City Council Candidate Out to Shake 100,000 Hands

One election you won't see on the ballot in Boston this November is the one for city council. That election is not until next year. But that has not stopped one candidate from going door to door to introduce himself to the voters.

Doug Bennett is running for city councilor at large. In next year's election, voters will pick four at-large councilors. Bennett wants to knock on 100,000 by then, and he's getting an early start.

More than a year before the election, we meet at 5:30 p.m., after his day job at the Suffolk County Criminal Trial Court. We meet at the corner of Broadway and Dorchester Street, in South Boston, where he shows me a map produced by the Republican National Committee.

BENNETT: So I use Voter Vault technology, right? What it does is it produces me a map of all the houses that we'll be hittin', OK?

The map shows the most frequent voters. Bennett has a huge packet of leaflets, and on each one, he's put the name of the voter he wants to contact, and the address, plus a little hand-written note. He got the map for free from the state Republican party. He is a Republican, but candidates for city hall aren't allowed to run under a party affiliation.

In the handouts that he leaves on people's doors, Bennett says he "understands the pains that Bostonians face today." He says the cards have gotten the attention of Mayor Tom Menino.

Bennett ran into Menino at an Eastie Pride event last month, and asked him for his vote. He says the mayor told Bennett he didn't like his campaign literature.

MENINO: It that's what he said, it must be true.

Menino says he doesn't agree with Bennett's positions.

MENINO: This guy's an interloper. ... This guy's from Nantucket, isn't he?

Bennett did move to Boston from Nantucket. He is 32. He and his wife, Kathleen, a Boston banker and the daughter of Papa Gino's CEO Thomas Galligan, live in the Boston Harbor Towers.

Bennett moved here from Nantucket. He has roots in Boston. His grandfather was abandoned at the age of three at the statehouse. But Bennett grew up in Allentown, Pennsylvania.

BENNETT: One of my best friends growin' up, he got involved in dealin' cocaine and gun trafficking, and what happened was he was murdered. ... It's a lesson I took. At the time, you think he was makin' all this money. It was comin' to him fast, but all of a sudden, that tragedy occurred, and he made me see, hey, I have this wonderful opportunity, and that's life, and I need to go out there and make the most of it.

Bennett and his wife met in Nantucket.

BENNETT: What happened was, so me and my wife, we met on Nantucket outside this bar called the Chicken Box, right? ... It was after the bar closed. People say you don't meet anyone at the bar. That's not true. I met my wife at the bar. So I always thought that was funny. I was a carpenter. That was my day job, and then I was elected selectman and county commissioner out there.

Along the way, Bennett knocks on Rep. Stephen Lynch's door. The congressman isn't home. Neither is State Sen. Jack Hart, across the street. But a few weeks ago, Bennett did run into a South Boston political legend, who gave him some advice.

BENNETT: I was in this neighborhood, campaigning, and I was walkin' by a funeral home. It was a Sunday afternoon ... and who walks out? Billy Bulger! All right? He just came from a wake, right? And he and I started talkin', right? And we talked for a good 20 minutes, right? He had a lot of real good wisdom, right? He said that in 1960, when he was running for the state rep. seat ... according to Billy, there were 19 people runnin' for that state rep. seat, for that open seat. ... He met more people than his opponents, and he won.

Somewhere on East 4th Street — he's not sure which door, exactly — he knocks on his 10,000th door.

BENNETT: You know, I got elected on Nantucket, and I had one-tenth of the amount of money that my opponents did, and I beat eight other people.

Beat them by knocking on doors. By 8 p.m., Bennett has knocked on 200 doors. He does this five days a week.

This program aired on October 13, 2008. The audio for this program is not available.


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