Was their dominant 2018 World Series victory good for the Boston Red Sox? This is a very strange and perhaps even insulting question, I know, but there’s something that fascinates me about the arc of the Red Sox, and I’m curious where that fascination might lead. And so we ask the question.

Let’s start with a few obvious thoughts.

First, for about 80 years, the Boston Red Sox represented unfulfilled longing. That was their whole story, really. One of my favorite-ever sports columns was written at the end of the Mets’ crushing victory over the Sawx* in the 1986 World Series by the great Mike Downey, under the headline, “Unite, Fans of Boston Strugglers.” I love it so much that I’ll post a chunk of it for you here:

I am part of this country, same as anyone, anywhere, and older than most. I am richly American. I am the son of a farmer, who was the son of a statesman, who was the son of a poet. My ancestors are tea drinkers and revolutionaries. I have Olde England in me and New England in me. In my bones. In my blood.…

I am Paul Revere looking for a lamp in a steeple, or at least for a pitcher in a faraway bullpen who can get somebody out…

I am Sweet Baby James Taylor, depressed by the snow on the turnpike from Stockbridge to Boston, though the Berkshires seem dreamlike on account of the frostin’.…

I am George Plimpton, a Harvard man, ready to go out there and play if they need me.…

I am Stephen King, buried alive in Maine, wondering if this horror story will ever end. I am the Boston Strangler, bringing new meaning to the word choking.

I am J.D. Salinger, secluded as always, reluctant to agree with the world that we could use another catcher.

I am Hester Prynne, ready as always to take one letter-high.

I am Bunker Hill and Beacon Hill and Heartbreak Hill, and Calvin Hill, gaining yardage for Yale. I am jazz at Newport, and sand at Cape Cod, and lobsters at Bangor, and sharks at Amity.

I am Boston. I am the Commonwealth. I am New England. Loser of the World Series once more.

New York City, have pity. Let’s play five out of nine.

*If you type “Sawx” into Google, the Red Sox will not come up, but the movie Saw X will. I cannot believe there have been ten Saw movies, but that’s okay. Saw 11 is coming out on September 27.

I posted more of Mike’s column than I originally intended because it’s just SO good that I couldn’t stop; it’s all of the Boston Red Sox heartbreak in 1,000 or so brilliant words. That’s what the Red Sox were for many, many decades—heartbreak—and while no fan base should endure such a fate for so long, well, I have this crazy theory that nothing in sports bonds fans quite like heartbreak.

“Strange how people who suffer together have stronger connections than people who are most content,” Bob Dylan wrote in “Brownsville Girl,”* and I believe that, and for so many generations baseball in Boston meant joining together over the near misses, the close calls, the emptiness that inevitably arrived.

*This is by far—like by 200 miles—my favorite Dylan song. To be fair, I would not call myself a Dylan fan. My friend Tommy Tomlinson has written that he admires Dylan more than he loves Dylan, and I feel that, too. But I truly LOVE “Brownsville Girl.”

It’s funny reading Mike’s column now because it has been almost a full 20 years since the Red Sox have been anywhere near Lonely Street, much less that far corner where Heartbreak Hotel stands. When they won the World Series in 2004, it was a triumph of the spirit; they did it in the most perfect way possible, coming back from oblivion against the vaunted Yankees in the ALCS, then sweeping the Cardinals in the World Series to avenge the torment of 1967 (not to mention 1946), and they did it with a bunch of lugheads who happily called themselves idiots and simply mocked the notion that Boston baseball was somehow cursed by ghosts.

Then the Red Sox won the World Series again in 2007, and it was pretty breezy, sweeping the Colorado Rockies, a team that baffled everybody then and now.

Then the Red Sox won the World Series again in 2013, once more beating the Cardinals, and even though this Series was superficially closer—the Cardinals led it 2-1 at one point—I don’t really recall many people thinking that Boston would lose it. I certainly never did.

world series red sox v cardinals game 4
Stephen Dunn//Getty Images
The Red Sox celebrate after defeating the St. Louis Cardinals 3-0 to win game four of the World Series on October 27, 2004, clinching the team’s first title since 1918.

Then, finally, came 2018. Though the Red Sox had now won three World Series in the previous 14 years, there was still this annual baseball anguish and drama all around New England. Old habits do die hard. After the Red Sox crumbled in 2014-15, general manager Ben Cherington was forced out and the team brought in Dave Dombrowski with the singular mission WIN NOW.

Fortunately, this is Dave Dombrowski’s specialty—he should put WIN NOW on his business cards—and he immediately took advantage of the incredible system that Cherington and company had built. He traded for Craig Kimbrel and signed David Price and traded for Chris Sale and signed J.D. Martinez and traded for Nathan Eovaldi and rode the terrific young players the Red Sox already had (Mookie Betts and Xander Bogaerts and Andrew Benintendi and Rafael Devers, among others), and Boston breezed to perhaps the easiest World Series season of the 21st century. There was never a single doubt all year that those Red Sox would win the World Series—they stayed healthy, they won 108 games, they easily dispatched the Yankees, they blasted through the Astros, and they never felt any danger at all in their five-game victory over the Dodgers in the Series.


Joe Posnanski has been called "contemporary sports writing's biggest star." For more stories from Joe, subscribe to his Joe Blogs Substack newsletter at joeposnanski.com, where he writes about sports, pop culture, life, and all manner of nonsense.


It was awe-inspiring… and absolutely the opposite of everything that the Boston Red Sox had long symbolized. This organization that was once the quintessence of suffering and trauma and hard-earned pessimism and heartbreak was now fat and rich, the kings of baseball, winner of four World Series since the turn of the century, and it must be said that none of those World Series triumphs was especially close or tense. Victory came pretty easily.

Merriam-Webster says words like “happiness” and “joy” and “jubilation” are the antonyms of “heartbreak.” But I’m not sure that’s exactly right. Sure, in the moment, it fits—winning the World Series sparks a huge amount joy in the same way that losing the World Series sparks heartbreak—but joy isn’t really the opposite of heartbreak because it lacks the power of heartbreak. Joy fades much more quickly. Joy is a rush, a surge, a dopamine hit.

Heartbreak, on the other hand, is a condition. Boston baseball for 80 years, like all deeply sad things, inspired poems, literature, music, art—“Great art is about conflict and pain and guilt and longing and love disguised as sex and sex disguised as love,” Philip Seymour Hoffman as Lester Bangs said in Almost Famous.

What did the 2018 Red Sox—and 15 or so years of celebrations and parties and ever-so-brief patches of ennui—inspire? Ten months after they won the 2018 World Series, they fired Dave Dombrowski and hired Chaim Bloom to rebuild the farm system. Fifteen months after they won the 2018 World Series, they traded away Mookie Betts rather than fight to keep one of the greatest and most beloved players in the franchise’s history. Less than two years after they won the 2018 World Series, the Red Sox social media team tweeted a photo of a RESET button, apparently celebrating the team’s ability to slash payroll to the point where they no longer had to pay the luxury tax.

Joy isn’t really the opposite of heartbreak because it lacks the power of heartbreak.

They have since fired Chaim Bloom as president even though he rebuilt the farm system (but didn’t win at the big-league level) and they have avoided spending any money on free agents and they have cut $25 million or so from the Opening Day payroll and they have talked glowingly about “the experience of going to Fenway… a special place,” and they have acted as if… well… as if they’ve won enough.

“I can tell you,” new team president Sam Kennedy says, “as a kid who grew up less than a mile from Fenway Park, if you think for one second that we aren’t passionate, committed, dedicated to the Boston Red Sox, you’re wrong, you’re a liar, and I’ll correct you on it, because it’s total BS.”

I respect that, and am certain that Kennedy and others are passionate, committed, and dedicated to the Boston Red Sox.

I also think… it’s just not the same. Joy simply does not motivate the way pain does. On the surface, sure, they’re still the Boston Red Sox—they still play at glorious Fenway Park, and they still have no one wearing No. 9 because of Ted Williams, and they still inspire angry radio talk show callers from Essex and Framingham and Medford and Walpole.

But they’re also a four-time World Series champion this century, the most recent only a few years ago, and they have some good players, and they have several exciting prospects on the way, and they have a rabid fan base that will fill up Fenway Park no matter how expensive the tickets get, and they’ll try to win, sure they’ll try, and they’ll fire people when they lose, and it will never matter quite as much as it once did.

Lettermark
Joe Posnanski

Joe Posnanski has been named the best sportswriter in America by five different organizations, including the Sports Media Hall of Fame and the Associated Press Sports Editors. He has also won two Sports Emmy Awards. He is the No. 1 New York Times bestselling author of six books, and he co-hosts the PosCast with television writer and creator Michael Schur.