It’s June 2001, and Boston sports fans are throwing a party. Ray Bourque has finally won a Stanley Cup. Not with the Boston Bruins, but with the Colorado Avalanche. Yes, the city of Russell and Orr—a city that runs on Dunkin’ and a they-hate-us-’cause-they-ain’t-us attitude—is celebrating the current success of a former player who had asked out of town two years before because of just how bleak he thought things looked. And as Bourque lifts the Cup before a crowd of as many as 20,000 title-starved fans at City Hall Plaza, it’s hard to disagree with his assessment. In fact, by this point, the fandom is so beaten down that a rally for another town’s title feels right. Things are so desperate that even a legendary contrarian like Dan Shaughnessy doesn’t have much to say. “Everybody liked him so much,” the famed Boston Globe columnist says of Bourque and the rally. “It would have really been pissing on the parade—literally—to come out strong on that being pathetic. In retrospect, of course, it is.”
Pathetic. That was the general feeling about Boston’s sports teams at the dawn of the 2000s. Those years were, of course, before unprecedented, century-defining success and the region’s accompanying sore-winner attitude took root. Instead, Boston was in the midst of something that would seem foreign to anyone who didn’t pay attention to sports until the new millennium: a championship drought. When Bourque won with the Avalanche, it had been 15 years since the Celtics’—and the city’s—last championship. The last time a fallow stretch lasted that long in Boston, the Patriots didn’t exist and Eisenhower was still president. But it wasn’t just the lack of championship hardware that wore on the fan base. It was the pervasive feeling of hopelessness—the idea that, as one radio host branded it, Boston had become “Loserville.”
Coming out of the ’90s, the then-ringless Patriots had an uncertain future with a new, cantankerous coach named Bill Belichick. The Bruins had gone nearly three decades without winning the Stanley Cup and made headlines more for the Bourque trade and for Marty McSorley’s on-ice assault conviction than for their play. Celtics fans were being reminded constantly—both by Rick Pitino’s words and by his team’s performance—that Larry Bird was, indeed, not walking through that door. And while the Red Sox—the team much of New England lived and died by at the time—may have been on the upswing with Pedro Martinez and Manny Ramirez in town, they still had to contend with both a Yankees dynasty and the most famous curse in all of North American sports. You could forgive the region’s fan base for being, as NBC Sports Boston’s Tom E. Curran describes it, fatalistic.
Take the vibes around the team Curran covers, the Patriots: After the dark days of 1-15, the Lisa Olson sexual harassment report, and a threatened move to St. Louis, New England spent the early ’90s turning things around under new owner Robert Kraft, new quarterback Drew Bledsoe, and head coach Bill Parcells, a two-time Super Bowl winner and perhaps the most respected sideline fixture of his generation. But even that seemed fleeting—as though, in Curran’s words, there was a “gauntlet of misery” lurking around every corner. The thinking was: “Bill Parcells … he’s a legend, he’s the best there is, and he’s going to come here?” Curran recalls. “Then five years later, he’s leaving in a snit after the team loses in a Super Bowl. Whatever you had, you were conditioned as a Boston sports fan that it’s going to end in a tragic way. Bledsoe was the best young quarterback in football, but by 1998, you’re like, ‘Something’s wrong here. He’s not getting any better anymore.’ Everything we had seemed to get ruined.”
And then, practically overnight, things changed for the Pats. Thank—or blame—Mo Lewis, Tom Brady, and the Tuck Rule, but mere months after Boston threw a parade for a member of the Colorado Avalanche, the Patriots transformed from the Browns of the Northeast to a feel-good story for a region (and, you may be loath to recall, for a country that felt battered after September 11). With a little bit of luck and some genius game-planning along the way, a team that Vegas projected to win six or seven games that season pulled off the biggest Super Bowl upset since Broadway Joe and the Jets. Some may have considered it a fluke. But even if you didn’t, there was no sense that the Pats were building the infrastructure for a new city of champions. “It was a lightning-in-a-bottle feel.” Curran says. “It wasn’t: Here comes the beginning of a dynasty. You just wouldn’t think they’re going to be the greatest team in football.”
And you would’ve been dramatically wrong. The Patriots won two of the next three championships, joining a very short list of teams that have won a trio of titles in a four-year stretch. Then the region’s other franchises got on the duck boat. All told, the city has won 13 championships in the major men’s pro sports since the dawn of the century, more than any other city in that timeframe (provided you don’t add the two Anaheim titles to L.A.’s 11, something no reasonable Angeleno would ever dream of). But beyond simple counting stats, Boston’s titles have felt more seismic. Maybe it’s the passion—or arrogance—of the fan base. Maybe it’s the towering figures that four major franchises have produced, both on the field and in the press box. Or maybe it’s simply the fact that whether you love them or hate them, these teams are responsible for many of the best on-field moments of recent years, win or lose. (For example, nine of The Ringer’s top 100—and five of our top 20—involve Boston in some way.) For better or worse, this has been the Boston sports century. “We’re looking at 13 parades since February ’02, and there’s a stretch of six years and four months when they all won—all four,” Shaughnessy says. “That hasn’t happened anywhere.”
Those 13 titles include a second trio of Patriots championships, two from the Celtics, and a single title for the Bruins. (Though given what happened in the city of the team they beat, it was certainly a loud solitary championship.) Most famously, that count also includes four World Series trophies for the Red Sox, whose fan base had previously discovered new, unthought-of levels of fatalism. This was a cohort that had lived through Aaron Boone’s home run and still showed the scars of the 1986 World Series—that shudders at the mere mention of the words “Bill Buckner,” “Carl Everett,” or “1918.” (It was also a fan base that threw an “Appreciation Parade” for the ’86 team that blew the World Series against the Mets—an event so much sadder than the Bourque rally that it’s essentially been written out of Boston sports lore. Shaughnessy does remember the jokes, however: “The float went through Buckner’s legs.”)
The Red Sox had become so synonymous with heartbreak and near misses that they also became romanticized—lovable in defeat, charming in their neediness, perpetually Charlie Brown chasing a low-and-away curveball. Their cause was so Sisyphean that the franchise attracted the pens of famous writers like David Halberstam and, fittingly, Stephen King. But Shaughnessy may have published the most significant piece of nonfiction on the team: The Curse of the Bambino, his 1990 bestseller that gave good branding to the team’s 86-year run of futility following the Babe Ruth trade. But even then, heartache proved to be a renewable resource: “I kept going back to print with new chapters,” he says. “It just got longer because more stuff happened.”
In 2004, Shaughnessy was able to write the decisive chapter in this story after the Red Sox pulled off the most improbable win in MLB history, roaring back from a 3-0 deficit against their bitter rivals and making folk heroes out of the likes of Dave Roberts, David Ortiz, and a literal red sock in the process. A week later, Boston completed a sweep of the Cardinals and banished the curse once and for all, inspiring region-wide catharsis—see another book, my boss’s first—and an awakening of latent pride. (As a cub newspaper reporter an hour south of Boston in Providence at the time, I couldn’t even begin to guess how many obituaries that winter included the phrase “lifelong Red Sox fan.”) “I’ve been at all 13 championships and every Patriot playoff game of Brady’s,” Shaughnessy says. “To me, the Red Sox is by far the biggest story I ever worked on. … I always say it’s a biblical tale and it just never goes away.”
But even a biblical title like the ’04 Sox was eventually subsumed by the greater Boston agenda. Eventually, it collapsed into the broader mosaic of New England dominance, where the needy, charming underdogs of yesterday became the front-running bullies of today. And that brash DNA has been imprinted on not only the pro sports landscape, but also popular culture. It’s seemed inescapable (we’ve all heard a “Yankees suck” chant in a place where it made no sense), and speaking as a native of New England, I understand if you’ve also found it insufferable. Because the story of Boston sports in the 21st century isn’t just about how Loserville became Title Town. It’s about how a city that made bestsellers out of T-shirts bearing lunch-pail slogans like “Cowboy Up” and “Do Your Job” also became Entitled Town.
As a Detroit native and a New York Jets fan, Fred Toettcher is used to sports fatalism. So when he arrived in Boston in 2006 as the cohost of the Toucher and Rich radio show, he expected to find some kind of masochistic camaraderie with the region’s fan base. After all, he didn’t recall seeing the Pats on TV much as a kid, unless they were getting blown out in the playoffs. But Toettcher quickly found that New England had no interest in trading sad-sack war stories. “When you’re out of town, you go, ‘Oh, the bumbling Red Sox fan,’ and Shaughnessy made a million dollars off of the curse stuff,” he says. “You thought, ‘Oh, how cute.’ And then when I got here, I’m like, ‘Wow, these Patriots fans are fucking assholes.’”
The entitlement, the sheer gall of it all—it was a shock to Toettcher’s system. Here was a fan base that had spent decades wallowing in misery—not unlike Lions or Tigers fans. But now Boston had gotten a taste of success, and it’d begun to act like it’d invented the very concept of winning. That meant routine calls from guys like Sully from Southie to trash-talk other teams or bask in Danny Ainge’s genius for assembling the Celtics’ Big Three championship team before dismantling it to lay the foundation for another title. Worse, as far as he could tell, many of these people didn’t even care before the winning started. “You’re acting like this is this generational dynasty,” says Toettcher, who now hosts Toucher and Hardy, a 98.5 The Sports Hub morning show that routinely ranks at no. 1 in the region for its time slot. “If you’re old enough to root for the first three Super Bowls, I guarantee you 90 percent of those fans weren’t watching every game. And then all of a sudden, you’re an expert in arrogance.”
The all of a sudden may help to explain some of the arrogance. There’s a certain whiplash that comes with going from worst to first—and rubbing your scars with a championship balm. “We were entitled to feel fucking good and to whip it out to everybody because we had gone through the wars,” Curran says. “Even if you didn’t, well, you knew somebody who had.” But there were likely some other factors at play. These teams—particularly the Sox, Bruins, and Celtics—are nearly as old as the leagues they play in, so they’d been more ingrained in the city’s culture than other franchises in other locales (to say nothing of how provincial New England can be at times). But, on an elemental level, there’s also simply something about sports in cold-weather cities, where people seem to live and die on playoff successes more than their fair-weather counterparts. When you’re spending three months a year scraping ice off your windshield before you go sit in traffic, what happens on the field seems to matter more. It’s part of the reason why the idea of the Chicago fan crystallized into something as indelible as Bill Swerski’s Superfans on Saturday Night Live, but also why there’s no stereotype of a Dodgers-Lakers fan that would land, unless it’s about people showing up late to the stadium. (Hey, rush hour on the 110 is brutal, as another SNL sketch will remind you.)
But “Da Bears” felt charming. What Toettcher was experiencing felt suffocating. The bandwagon quickly became overstuffed with what Sox diehards would call “the pink hats” (an epithet that is at best exclusionary and at worst something more insidious). Then movies and media began crawling with people with 617 area codes—and the spectrum ran from the highbrow (Scorsese finally winning an Oscar with The Departed) to the lowbrow (Barstool Sports) to whatever the hell you consider Ted. In the process, Boston sports fans seemed to treat their story like it was everyone else’s, too. For example: The ’04 Sox were the subject of not just a handful of books and documentaries, but also a Jimmy Fallon–Drew Barrymore rom-com. Contrast that with Bill Swerski’s beloved Cubs, who ended a 108-year, curse-laden title drought by winning perhaps the greatest World Series game ever in 2016 and didn’t even get a Vince Vaughn straight-to-Netflix vehicle.
As Boston and its sycophants became omnipresent, a caricature began to emerge: a Skoal-packing, slur-dropping loser who shouted “FACK YOU” at opposing fans. It’s undoubtedly an exaggeration, but there’s sometimes a bit of truth in a stereotype. Shaughnessy talks about “the braggadocious, thumping-on-your-chest” brutes taking over other ballparks. Curran likens it to finding new money and not knowing what to do with it: “They hit the fucking sports lottery, and they were going to just walk down the street with hundreds falling out of their pockets and say, ‘Clean that up, have that taken away.’”
Understandably, other fans got sick of it. Virtually any survey from the past 25 years has shown Boston sports teams among the most reviled in America. The most exemplary, however, came in 2019, just after the Pats’ sixth championship and the Sox’s fourth this century. Thirty-five percent of respondents said that Patriots fans were the most obnoxious in the NFL—20 points higher than the second-place Cowboys. Bruins fans also took top honors in the NHL, while the Red Sox placed second and the Celtics placed third in their respective leagues. (It’s worth noting that at the time of the survey, both the Celtics and Bruins had won just one title this century—far fewer than less hated teams like the Spurs, Heat, Blackhawks, and Penguins.) The kicker, however: A separate question had the Pats as the most obnoxious fan base of any North American team, regardless of sport, while third place went to “All of Boston”—just behind the Lakers and just ahead of the Yankees. The one bright spot: Boston doesn’t have any college sports teams popular enough to be hated, or else it might’ve given Duke a run for its money.
Perhaps it’s simply a matter of either dying a hero or winning enough titles to see yourself become the villain, especially in the always-on social media era. (See also: the Kansas City Chiefs, ca. 2025.) But it may have also been a matter of how a few of these championships were won—or at least, the outside perception of how they were. Specifically, we’re talking about the Patriots, who prided themselves in being smarter than the other 31 teams in the NFL but also found themselves at the center of two of the dumbest sports scandals of the century: Spygate and Deflategate. And the only thing people hate more than a winner is a cheater—even if the degree of cheating and the benefits of it remain an open debate.
Deflategate in particular gave New England something to rally around—a hatred of NFL commissioner Roger Goodell, who many thought was on a witch hunt. It became personal for the fan base, Toettcher says, as Sully switched from being an armchair NFL expert to an upstart scientist. It was, as Toettcher describes it, “the boulder going downhill and taking out the town.” “Because now you’re these glorious victims,” he says. “Now you’re these heroes that are being cast stones upon, and they’re so successful that the league is trying to figure out a way to undercut them. … People would call in to radio stations and be like, ‘You know the ideal gas law. It was cold and the air molecules get smaller.’”
I moved out of New England 10 years ago, shortly after the Malcolm Butler interception and before the Tom Brady court sketch went viral. I didn’t live through the worst of this. But when I hear Toettcher put an affected Boston accent on the word molecules, I completely understand why he nearly lost his mind taking calls about air pressure.
If there’s a through line for Boston sports so far in the 2020s, it’s watching the city’s former superstars win titles with other teams. In 2020, Mookie Betts—the prize of the decade’s worst major sports trade, non-Luka division—got a ring with the Dodgers before collecting another last fall. Most famously, Brady and the Tampa Bay Buccaneers beat Patrick Mahomes and the Chiefs in the Super Bowl the very season after the Patriots discarded him. The Bruins could soon join that list: Just this past week, the team traded legend Brad Marchand to the Florida Panthers, who are now the cofavorites to win the Stanley Cup this June. Sure, last June the Celtics may have ended the region’s longest title drought since Y2K—five years!—but the other three pro men’s teams are in a decidedly different place: The Red Sox are looking up the standings at the Yankees, the Bruins appear to be tanking after failing to turn historic regular-season success into a championship, and the Pats have been mostly banished from national TV, just like in the days of Toettcher’s youth. New England may be spiritually closer to the Bourque rally than we would have thought possible, even a few years ago.
Maybe on some level, that’s for the better. Entitlement has its roots in insecurity, and Boston sports fans started the 2000s as insecure as they come. They were the little brothers and the peons, so they puffed their chests out to prove they belonged. But along the way, they became scared of that adage about how winning doesn’t feel as good as losing feels bad. The wins stopped bringing much exaltation—only exhales. And the losses kicked up those old feelings of inferiority. “There’s no enjoying the ride,” Toettcher says. “When they didn’t win the Super Bowl, I know someone who was at a bar, and a guy just threw a glass through the window. There is this expectation that if you don’t win a championship, it’s worth nothing. There’s no second-place phenomena here. If you lose a championship, it’s almost worse than not making it at all.”
To a fan in Minnesota or Buffalo—or hell, most fans of most teams in any sport—these sound like Champagne problems. (Or Sam Adams problems, as it were.) But there’s something to letting go and realizing that your team is just like any other team. If you spend too much time worrying about falling off a cliff, you’ll miss your chance to admire the scenery. And when you have to claw your way back up the side of that cliff—say, with Drake Maye and Mike Vrabel leading the way—you learn to appreciate the journey. And maybe the fan base becomes a little less obnoxious in the process, as people start to fall off the bandwagon and leave only the lifers behind, much to the lifers’ delight. (As Curran succinctly puts it: “If you ask a Red Sox fan, do they like ‘Sweet Caroline’? No, they do not.”)
Plus, as the lifers can attest, a little losing can be good for the soul. The next chapter of Boston sports should bring fewer parades, a lot more pain, and hopefully, a little humility. That may be a tough but necessary pill to swallow for a kid born in the mid-’90s who’s known nothing but their teams winning their entire life. “It’s like being born on third base,” Shaughnessy says. “You’re born a rich kid, so you just don’t know what it’s like to wait and to really invest your loyalty and emotion, to have that crushed. You didn’t feel the soul-crushing defeats that we lived with or the long droughts or the clown shows. It’s not your fault, but you just can’t possibly appreciate how great this is the way us oldies can because we paid the dues to enjoy it and really relish it.”
The reality is that winning and arrogance go hand in hand. I don’t know many members of Crimson Tide nation, but I suspect that other SEC fans don’t consider them humble. And I’ve now lived in L.A. long enough to know exactly how Lakers fans feel about the woebegone Clippers (truly not fit for print on a family website like this). Sports fandom is about bragging rights, and the reason Boston fans seemed uniquely cocky is because they had a right to be—the 21st century brought them shocking, unprecedented success and a megaphone with which to shout about it. Any fan base in that situation would’ve almost certainly behaved similarly. So it’s OK to celebrate now that the city has been mostly vanquished, but it’s also OK to admit that deep down, maybe you do hate them because you ain’t them.
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