Scaling the City on a Hill


In the fall of 2021, the New York Times sent their New England bureau chief, Ellen Barry, to Boston, so she could report on one of the most unusual spats in local politics. Councilor Annissa Essaibi George, the hardy, local-grown challenger to progressive star Michelle Wu in the mayoral election, had inspired cheers, jeers, and more than one strongly-worded statement with the habit she’d picked up after the primary. The shtick itself — Essaibi insisted it was anything but — was perhaps the most prominently-placed article on the election that the Times had run all year. Beantown was, if I may be so grandiose, in an uproar.

What, you ask, was the nature of Essaibi’s revolutionary act? What was the cause for all this commotion? Unfurl the October 9, 2021, Times and read her ploy in all of its glory: “Candidate for ‘Mayah’ Proudly Leans in to Her Boston Sound,” thundered the headline for Barry’s profile. During campaign appearances, Essaibi’s thick Dorchester accent often shone through, never more than in her recurring pledge to be “the mothah, the teachah, and the mayah this city needs.” Eventually, her supporters took to chanting the slogan, letting their own accents hang wild and free as they shouted, The Mothah! The Teachah! The Mayah! It was about an accent.

You can probably guess by now that this wasn’t just about an accent. Michelle Wu, the jovial progressive warrior in pole position to take over City Hall, wasn’t born in Boston. She hadn’t grown up in Boston, either — she’d moved to Boston Common in 2003, at 18 years old, to attend Harvard University a stone’s throw away in Cambridge, Massachusetts. But even then, Wu didn’t stay, opening a coffee shop and caring for her family in her hometown of Chicago before starting law school at Harvard in 2009. Anissa Essaibi George, 12 years Wu’s senior, had been in Boston the whole time. This was about Boston people, and whether the smiley, Midwestern-voiced Councilor Wu was Boston enough to speak to their concerns.

In case this was at all subtle, Essaibi sat down for an interview with Boston public radio and said that Wu’s Windy City history was a big deal for her, and a big deal “for a lot of people.” As for the accent? “This is just how I talk,” the councilor told Barry in the Times profile. Point being, she talked like a Bostonian. Shots fired.

Wu, or at least her campaign, wasn’t happy about the implication, at one point firing off a press release that pointed out that two-fifths of Bostonians weren’t even born inside the boundaries of Massachusetts state, let alone the city itself. “We need a mayor for ALL Bostonians,” Wu sermonized on her squeaky-clean Twitter account, “whether you were born here, or chose to call this city home.” Shots returned.

This was not a petty dispute. Boston is venerated as one of the nation’s oldest, most illustrious, and greatest cities, punching far above its 700,000-person weight in education, medicine, technology, finance, and sports — they’re way above their weight in sports. Massachusetts, after all, the place where the Puritans set up shop after they booked it out of Europe, prompting William Bradford to prophesy, “We shall be as a city upon a hill; the eyes of all people are upon us.” Boston’s been a spinning jenny of immigrant success stories ever since, most famously the Irish who rafted across the Atlantic and rebuilt the town in their image in the 19th and 20th centuries.

When Michelle Wu first walked into Boston’s City Hall, she later wrote, “I felt invisible, swallowed up by the cavernous concrete hallways and shrunk down even more with every checkpoint and looming government counter. My immigrant family tried to stay away from spaces like these.” She, too, felt for all the world like a Boston success story, as one descended from oceans afar to make something of herself in the city. And, at least for her, the attacks were about that, too.

Lest you think that the Boston mayoral election was some kind of dogfight for the future of democracy, let me assure you that the race was not particularly close at any point. Wu, the daughter of immigrants from Taiwan, couldn’t have picked her local friends any better if she had popped out of the womb trying to run for mayor. She was one of Elizabeth Warren’s star pupils at Harvard, and the two became close when Wu opened up about her complicated relationship to her mom. So, when Elizabeth Warren started driving hard to unseat Republican senator Scott Brown, she picked Wu to coordinate parts of her outreach operation. Wu was also en ligue with Ayana Presley, the local councilor who became the first Black woman to represent Massachusetts in Congress during the 2019 cycle. (One other Black person had pulled this off: Senator Ed Brooke — in the sixties, no less!)

When Michelle Wu ran for City Council for the first time in 2013, she was the second most popular at-large candidate in the birthplace of the Revolution, behind only Presley herself. That was Essaibi’s first run, too, and she was all the way down at number five — not even enough to win a seat on the city council.

After Essaibi finally won a seat in 2015, Wu became City Council President in 2016, and was the number-one at-large candidate in 2017, ahead of even Presley. (In 2019, Wu led again, but there was a fresh face in second place — Essaibi.) Wu did work: She severed the city’s ties to health insurers who wouldn’t work with transgendered patients. She passed an ordinance to ban plastic bags. She introduced rent control. She even convinced the City Council to applaud a version of the Green New Deal when it was still a running joke in Washington. (Massachusetts’ own Senator Ed Markey, who co-sponsored the resolution in Congress, actually voted against it when it came to a vote. Lesson: Never introduce anything you aren’t ready to vote for.) Wu was a regular Clement Atlee, grinning her way to a brick-by-brick renovation of Boston’s economic playing field.

Essaibi, on the other hand, didn’t get involved with the headline-grabbers. The daughter of a Polish Bostonian mother and an Arab Tunisian-American father, she’d gone to the city’s commuter schools and graduated from BU in 2001 to teach high school social studies in Eastie. Instead of landing on the political Jumbotron, she passed bills to make Boston’s bigger pharmacies put their used needles in disposal bins, and got the city to hire a social worker and a nurse for every public school in Beantown. She plugged away on local issues, and the local voters rewarded her for it.

Wu and Essaibi existed like this for some time. But, in March 2021, another big-time Boston public servant got beamed up to the Beltway. Incoming President Joe Biden called the city’s mayor, a middle-of-the-road moderate and childhood friend of Essaibi’s named Marty Walsh, and asked him to become the US Secretary of Labor. He did. Walsh became Secretary of Labor, Wu’s successor as City Council President — Kim Janey, an ally — became the interim mayor, and the November election became wide-open.

Janey decided she didn’t want to only be the interim mayor; she wanted to be the city’s first Black mayor, first female mayor, and first female mayor of color, in one fell swoop. Wu, who already made history as the first councilor ever to give birth in office — twice, no less! — decided she wanted to be mayor, too. And Anissa Essaibi George? Aw, what the heck; everyone else was running. Why shouldn’t she?

There are no major Republicans capable of winning office in the city of Boston, and so the municipal elections are nonpartisan. Any two candidates, regardless of party, can advance to the general election if they are among the top-two vote getters in the primary. (Republicans and Democrats alike can vote in the primary, by the way, as can independents. Independents! What a city!) If a candidate wins more than half the votes in the first round, however, the election is over — they won a majority, and the job is theirs.

When the votes tallied on primary night in Massachusetts, Wu was in first place, with nearly a third of all votes cast. Of course, she was. But interim mayor Kim Janey wasn’t the second-place candidate. That honor belonged to none other than Anissa Essaibi George, the muthah, the teachah, the mayah.

Did Boston’s voters think that they were setting up a clash of planets? Probably not. No matter; a clash of planets it would be.


Someone will hit Donald Miller.”

2008’s Doubt, starring Meryl Streep as a midcentury conservative nun in charge of a freshly-integrated Bronx parochial school — integrated, because Donald Miller is there — is one of the great cinematic productions of all time. Every explosion over issues of race, culture, and religious responsibility etches itself across the actors’ faces like the dynamite that carved Mount Rushmore. Nearly every speaking adult in the movie got an Oscar nod, and the film itself stands the test of time as a story of faith in flux during troubled times.

But there’s one scene in particular — the explosion of explosions — that gets to the heart of the conversation Doubt demands to have with itself: Streep’s nun, convinced that a sterling embrace of Miller signals grave misdeeds from the progressive parish priest, played by Phillip Seymour Hoffman, complains of the priest making certain kinds of changes to the Christmas pageant. Why do you want to include secular songs, she wants to know, or introduce a wintrier theme? This is a house of worship! (Implication: Not a Bing Crosby special.)

Hoffman’s priest has heard enough. “I’m trying to show the working-class people of this congregation,” he wails, his hands flapping through the air like eagles’ wings, “that we’re not different!”

Streep is masterful at this moment. The nun, simultaneously sniveling and regal, rises from her principal’s desk and uncorks a New York roar, the kind lost on the modern age’s drive for the genteel, relegated to the city’s beam-bearing, corner-clubbing, hard-hat-clad backbone. “The working-class people of this congregation,” she hisses, with the perfect marriage of reverence and ridicule. “Are counting on us to be different.”

You’d have to see the movie to understand Streep’s inference: Hoffman’s priest, for all his concern for the local populace, doesn’t really know what they want, or what they need. He has, in her eyes, no concept of the glue that actually holds the congregation together. (She’s not even that hostile when discussing the new kid, Donald Miller. She simply prophecies his persecution as the wetness of water: “This parish services families of Irish and Italian stock,” she informs an underling at the crux of the film. “Someone will hit Donald Miller!”) It’s not quite the glue of race, but it is a kind of cultural glue, a social fabric that depends in part on the local parish’s iron spine.

Culture. The word, at times, is fraught — it so often looks like race, or feels like race, or even acts as race’s dapper dance partner in the waltz of anxious change. It doesn’t capture what we are — the color of our skin, the shape of our genitalia, the house of worship in which we sit — but what we do, and what that means, and who we are, the things our race, or gender, or religion can be shorthand for. “Someone will hit Donald Miller,” simply because his skin is darker than theirs, yes, but someone might not hit Donald Miller because he’s an altar boy, because he’s friendly with the parish priest, because the sculpting of his mind, body, and soul has sliced a corner of him from the same cloth as theirs.

Doubt takes place in 1964, between the March on Washington and the March to Selma, at a time when John F. Kennedy’s body still clung to chunks of decaying flesh as the presidential cadaver rested in honored glory. The Earth was shifting underneath the feet of working-class people in the Bronx, spinning before their very eyes. Changes had visited themselves upon the parish, some good, some bad, all incredibly disorienting, and the world to which each parishioner awoke was not the one in which they’d fallen asleep the night before. “The center,” to quote Joan Didion, “would not hold.”

Hoffman’s priest thinks the best thing the church could do is to join in that change, stylistically as well as demographically. They can certainly welcome the Donald Millers of the world into their ranks, but why stop there? Why not bend the contours of the church itself to meet the denizens of a new and changing world? What better time than right now, with everything else changing and new faces roaming the halls, to change the church?

This is where the nun’s point becomes salient. She’s not actually opposed to Miller’s presence — her prediction is to prepare a younger nun to exact judgment on the person who does hit Donald Miller. But she is opposed to the idea that Miller’s arrival should herald a vast cultural transformation in the church. You could say that she’s a curmudgeon, sure, one of many conservatives slowly choking American religion to death. But there’s more to the nun’s conservatism than that, surely. Might it be that her attempts to seal the rest of the church in operational amber are actually noble, if misguided, attempts to make Donald Miller’s life easier?

Think about it. Although the parish services families of Irish and Italian stock, the parish ultimately services families of Catholic stock — the O’Connell types, and the Mattarella types, sure, but also Donald Miller’s family. The theory of small-L liberalism holds that this has nothing to do with Miller’s color, of course; you should be accepting of different kinds of people, regardless of whether you think you have anything in common. Free societies are built on the acceptance that not everyone is alike, and that the only commonality that matters is the commonality of soul, of spirit, of humanity. In a big, diverse country like America, the civic bonds won’t hold together if people start to reject this framework en masse.

That’s the free society in theory. In practice, however, most people do not try to form their opinions of the new kid at school or the new guy across the street by reading the Treatises of Government, John Locke’s prose on the “sentiments,” or I Have a Dream. They form their opinions of each other in real life — by existing in similar spaces, and doing similar things, and realizing that the gaps from one person to the other aren’t vast enough to justify the ways in which we enforce them.

If Donald Miller walks in to a church that shortly thereafter dissembles itself and transforms, he will be lumped in with the rest of those transformations: A loss for the Christmas pageant would function as a loss for Donald Miller, and someone, incensed over their changing church, “would hit Donald Miller,” physically, or verbally, or spiritually. But, if Donald Miller exists as a fellow Catholic, consuming the elements, confessing his transgressions, sharing in the life of Christ among the rough-and-tumble working-class boys of New York, then the working-class people of this congregation will see that the only thing separating them from the Millers is the weight of American melanin — and, coincidentally, the working-class people of this congregation.

In some ways, Doubt is a parable of the American city: a place where police officers from Ireland, construction workers from Italy, Black autoworkers from the Deep South, and grocers from Puerto Rico came together to build a place where they tap-danced, sometimes gingerly, on the webs each had weaved atop an economy, a polity. They came together in the throes of difference, and they almost came apart in competition over issues like jobs and political influence — the things in a city that always feel limited. But slowly, surely, and sometimes reluctantly, they learned to live together. We learned to live together, all of us, combustible as that living might have been. Forever and always, we’re still learning. Someone will hit Donald Miller, and it won’t be okay, but it will mean that the learning continues, that the marring of Donald Miller’s humanity, horrendous as it is, becomes a cavity for courage and change to wash away the bruises.

Working-class Americans, fused together by the iron spines of proximity and necessity, built this country’s cities as we currently see and understand them. Theirs is the skyline that fell on 9/11 and rose laboriously thereafter, the houses that changed hands after the 2008 crisis, the street-level sentiments that continue to shape the contours of politics on both sides. And, as America’s cities welcome even newer kinds of Americans, through the processes of education and gentrification, it’s often the working classes who have to either move over and move out or get moved over and out. There’s an old Baltimore and a new Baltimore, an old Philadelphia and a new Philadelphia, and — most importantly, for us — an old Boston and a new Boston.

Political conservatism, as a rule, isn’t particularly popular in cities. Among the white working class, it’s still associated with the people Hannah Ardent called “landed gentry,” the business class with whom the everyman has to haggle and fight. For nonwhite urbanites, it’s associated with Nixon, and the law-and-order pejoratives that often masked a disdain for the struggles that coincided with — and outlived — the civil rights movement. Politics evolves, and the polity, the people, with it, but that’s a lot for any ideology to overcome when it’s shut out from the ranks of the educated upper class.

There’s only one problem: The educated upper class is getting harder and smaller. A college education, once a guarantee that midcentury Americans would have better futures than their forbears, is barely enough to keep us treading water in the new century. Amazon, Starbucks, and the whole of the tech sector, while embracing progressive motifs and messaging, often work in the dark against their own workers — internal emails at Amazon appeared to show the company working to stoke racial resentment in their warehouses, to prevent Black and white workers from joining hands in the labor movement.

For many of these companies, social justice is a matter of the right words, of progressive, uplifting images on the sides of skyscrapers or splashed across the latest smart TVs during commercial breaks. But those buildings often stand atop or even inside buildings from another time, that once stood as pillars of the Black community, before those communities were cleared by the nightstick and the checkbook. Those televisions were often made, processed, and delivered by underpaid, nonunion members, in flaming factories segregated to keep them underpaid and non-union — whether they’re in America or overseas. And yet, the new America, allegedly enlightened and supposedly multicolored, preaches on.

Inches from the spittle of the preacher’s mouth, hypocrisy can get a little easier to spot. Whether across the country, where eighty million continue to support the most morally-dubious figure to hold the office in two decades, or in New York, where the voters passed over the favorites of the hipsters and the intelligentsia to elect a former policeman from the Black working class who decried gentrification while earning likes from the likes of Tucker Carlson, the people have noticed that, at the levels we all see and touch, the Left’s bite often falls short of its bark.

Boston’s history is complicated, too. It’s not just the city where the original Puritans fled one repressive regime to build another. It’s the city where John F. Kennedy recalled his father rolling away by train, as signs bearing anti-Irish sentiment rose like roadblocks of the soul in the windows of local businesses. But Boston’s rising population proved too powerful for the bigotry to last, and soon they were asked to make room for new students — Black students — in the public schools of Southie. There were riots, wounds, and the city’s most infamous mayoral campaign, in which a school board member named Louise Day Hicks became the very soul of segregation on the city’s ballots. Perhaps those wounds have been stitched up, the blood that flows from them drying with time, but the scars are still there — enough so that Boston Celtics’ backbone Marcus Smart recalled being called the N-word while leaving a game in 2018, and the city’s flagship magazine asked, in cover-story form, if Boston was “the most racist city in America.”

Into this world walked the aspiring mayors of William Bradford’s City on a Hill.


A few weeks before Boston’s voters decided her suddenly-insurgent campaign’s fate, Anissa Essaibi granted one last interview to WBUR in Boston. The interview explored her rise in the city’s politics, her status in the mayor’s race, her reputation as the “moderate” against Wu’s happy progressive warrior, and her complicated relationship with the Boston real estate scene, including accusations that she leveraged her office to help her husband, a local developer. It wasn’t her last interview, but it was among the most somber: With the election less than two weeks away, the gap between Wu and Essaibi was wider than it had ever been, thanks to the latter’s growing reputation as a favorite of Trump supporters. (New Balance’s chairman, a supporter of the former president’s re-election, had engaged in campaign activities on Essaibi’s behalf.)

I told you this race was never a dogfight, and I told you the truth. Essaibi’s accent wasn’t an advantage in the race; not even close. The candidate herself spent a lot of time being dogged by allegations of corruption involving her husband’s gig as a building developer and facing the fury of the people over her pro-police stances in these unprecedented times. Everything that made her, and her campaign, distinct and newsworthy, everything that put Ellen Barry on her trail in the fall, became an anchor that kept candidate and campaign out of Councilor Wu’s stratosphere.

Michelle Wu cruised to victory in a 64–36 blowout, making her perhaps the most comfortable politician on any ballot, anywhere, on the evening of November 2, 2021. Chances are you didn’t notice, or particularly care — as Essaibi conceded, political earthquakes were unfolding in Virginia and New Jersey. If you were interested at all in politics, it sure looked like you had bigger fish to fry. But Michelle Wu did indeed make history as the first woman of color to win a mayoral election in Boston — mere weeks later, she became their first woman of color to serve as mayor.

On November 16, 2021, the eve of the inauguration, an op-ed appeared in the Globe. It’s principal author was the 56th Mayor of Boston, Michelle Wu, asking her constituents to “march together into our shared potential.”

It was here that she told of the architecture of City Hall, and what her rise to power would mean for families like hers. But it was also here that she told the story of her victory — one where ordinary people from all walks of life organized around a campaign that promised to move the city of Boston into a new era. It was here that she lamented the great city’s contradictions: A global capital of academics, the smartest metro area in America, pockmarked with subprime schools; a locus of healthcare research, still digging out of COVID-19’s quicksand; the very embassy of heaven, greenhouse of knowledge, seedbed of healing, singed by the scars of “substance use, mental health, and homelessness.”

It would be her job to fix these problems, Wu wrote, the modern problems of every great American city. “Block by block,” she inscribed, “street by street, our city has the resources, the activism and the ideas to meet these challenges if we act boldly and reshape what’s possible.”

Here I must warn you, and the mayor, that history is often the graveyard of idealism — for perfection is the domain of the perfect, entities that simply do not exist here below. In governments at all levels, money is mismanaged, duties are neglected, and entire populations lend ear to the devils whispering on all of our shoulders, turning moral no-brainers into political non-starters. Wu, undoubtedly, hopes to be different, wants to be different, needs to be different, relying on the activists who were the engine of her rise to make the future city in her image.

But the old Boston still, very much, exists. Many of its buildings, much of its police force, and most of the things that set it apart from the ranks of American cities are thanks to the old Boston, but so is a great deal of the city’s terrible reputation — a reputation as a place hostile to Americans who weren’t white, where segregation was defended with violence and political organization. Maybe that’s what Ellen Barry was getting at when she noted that Essaibi’s accent was “really a white, working-class accent.”

The eyes of all people aren’t upon her now, but I have a feeling we haven’t heard the last of Mayor Wu. If she wants to forge a better Boston, Michelle Wu needs to keep the hearts of the young, and the idealistic, and the activists, those who first embraced her as a politician. Of course, she does. But she cannot commit herself to the new Boston, a Boston that has arisen while somehow having yet to rise, or else her vision will be built on a shell of former glories — a dangerous place to be, if we’ve learned anything from the last four years. Mayor Wu, scaling the city upon a hill, has to build on what’s already there to be proud of, while pointing her city to build even more.

Let’s hope, for all our sakes, that she can.



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Jadon George

Full-time student, sometime scribe. (Photo credit: David Anderson)