The shape of Boston’s recent City Council election allows us to configure the upcoming Mayor election– which campaign has already begun. Unless miracles drop, Councillor Michelle Wu will run. So might others, but Wu has the challenger’s pole position. She received more than 41,616 votes (tally is still unofficial) from 66,884 voters — well over 60 percent. (No one was close. Annissa Essaibi George and Michael Flaherty fell 7000 and 8000 votes short, respectively.) Wu was the Council’s President and, you might say, was and still is its most outspoken policy proposer. At the end of October she reported $ 344,157 cash on hand — a massive sum for a City Councillor.

Mayor Walsh reported $ 3,930,051 — more than times as much as Wu has, but that’s to be expected. He has the power. There’s plenty of room for that funds imbalance to change drastically. Let Wu actually announce, and there’ll be plenty of funds coming her way.

Can Wu win ? She certainly can. Let’s look at the state of things :

( 1 ) In the Council election just held, non-union “progressives” — Wu’s chosen constituency — outvoted labor-endorsed candidates across the board, both city-wide and in the District 5 race. Wu endorsed the District Five winner and also Alejandra St. Guillen, who lost to independent “progressive” Julia Mejia by one ( 1 ) vote, 22,792 to 22,791, for the fourth Council at-Large seat. Meanwhile, Walsh endorsed only a safe choice, Annissa Essaiabi George, and St. Guillen, whose campaign seemed to stall the day after Walsh decided to endorse her.

( 2 ) Wu’s policy proposals have certainly electrified “progressives.” She called for the MBTA to be fare-free. She proposed a $ 25 annual fee for resident parking stickers. She whole-heartedly supports burdening car owners sufficiently to force as many as possible into using public transportation. She may very well support attempts to bring back rent control to Boston (as of today, State law bars it), and it would not surprise were she to propose some sort of voting rights for 16 and 17 year olds. If there’s a priority initiative on the organized progressives’ agenda that Wu does not champion, I have not seen it.

( 3 ) Plenty of voters who might not like this or that Wu proposal — or any of them — still give her credit for trying to bringing change to a City government that, to many, seems resistant to change of any kind and determined to go its own way no matter who doesn’t like it. First to mind is the Mayor’s attitude toward development : he wants lots of it and seems willing to bend every zoning rule in order to get as much of it as possible built. The more aggressively Wu’s proposals unsettle the Mayor, the better she is liked by the many, many voters who are fed up with seeing their neighborhood bullied by developers. Lastly, an enormous number of voters lack confidence in the Boston School Department — for many very good reasons. Those who can move to towns with better-run schools, often do so. The rest stay — and are unhappy. Mayor Walsh cannot count on their votes, no matter how many Schools policies are voted unanimously by his appointed School Committee.

( 4 ) the most recent citywide, major election, for Governor in 2018, saw Governor Baker take 49.3 percent of the City’s vote to Jay Gonzalez’s 50.7 percent. It would not surprise me if the 2021 Mayor election were similarly close. Baker assembled his 108,000 votes by winning ( a )  the new-breed, Downtown and adjacent areas populated mostly by tech and institutional voters ( b ) the “old Boston” voters of Charlestown, Southie, Bayside Dorchester, Hyde Park, upper East Boston, and West Roxbury and ( c ) 36 to 46 percent of Black and Latino voters. Against him were ( a ) the “progressives” Of Jamaica plain and parts of Roslindale ( b ) Brighton-Allston and ( c ) 54 to 64 percent of Black and Latino voters — 112,000 votes in all.

I doubt that Mayor Walsh can build a win via this coalition. Michelle Wu won a very large percentage of the Downtown and adjacent vote, and Walsh has never been strong in Charlestown and East Boston. Baker is himself an institutional, Downtown-ish man; Walsh is anything but. His background is in labor, and a labor guy he still acts the part. Unions form a significant part of Baker’s support, but for Walsh they are more than that, they are identity. Which is a problem, given the weak showing by labor candidates in the recent Council election. That said, Walsh has no choice : labor will be his bedrock, and the neighborhoods of his traditional base : South Boston and Dorchester, some of Hyde Park, and about one third of West Roxbury. This is far, far from enough, but Mayor Walsh has one huge advantage : he can go to events everywhere in the City, as Mayor, bring City funds for this project and to that organization, and just flat-out meet everyone he can, as Tom Menino did. Michelle Wu can’t come close to matching Walsh’s ubiquitous star power, nor his money grants. He can cobble together votes ten or twenty at a time from almost every part of the City, from business people who need City licenses, from those who use the City’s libraries, parks, youth activities, and Main Streets, or just from people who can tell their kids “I met the Mayor !”

Will this, then, be enough? Against it I see Wu’s aggressive change agenda, her status as a non-Caucasian, and the momentum that “progressive” organizations and pointedly non-White campaigns have built up ever since Ayanna Pressley’s 7th Congressional defeat of defeat of Mike Capauno. More than that, Wu has the look of today — of social media — as the extremely local, Dorchester-guy Marty Walsh does not. There’s a bit of a social class thing going on here, though no one will say it, but appearances matter in the Age of Instagram. Here, Governor Baker held a huge advantage. At six foot six, with the sleek build of a pro athlete and a gentle and well-spoken affability, the non-ethnic Baker dominates every room that he enters without being in the least bit domineering. Walsh is of ordinary height and not an easy conversationalist; he does not dominate unless accompanied by several aides who, crowding around him, convey importance by implication.

Will that be enough, along with all the money and licensing power that a Boston Mayor has ? I’m not sure. You can’t win an election by implication.

—- Mike Freedberg / Here and Sphere

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