The Battle for Eastie’s Soul

Old-timers. Immigrants. Millennials. Developers. Who will win in the fight for the city’s last frontier?

Get a compelling long read and must-have lifestyle tips in your inbox every Sunday morning — great with coffee!

Traffic! Crime! Construction! There are a lot of ways to size up life in East Boston today. Maggie Simeone and her husband, Derek Edwards, are as good a place to start as any. Two years ago, the couple bought a condo in Jeffries Point, just a few short blocks from the shore of Boston Harbor. Neither Simeone, a teacher, nor Edwards, a software engineer, knew much about the neighborhood when they moved in, other than that it was close to downtown and affordable. In fact, they had never spent any time in the area until they went house-hunting. But when they came across an 800-square-foot two-bedroom condo in a newly renovated walk-up for $420,000—a total steal in Boston—they snatched it up, knowing this was one of the city’s last neighborhoods they could actually afford to buy in.

As the lovebirds settled in, they were thrilled with their investment and their new neighborhood. The longtime geographically and socially insular neighborhood, though, was less than thrilled with them. “I felt very much like an outsider when I first moved here,” Edwards says, adding that he went to the local bars and tried to chat up his neighbors, but the reception wasn’t exactly an offering of home-baked cookies. “One guy got really, really mad at me for moving here and started cursing at me.”

That pretty much sums up the sentiment in East Boston when it comes to the radical changes taking place on the city’s last frontier of underdeveloped waterfront property. Long the home of successive waves of immigrants from around the globe, this isolated, often ignored and trampled-upon appendage of Boston has, in recent years, emerged as a highly profitable playground for developers and the latest destination for upwardly mobile millennials, who are flocking to Eastie like rats to a dumpster full of gluten-free artisanal doughnuts.

Many of these new arrivals have planted themselves in the luxury digs on the western waterfront in Jeffries Point, which began sprouting up in the past few years. They offer unparalleled views of downtown Boston and are a short walk from Maverick Station, from which the Financial District is a measly one or two stops away on the Blue Line. “Demand is just incredible,” says Ivan Baron, chief legal officer for Roseland Residential Trust, the New Jersey and Malden–based development company behind Portside at East Pier, a luxury development that boasts nearly 500 apartments with monthly rents ranging from $2,290 for a studio to more than $5,000 for a two-bedroom.

Along the way, the population has swelled, parking spaces have grown scarce, and commuter traffic has slowed to a crawl. But beyond the vast physical changes, the culture of Eastie is transforming into something unrecognizable to those who have long called it home. A battle is under way between the old Eastie, the launch pad for generations of new Americans, and the new Eastie, the landing spot for more-affluent and aloof newcomers. “It’s a lot of growing pains, and a lot of change,” says City Councilor Lydia Edwards, who represents the area. “People are trying to make sense of it.”

It’s too early to say who will win, but rest assured that the old guard isn’t going to simply wave the white flag. After all, the very fabric of their community is imbued with a fighting spirit. They have fought against Massport’s expansionist designs for Logan, Eversource’s ambitions to install an electrical substation, and ExxonMobil oil spills. And despite being one of the largest neighborhoods in Boston geographically, they’ve fought against neglect and abandon at the hands of state officials. They have fought for green spaces, a new library, and the American Dream (and won). Now, as their beloved Eastie faces the greatest cultural transformation in its recent history, they are fighting again—not just to be able to afford to live here and enjoy the spoils of their victories, but to preserve the fighting culture of Eastie itself.

It’s around 7 p.m. on President’s Day, and a steady snowfall is coating the city. While most folks are curled up on couches, winding down from the long weekend, 50 or so people—mostly white, many over the age of 50—have filed into the basement of a YMCA in East Boston’s Orient Heights neighborhood. I’ve forgone the lure of my own couch north of the Charles to check out the dynamic of discord in Boston’s hottest new real estate market.

On the docket tonight are three proposals from three small developers who are all eyeing different projects in this quiet, residential part of town, about 2 and a half miles northeast of the new waterfront developments. The first presentation flashes by with hardly a murmur, and I start to wonder if perhaps everyone here is far more accommodating to developers than I’d initially thought. By the second proposal, I am disabused of that notion. Local residents are angry, and they’re starting to yell. “So when I sit on my deck, there’s gonna be 10 cars drivin’ in and out of the parking lot,” a woman near the front of the room complains. Then a heavyset man with a comically thick Boston accent bellows, “We fight amongst each other—amongst each otha—right now over parking.” Another woman joins the chorus: “It’s too many units!”

All of this uproar is over a relatively modest proposal to tear down an outdated 980-square-foot single-family ranch home that sits on a mostly vacant 6,200-square-foot plot of land and replace it with a bigger, more modern building that will have six condominiums and six parking spaces. The building won’t be any taller than the homes around it, and the architect went to great lengths to ensure it fits into the neighborhood, down to the pitched roof. From the perspective of a city that’s wrestling with an acute shortage of housing, the plan seems sensible and, quite frankly, like small potatoes in the grand scheme of Boston’s development bonanza. Given the reaction of the crowd, however, you’d think someone was trying to build a brothel on a playground.

Sure, the people in the audience are upset about traffic and parking, and rightfully so. After all, in a neighborhood where Waze-guided Audis and BMWs from North Shore suburbs converge with Logan-bound Ubers and Lyfts during the daily commute, Eastie has some of the consistently worst gridlock in the country. “It’s explosive growth, unlike we’ve seen anywhere else,” says Jonathan Gulliver, highway administrator for the Massachusetts Department of Transportation, who notes that traffic in and out of the Sumner Tunnel—the main corridor connecting Eastie with mainland Boston—has increased nearly 47 percent in the past five years. So of course, every extra car that calls Eastie’s streets home is going to irk the neighbors. But the longer I sit in this YMCA basement, the clearer it becomes that the anger isn’t just about traffic and parking, but about the cultural shift that’s under way. It doesn’t matter if it’s a proposal to erect a hulking waterfront tower or do a gut reno on a triple-decker down the street—each project that’s green-lit marks the end of the community as these people know it. “We raised our families here. This is a family neighborhood,” a woman in the crowd pleads.

It has also long been a neighborhood of new Americans. Canadians and Irish came here first. Then the early 20th century saw waves of Jewish immigrants from Russia and Eastern Europe set up shop (and build the first Jewish cemetery in Massachusetts). Italians followed, and in their wake came immigrants from Southeast Asia, followed most recently by families from Latin America. Today, 58 percent of East Boston’s population identifies as Hispanic or Latino. “When I moved here 35 years ago, it was only Italian people,” says Consuelo Tizon, a 60-year-old Peruvian immigrant who has lived in East Boston since arriving in the United States. She worked multiple jobs, put her daughter through Catholic school because she says the public schools were too violent and too neglected, and eventually purchased a three-family home in Eagle Hill. At first, Tizon says, the Italian-American families and the newer Latin-American immigrants didn’t always get along. As time went on, though, and the Latino community grew, the tensions largely faded.

The reason Eastie has always been a magnet for immigrant communities is because, up until very recently, it was affordable. In fact, most people just saw it as the airport’s backyard. That meant rents were cheap and there were plenty of vacant apartments and homes. Now that East Boston is a destination, the immigrant community is feeling the squeeze. “Everything is developing,” says Tizon, who rents one floor in her house for $1,200 and another for $1,500, both to families from Latin America. Her rates are well below market value, “super-cheap” as she puts it, because she “has to have a heart.”

Plenty of “melting pot” references have been made about East Boston over the years, but in reality it’s less of a melting pot and more of a tidal pool—a delicate ecosystem where the inhabitants change with the ebb and flow of the city. Though it’s constantly shifting and evolving, there’s always been a firm natural order, an instinctual way things work, and an immigrant and working-class ethos. Now, with a monsoon of newness—and, more to the point, wealth—everyone is on edge. “It makes me angry,” Tizon says of Eastie’s newfound gold coast. “It’s no longer East Boston.”

Next on the docket at the neighborhood meeting is attorney Richard Lynds, clad in black with his dark hair styled off to the side. It’s the last presentation of the night, and for a slightly more ambitious project than the others. Lynds represents a developer that wants to raze a six-unit eyesore of old brick and cheap windows and replace it with a six-story, 33-unit building. When an older gentleman in the crowd asks Lynds what gives him the right to do the project, Lynds fires back that he never claimed to have the right to do anything. “Don’t put words in my mouth,” he barks.

It strikes me as a particularly aggressive style of community engagement, and one that’s not likely to win over the locals. Then I learn that Lynds’s parents grew up in public housing near Maverick Square during the 1950s and that he was born and raised in the neighborhood. Intrigued by Lynds’s straddling of both Easties, I arranged to meet up with him a few days later at Cunard Tavern in Jeffries Point, a stone’s throw from the new waterfront condos. It’s early afternoon on a Saturday, and every table in the joint is packed. Young professionals who live nearby are making the most of their weekend, sipping on cold-brew coffee spiked with Canadian whiskey and wolfing down orders of sweet-potato-and-chorizo hash.

Lynds knows Cunard Tavern well, and he picked it as our rendezvous point for a reason: It’s a brick-and-mortar metaphor for the whole of East Boston. Just a few years ago, the building was a defunct two-story warehouse that nobody in their right mind would opt to live next to. Now, after a development project for which Lynds acted as the primary attorney, it’s a four-story mixed-use building with a sleek brick-and-wood façade. The first floor is the restaurant, the second floor is, of course, a barre and yoga studio, and the upper two floors are split into four apartments that look like something you’d see in the pages of Dwell.

After we chat at the restaurant, Lynds takes me on a brief walking tour of Jeffries Point. He leads me over to Piers Park, which is stunning even on a windy winter day, and then points to a massive dirt lot that Massport will soon convert into more public park space. Next to that will be more high-rise luxury apartment buildings. We walk a bit farther to where we have a clear view across the harbor of the Institute of Contemporary Art, which opened up an East Boston offshoot called ICA Watershed last summer at the shipyard just up the road. Lynds tells me he remembers as a boy watching the bicentennial Tall Ships from the busted-up piers. “It was, ‘Watch your step, don’t fall in that hole, don’t step on that glass,’” he half-jokes. The Eastie he grew up in was safe and close-knit, but it wasn’t the type of environment that most people today would aspire to live or raise their kids in. “I used to swim in the Chelsea Creek where the Hess oil tanks were,” he says. “From a nostalgia standpoint, sure, those things were fun. But the new East Boston is certainly better.”

In hopes of warming up, we head over to Downeast Cider House for a few drinks, but a line that’s at least 60 people long sends us back into the streets, where Lynds leads me to a residential road and starts pointing out various projects that he’s represented in recent years. Within a few hundred feet of each other are a beautifully rehabbed gray Victorian with a mansard roof and a half-torn-down single-family that will soon become condos. The backstories for all of these new buildings follow the same arc: What was once a dumpy and dated one- or two-family home is now spruced up, modern, and consists of multiple units.

Our walk lasts less than an hour and amounts to little more than a big loop around the block. But in that short time and distance, Lynds points out so many buildings that have either been built or fully renovated over the past five years that I lose count. And there are no signs of the rush subsiding. Lynds is one of the first people developers call when they’re interested in buying a plot of land or an old triple-decker to demolish in Eastie. When those calls taper off, it’s a sign that things are about to cool down or go bust. But these days, he says, the phone hasn’t stopped ringing.

This is likely just the very beginning. There are much bigger changes on the horizon for East Boston, from Suffolk Downs, where the current proposal includes building 10,000 housing units, to Maverick Square, which is poised for a retail makeover that might welcome a recreational marijuana dispensary. The city has launched a “Plan: East Boston” initiative with an eye toward updating zoning for the area for the first time in a quarter-century. There’s also chatter that the state may reconsider restrictions that prohibit residential developments along most of the coastline, which is currently classified as a Designated Port Area. If that happens, the whole of Boston Harbor will change.

Lynds knows that affordability, traffic, and parking are all serious problems—but that they’re not exclusive to East Boston and they shouldn’t be used as excuses to stop the neighborhood from riding the wave of prosperity that has lifted Charlestown, South Boston, and the Seaport to such extraordinary heights. For years, he says, the baby boomers in the neighborhood have watched property values soar in those places and wondered when it was going to be Eastie’s turn. Now they’re sitting on some of the hottest real estate in Boston, and they want to fight every project tooth and nail. It doesn’t make sense to him. Change is always a bitter pill to swallow. But the way Lynds sees it, change is exactly what East Boston needs—and deserves.

Those with roots in Eastie have every right to feel defensive and even paranoid when it comes to outsiders, especially the ones who are snatching up land in the name of progress. If old-timers feel like they’re owed something, it’s probably because they are. Since at least the ’50s, the residents of East Boston have been in a prolonged conflict with the Massachusetts Port Authority and sundry government agencies and politicians who prioritized Logan above all else. “Everybody just expected we were living here on borrowed time because the airport was so aggressive in its expansion, especially under Ed King,” says Roberta Marchi, who was born in East Boston and has lived there for the past 75 years. “He just broke people’s spirits.”

King, who was appointed executive director of Massport in 1963 and later became governor, had a reputation as a ruthless career man who couldn’t have cared less about what the residents of East Boston wanted. Among the more pernicious assaults carried out on his watch was the seizure of Wood Island Park, the 46-acre crown jewel of Eastie that cut along the harbor. Designed by Frederick Law Olmsted—the mastermind behind the Emerald Necklace and New York’s Central Park—it was the place for families and friends to get out of their cramped apartments and gather on weekends. As the story goes, on the morning of April 23, 1969, King, without giving notice to the neighborhood, sent in a barrage of bulldozers and state police, along with a few dozen men toting heavy-duty chainsaws, to commit what can only be described as arborcide. They blocked the entrance to the park with construction barriers and buzz-sawed their way through dozens of historical elm trees in just a few hours. “We all felt so flattened when they took that,” Marchi says. “After that, we really didn’t have any nice parks.”

That hostile takeover, however, galvanized a fierce and clever band of local activists who helped define East Boston—and whose spirit is very much alive today. The people yelling into megaphones and leading the charge may have changed over the years, but each generation has known that if anything is to change for the better in Eastie, they’re going to have to fight for it. In recent clashes with Eversource over the proposed substation, residents have gotten creative and installed a light-up art display adorned with skeletons and lightning bolts. And they’ve done their damnedest to make sure Massport atones for its past sins. They don’t win every fight—far from it—but they have come out on top plenty of times, especially with regard to the re-greening of East Boston.

Take a walk through East Boston today, and it feels like you’re never more than a few blocks away from a park. There’s the snaking 3-mile East Boston Greenway, the American Legion Playground overlooking Chelsea Creek, and Belle Isle Marsh, to name just a few. Perhaps most important is Piers Park, the lushly landscaped waterfront plot that’s funded, maintained, and operated by Massport. “In the last 20 years,” Marchi says, “we’ve become the recreation capital of the city. But all these things were hard-fought for.”

The irony is that these victories, and the improvements they have wrought, are in part what has made the area attractive to developers, hastening the changes old-timers say are now threatening the culture that produced them. Some contend that razor-sharp tensions in Eastie right now have little to do with the fact that the newcomers have six-figure salaries and are up to their eyes in amenities. Magdalena Ayed, an environmental organizer who was born in Argentina and has lived in East Boston for 13 years, speculates that the real source of frustration is that many of the wealthier newcomers are oblivious to all that East Boston has endured. The hard-fought victories that Marchi speaks of might as well be ancient history to them. It doesn’t matter that Massport seized a beloved park back when Nixon was in office or that a band of mothers shut down Maverick Street to protest the disruption caused by Logan’s expansion. All that matters is that there’s a nearby dog park, a running path along the water, and a short commute downtown. “There’s a disconnect,” Ayed says. “These upper-income newcomers are arriving with a sense of entitlement because they pay $3,000 a month in rent.”

In other words, it’s what we have all heard before: Millennials simply don’t care. “The old-time residents of East Boston and the Latino community are pretty much fully engaged,” says Jerome Smith, chief of civic engagement and director of neighborhood services for the mayor. As for the young professionals along the waterfront? “I don’t want to cast a shadow on a whole demographic, but they’re just not interested,” he says. “They like East Boston because the waterfront is hot, there’s new restaurants, and there are parks and they have access to the water. They like living in their new neighborhood—they’re not necessarily wanting to roll their sleeves up.”

That’s a shame, considering there are big issues to deal with now and in the future—sea-level rise, Suffolk Downs, and traffic, for instance—that will affect everyone living in East Boston, no matter their station in life, no matter which Eastie they inhabit.

Only a very small portion of the waterfront has been developed, and already a bright line has been drawn—the outer ring where the well-to-do millennials live, and everywhere else. Central to the appeal of the new developments on the water is a bevy of amenities that ensures tenants never have to stray more than a few hundred yards to get what they need. Where not long ago there were dilapidated docks and vacant lots, there’s an indoor pool and a nautical-themed eatery pushing a $13 cocktail aptly named “Skinny Jeans.” Not only do the newcomers not have to get involved in the ongoing battles and issues that affect the neighborhood where they now reside, but they don’t even have to interact with Eastie’s longtime residents or the old way of life.

It’s all but certain that more change is coming to East Boston. Rents will keep climbing. Luxury apartments and condos will continue rising, and the kaleidoscope of vinyl-sided homes that have been a staple in the neighborhood will fade into history. What’s less certain, and maybe more important, is whether the new residents will ever feel invested enough to treat the neighborhood like it’s their home and fight for its future.

On a Tuesday night in March, I found myself in the gymnasium of East Boston High School for a “Plan: East Boston” event focused on transportation. Boxes of Santarpio’s pizza were piled high on a table, and all around the gym were poster boards with facts and stats and pie charts showing how much East Boston is changing. I saw Ayed, who was walking around and live-streaming the event on Facebook, and Lynds, who was shaking hands and making small talk.

After a few minutes, I spotted Derek Edwards, who had gotten the Eastie un-welcome at the bar after moving in, along with his wife, Maggie Simeone. For them, lots of things have changed in the two short years they’ve lived here. Their home has increased in value so much that they aren’t sure they could afford it if they were looking to buy today. And they’ve seen East Boston transform physically every day. “The view out our back window when we moved in was of an auto-body shop,” Edwards said, “and now it’s of a building with $600,000 condos.”

They didn’t let the initial cold shoulder stop their efforts to become part of the community. Simeone, who’s 32, says that for the past year or so they’ve been going to every monthly Jeffries Point community meeting they can. “That’s made me feel like much more part of the neighborhood,” she said, noting that she and Edwards are more familiar with their city councilor and state representative than anywhere else they’ve ever lived. They’re almost always among the youngest people at the meetings, so it’s an important forum to counter some of the preconceived notions that the longtime locals have formed about East Boston’s newest demographic. Simeone says she supports most of the development going on here, especially in light of the city’s housing crunch, but she does worry that some of the existing small businesses and families are inevitably going to get priced out.

They’ve also stitched themselves into the social fabric of East Boston and now feel like they firmly belong. “It’s very neighborhood-y here. You go to the restaurants and bars and you see the same people. The bartenders here know me, and you get to know the people around you,” Edwards said. “I lived in Davis Square for almost four years and went to the same four or five bars over and over, and every time I walked in, it was like I was meeting strangers.”

It’s heartening to know that people like Simeone and Edwards are doing their best to make their neighborhood their hometown. But others are likely to be more transient. Outside of the meeting, I met a young, handsome man on the street named Brian Henry. He’s in his twenties and moved to the Eagle Hill neighborhood—not the waterfront—in September. He loves it, he said. There’s great Latin-American cuisine, he and his girlfriend live in a newly renovated apartment in a triple-decker that’s $1,850 a month, and the commute to his job in the Financial District is a breeze. When I asked what he thinks of what’s happening along the waterfront, he lit up with excitement. He’s hoping for a promotion in a few months, he explained, which would come with a good pay bump. When that happens, he and his girlfriend are going to lease an apartment in one of the new high-rises on the waterfront.

“It’s even closer to work,” he said. “And it’s obviously a lot nicer.”