^ soon a Boston City Councillor : Althea Garrison, flag pin and all (WGBH photo)

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Because Ayanna Pressley is moving on to represent our state’s 7th Congress District, Boston’s City Council, in next year’s election, will be choosing a successor to the person who had, for three terms, been its top or second-place vote-getter. Not having Pressley on the Council ballot allows her three at-large colleagues each to aspire to “top the ticket.” At the same time it offers an open at-large seat to all and sundry aspirants. There appear to be plenty.

To call Pressley’s Council seat “open” perhaps disrespects the woman who will move to occupy it per the City Charter, which dictates that the fifth lace finisher in an at-large council election –we choose four — fills any vacancy. In the 2017 election the fifth finisher was Althea Garrison. She won 18,253 votes, way behind four place finisher Annissa Essaibi George — but a winner after all, thanks to Pressley and her voters. Can Garrison win election to a full term ?

This is a question that many observers mishandle, in my opinion. It is widely assumed that Garrison is only a gadfly, a perennial candidate — which she is– who is not to be taken seriously as a Councillor. I’m not so sure. I also dislike the background of much of the dismissing. No one will say it, but it’s hard not to sense that much of the dismissing arises from  Garrison’s status as a transgender person who does not talk about it or wear it as an identity slogan, and whose positions on many issues does not conform to what the conventional wisdom expects a transgender person to hold. Garrison is a conservative, as the term is now commonly used, and Black. That alone casts her outside the bounds of Boston’s political community.

Is she a Republican ? A Democrat ? An independent ? Over her at least 25 years of political visibility, she’s run as all three. To say the least, this is unusual; in Boston, it’s out of bounds. In Boston, one is expected to identity as a “Democrat,” which, once you do that, frees you to hold any sort of political views you feel best serves your interests. But Garrison has run as a Republican, more than once, and in 1992 she won, as a Republican, the contest for 5th Suffolk District’s State Representative seat. In 1994 she was easily defeated by the Democratic nominee — which does not surprise, as there is just about zero Republican presence in the “5th” — even this year, while winning 49.5 percent of Boston’s vote, on the way to a two to one state-wide win, Governor Baker secured barely 35 percent of the “5th”‘s votes.

Defeat in 1994 did not stop Garrison. Just the opposite. She has run for city office many times since then — I have lost track of the count. Curiously, she is not the only candidate in her part of Boston who does this : Roy Owens has, I believe, run for office even more often than Garrison, always with underwhelming results. Owens is also a “conservative.” He and Garrison are politically close. It makes sense that Owen has been mentioned as a possible staffer in Garrison’s forthcoming Council office.

Yet Garrison isn’t as predictable a conservative as Owens, partly because as a transgender person she supports the state’s 2016 transgender civil rights law. It isn’t easy to predict what position she takes on issues. As much as any Boston politician, if not more so, she thinks for herself. Unfortunately, that independence of mind also means she has few if any political friends.

Still, in one month she will take the oath as an t-large City Councillor. She’ll represent not only Ward 15, in which she won 492 votes, or Ward 12, where she finished third (!!) with 868 votes, or Ward 14, where she won 938, but also West Roxbury and Roslindale (1886 votes), East Boston (608 votes), and Brighton-Allston (1795 votes) and Beacon Hill, Back Bay and the South End (1645 votes), among others. In  2017 she had to compete with four incumbent Councillorts seeking re-election yet still found 18,253 voters supporting her. She may well  need to double that total in 2019 — maybe more, if turnout increases over the usual Council off-year. Can she ?

She’ll certainly finish in the top five in the upcoming primary. No matter who, of the many  names being mentioned, seeks the office, Garrison starts way ahead of any of them. Even if the City’s numerous collections of activists — not to mention City employees and their families — all pass Garrison by, there’s plenty of non-insider voters who might find a :thinks for herself” Councillor worth supporting, if only because there ought be at least one voice on the Council that doesn’t vote like all the others. (to cite just one example : the 2015 Council voted unanimously to make Boston a Sanctuary City. I’m pretty sure there’s a substantial number of voters who do support that move and would gladly vote for a Councillor who would vote No.)

Garrison can also count on some favor as a woman of color. With Pressley leaving, the 2019 Council will not have a city-wide member who is African-American (or Caribbean).

Frankly, Garrison’s fate is entirely in her hands. I’m not here to advise her, but if i were, I’d say “run against the Council majority.” The Council has taken many issues positions that lots of voters dislike — think the controversy about Air Bnb, or the moves to impose a higher “contribution” assessment on the City’s tax-exempt institutions. Even Garrison’s conservatism might be a fruitful avenue for attracting votes : shouldn’t the Council, — most of whose members are all seeking to appease, or lead, the “progressive’ vote that defeated Congressman Mike Capuano and State budget chief Jeffrey Sanchez and saw reformer Rachael Rollins defeat the presumed favorite in last year’s Suffolk District Attorney contest — have at least one at-large voice that speaks for those on the other side ? Mike Capuano won 22,914 votes in the primary even while losing, and about 49,400 Boston voters did not vote for Rollins. Might not Garrison find strength in said numbers ?

She’ll have to convince potential supporters that she means business, that she can do all of the job, that she will reach out, constantly, and make her Council staff do all the usual tasks. It won’t be as easy as simply getting a few signatures and having her name on the ballot. She’ll have to raise significant money — and know where to seek it — and work every neighborhood. It will be exhausting. Is she up to it ? Does she want to even do it ? Her “OCPF” file shows her having raised almost no money except from herself, for all of the past six years. It also shows over $ 98,000 in liabilities. This is not a good look for a serious candidate who will likely need to raise $ 200,000, not to mention enough money to pay off that huge $ 98,000 liability.

The money mountain in front of garrison is steep and high. The outreach and issues task is exhausting and requires enormous discipline. can Garrison do any of this ? She has the opportunity; but opportunity does not give away gifts to those who can’t struggle to success.

—-  Mike Freedberg / Here and Sphere

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