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    In Boston, is there life after challenging the mayor — and losing?

    Then-City Councilor Peggy Davis-Mullen ran against Mayor Thomas M. Menino in 2001 — and lost.
    Globe Staff/File
    Then-City Councilor Peggy Davis-Mullen ran against Mayor Thomas M. Menino in 2001 — and lost.

    TITO JACKSON WAS HARDLY the first Boston city councilor to make a long-shot bid against a popular incumbent mayor. Peggy Davis-Mullen played the theme song from “Rocky” when she launched her candidacy against Thomas M. Menino in 2001. She knew what she was up against. Taking him on was like “climbing Mount Everest in ice skates,” she said back then.

    Even so, she felt she had no special reason to be anxious about her future. “I have a law degree, two master’s degrees, and I’m finishing up a master’s in public policy at the Kennedy School,” she told Boston Magazine before the election. “I’m not worried about what’s going to happen to me after this.”

    Maybe she should have been. Before her failed mayoral run, Davis-Mullen was a four-term city councilor who used her voice to champion gay rights, early education, and Shakespeare on the Common. At campaign’s end, she got just 23 percent of the vote, and she was tarnished by revelations about unfiled tax returns, late payments on student loans, and large personal debts. Trying to protect her then-young children from her loser status, she left Boston for Dedham, and ultimately left the country to start a family fishing business in the Caribbean.


    About 18 months ago, she moved back to Massachusetts, and is looking for work. Her recent jobs include cutting fruit at a South Shore Stop & Shop; a short stint in the state Department of Health and Human Services; and substitute teaching. “You pay for your sins,” said Davis-Mullen. “You rock the boat, and you’re ostracized.”

    She believes her decision to challenge Menino haunts her job prospects even now, three years after his death. Once you’ve become a political persona non grata in your own city, it’s hard to make a comeback.

    Do sour grapes factor in? Maybe a little. Still, under Boston’s city charter, there’s just one center of authority: A strong mayor has direct control over police, fire, housing, development, public schools, and some 18,000 municipal jobs — plus far-reaching influence over private businesses, nonprofits, and other civic organizations that interact with City Hall and might think twice about hiring his political enemies.

    The idea that Boston’s last mayor punished those who defied him is accepted dogma by political insiders; indeed, admirers cite the way Menino froze out opponents as a skillful use of the ample power accorded to Boston’s chief executive.

    With her missteps and personal hardships, Davis-Mullen had more vulnerabilities than the typical mayoral candidate does. But she isn’t the only cautionary tale. Soon after Menino won a record fifth term in 2009, Sam Yoon — who didn’t even make it past the preliminary election — was headed to Washington, D.C., because he couldn’t find work in Boston. “I got signals, mixed signals,” he told the Globe in 2010. “To the extent that I was looking for a leadership position in the city, there were signals sent my way. It was subtle, but clear, that the fact I had run on a reform platform” — that is, a platform critical of the incumbent — “left some employers not willing to take a chance on me.”


    Tito Jackson, who won 34 percent of the vote against incumbent Martin J. Walsh, has not yet revealed his plans. As Walsh begins his second term Monday, all eyes are on what the re-elected mayor will do with the political capital he has amassed.

    But what Jackson does next will also be something to watch. (By press time, he didn’t respond to my requests for comment.) If history is any guide, Walsh will be scrutinizing the path taken by his vanquished foe. The decision to leave a little room for other leaders — or stamp out potential rivals — is up to the incumbent mayor.

    One measure of the state of Boston politics is the quality of life a candidate experiences after running for mayor and losing. If it’s terrible, that discourages others from even trying. That, in turn, cuts off meaningful conversation about the city’s future.

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    granted, losers of any sort can expect little sympathy in Boston. Jack Beatty, author of “The Rascal King: The Life and Times of James Michael Curley,” cites John F. Fitzgerald as the clearest example of a pol who had a tough time after a failed mayoral candidacy. In 1913, Fitzgerald — the incumbent, no less — dropped out of the race after Curley exposed his dalliance with a 23-year-old cigarette girl named “Toodles.” Sidelined by scandal, Honey Fitz never held elected office again, although he did help guide a future president, his grandson, John Fitzgerald Kennedy.

    If Curley successfully drove one incumbent out of office to launch his own political career, he was also the last incumbent Boston mayor to lose an election. Of course, when that happened, in 1949, it was after he served time in federal prison. No incumbent mayor since then has been knocked out of City Hall.


    For much of the Curley era, a Boston mayor couldn’t serve consecutive terms. Once that law was repealed, mayors could truly begin to consolidate power. All those city workers represent a vast, built-in field organization that discourages strong challengers and makes quick work of weak ones. Ironically, this old-school style of politics works just as well today — and maybe even better. Over the past three or four decades, turnout in municipal elections has plummeted, from over 200,000 to half that amount in 2017. Voter apathy “allows incumbents tremendous power to crush their opposition and grind them into the dust,” said Thomas J. Whalen, an associate professor of social science at Boston University, and expert on local political history.

    Because of the length of Menino’s reign, all the recent evidence for that proposition revolves around him. In 2005, he beat City Councilor Maura Hennigan by more than 2 to 1. She’s still paying off the nearly $700,000 in debt she incurred by borrowing against two properties she owns. A 24-year veteran of the council who hails from an old Boston political family, Hennigan did manage to find her way back to public office — as clerk magistrate of the criminal division of the Suffolk County Superior Court — but over stiff resistance from Menino’s machine.

    When Michael Flaherty ran against Menino in 2009, he won 42 percent of the vote, doing better than any challenger since Menino first took office back in 1993. After conceding defeat, Flaherty, a former assistant district attorney who grew up in South Boston, quietly practiced law. When he tried to regain his council seat in 2011, the Menino machine, according to a Globe report, “mobilized a citywide effort” to stop him. Flaherty won back his seat in 2013, when Menino was no longer on the ballot. “I ran against a dictator,” said Flaherty of his race against Menino.

    Jim Brett, who lost to Menino back in 1993 when Menino was acting mayor, managed to carve out a meaningful role in civic life afterward — but credits that to his own willingness to eliminate himself as a threat. When he conceded defeat, Brett offered “a prayer and a promise. . . A prayer that Tom Menino succeeds. And a promise that I’ll work shoulder to shoulder as his partner on Beacon Hill.” With that, Brett returned to his job as state representative from Dorchester, and eventually became president and chief executive of the New England Council, a position he still holds. Menino knew his former rival had no interest in running for mayor again. “He was happy if you moved on,” Brett said.

    Outgoing Boston city councillor Tito Jackson at his 8th annual Turkey Giveaway at the Reggie Lewis Center in Roxbury on Nov. 19.
    Dina Rudick/Globe Staff
    Outgoing Boston city councillor Tito Jackson at his 8th annual Turkey Giveaway at the Reggie Lewis Center in Roxbury on Nov. 19.

    For now, Walsh seems more conciliatory than his predecessor. After winning an open mayoral seat in 2013, he brought three rivals — Felix Arroyo, John Barros, and Rob Consalvo — who ran against him in the preliminary contest into his administration. Having won that contest by a mere 2,445 votes, you can argue that Walsh needed the constituencies represented by those rivals to build a governing coalition.

    After handily winning re-election, Walsh’s hold on power is far stronger than it was four years ago. If he wanted to crush Jackson politically, it’s likely he could. Still, Flaherty, who knows what the Menino machine felt like, doesn’t see the same forces being marshaled under Walsh. “There’s life in Boston for Tito Jackson, post-mayoral race,” Flaherty says.

    Indeed, Walsh is treating Jackson — the first African-American candidate in 34 years to make it to the general election ballot — with respect. At the year-end meeting of the City Council, Walsh gave his opponent a silver Revere bowl and a hug. If anything, it’s Jackson who’s keeping the rivalry alive. At the same council meeting, Jackson said he will continue to address issues he raised during his campaign and introduced a resolution challenging a decision by the Walsh administration to significantly change start times at Boston schools. In his farewell speech, Jackson also urged the city councilors he’s leaving behind “to use the most important bone in our body — our backbone.” Since then, the Walsh administration backed off the new starting times.

    When other politicians openly challenge the mayor, the public dialogue is richer for it. In questioning the incumbent’s record and vision during her mayoral campaign, Davis-Mullen argues, she raised valid issues about a city she loved. “The trouble I made was not bad trouble,” she said. “The trouble I made was for things I believed in.”

    As long as Boston’s chief executive enjoys such far-reaching powers, the fate of anyone uppity enough to challenge the status quo depends mostly on the mayor’s good will and sense of restraint. Challengers like Davis-Mullen and Yoon paid a big price for failing to topple Menino — and the charter hasn’t changed. “That’s politics,” Davis-Mullen says. “It’s a rough game, especially in this city.”

    Joan Vennochi can be reached at Follow her on Twitter @Joan_Vennochi.

    Correction: An earlier version of this piece misstated the timing of former Boston mayor James Michael Curley’s time in prison.