Fueled By Outside Money, Boston’s Mayoral Slugfest Gets Personal

The first competitive race to run Boston in two decades has become a union-funded fight over identity politics

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Photo by Wendy Maeda / The Boston Globe / Getty Images

Boston Mayoral candidate John Connolly held a press conference outside Madison Park High School in Boston, on Oct. 16, 2013.

John Connolly sat in an SUV littered with the detritus of a long political campaign — old coffee cups, empty doughnut bags, campaign fliers printed in English and Chinese, a bruised banana, a tub of hand sanitizer — and tried to make sense of the wringer he’s squeezing through. Not long ago, Connolly, a 40-year old Harvard-educated city councilor, had looked like the favorite to become Boston’s next mayor. The weeks since September’s preliminary election have not been kind.

Connolly has been unable to beat back an autumn surge by his opponent, Marty Walsh, an affable state legislator and former labor union official. The race for Boston mayor has become a chippy, intensely personal affair that’s breaking along cultural and class fault lines, and fueled by an unprecedented influx of outside super PAC money. Connolly has gotten the worst of these exchanges; by the time he sat in his debris-strewn campaign vehicle days before Tuesday’s election, shuttling between an interview for a local access TV show and a meeting at a senior citizen center, he sounded spent and confessed to feeling numb. He admitted that he’ll be outgunned on the ground, but found hope in internal polls that had the race tied. In the last days of a campaign, you take hope wherever you can find it.

Boston hasn’t had a real, hotly contested race for mayor in 20 years, since the current officeholder, Tom Menino, won the first of his five terms in office. It’s been 30 years since the city’s last open mayor’s race. So the current contest is as historic for the fact that it’s happening at all as it is for what Walsh and Connolly are saying on the campaign trail.

The contest itself has been an odd tweener of a race. Boston retired old-school, machine-dominated politics when Menino declined to seek a sixth term early this year. At the same time, seismic demographic changes in the city haven’t yet re-molded its ways. Boston is a rapidly growing, gentrifying city. Young, educated, and relatively wealthy residents are streaming into the city’s core. These new residents are driving Boston’s economic future, but most of the political power still rests in the city’s clannish outer neighborhoods.

Both Walsh and Connolly have taken great pains to straddle these two worlds. They’ve each tried to graft enough of the new Boston onto the city’s old, politically active base to cobble together a winning coalition.

Walsh is the son of Irish immigrants and a second-generation construction laborer. He speaks with a ragged Boston accent. The 46-year old state legislator measure the success of his days on the campaign trail by how much his right hand aches at night, when he’s done shaking hands. He’s a former alcoholic who has touched a vein of fervent support in the city’s recovery community. There’s plenty of Tom Menino in Walsh: He won’t stun anyone with oratory, but he combines a fierce work ethic with a unique ability to connect personally with voters.

Walsh entered the mayoral race vowing to out-hustle field, and he topped September’s 12-person preliminary election. Walsh will never out-debate Connolly on policy minutiae, but along the way, he’s surprised skeptics. He wowed a room full of downtown business executives recently with a riff about how he’d never imagined, when he first ran for the State House, that he’d be a key vote against the death penalty, and for gay marriage, but he’d grown with the job. “You grow and evolve,” he says. “You learn.” He argues that he has traction in the mayor’s race because “my upbringing is resonating. I keep hearing the theme, I’m a regular guy.”

Connolly, a three term city councilor, has built his campaign around education reform. A veteran of battles with Boston’s entrenched teachers union over extending the school day, loosening seniority protections, and upending a school assignment system that’s a legacy of the city’s old busing days, he argues that the issue is central to both the retention of young, middle-class families, and to the advancement of the lower-income students who fill Boston’s schools. “This is a young city,” he says, “and we want to nurture all that young talent, all that diversity, to really go to a place where the city’s never gone before.”

The two candidates share broad agreement on the urgency of improving city schools; on the need to ramp up housing construction while spreading wealth out of the booming downtown, and into the neighborhoods; and on the danger that Boston is losing its middle class, and becoming a city exclusively of rich and poor residents.

But messy identity politics lie underneath these broad policy agreements. Boston is an overwhelmingly Democratic city, and its mayoral contest has become a tortured referendum on the city’s evolving identity.

Walsh enjoys deep support in the blue collar Irish enclaves along Boston’s eastern edge. At the same time, he has also become the darling of the progressive activists who catapulted Elizabeth Warren past Scott Brown. He’s pulled together an odd-looking coalition of lunchbucket Democrats, black and Hispanic politicians, union activists, and ultra-liberal whites from outside the downtown core. These folks have nothing in common, except for Marty Walsh.

Connolly, for his part, enjoys support from the two-toilet Irish who live on the city’s leafier western side, along with school parents, black ministers, and downtown professionals.

The divide between these coalitions owes more to identity politics than policy. Many Connolly supporters distrust Walsh’s close union ties, and fear he’d hand out platinum-plated contracts to cops and firefighters. Walsh supporters, who see their candidate as a crusader for the poor and the working class, have countered by painting Connolly as the lost Koch brother, a wealthy interloper who can’t be trusted.

The notion of a class divide between the candidates is inaccurate, but in the absence of many bright-line policy distinctions, it has become pervasive. And it’s clearly wearing on the Connolly camp. Late last week, Connolly’s wife broke down in tears at a campaign event while trying to disarm her husband’s critics. “The character piece gets under my skin, but I try not to let it,” Connolly says. He pauses, then adds, “I used to love Twitter, and now I hate Twitter.”

Walsh, a die-hard Bruins fan, compares the race’s sudden nasty bent to playoff hockey: The higher the stakes get, the more physical it gets. “Within the last 10 days, it’s gotten very chippy,” he says. “Now it’s real. The winner is the mayor of Boston.” In the race’s last days, Walsh says, “Every move matters. Every word matters.”

The hardest hits haven’t come from inside Walsh’s campaign, though. They’ve come from the super PACs that are flooding the Boston race with outside money.

To date, unions and super PACs have made $3.6 million in independent expenditures in the race — an enormous amount of money, given tight Massachusetts campaign finance laws that cap individual campaign contributions at $500. Since early August, when the spending began in earnest, outside groups have outspent the combined Connolly and Walsh campaigns by more than one-third. Recent mayoral races in Los Angeles and New York have also attracted heavy union and super PAC spending, but both those cities are considerably larger than Boston; on a per-capita basis, outside spending in Boston’s mayoral race is twice what it was in Los Angeles, and six times the levels in New York.

Working America, the AFL-CIO-affiliated super PAC, has poured hundreds of thousands of dollars into a field operation for Walsh. The group has housed a small army of paid political canvassers at a Holiday Inn alongside a busy highway since early August. The PAC has also dialed up the class issue, producing a series of mailings in which salty-looking Bostonians claim that Connolly is “trying to fool people,” “doesn’t understand us,” and “isn’t one of us.”

Walsh has sworn off the negative mailers, but he’s also declined to ask the outside PACs to leave the race. Three-quarters of all outside money has been spent promoting Walsh’s candidacy, and in a tight race, it’s given Walsh a tremendous spending edge. In addition to Working America’s ground game, a pair of other super PACs has spent more than $1.5 million airing television ads on his behalf. Pro-Walsh PACs have spent 45 percent more on the race than Walsh’s own campaign committee has. Boston’s mayoral race has become a rallying cause for organized labor nationwide — a chance to flex its muscles and show it still has political juice, Chris Christie and Scott Walker be damned.

Groups like Democrats for Education Reform have lined up behind Connolly, and are spending money at a furious pace in the race’s final days, but they’ve been outflanked both on the air, and on the ground. And Connolly is expecting a crush of paid super PAC organizers to flood the streets on Walsh’s behalf on Tuesday.

“Boston campaigns are inherently local, so much of it has to do with field organization and message,” Connolly says. “That’s the good part. I don’t think any of this stuff is unexpected, with the outside money, but it’s sort of like watching the car wreck in slow-motion. There’s nothing you can do to stop it. I knew it would happen. Everybody knew it would happen. But you have to live with it. You just keep on moving.”