The Red Sox's Brutal Transformation to AL East Doormat

Listen up, kids. It's time for a history lesson on how the Boston Red Sox used to be the gold standard of MLB franchises.

It sounds ridiculous, but it's true. John Henry and his ownership group bought the team in 2002, and they won more games between then and 2018 than all but one other team. That's not even counting the four World Series titles and .606 winning percentage in October.

That was before the dark times. Before the fallen empire.

The Red Sox ranked 16th in wins between 2019 and 2025, and mediocrity reigns again in 2026. They're somehow only 4.5 games out of a wild-card spot but given their 27-38 record, to point that out is to reach for lipstick while face-to-face with a sickly sow.

Which brings us to what this lesson is all about: How did the Red Sox go so wrong?

They're Not a Big-Market Team Anymore

The Point: Follow the money.

The Red Sox play in the league's seventh-largest market, and they're a hugely valuable asset. When Henry bought the team, it was for $700 million. Forbes now values the franchise at $5.25 billion.

What matters, though, is that Boston has ceased acting like a big-market team. Since running top-five payrolls annually between 2004 and 2020, these are their Opening Day ranks for the last six seasons:

• 2021: $180.1 million (8th)
• 2022: $206.6 million (6th)
• 2023: $181.2 million (12th)
• 2024: $171.2 million (12th)
• 2025: $195 million (11th)
• 2026: $190.6 million (12th)

As Joon Lee covered in his YouTube video with More Perfect Union, behind all this is a complicated story about the influence of private equity in pro sports, as well as how owners' motives have evolved. Whatever the case, what it absolutely is for Boston fans is infuriating.

And certainly, that much more so when this lens is applied to departures of guys like Mookie Betts and Alex Bregman. What actual shopping Boston has done this decade has exclusively been on shelves below the top one, and it's how they waded into disasters like Trevor Story and Masataka Yoshida.

They're Not a Well-Run Team Anymore

The Point: The run of innovative executives is over.

As much as Henry's spending helped, the Red Sox were a powerhouse in the 2000s and 2010s just as much because the three guys who built World Series winners in 2004, 2007, 2013 and 2018 each brought something to the table:

• Theo Epstein, 2002-2005, 2006-2011: Basically the first to do Moneyball with a big budget
• Ben Cherington, 2012-2015: Built an excellent farm system and had one of the great masterstroke offseasons of all time in 2012
• Dave Dombrowski, 2015-2019: Had the audacity to commit the team's resources to star players

Even Chaim Bloom deserves some flowers. His return in the Betts trade is an infamous calamity, but he at least rebuilt a barren farm system that has since yielded such fruits as Roman Anthony, Jarren Duran and Wilyer Abreu.

The guy tasked with picking up Bloom's ball is Craig Breslow, who Boston hired as chief baseball officer in October 2023. And though Tim Healey of The Boston Globe reports Breslow's job is ostensibly safe, his work has rightfully landed him on the hot seat.

Some of his crimes (i.e. not re-signing Bregman) can be referred back to ownership. Others are more subjective, such as his alleged roboticness and overreliance on analytics.

You can even make the case that Breslow deserves more credit for his wins. The trades for Garrett Crochet and Sonny Gray and the signing of Ranger Suárez count. The arrivals of Payton Tolle and Connelly Early do, too.

That the 2026 Red Sox are nonetheless hamstrung by a 29th-ranked offense is also on Breslow, however. He just plain neglected an offense that obviously needed help over the winter, which makes it almost funny that the team is now reportedly desperate to add a bat.

It's also hard to look at this roster and miss the roles that Anthony, Marcelo Mayer and Kristian Campbell aren't playing. They were meant to be the vanguard of a game-changing hitting lab installed under Breslow. Instead, Anthony is hurt, Mayer has a .600 OPS and Campbell has been banished to the minors for nearly a year.

If one had to find a common explanation for how Bloom and Breslow have turned the 2020s into a wasted decade, where they came from says a lot. Bloom was hired from the Tampa Bay Rays. Breslow came from the Chicago Cubs, who are like the Red Sox in that they stop short of using the full might of their resources.

Clearly, they're guys you hire when you want a job done cheaply first and right second.

They're Not One Big Happy Family Anymore

The Point: Boston is beyond impatient and just plain pissed.

Up until the Curse of the Bambino was broken in 2004, the standard Red Sox fan's mindset was fatalism with a garnish of hope. The fatalism went away for a while, but now it's back with a new garnish.

Hope is out. Outrage is in.

It isn't all about how the 2026 club is 10-21 at Fenway Park, even if that is on track to be Boston's worst home record in 100 years. It's also how many bridges have been burned.

Mookie Betts, Alex Bregman and Rafael Devers—whose trade to San Francisco last June was adequately described as a "s--t show" by one staffer—all went from fan favorites to castoffs. Alex Cora got the boot as manager this April after losing a power struggle with Breslow. Perhaps the real shocker was that beloved Red Sox mainstay Jason Varitek also got canned (much to his wife's dismay).

It would be nice to hear from the man at whose feet the buck stops, but good luck with that. Henry simply doesn't talk to the media. The best anyone has is David Ortiz's word that he is "worried."

Well, that makes Henry and every Red Sox fan under the sun. But at least fans have an idea for what should be done, and it's the same message that has been heard loud and clear at Fenway Park this year: Sell the team.

That can be fans both lashing out and giving good advice. Henry is 76 years old and, for as sour as things have gotten, he should be proud of his legacy. And if he cashes out now, he stands to walk away with billions of dollars.

Whether an ownership change actually happens is anyone's guess. But especially when compared to the teams the Red Sox are fielding, it's worth rooting for.

Stats courtesy of Baseball Reference, FanGraphs and Baseball Savant.