^ in pink, upper right, District 2 : contains all of South Boston, the South End, Bay Village, Chinatown, and the Downtown area that today is vastly more populous than it was ten years ago, much less 30.

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For the first time since 2007, the City Council seat representing District 2 is open. The voters of South Boston, Chinatown, Bay Village, and the South End have only had two Councillors since district representation was established in 1981 : the notorious but charismatic Jimmy Kelly and the soft spoken Bill Linehan, Now, as Linehan is retiring, the area’s communities — much changed since Kelly first took office, with all of the Downtown core of high-rise condominiums now added — will elect a new face.

Well, maybe not a face all THAT new. Of the three leading candidates, one in particular bears a face known best of all to long term residents : Ed Flynn, son of former Mayor Ray Flynn.

Certainly Flynn starts the race as a favorite; but by no means is his election assured, any more than Billy Bulger, Junior’s election as South Boston state representative was assured, many elections ago, when a newcomer to politics, union activist Stephen Lynch, ran and defeated him. If Flynn hopes to win, he will have to earn it the hard way.

His task will not be easy. Among the likely candidates — OCPF lists a total of four so far — we find two who come to the race with substantial followings : Cory Dinopoulos, of 300 K Street in South Boston, one of the founders of the Boston 2024 Olympic idea, and Michael Sean Kelley, of 100 Arlington Street in the Bay Village region, a veteran of the late Mayor Tom Menino’s operation. Kelley knows his way politically, and his facebook page has 2,152 friends. Dinopoulos may be even more social media aware: he’s very active on twitter and  facebook, and his campaign kickoff, on March 2, 2017, at Capo Restaurant, drew a large crowd of not the usual suspects. (There’s also a fourth candidate, Peter Lin-Marcus, of Tyler Street in Chinatown. I have yet to meet him or talk with him.)

When this District was created — disclosure : I was a key advisor to the City Council Redistricting Committee that created the current nine-district map — the goal was to assure South Boston a seat. “Southie” was one of Boston’s most powerful political communities; it to anchor a District. The problem was, what precincts to add, because “Southie” had about 37,000 people, and Districts had to contain about 70,000. We understood that the “added precincts” would likely be “filler,” which made the decision a painful one : who would get screwed ? The South End was the easier choice — the other suggestion was Back Bay and Beacon Hill, and they had too much clout to accept being pawned off. The South End had scant political clout; we saw it, more or less, and maybe unfairly,as a hotch potch of vacant buildings,. underserved populations, and elderly life-long South Enders.

Today the South End is very high-end, as are the precincts north of it, and together they form a seriously powerful constituency of high income movers. To add to the mix, an entirely new neighborhood, the Seaport District, has filled two formerly empty precincts (Ward 6, Precinct 1 and — to a lesser extent — Ward 3 Precinct 8) with about 12,500 voters who weren’t there when Linehan was first elected.. Given this influx, there’s no guarantee at all that a highly respected, lifelong “Southie” candidate like Ed Flynn can carry the day. Bill Linehan himself barely survived a Chinatown challenger, Suzanne Lee, in 2013. How will Ed Flynn stave off Dinopoulos, who lives in South Boston and has widespread support in the upscale precincts, or Michael Kelley, who knows everyone and lives in Bay Village, a very populous singe precinct ?

Is it possible that Flynn won’t even “make the cut” in the primary by finishing in the top two ? I think it is entirely possible. South Boston used to turn out 7000 votes on primary day — you could count on it. Recently the number’s been more like 3700. How good is that, when the Downtown Precinct alone (Ward 3, Precinct 6) lists almost 7500 voters by itself ? Flynn’s people might answer that newcomer voters who live in a tower and have no neighborhood feeling at all aren’t likely to turn out 50 percent for a primary. I would agree. But if this precinct turns out just a quarter of its votes, 1875, that’s worth three or four of Southie’s 14 precincts by itself. Now add in the Seaport precinct’s 1500 votes, almost all of them new to Boston, much more attuned to Dinopoulos than to Flynn, and Flynn is already in big trouble.

Flynn of course knows all of this as well as I do. I trust he is working like crazy — has been working — to dig some serious roots in the non-South Boston precincts that whelm so large. Being the son of a Mayor surely helps; but when Ray Flynn was Mayor, 1983 to 1993, neither the Seaport or the Downtown high rises existed, and the South End had only partly become what it is today. There isn’t much that Ed Flynn’s Dad really can do, “across the channel” to break the ice for his son.

One other curious situation about this race : not one of the three “major’ candidates was an obvious  supporter of Mayor Walsh in his 2013 campaign. The Flynns supported John Connolly; so did Cory Dinopoulos. (So, too, did South Boston’s state representative, Nick Collins, and his Dad, who was himself a state representative, albeit from Charlestown.) Of Mike Kelley’s allegiance, I am uncertain. He is said to be a Walsh ally now. As Walsh is running for re-election, and as South Boston — but not at all the District’s non-Southie precincts — were a Walsh stronghold, having an alliance with Walsh might make  a difference, at least in South Boston, where alliances are valued as “being on the other side”is barely begrudged

The Connolly-Walsh battle has not been forgotten in South Boston, and the Connolly people may just be numerous enough to provide Ed Flynn a base, big enough, when added to his family’s supporters, to get him one of the two top spots in the primary.

I say “maybe.” Nothing about this race is etched in stone. There’s no obvious favorite, despite what old standards may suggest. Let’s see what the campaigns make of it.

— Mike Freedberg / Here and Sphere