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    The best mayor we didn’t elect

    Lawrence DiCara (center) ran for mayor in 1983.
    Bill Greene/Globe staff/file 2003
    Lawrence DiCara (center) ran for mayor in 1983.

    Attorney Lawrence DiCara, the former president of the Boston City Council, has few rivals when it comes to knowledge of the city’s political history from the ground up. His recently published memoir — “Turmoil and Transition in Boston’’ — arrives at a good time to provide historical context to the current mayor’s race in Boston.

    In 1983, DiCara was the sharpest of the nine candidates seeking an open mayoral seat. The Dorchester native had set his sights on the office while still in high school. Seriously. He was consciously creating networks for future campaigns while running for senior class president of Boston Latin School in 1967. I remember pieces of DiCara’s campaign literature landing on the desks of my classmates. And we were juniors who weren’t eligible to vote for the senior class president.

    DiCara would go on to become the youngest person, at 22, ever elected to the Boston City Council. Over the next few terms, he solidified his power and assumed the presidency of the council. DiCara was convinced that his years of political preparation would pay off. He pulled himself up to his full height of 5 feet 4¼ inches (by his own meticulous measurement) and prepared to stride into the office that would soon be vacated by the late Mayor Kevin White.


    DiCara came in fourth — a distant fourth — in the 1983 preliminary election that sent eventual winner Ray Flynn and former state representative Mel King into the November runoff.

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    “I naively thought that my 10 years of City Council votes, the countless appearances at dinners and events, the many summer jobs and other favors would translate into votes for mayor,’’ wrote DiCara. “I was wrong.’’

    The five Boston city councilors who are currently running for a truly open mayor’s seat — the first such opportunity since 1983 — can’t feel good about that revelation.

    The backdrop of DiCara’s book is the tumultuous period beginning in 1974 when a federal judge ordered the desegregation of the city’s school system. But his best material focuses on how candidates toggle between exhilaration and exhaustion. At times, DiCara literally collapsed from the strain of campaigning. And despite DiCara’s grasp of issues and brilliant debating style, he failed to drum up interest at scores of candidate forums, where most attendees were already committed to one of his opponents.

    “I could have been the second coming of Demosthenes and my performance would not have persuaded a single one of them to support me,’’ he wrote.


    Had he won, DiCara would likely have been a superb mayor. He believed passionately that no Bostonian should be marginalized. He enjoyed good relations with the city’s business community and was prepared to push for a responsible development policy. He knew enough not to get rolled by municipal unions. And he was proud of the excellent education he had received in the city’s public schools and was determined to provide the same opportunity to all students.

    Boston certainly made progress during the administrations of former Mayor Flynn and soon-to-depart Mayor Menino. But DiCara was more nimble than both of them and might have pushed Boston further and faster in the right direction.

    Some candidates in the current, crowded field of 12 are reminiscent of DiCara. They are pegged as second-tier candidates despite their obvious abilities. DiCara fought against similar perceptions. They want for a reliable geographic base. In 1983, DiCara was too liberal to carry his own Dorchester ward.

    Candidate Bill Walczak is a policy expert with a common touch and a deep devotion to the city. Walczak’s white papers on key issues such as housing, education, and public safety provide a clear idea of what his administration would look like, just as DiCara’s did 30 years ago.

    Boston City Councilor Michael Ross is another example. Like DiCara, he has a strong grasp of the city’s development potential, gets high marks from Boston’s business community, and is willing to work around the clock.


    Candidate John Barros followed a similar path to DiCara’s that led from a modest upbringing to an Ivy League college. And each displays an almost courtly demeanor and wise-beyond-his-years presence.

    DiCara, incidentally, won 15,148 votes in the 1983 election, a third of what he needed to make it to the final. “In the years since that election,’’ he wrote, “I have met far more than 15,148 people who swear they voted for me.’’

    As if bruised egos, exhausted bodies, and crippling campaign debt weren’t enough.

    Lawrence Harmon can be reached at harmon@globe.com