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Flynn's low-budget campaign intends to use the remnants of his once mighty grass-roots operation to get out the vote. But the residual goodwill from his 10 years as mayor is ebbing. After he left office, two of his top aides were convicted of fund-raising-related crimes. And Flynn's tenure as an ambassador earned him a reputation for erratic and often unstatesmanlike behavior in Washington and Rome. After the Globe published an eyewitness account of him appearing drunk in the late afternoon, Flynn went on 60 Minutes to rebut the charges. Now he dismisses the controversy. "I don't think [voters] take it seriously," he says.
Clapprood, 48, is the only other candidate who can match Flynn's backslapping style. When a motorist honks approval at an intersection in East Boston, she shouts, "I love you," then totters after a voter on her 4-in. heels. Suddenly, she stops short, whirls around and asks her campaign adviser, Jim Spencer, "Do I have schmutz on my face?"
Spencer shakes his head no, and Clapprood accosts two women on the sidewalk, one of whom has just declared, "It's her!"
"This is very important," Clapprood tells them. "You gotta help me win, O.K.?"
Spencer, who worked for Joe Kennedy, insists that Clapprood is more than a celebrity. And he's right. She served six years in the state legislature, then ran a credible race for Lieutenant Governor in 1990. Her loss was blamed on her famously acerbic running mate, Boston University President John Silber, who was defeated by William Weld. Clapprood has a record of involvement in groups that help poor women and children, and she is trying to exploit Flynn's biggest vulnerability in such a liberal district, his opposition to abortion. She touts herself as the pro-choice candidate who can beat Flynn, and in last week's debate, she essentially asked voters to elect her because of her gender. "We've never sent a woman to Washington to stand for us," she said. "I'd like to be that woman."
Of the eight others angling to sneak by Flynn and Clapprood, the most visible is Gabrieli, 38, a nerdy, prematurely gray father of four. Gabrieli has visibility because he paid for it. Since early summer, the multimillionaire has spent more than $2 million of his own money, most of it on television. But unlike other self-financed candidates, who spend their early money on get-to-know-me ads aimed at raising their name recognition, Gabrieli has been running substantive spots about issues like setting standards for teachers and HMO reform. He wants voters to associate him with progressive ideas, even ones that are controversial in traditional Democratic circles, such as charter public schools. Gabrieli distinguished himself in the debate, promising "to step on some toes" to get things done. His strategy seems to be working. At a subway "T" stop in Somerville, most of the morning commuters who pause to take a leaflet recognize Gabrieli and know his positions on the issues. Some are not impressed, like the woman who badgers him for being "against teachers." But others are more positive. "My husband just said he's probably gonna vote for you," says Cynthia Close, 53. "I might too."