If you’re wondering who’s responsible for bringing the FIFA World Cup to Boston, it isn’t Robert Kraft, or the Healey administration, or the mayor’s office, or the loose confederation of pols, boosters, sports fans, glory-hogs, and straight-up opportunists that instinctively forms at the prospect of such events.
No, the credit lies with a man named Jason Waddleton.
Waddleton grew up in Scotland, outside of Aberdeen. Twenty-eight years ago, he attended Scotland’s last World Cup appearance, a 3-0 loss to Morocco. Twenty-five years ago, he immigrated to Boston. Sixteen years ago, he opened a beloved Scottish bar called the Haven in Jamaica Plain. And four years ago, he moved it from its original location in Hyde Square to the redeveloped brewery complex off Armory Street in J.P.
At some point during those years, Waddleton began willing into existence, with his mind, a Boston World Cup, featuring the Scottish national team. Last year, his efforts paid off. Scotland qualified for the Cup in November. And while some may have wondered where the team and its attendant Tartan Army would end up, Waddleton knew it would be Boston. After all, he says, “I had already manifested that to be the case.”
When we spoke in late March, Waddleton was in the middle of preparing a giant World Cup party in the bar, around the bar, and in the parking lot of the bar: “A three-day festival of food, drink, music, and whiskey,” he calls it. Many Scots are expected to turn out, and Waddleton is thrilled at the opportunity to introduce people from his native land to neighbors from his adopted home. In fact, he had already placed an order of Tennent’s beer so large—120 kegs—that the Scottish newspapers covered it. And that’s just the first wave. “We’re going to be swamped, mate,” he says.
It’s a lot, but Waddleton has had decades to prepare. “I’ve been manifesting this for a long time,” he says, laughing.
THIS IS A BIG SUMMER for Boston. The World Cup may be sucking up most of the oxygen, but it’s only one of several high-profile and likely well-attended events the city will be hosting this season. There’s also the return of Sail Boston, featuring a flotilla of tall ships from around the world, and Boston 250, a yearlong, citywide commemoration of Boston’s role in the American Revolution. Combined, these events are expected to attract millions of visitors, on top of the usual throngs who come to attend the Fourth of July festivities, see the Sox, or participate in that time-honored ritual of death-marching clutches of damp, unhappy children down the Freedom Trail in 98 percent humidity.
Boston isn’t great because it’s the best at everything. It’s great because it’s its own thing.
We’re told these events will generate more than a billion dollars in revenue for the city and state, all while showcasing to the world all that is great and good about Boston and Massachusetts. Wildly irrational projections are the oxygen of mass events, so those numbers are to be viewed with skepticism. But, on the whole, these are positive things—potentially enjoyable, edifying, and maybe even an occasion for genuine civic pride. Right? Aren’t they?
Because even as I write those words, an old ambivalence begins to creep in: Is this whole thing going to be a pain in the ass? A money pit? A traffic nightmare? Will the city’s narrow arteries be choked with the plaque of wayward French? Is the T going to crumble like a cracker under the added poundage? “Screw this,” writes a Reddit user. “We’re in no shape to host a global party.”
Many residents are understandably wondering who all of this is actually for. Is it for locals, or is it all just a sop to rich tourists and international travelers? If the latter, what are we even showing them? As Paul Ford, a 69-year-old lifetime Southie resident and small-business owner, put it, “Are they trying to show off the city, or are they showing off the real estate value because they’re looking for tax money?”
These sorts of concerns are, of course, part of Boston’s DNA, rooted in a deep and justified suspicion of overt boosterish activity. Boston never fares well when it tries to compete on the terms set forth by a New York, or a Los Angeles, or a Paris, or a Tokyo, or a petro-state nightmare like Abu Dhabi. There is nothing more third-rate than a second-rate city trying really hard to be a first-rate city
I’m on a group text chain with a handful of prominent former and current Bostonians. Recently, while discussing why Boston even wanted this thing to begin with, an ex-Bostonian argued, “There’s a case to be made that Boston as a people don’t really give a fuck about being seen as a top-tier metropolis. Perhaps only its leadership still longs for that status. It is a great city. It has excellent food, sports, history, architecture, schools, et cetera. And in recent years, it seems to have only improved on a number of those fronts. But it’s always punched above its weight class. Maybe the people of Boston just want to be a great place to live and not have to act like they’re on the same status as NYC and L.A. Maybe they’re done status-chasing.”
Maybe they are. Or should be. A disinclination to participate in these sorts of pageants is understandable. Even honorable. I don’t consider it a failing. Boston isn’t great because it’s the best at everything. It’s great because it’s its own thing. Just like biologists measure animal intelligence by how well animals succeed at being animals, not by how well they act like people, we should judge Boston by how well it succeeds at being Boston. And we should only do things that enhance its Boston-ness, whatever that may be right now.
How will the events of this summer do that? Who are they actually for? What are we actually showing? And what does it all say about what this city has become—and is becoming—in the year 2026?
Photo by Ken Richardson
WITH APOLOGIES to Sail Boston, I’m going to only briefly address the tall ships. They’re coming from July 11 to 16. The city has hosted them multiple times, it always draws a good crowd, it looks cool, kids like it, it gets people outside, it’s not ruinously inconvenient to locals, other neighborhoods like Eastie and Charlestown get a piece of the action, and it’s fun to see Italian sailors getting plastered for free in the North End. Organizers are estimating the event will attract millions of visitors, which—who knows? Probably not? But it doesn’t matter. The tall ships are fine. We probably don’t have to worry about the tall ships. Go see them.
The World Cup, going from June 13 to July 9, is another matter. It’s expected to attract some 2 million visitors and generate more than $1.1 billion. To put it nicely, the preparation for the seven games planned for Gillette Stadium has been uneven. To put it accurately, it has been a goat rodeo. By spring, as most other host cities were hysterically setting whole dumpsters of cash on fire and sewing the last sequins on their pageant gowns and practicing their best smiles, we were still fighting in the mud over who was supposed to be doing what, and who would be responsible for paying the bill, and how any of this stuff was supposed to actually work. For a minute, it wasn’t even clear if the World Cup was going to happen here at all. The Athletic memorably called Boston’s preparations the “most fraught” of all World Cup host cities. But while it remains to be seen whether it’s reasonable to expect millions of foreign tourists to attend your party in the age of ICE, or sane to mount a World Cup whose success relies heavily on a flawless performance by the MBTA, or cruel to inflict the Gillette Stadium fan experience on a legion of unsuspecting foreigners, the World Cup will happen.
And it will probably all be fine. Chris Dempsey is the cofounder of Speck Dempsey, an urban design and city planning firm headquartered in Brookline. In a previous life, he was one of the founders of No Boston Olympics. That was the group that masterfully torpedoed Boston’s bid to host the 2024 Olympic Games a decade ago. While in some quarters that effort was seen as the handiwork of parochial killjoys lacking in vision, the city owes Dempsey and company a great debt for steering Boston away from what he estimated would have been a $10 billion boondoggle, destined to become a permanent feature in the fiscal lives of taxpayers for the next several ice ages.
Dempsey doesn’t buy the estimates that the state will reap $1 billion in revenue from the Cup, and he predicts it’ll end up costing far more than officials believe. He wishes that money and care and time could have gone toward things like schools and public health centers, but on the whole, he’s okay with the World Cup. “I’m pretty confident it’s all going to work out in the end, and there’s not going to be some embarrassment or disaster,” he says.
Okay, so what about the locals? What’s in it for them? Can they go to the games themselves? Or, as Southie’s Paul Ford put it, “How many people have $5,000 to toss away to go see soccer games?” As of April, tickets are mostly spoken for. You could still get a ticket to Haiti-Scotland on StubHub for between $700—for a seat so far from the action it might as well be in a bar in Mansfield—and more than $40,000 for one that allows you to see that the players have faces. You can also get a “hospitality package” for all seven games for $11,150 per person or rent a private suite at Gillette for between $102,000 to $162,800. It’s all just another opportunity for the rich to spend richly, in a city that does not lack for such opportunities. Maybe after the game, everyone can go try the $95 lobster tail at Nine restaurant on Beacon Hill. Maybe grab a spare to feed to the ducks in the park after. Maybe the ducks will give some to the homeless.
So no, the games themselves aren’t really for the locals. Their World Cup experience is likely to take place closer to home. In February, Boston’s host committee announced a fan festival on City Hall Plaza, promising a space in which “Fans will enjoy live match broadcasts, highlights, interactive games, activities, and a food and beverage program that reflects Boston’s local flavor.” As of presstime, no one has been able to give me any specifics about what the festival will actually entail. But the festival is happening. You will be able to go to the festival.
More promising than the prospect of hanging out in the wind-blasted wasteland that is City Hall Plaza, however, are the smaller events. These are also coming together higgledy-piggledy. Only in late March did the state award $10 million in grants to support community gatherings around the region, including viewing parties and neighborhood activations.
“The real question is: Are these events for locals?” says Ruthzee Louijeune, an at-large city councilor and daughter of immigrants who grew up in Hyde Park and Mattapan. Louijeune is pushing the city to include Black-, brown-, and veteran-owned businesses in the festivities, and pressing City Hall to support more events in the neighborhoods, particularly for Boston’s sizable Haitian and Cape Verdean populations (both countries will be playing in this year’s tournament). While Louijeune admits the city’s planning “is happening slower than any of us would have wanted…I do think that there’s still going to be really phenomenal events.”
These sorts of gatherings and the connections they may foster are also what excite Sam Mewis. She’s a women’s soccer legend from Massachusetts who played on the Women’s National Team in the 2019 World Cup, among many other accomplishments, and hosts The Women’s Game podcast. Mewis grew up in Hanson, a blue-collar community that placed a heavy emphasis on family and hard work. “I have a lot of pride in being from Massachusetts,” she says. “The opportunity to have soccer bring more people to the area, or help us stand out, feels like a convergence of my home and the thing that took me away from home,” she says. “For me, it feels like a really special opportunity to have all the people who made me the way I am cross paths with this huge global event celebrating the sport that has taken me to so many places.”
In other words, for Mewis, the World Cup will reunite the place that made her who she is with the person she has become. The past, the present, and the future will meet, and a newer, better, richer story will emerge.
Which brings us to Boston 250.
Illustration by Neil Jamieson
BACK IN MARCH, I walked the Freedom Trail for the first time in probably 40 years and listened to the National Park Service’s audio tour. At one point, the Northeastern professor Bill Fowler, a guest speaker on the tour, told a story about the Puritans. At the end, Fowler remarked, “It made for an interesting, if somewhat raucous, community, which is what Boston has always been.” I emailed Fowler to ask him what he made of the confluence of big events coming to Boston this summer. “Boston loves to celebrate!” he replied. He loves these parties, he said, “But celebrations should also be cerebrations. After the bands have gone home and the last firework has been sent off—what’s left?”
Boston 250 can be that cerebration. (Which is a word. I checked.)
But before we continue, a couple of caveats. Reporting on Boston 250 was…complicated. No one at City Hall was able to give me a definitive schedule of upcoming events, nor much by way of specific detail on what Boston 250 would entail, beyond a PowerPoint presentation and a couple of press releases. Mayor Wu wouldn’t agree to an interview. Nor would she answer emailed questions on the city’s preparations for the events of the summer in general, or Boston 250 in particular, or take a swing at what she considers singular about the city she governs. The mayor’s office did allow me to take a stroll with some officials working on Boston 250, who were passionate, intelligent, articulate, and a credit to the city and its mayor. But they weren’t authorized to speak on the record, so you’ll have to take my word for it. You can maybe request a transcript from the aide who followed us around recording the whole conversation on their phone. The paranoid ghost of Tom Menino, it seems, still stalks the corridors of City Hall.
Okay. That being said, let’s continue.
The theme of Boston 250 is “everyday revolutionaries.” The idea is to highlight the standard Revolutionary history that everyone learns in school, weave it together with the local histories that haven’t gotten as much attention—Black history, immigrant history, cultural history, scientific history, and oddball history like how the disco ball was invented in Charlestown—and place it all firmly in the context of how Bostonians live now.
There are a few things comprising Boston 250. By the time July Fourth rolls around, City Hall expects to mark a few dozen new historic sites around the city. They’ve established a $300,000 grant program, which community organizations can apply for to research and propose community markers in neighborhoods around the city. The city is working on a new app that will allow people to visit these historic sites, read the plaques, and then scan a QR code and listen to a story, or even enjoy an augmented reality presentation. All cool, and overdue. The city is also preparing a marketing push to introduce visitors to the city to Boston’s layered history.
There are also events. These are aimed at displaying history not as a thing that happened once upon a time, but is still happening, a continuum that modern Bostonians are very much a part of. For instance, in March, Boston 250 re-created part of Henry Knox’s famous march from Fort Ticonderoga to Roxbury with 59 stolen British cannons. The Boston event featured reenactors, horses, drums, fifes, and cannons—all the usual stuff—but they also wove in stories about Roxbury’s history as a cultural hub, showcased work curated by local artists, and brought in a drumline from the Hamilton-Garrett Center for Music & Arts.
I can’t offer much more about Boston 250 by way of specifics, as I don’t really have them as of presstime. But having discussed it with nameless individuals at a nameless City Hall, I have come to believe Boston 250 could actually be quite valuable, though as much as a thought exercise as an event. If the world is indeed coming here to see the best of this place—and not, you know, checking into a hotel, paying a fortune to ride the commuter rail, paying a fortune to attend a game, returning to their hotel, and flying home—what does Boston want them to see? To answer that, we have to ask, What is Boston? And to answer that, we have to ask, Who are Bostonians?
The fact is, I don’t have an answer to that question. I used to. But I haven’t for years, as the city changed so radically. Gentrification is a boon to a city’s finances, and diversity is a godsend for its dynamism, but both—separately or in tandem—can scramble a city’s identity and weaken its social fabric. What is a Bostonian in 2026? On the most basic level, a Bostonian is someone who can afford to live in Boston. But a city needs more than economic means to build its identity on. It needs something people can be proud to be a part of.
Boston 250’s idea of “everyday revolutionaries” is a good starting point. It draws from a past where ordinary Bostonians did extraordinary things, as a way to inspire modern Bostonians to see themselves as part of that lineage—to show them that they’re capable of similar feats of great daring in the face of cruelty, stupidity, and injustice, just by dint of being Bostonians, whether they grew up in Southie in the ’80s or came from Sulawesi a year ago.
“There are stereotypes that exist,” says Louijeune, “but I think that we are curious people, and we are interested in helping out our neighbors. I try to fight for a city that is warm and welcoming to all, and that doesn’t take any bullshit from people who are trying to bring us backward.”
As the world comes to Boston, show them that.
Back at the Haven in J.P., Jason Waddleton is ready. The kegs are ordered. The Tartan Army is coming, and so are the neighbors, and anyone else who wants to join.
He says it doesn’t matter where they come from. All are welcome. After all, that, to him, is the essence of the city. “If you walk into a bar in Boston and start talking,” he says, “you’ll have a conversation.”
And that’s a great place to start.
First published in the print edition of the June 2026 issue, with the headline,“The World Is Coming. Now What?”
