Obama. But many city observers associate Flaherty with positions against rent control, affirmative action and school busing.

Myriam Ortiz runs the Boston Parents Organizing Network and is skeptical of Flaherty when it comes to schools.

"When an elected official goes back and forth on issues that are so fundamentally impacting the lives of low-income children and children of color in Boston public schools, I tend to be cautious," she said.

That's because, around 2004, Flaherty led the charge to stop busing in the Boston public schools, to save money and so more students could attend their neighborhood schools. But, this year, he's scaled back that plan, saying the city has to improve the quality of education first.

Flaherty said he changed his position because he learned more.

"I didn't realize that we had so many under-performing schools until I presided over the education budget hearings," he said.

Flaherty said some people unfairly demonize him because he's from South Boston, the neighborhood associated with the busing riots in the 1970s.

"The topic of education and school transportation is and can be a very polarizing argument the minute someone steps up to the plate and says, why are we spending this money, and why don't we spend it in the classroom?" Flaherty said. "There are some people who take it one way and there are others who take it another way."

FLAHERTY HAS MADE A NUMBER OF OTHER SWITCHES, on the death penalty, affirmative action and Boston University's plan to build a Biolab in Roxbury. Flaherty supported building the Biolab until a few years ago, after Hurricane Katrina hit.

The government's slow response to that disaster made Flaherty wonder how the government would react if a disaster struck the Biolab, where they plan to store dangerous pathogens like the Ebola virus.

If you take Flaherty at his word, he sounds like a guy who takes a strong opinion, but might bend after more experience with the issue. But others wonder if it's a strategy to become more electable.

His colleagues, including Councilor John Tobin, describe Flaherty as ambitious and a risk-taker with remarkable behind-the-scenes political skills.

"Being council president, getting there, is like herding cats," Tobin said. "It's a situation that's not over until it's over, until the final vote is cast. You have 12 people that you're dealing with and their personalities, and people going back and forth, and they're going back and forth, and he held on to that for five years. That's remarkable."

Tobin said Flaherty was effective getting work done on the council. But the flip side of being so efficient was that he sometimes alienated his colleagues, according to current and former councilors.

FLAHERTY WAS THE RINGLEADER of a group of six young city councilors, all white men, that the news media dubbed the "young turks." There was a generational divide between this group and everyone else who was over 40, including the only black and Latino councilors.

Many in this group complain that Flaherty was an autocratic leader, who didn't reach outside of his clique. Councilor Charles Yancey said he didn't like the way Flaherty treated him early on.

"Some of the things that he did verged on disrespectful, but I chock it up to inexperience," Yancey said. "There were those signs early on — I don't see him that way now. I think he's grown and matured a bit."

But former Councilor Maura Hennigan said she never saw Flaherty lose his cool. "He may have disagreed with us, but he was never disagreeable," she said. "He was respectful, but once he made his mind up there was nothing more to be said about it."

For Hennigan, Flaherty's attempt to unseat Mayor Menino has an ironic twist.

"Councilor Flaherty, I viewed as part of Tom Menino's team," Hennigan said. "He would refer to the mayor as 'his mayor,' and say, 'we have to work together.' so it actually is a bit humorous to watch it now."

And perhaps that's the biggest curiosity about Michael Flaherty. It's been said for years that he was the heir-apparent to Menino, that Menino would retire from politics and endorse and help Flaherty.

Now, Flaherty's running as his own man, and still defining who that man is.


This is the first of two profiles of the Boston mayoral candidates. Click here to read and listen to WBUR’s profile of Thomas Menino.

This program aired on October 16, 2009.

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