Diary of a Political Education, Or How to Change Some of the System Without Taking to the Streets

Years and years, and years, ago I was a reporter who wrote a lot about politics and public policy. I did not pretend to objectivity but there was a line I would not cross: I didn’t ever work for a political campaign. No matter that my reporting was sometimes ferociously opinionated and perhaps even useful to one side; I myself was never actually connected to a campaign. My objectivity, in my mind, was intact.

Looking back, I realize I was only truly interested in national politics and national policies. National party conventions were the best parties I ever attended and national campaigns were fabulous blood sports. The closest I ever got to local politics was a dim, shabby little office on the second floor of a dim, shabby little building on upper Broadway in New York City, where I lived. The tenant was in possession of some statistic I needed on local welfare. The building is long gone, and so is that part of my life, but I remember so clearly the dust, the ancient dial telephone marked by a thousand turns of a pencil stuck into the dial holes, the mangy cardigan left hanging for years behind the office door, and the selection of immersion heaters tossed in among the file cards in the middle desk drawer. It was the office of some kind of elected upper west side Democratic Party official. I thought it would make a great set in a play about a murder, but it never occurred to me that it might be what it actually was: a basic building block of the democratic system.


In 1995 I moved away from New York, and away from reporting, to a Vermont town with a population of 650 people. I settled in, volunteering here and there, figuring things out. I was amazed to learn the considerable size of our town government. A State Senator and a State Representative spoke for us in Montpelier. The town business was run by the Town Clerk, a five member Selectboard, a town Treasurer, one Road Commissioner, three Listers, one Tax Collector, five Justices of the Peace, a town Moderator, a Planning Commission, five library trustees, a Constable, two Trustees of the Church and Cemetery Funds, three Trustees of Public Monies, a Town Grand Juror, and a Town Agent. And those were only the people who had to be elected. More than a dozen other offices were appointed, such as the Tree Warden and the Town Services Agent.

I observed the procedures of the really difficult jobs, Selectboard and Schoolboard, and realized to my embarrassment that they were way beyond my level of competence, or patience. I also realized that I would have been a better reporter if I had actually tried to put together a town’s annual budget before I wrote so many opinions of people who did. I am not ready to admit that I might have been wrong. I am just saying I would have been more … understanding. Being a Justice of the Peace looked good to me. Easy. It would be fun to marry people.

I had to attend a party caucus (of course I was already a registered Democrat), which turned out to be a group of five huddled together in the back hall of the Historical Society during a break while serving the autumn potluck supper. We elected each other to party posts, and then nominated each other for town posts. All of us were nominated for the job of J.P. We were unopposed and we won big. It was indeed tremendous fun marrying people. My personal experience of marriage in no way dimmed my delight in being legally entitled to declare, “I now pronounce you man and wife.” One daring feminist bride even requested that I declare, “I now pronounce you wife and husband,” and the assembled guests gasped.

The Justice of the Peace job turned out to be less inconsequential than I had assumed. It also involved becoming a member of the Board of Civil Authority, which, among other things, settled disputes between the Listers (property tax assessors) and the owners. A delicate process. I was also part of the rather elaborate group charged with overseeing elections, which seemed to happen with remarkable frequency. I mostly remember an admirable and entertaining group of Town Grandmothers, who sold baked goods and played ferocious poker in the firehouse kitchen while the rest of us sat at our tables and booths amid the fire engines, waiting for voters. In time, I became a Town Grandmother myself.


Then, ten years ago, I had to move to Boston (not the Boston of my ivy covered college years, but an entirely different Boston) to a neighborhood where an enormous percentage of immigrants to the United States have always, from the city’s 17th-century beginnings, landed, but where no tall Lady Liberty honors them. This section of Boston entirely surrounds Logan International Airport, a continuous bone of every possible variety of community contention, an entity dedicated at all times to expansion.

It is a voting district where the immigrant group before last, the Italians, has dropped in the last twenty years to less than 25 percent of the population, but still holds virtually all of the elected offices. (They are universally called “The Electeds.”) The newcomers are a very diverse group of Latinos (near 70%), increasing numbers of Moroccans, and some South Asians. The very newest arrivals are people looking for a place they can afford to live when they think they would much rather be able to live in Cambridge or Somerville or even Medford. People politically sort of like me, but mostly much, much younger. They aren’t yuppies. They are – at least the ones I like best – progressives.

Our particular bit of Boston has no bookstore, no movie theatre, no good grocery store (but great bodegas), and, despite our delicious Colombian coffee, scarcely any cafes as the word is understood in Cambridge. Our high-end shopping store is Marshalls (I recommend it) and our restaurants are cheap and cheerful and not especially good ethnic. Perhaps a third of our immigrant population is unregistered, and they all, ‘legal’ or not, need to work two to three jobs to survive. We are poor, statistically and actually. We don’t have enough room in our below-standard schools for our population of children. This morning I read about a five-year-old girl the Boston Public School system has offered to accommodate in a kindergarten if her family is willing to let her be bussed 45 minutes away out of the neighborhood.

We do have a few very nice parks, a beach, a low roofline and a very wide sky; one subway line, a couple of nice districts of historic houses cloaked at the moment in asphalt and vinyl, and the entire eastern edge of Boston Harbor. It is a known fact that the people who live here are much nicer than any other Bostonians, especially the ones from the south side of Beacon Hill.

Our edge of the harbor, once lined by docks and warehouses and factories, has been empty for years. It could have been a magnificent urban amenity, like Brooklyn Bridge Park or the San Antonio River Park, or even the two riverside parks that already exist along Boston’s Charles River. But it never will, because my part of Boston is now “happening,” meaning the land has been turned over to developers of “luxury condos,” tall and blocking the views and the breezes, built with no master plan and multiple variances, with no street level vitality and no possibility of being afforded by the people who already live here. For a while, my entire social and political life consisted of going to Neighborhood Planning Committee meetings and objecting. It was a nice way to meet people, but extremely discouraging.


One Sunday morning, a few years after I moved here, I was enjoying breakfast at a food truck on the pier overlooking the harbor and I met a group of nice young people and attached myself to them. They were talking about stopping a plan to build a casino on the site of a failing racetrack stretching across my part of Boston and a neighboring town. The efficacy of casinos in restoring life to fading economies has by now pretty much been demonstrated as having low to negative results. My new anti-casino friends had a leader, a group, a slogan, and they were so smart, and so competent, and so aware, and so progressive, and so quick, and working so hard at building alliances … well, I thought they must have all gone to Harvard. I went to Harvard. Or Radcliffe. It turned out they had not, except for one or two, gone to Harvard. They had gone to schools I had never heard of, in places I had barely heard of. I was surprised. How Cantabridgean of me. How Beacon Hillish. How 19th-century. How very embarrassing.

Anyway, we won. We won! No casino for my neighborhood. Not yet, at least. Casino projects are like civic plaque; they have to be scraped back regularly. We have had to keep fighting new ballot initiatives and blocking end runs around regulations, but so far, so good. We began considering how best to use our new skills and energy.


It was pretty clear to me from the beginning that Boston politics are not like Vermont politics. In Vermont there is relatively no corruption because there is relatively no money. There are feuds and grudges going back generations, there are smart-aleck newcomers who think they know better and find out they don’t. There are always people who hold onto an elected office too long because they like to run things. But it wouldn’t be possible, in most of the towns in Vermont, to parlay a town office into a retirement fund or favors for nephews. At least, not on the scale of the way things are traditionally handled in Boston. I lived in New York City for nearly forty years, and I thought I had seen some amazing political stunts, but it has been a revelation watching the micro-machinations here. People win elections running as a member of one party, and unapologetically switch parties if the other party wins the top jobs. They hand off offices with a skill the Patriots would envy. Just resign a job barely a legal amount of time before an election, get their guy appointed to the vacancy, their guy runs as an incumbent, wins, the first guy gets appointed to a new job; loyalty shakes all around.

It’s textbook stuff. Bestseller stuff. Boston politics has spawned a long and large literary tradition. Boston has the best writers, although every city of any size in the United States has its own system. Otherwise known as The System. Aka Democracy.


So. What did we do next? Pretty much we did the usual: put up a few candidates, worked hard for some more, kept each other informed and showed up at local meetings.

A few of us tried, during the last presidential election year, to take over the local Democratic Ward Committee. That was fun. A member of our group who actually understood the state regulations (and thus understood that the chance for a takeover only comes once every four years, the presidential years) hounded us to attend the local Ward Caucus meeting to elect delegates to the state Democratic convention. There, a lucky few would be elected to go to the big gala Presidential nominating convention. We were supposed to arrive early, and without warning. We would be a surprise. And then elect ourselves. We weren’t. A gauntlet of fairly determined looking men stood at the door. Big guys. Glowering. I am not sure they knew why they had been called out, but they didn’t stop us from entering. Or even try.

Inside, chaos reigned. It seems our Ward Democratic Committee was so accustomed to being in charge that they arrived – those who bothered to attend – with ready-prepared ballots, and an easy assumption that they would get it all over within a few minutes. One gentleman demanded loudly: “What the hell is going on, I have to pick up my grandchildren in ten minutes. Why is this taking so long?”

It was taking so long because there were enough of ‘us’ there to demand nominations, ballots listing the subsequent nominees, and an official count and announcement of results. Some of us were nominated, some of us won, and some of us actually were delegates to the state convention, which in its turn nominated Martha Coakley for governor. She was a terrible candidate. She lost and we like to think she never would have been nominated if more of us had been there. Maura Healey was nominated for Attorney General. She was a splendid candidate. She won, and we think she would never have been nominated if some of us hadn’t been there. Win some, lose some. On the plus side: I met a lot of “them” and they seemed pretty friendly. We smile now when we see each other in the grocery store.

Maybe they will vote for me next time. I want to replace anyone who changes party so they can vote for Donald Trump. It happened this year. Not my idea of a Democrat. I want to be elevated to a dusty room! It is a pretty easy process. Everything you need to know is probably online. In Massachusetts, I can get a block slate for my local Ward onto the top of the ballot with only five signatures of registered voters. Poof! Power! It will be much harder if you live in a state where the Republicans have already succeeded in blocking your voting rights. But if they did it, you can undo it.


The other thing “we” did to keep up our energy as progressives was to organize a progressive network for the neighborhood. We had been envying the progressive network in Jamaica Plain, and we wanted one for ourselves. We spent months organizing according to a system of mediation the young seem to favor, especially the well-meaning young working for non-profit organizations or the more benevolent branches of government. Hours of meetings were spent taping long sheets of paper to the walls and then recording, in multi-colored pens, our responses to prompts such as “core values,” “mission statement,” “vision of future” – suggestions that ran along the lines of tax the rich, diversity, immigration reform. From the very first meeting, everyone agreed on almost every issue, which we knew probably meant we needed to include a lot more people from the wider community but we would get to that.

Except for one thing. When someone suggested we consider pledging to vote for Democratic candidates, the reaction was pure horror. One would have thought that the words Democrat or Republican and even Party Politics seemed as menacing as, just for example, Gerrymandering, Poll Tax, Tea Party, Koch Brothers. Independent was the only good word.

Sure, they can vote as Independents, depending on the state and district in which they live. But, alas, they are absolutely useless in changing the basic system that actually runs electoral politics. They are voting after most of the choices have already been made.

Party politics is really hard, and does involve intractable systems – often corrupt, often wrong. But that’s how democracies run, everywhere there is democracy. Democracy is a miracle, but only if everyone is part of it. If you want to change the system, be part of the system. At the ward level. The local ward committee members, the denizens of the dusty rooms, decide who, in my little neighborhood, goes to the big caucus, and the big caucus decides who gets nominated for big offices. The outgoing President of the United States and the new Mayor of Boston both started as State Representatives. But the local ward also decides who gets party support for people running for jobs such as Sheriff, Registrar of Deeds, Registrar of Probate and Clerk of Courts. Those are people who help determine how your community benefits, or doesn’t, from your government. Maybe the Electeds in my neighborhood seem to do a lot of favors for people they know (okay, they do do a lot of favors), but do they know you? Maybe the deck is stacked, but you certainly won’t win if you don’t play the game.

In the immortal words of a candidates’ guide published by the Massachusetts Secretary of State:

Don’t Just Stand There … RUN!



Author's Comment

This whole election season has made me pretty sick and tired of the thing I used to like best: politics. People (meaning the so-called press; the folks encountered at the dentist office; people overheard on the subway; people paid to natter on, ignorantly, about presidential candidates) – everyone seems to have lost all track of how things work. A President cannot and does not and should not fix or often even affect everything that could possibly be considered an issue in the United States. Voting as an independent is not a principled alternative to joining a party; it is just plain dumb. The parties run politics and politics decides the policies and the policies determine our lives – everywhere, at every level. Get real, people.



After a long career of writing too much, too fast, Jane O'Reilly burnt out and spent the last thirty years doing other things: teaching, making prints, gardening, being a grandmother, outliving her dogs. She has recently been brought back to the electronic plow by Persimmon Tree Editor Sue Leonard and in celebration is looking for a new dog. All her grandchildren are very much smarter than she is, which is as it should be.


  1. It is so wonderfl to have so many (very nice) comments. Hooray for PersimmonTree, which obviously has a very special readership. Thank you.

  2. Wonderful! Inspiring! As first cousins, Jane and I share some DNA and I can write–not as well as J. but that DNA must mean something! I think I’ll paraphrase: Don’t just sit there-WRITE!

  3. Thank you Jane O’Reilly for true, candid contrasts between politics in small town Vermont and big town Boston. Your savvy commentary on the electorate young and old is appreciated. Your reminders that Democracy is wonderful but complicated are timely. This is a fine piece of writing.

  4. I am so glad Jane has taken up writing again. And so brilliantly, and with such trenchant observations and clear-headed grandmotherly directives. The old things are equally good — and I recommend them to anyone who has somehow missed them. But – wonderful as they were — and are — it is a pleasure to know they weren’t Jane’s last word on the subject.

  5. Jane, As always I love your voice and your ability to bitch, protest, and be funny at the same time. Great article. Leigh

    1. Outstanding!! And a great representation of the differences in “Politicking” in different geographic, economic and ethnic areas of states, towns and national government. I too cannot wait for this to be over — except at the same time I fear the backlash that can be the result. Your sister Mary sent this to me. Keep writing Jane! We need both your wit and your wisdom.
      Pam (Morris) Clark

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