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We all know the history.

Angry mobs hurling rocks at busloads of Black schoolchildren. A city too willing to believe a white murderer, Charles Stuart, who pinned his pregnant wife’s killing on a phantom Black assassin.

Even as the worst of the bigotry receded in the 1990s and 2000s, our civic life felt exclusionary. Unyielding.

Boston is marked.

And the new generation of political leaders who began to emerge a dozen years ago know that as well as anyone: Ayanna Pressley, who became the first woman of color elected to the Boston City Council and later won a seat in Congress; Michelle Wu, who took her own spot on the council in 2013; councilors Andrea Campbell and Lydia Edwards and Kim Janey, who followed.

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They all understand the symbolic value of their rise. They revel in it, campaign on it.

But symbolism, they have always insisted, is not enough.

A new politics is required. Something more attuned to Black and brown Boston. More focused on equity and justice. More urgent.

And the extraordinary events of the last few years — the election of Donald Trump, the onset of the pandemic, the murder of George Floyd, and the fires and floods of climate change — have provided a runway for that politics like never before.

What seems possible — what seems necessary — in a city like Boston has shifted.

In the last year, Wu has proposed a sweeping Green New Deal for the city. Campbell is pushing to cut the police budget by at least 10 percent and move the money into social services. And there has been insistent talk of narrowing Boston’s shameful racial wealth gap.

Former Mayor Marty Walsh’s decision to leave office five months ago and join President Biden’s cabinet threw open the doors to power.

Now, with a highly competitive mayor’s race, this new cohort of progressive leaders face their most important test yet.

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Adobe/Globe Staff/The Boston Globe - The Boston Gl

The candidates need to demonstrate that they have the policy chops — that they have bold and achievable plans for the sort of transformational change they envision.

With voters set to narrow the field of five major contenders to two in the preliminary election next month and to pick a winner in November, the candidates also have to show they can build electoral coalitions in a city that still has a sizable share of moderate and conservative voters.

And if one of the progressives wins, the new administration will have to prove that it can deliver on the promise of this breakthrough group of leaders, that it can make the new politics real.

That it can move the needle in one of the wealthiest and least equitable cities in the country.

The case for change

Michelle Wu orders a chicken salad sandwich and a smoothie and sits down with me at a café a couple of blocks outside Roslindale Square.

She’s here to make the case that Boston is ready for change. That it can change. And the story of her own ascendance in local politics is Exhibit A.

When she was exploring a run for an at-large city council seat in 2013, Wu says, people she trusted — people with her best interests at heart — told her she couldn’t win.

Boston Mayoral candidate Michelle Wu.
Boston Mayoral candidate Michelle Wu. Jessica Rinaldi/Globe Staff

She is Taiwanese American. A woman. A Chicago native. Back then, she was only 28 years old. And when she got out on the campaign trail, she encountered a deeply parochial politics.

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“The question I was asked most often was ‘What neighborhood do you live in?’” Wu says. “And second most was probably ‘What neighborhood did you grow up in, where does your mom live, where did you go to school? How do you fit within the tribes of Boston?’”

Her victory that fall was evidence that the city’s political culture was shifting.

But Wu says the change really hit home in the 2019 election cycle, when a new batch of progressive advocacy groups greeted a new clutch of council candidates with a new kind of question. Not where did you grow up or where did you go to school, but “What change will you deliver, what issues are you going to champion, what communities will you fight for?”

The Boston City Council is weak by design; power here is centered in the mayor’s office. And the new, more diverse, more progressive iteration of the council had real limits on what it could do.

But it became a notably feistier body — what Wu calls “a platform for activism.” A place to organize and push the Walsh administration into action.

Now what Wu is asking the voters to do is move that activist impulse into the mayor’s office. And she seems to be making headway.

The most recent public polls show her neck and neck with Janey, the city councilor-turned-acting mayor, at the top of the pack.

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Wu’s most ambitious proposal is a city-level Green New Deal, spelled out in a 46-page manifesto she released last summer.

Like its federal cousin, championed by Senator Edward Markey and Representative Alexandria Ocasio-Cortez, the plan aims to combine climate justice, racial justice, and economic justice in a sweeping package of reforms.

“We have a moral obligation to act,” Wu’s blueprint reads, “making the transformative changes we need to de-commodify, democratize, and decarbonize our lives.”

Wu imagines fare-free electric buses and an Urban Climate Corps that would boost the city’s composting capacity and restore wetlands.

She envisions thousands of new trees shading low-income neighborhoods and the establishment of “green zones,” where developers would get expedited permits and density bonuses in exchange for erecting net-zero-emissions buildings and setting aside large numbers of units for affordable housing.

Rent control would ease the burden on Boston’s tenants. And residents facing eviction would have a guaranteed right to counsel.

Her plan is peppered with examples of cities that have already put similar policies in place: a right to counsel in New York City, green zones in Minneapolis, and free transit in Park City, Utah. But if the copious footnotes lend an air of practicality to her transformative vision, there are undeniable obstacles to making it a reality.

Wu has pitched green bonds as a way to pay for some of her plan. But other sources of revenue could be hard to come by. In Massachusetts, cities and towns can’t levy taxes without approval from the state Legislature, and it often doesn’t come.

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The state would also have to sign off on a right to counsel and rent control. And the mayor has no control over the MBTA. Wu would have to talk the perpetually cash-strapped agency into a broad program of free bus service.

But she insists she could bring others along. And, as she’s quick to point out, she’s already made some progress.

For years, Wu says, the debate over public transit fares boiled down to how much the T should raise them — a lot or a little.

But her call for free public transportation in a Globe op-ed in January 2019 helped shift the conversation. And after hearing about Wu’s advocacy, the mayor of Lawrence launched a free bus pilot that was so popular, it was recently extended.

“One way to shift the boundary of what’s possible through policy is by demonstrating it works,” Wu says.

Boston could pitch in some money for a pilot of its own, she says between bites of her sandwich. Carve out more dedicated bus lanes. Make this thing a reality.

It’s an idea she’s been pitching for some time. It has built momentum.

Acting Mayor Kim Janey.
Acting Mayor Kim Janey.Craig F. Walker/Globe Staff

And a couple of weeks later, Acting Mayor Janey announced just such a pilot on the T’s Route 28, which shuttles thousands of riders a day between Mattapan Square and Ruggles Station.

It’s good to be mayor.

‘Madam Mayor’

Janey meets me at a tavern on the edge of Faneuil Hall and orders her usual — an arugula salad with shrimp and a squeeze of lemon.

A press aide sits across the table. Security is nearby.

We’re just steps from the office she inherited from Walsh in March. And she’s made ample use of her megaphone.

Just days after her swearing-in, Janey announced $50 million in rent relief for Bostonians hammered by the pandemic. And she was the only politician to speak from the podium at the free-fare bus announcement.

She has also worked to tap the excitement surrounding her as Boston’s first Black woman mayor.

In an introductory video on her campaign website, Janey laces up a pair of high tops and strolls through time — from her days on a school bus, when she endured the rocks and rage of segregationists, to a triumphant march up the steps of City Hall.

“Madam Mayor” totes and t-shirts sell for $30 in her online store. And sticker packs — in purple, yellow, and tangerine — go for $5.

The image-making has drawn some tart responses from her campaign rivals.

After the Globe ran a story on Janey’s stylish swag, City Councilor Andrea Campbell posted a tweet labeled “Priorities,” with green check marks next to “Equitable Public Schools,” “Transparent & Accountable Police,” and “Addressing the Opioid Crisis on Mass & Cass,” referencing the large number of people addicted to opioids who gather near the corner of Massachusetts Avenue and Melnea Cass Boulevard. At the bottom of the list: A big red X next to “Launching a merch store before a policy platform.”

Janey has, indeed, been light on policy prescriptions.

Her preferred formula is to speak about a problem like the racial wealth gap in Boston, mention her own life experiences — living in a shelter for a week as a child or making use of a Section 8 voucher as a single mom — and point to something concrete, if incremental, that she has done as acting mayor to address it: boosting funding for the city’s first-time home-buying program, for instance.

This combination of biography and incumbent power may well work as a political strategy. But it leaves some fair questions about what she would actually do to fulfill the promise of the new Boston politics if she won a full term as mayor.

At lunch, I push her a bit. I want to know how far she’ll go.

Would she be willing to pursue something like the $10 million reparations program that the multiracial suburb of Evanston, Ill., has launched — providing housing grants for Black residents who can show that they or their ancestors were subject to redlining or other discriminatory practices?

It’s “worth exploring,” Janey says. “It is the legacy of slavery in this country, and what happened post the enslavement of people of African descent, that has led to this racial wealth gap in Boston. Redlining is just one piece of that.”

That puts her on the left flank on this issue, though she’s not alone there.

Mayoral candidate John Barros.
Mayoral candidate John Barros.Craig F. Walker/Globe Staff

John Barros, who stepped down as the city’s economic development chief several months ago to run for mayor, tells Ideas that he would consider a reparations program of some kind. Wu supports the idea, too. Campbell speaks of a truth and reconciliation commission that would explore Boston’s history on race and inform policy change; she says that the relevant policy could take many forms. City Councilor Annissa Essaibi George, the fifth major candidate for mayor, eschews talk of reparations, saying the city should instead pursue broad policies to assist Bostonians in need.

If Janey flirts with the idea of reparations, though, she isn’t committing. What about rent control? I ask.

The acting mayor says she supports state legislation giving cities the option but demurs when pressed about whether she’d actually impose it on the city.

To be fair, these aren’t easy calls.

Reparations are politically fraught. And research suggests that putting limits on escalating rents can backfire in a number of ways — leading landlords to convert apartments to condominiums, for instance, and deplete the rental stock.

But these kinds of ideas get at the core questions for this new generation of political leaders: What are you willing to do? And what can you really get done?

The conundrum

Housing is everything in the 21st century American city.

It is the neighborhood we live in. The schools our children attend. It is the difference between violence and safety. Hot asphalt and cool shade. It is walking home from work at 6 or lurching from one subway stop to the next while the kids finish up dinner and turn to their homework without you.

And Boston is in the midst of a full-blown housing crisis.

Young families are fleeing the city because they can’t afford to buy. And many renters are teetering on the edge of financial crisis.

Nearly half of the city’s tenants spend more than 30 percent of their income on rent. A quarter shell out 50 percent or more. The economists’ term for that latter group is “extremely housing burdened.”

If there is one issue crying out for a bold new remedy from a new batch of Boston leaders, this is it.

But here’s the reality, both heartening and distressing: It’s not clear that the city can do much better on affordable housing.

Boston already has a much larger share of subsidized housing than its peers. A remarkable 1 in 5 housing units in the city is income-restricted. And in some neighborhoods, the share is substantially higher. Fully 44 percent of units in Roxbury are set aside for lower-income residents.

The city is making good progress on plans to build almost 16,000 new affordable units and 69,000 units overall by 2030 (though it could probably up its production targets). And housing officials are making creative plays to hold onto existing moderately priced housing stock.

Last summer, when tenant leaders at the Morton Village Apartments in Mattapan learned their aging, 207-unit complex was up for sale, they started organizing and reached an agreement with the buyer to keep rents affordable for five years.

The city, sensing an opportunity, chipped in $4 million to extend affordability beyond the five-year term.

Still, if something more ambitious is possible, now is the time to pursue it.

Congress, after decades of underinvestment, has poured billions in federal relief funds into housing, providing a once-in-a-generation opportunity to go big.

“My field has never been resource rich,” says Priya Jayachandran, chief executive of the National Housing Trust, a leading affordable-housing advocate. “And now cities are swimming in dollars.”

The trouble is, she says, a sector long accustomed to patching things together with limited funds — building a few new units here, saving an affordable apartment complex there — isn’t all that adept at innovation.

So for now, the market is awash in clever but incremental ideas. And that’s reflected in the Boston mayor’s race.

Barros is calling for a Neighborhood Investment Fund, seeded with money from the city, foundations, and university endowments and open to small investments of $100, $200, or $2,000 from residents.

The money, he says, would be used to redevelop lower-income neighborhoods. Locals would get a say in how their blocks change — and a shot at a small return.

Mayoral candidate Andrea Campbell.
Mayoral candidate Andrea Campbell.Craig F. Walker/Globe Staff/The Boston Globe

Campbell, meanwhile, is pledging to open up 100 city-owned vacant lots to development in her first 100 days as mayor.

Standing in front of one such property at a press event in Dorchester last month, Campbell imagined scores of mixed-use developments with locally owned businesses on the bottom floor and apartments above.

The effort, she said, would build on one she launched as city councilor to activate 30 lots on the Blue Hill Avenue corridor — the alternately lively and forlorn spine of Black Boston.

“I am the only candidate in this race that has a housing plan that is specific, that is practical, that is doable, that is creative, and frankly builds on a long record of accomplishment,” Campbell said.

This is not the language of radical change.

But it is intriguing nonetheless. As the campaign enters the homestretch, Campbell is positioning herself somewhere between the visionary and the grounded.

She’s talked of providing housing vouchers for moderate-income families who don’t qualify for low-income housing.

Her pitch for redirecting at least 10 percent of the police budget to social services isn’t defunding, exactly, but it’s no small change either.

And the long-time critic of the Boston Public Schools administration is calling for a decentralization of power — a devolution to individual schools.

Barros is claiming a similar spot between practical and far-reaching.

“I’ve been in government for seven years and this is a different time,” Barros says. “People are asking for change at a quicker pace. There’s an appetite for that.”

But, he adds, “people are afraid that there’s going to be too much change.”

Barros would separate the long-struggling Madison Park Vocational Technical High School from the school department — giving it a budget and board of its own in a bid to turn it around.

And he’s calling for a new agency — alongside the police, the fire department, and emergency medical services — that would handle mental health calls and behavioral issues in schools.

Not a wholesale reimagination of city government, but a palpable shift. One that may still go too far for some voters.

Those voters have another choice.

The alternative

Councilor Annissa Essaibi George had a thing for porcelain unicorns when she was a kid.

“I had quite the magnificent collection,” she says. “Probably made my mother crazy.”

But these days, when she talks about unicorns, she isn’t referring to the shiny figurines of her youth. She’s talking about the shiny ideas of her more liberal mayoral rivals.

“We always have to be aiming toward the ideals of . . . you know, unicorns and rainbows or, someone said, ‘it’s like cupcakes and puppies,’” she said. “That’s great. But we have real work that has to be done.”

Mayoral candidate Annissa Essaibi George.
Mayoral candidate Annissa Essaibi George.Craig F. Walker/Globe Staff

Essaibi George is the outlier in the mayor’s race — the one candidate who has separated herself from the self-consciously progressive cohort of new Boston leaders.

For her, the “real work” of the city is fixing special education and keeping neighborhoods safe. It’s filling potholes and rebuilding playgrounds.

“We think about our responsibility as a city, as a municipal government — it is those basic city services,” she says. “It is nothing terribly fancy.”

Essaibi George’s supporters take heart in Eric Adams’s recent Democratic primary victory in the New York City mayor’s race.

The former police officer outflanked his more liberal rivals with a focus on public safety and an appeal to working-class voters in the outer boroughs.

Boston is different, though.

Crime hasn’t registered as a major concern in polls. And while Adams, who is Black, fared very well among voters of color, Essaibi George may struggle to do the same.

She identifies as a person of color; her father emigrated from Tunisia and her mother is Polish-American. But she has not performed well with Black or Latino voters in public opinion surveys. And if she makes it through the preliminary election in September and winds up in a one-on-one contest with a candidate like Janey or Campbell in November, her problems could be compounded.

David Paleologos, director of the Suffolk University Political Research Center, which conducted a June mayoral poll for the Globe that had Wu and Janey in the top tier and Campbell and Essaibi George in a second tier, says her best hope may be drawing more moderate and conservative white voters to the polls than expected.

It’s anyone’s guess how realistic that is.

In the last two mayoral elections in 2009 and 2013, according to estimates provided to Ideas by the Democratic voter data firm TargetSmart, about 65 percent of the voters who cast ballots in the general election were white.

But Paleologos expects a substantially smaller share — on the order of 50 percent — given the shifting demographics of Boston and the composition of the mayoral field.

And a sizable chunk of Boston’s white voters — more than half, according to the Globe poll — identify as “liberal” or “very liberal.”

Indeed, it was Wu — not Essaibi George — who was the top choice of white voters in the survey.

But even if Essaibi George is unable to pull off an upset, the constituency she represents is a substantial one.

The Globe poll found that nearly half of Boston voters identify as either “moderate” (38 percent), “conservative” (9 percent), or “very conservative” (2 percent).

And any mayor who wants to pursue a controversial policy like siphoning money away from the police will have to contend with that segment of the public.

Old Boston isn’t as potent as it once was. We know that. And after this election, the world may know that, too. But it isn’t entirely transformed, either.

This is a transitional moment. A moment of activism and hope and misgivings about the new direction of Boston politics.

The city is ready for change. The question is: How much?


David Scharfenberg can be reached at david.scharfenberg@globe.com. Follow him on Twitter @dscharfGlobe.