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HIS WORKOUT IS OLD SCHOOL. It's sit-ups. It's push-ups. It's jumping rope. It's the stuff Michael Flaherty did growing up in gym class in school. Only when he was at Boston College High, the workouts didn't start at 5:20 in the morning.
Flaherty clearly likes a challenge. If the City Council is often derided, especially by Mayor Thomas Menino, for its light workload and responsibilities, Flaherty's day is anything but light. He gets to the hard-core workout at the gym on Dorchester Ave. in South Boston on less than six hours of sleep.
It's hard work to run against Boston's longest-serving mayor, but Flaherty faced an uphill challenge when he ran successfully in 1999 against the entrenched Dapper O'Neill for an at-large seat on the City Council.
Wherever he goes — Charlestown, East Boston, Jamaica Plain, Roslindale — Flaherty becomes a magnet for people eager for change: city workers, families of firefighters and police officers, young parents and, it seems, just about all the shoppers at Roche Brothers in West Roxbury.
"Think it's time for new leadership in our city?" Flaherty asks one woman.
"Are you kidding?" she responds. "Definitely!"
"Most definitely!" chimes in another woman.
"After 16 years?" asks the first woman.
"Definitely!" says the second woman. "What gets me is nobody can beat him. Nobody can beat him."
"You're looking at him," Flaherty says. "I happen to think that after 16 years, it's time for new leadership."
"It's more than time," says a third woman, laughing. "My dog could run this city better than that one could. I just don't know how you're going to do it."
"We're working hard," Flaherty says. "I need your vote. We're working one person at a time."
"The vote's not a problem," the woman says.
IN WEST ROXBURY, Flaherty meets countless people who, like he, grew up in South Boston. He lives at Columbia Road and M Street, by the beach. His father was the neighborhood's state representative for 12 terms. BC High has graduated a lot of talented politicians, but if he wins, Flaherty would become the school's first graduate to become mayor of Boston.
After BC High, Flaherty went to Boston College, then Boston University Law School. To put himself through law school, he went to work for the Teamsters, delivering freight at the airport. After law school, he worked as an assistant Suffolk County district attorney under Ralph Martin. Flaherty had campaigned for Martin, working Southie for the African-American Republican candidate.
As an assistant DA, Flaherty was assigned to Roxbury, where he worked with his friend Dave Breen, an assistant attorney general. "It was a collaborative effort to basically target certain neighborhoods and deal with quality-of-life type of issues," Breen said.
Earlier this summer, Breen wrote an op-ed article in Bay Windows, the gay newspaper, endorsing Flaherty, in part because Flaherty was the first city-wide elected politician to support gay marriage. One of Flaherty's cousins, whom he called an uncle growing up, was discovered to be gay only when he was murdered.
BREEN BELIEVES THAT TRAGEDY SHAPED FLAHERTY'S OUTLOOK. "I know from talking to him that it had a deep impact on him" Breen said, "and I think the idea for him that anyone would have to lead a closeted life and lead to what happened to his uncle, it was too much to bear."
"I think back about it," Flaherty said of the murder, "and wonder if Boston back in 1994 was like Boston in 2009, maybe he'd be alive today."
When Flaherty proposed that Boston support gay marriage, the city couldn't even get domestic partnerships approved by the state legislature because Tom Finneran, the speaker at the time, opposed it. So Flaherty was taking a political risk by calling for same-sex marriage.
"For me, being from South Boston, I think it took quite a lot of people by surprise," Flaherty said — "but obviously, it didn't take people who know me by surprise," he added.
"It sort of paved the way, and it made it a little bit easier for other colleagues in government to look at me as a case study and say, 'Look, here's a guy from a traditional neighborhood base and he's the top vote getter citywide, and he takes these positions, and it hasn't hurt him on election day,' " Flaherty said, "and I think it went a long way to sway other leaders to cast a vote in favor of gay marriage."
Flaherty's friend, Dave Breen, gives the city councilor credit for switching the votes of several Boston legislators on the issue of gay marriage.
WHEREVER FLAHERTY GOES, he is approached by young professionals worried about the direction the city is taking. On City Hall Plaza, he hears from Alex Rodriguez, who just moved to Boston a year ago from Texas.
"I've seen businesses grow down there because the taxes are so low," Rodriguez tells Flaherty of his former home. "The costs are so low, and there's no growth here."
"No," Flaherty says, "I agree with you."
"There's nothing that can happen here" Rodriguez says, "and quite honestly, the local Democratic Party here, Beacon Hill, is slamming people. I know you're not on Beacon Hill, but it's slamming people over and over and over again, and people can't afford it here anymore."
"I agree," Flaherty says, again.
"And so," Rodriguez asks, "from a city perspective, how do you plan to bring relief to the people of Boston?"
A few minutes later, Flaherty meets Alex Pelletier, who is trying to figure out where her two-year-old should go to school in a few years.
"Put it this way," Pelletier says, "I don't want to move. I love Jamaica Plain, but at this stage, I've got three years to decide whether I'm going to pay city taxes to Newton."
"That's a dilemma that most parents have to go through in Boston, sadly," Flaherty says. "That should never be the case. Give me some thoughts around education as to what you think would be a great thing for Jamaica Plain."
"Options that work for kids that do speak English, that do come from an educated family," Pelletier says. "Me and my partner both have masters' degrees. I don't want her sitting there with people that are learning English."
"Exactly," Flaherty says. "This is an outrage. More young families leave our city in search of quality education."
This is a discussion that Flaherty has with young parents throughout the day. Two months ago, he proposed lifting the cap on charter schools. Soon afterward, Mayor Menino withdrew his opposition to charter schools, a change that Flaherty now takes credit for.
If nothing else, he says, the fact that he's in the race is forcing the mayor to consider new ideas.
"You're a resident," he tells Pelletier. "You're a taxpayer. Your kid's not good enough?"
This program aired on August 10, 2009.
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