The Creeping Enshittification of the Boston Red Sox

The greatest ownership team in Boston Red Sox history seems determined to also become the worst ownership team in Boston Red Sox history.

Photo by Yassine Khalfalli on Unsplash

Last year Cory Doctorow coined the term “enshittification” to describe how Internet platforms like Facebook and Google were getting objectively worse in terms of the services they provided. He elaborated his argument recently in the Financial Times: “It’s a three-stage process: first, platforms are good to their users. Then they abuse their users to make things better for their business customers. Finally, they abuse those business customers to claw back all the value for themselves. Then, there is a fourth stage: they die.”

As I was reading Doctorow’s essay — and it’s a compelling read — my mind kept wandering to a possible non-Internet example of enshittification: my beloved Boston Red Sox.

John Henry led the purchase of the Boston Red Sox in 2002, and as a result they have been the most successful baseball franchise in this century. They have won four World Series titles, including an epic, curse-ending, down from 0-3-against-the-New-York-Yankees victory in the 2004 American League Championship Series. Henry’s ownership group completely refurbished Fenway Park in the process. The last Red Sox World Series team, in 2018, represented the culmination of excellent management, as a combination of talented home-grown players, high-priced free agent signings, and savvy trades created a 108-win season ending in a World Series.

So why am I throwing around the word “enshittification” when talking about the Red Sox? It’s mostly due to everything that has happened since that 2018 World Series.

The 2019 team underperformed, causing Henry to fire Dave Dombrowski and bring in wunderkind Chaim Bloom to right the ship. To be fair to Bloom, he inherited a team with a bloated payroll and a bereft farm system. Bloom responded with successes in small trades and rebuilding the farm system. Fangraphs currently gives the Red Sox five prospects in their top 100 ranking, which is pretty good! Their young major-league talent like first baseman Triston Casas and pitcher Brayan Bello are also encouraging.

In the end, however, Bloom’s time running the team will be known for two things:

1. The Red Sox finishing dead last in the AL East in three out of his four seasons;

2. Bloom trading Mookie Betts to the Dodgers for… let’s say an “underwhelming” return.

With Bloom’s firing in late 2023 and the hiring of Craig Breslow as the new head of baseball operations, it seemed ownership has decided to shake off their collective torpor and re-dedicate themselves to putting a winning team on the field. When Breslow was introduced to the media back in November, Red Sox chairman Tom Wener told the press, “We’re going to have to be full throttle in every possible way.” In January, Red Sox team president Sam Kennedy said, “I can tell you, 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.”

Fair enough! So with spring training now under way, how has that “full throttle” Red Sox offseason gone? Let’s just go to MLB Trade Rumors’ Darragh McDonald:

The club has been searching for starting pitching all winter and hasn’t really found it. They did sign Lucas Giolito but also traded away Chris Sale, leaving them roughly where they started. One might argue that Giolito is an upgrade on Sale but that substitution doesn’t address the overall depth.

The Red Sox have also been quieter than some other traditional big spenders. While clubs like the Yankees and Dodgers are well beyond the fourth and final luxury tax tier, the Sox aren’t even above the lowest threshold of $237MM. Boston’s competitive balance tax figure is at $202MM, per Roster Resource, which gives them plenty of room to theoretically make a big splash and still avoid the tax. Some other clubs like the Padres, Rangers, Mariners and Twins seem to be operating with diminished spending capacity this winter due to uncertainty in their TV revenue situations.

All that could perhaps put the Red Sox in a position to strike, but there are also reasons to suspect it won’t happen. The club’s president Sam Kennedy was recently present as Spring Training facilities and spoke to the media, with Christopher Smith of MassLive relaying some video. “We have set parameters for him,” Kennedy said in response to a question about whether chief baseball officer Craig Breslow has a hard budget. “He’s operating under those parameters.” He declined to elaborate with specifics.

Anyone who follows baseball knows that winning the offseason does not necessarily translate to winning on the diamond. But the 2023 version of this team finished in last place, and they obviously needed some quality pitching real bad. And yet they have basically treaded water in that department.

Needless to say, the fan base ain’t happy. I have read SBNation’s Over the Monster (OTM) for quite a long time now, and they have usually been pretty bullish on the Red Sox even during the lean years. But over the last month of so they have been pissed, man. Here’s OTM’s Jake Devereaux from last month:

At this past week’s Winter Weekend, Sam Kennedy and Tom Werner tried their best to enter into damage control mode. The fanbase (at least those of us who are realists) is frothing at the mouth with anger over the lack of spending. The fans demanded to know how this roster reflects Werner’s “Full Throttle” offseason and how the team can possibly justify the highest ticket prices in the game. For the first time we finally got some honest answers.

Werner, in his own words, admitted what we had long assumed: Fenway is a tourist trap that will make money regardless what type of team is on the field. Kennedy, in a moment of lucidity, breaking from his programming, even said that the team’s payroll was likely to be even lower than last year. No longer do we need to pull out our hair at why the Red Sox aren’t signing such obvious fits as left hander Jordan Montgomery and right-handed power bat Jorge Soler, this team isn’t really trying to win so much as they are trying to make money.

As depressing as these answers were to hear, it was refreshing to finally get the truth, rather than just spin meant to deceive the idiots among us.

Or Matthew Gross, comparing John Henry to — gulp — Harry Frazee, the Red Sox owner who sold Babe Ruth to the New York Yankees:

Once again, after starting the century off as the best franchise in the sport, the operation appears to be getting stripped to the ground because the owner wants to use the ballclub as a mechanism to funnel cash into his other ventures. Namely Fenway Sports Group (FSG) and all the features that come along with that bloated conglomerate….

In one sense, Henry’s actions make perfect sense from the perspective of a billionaire. (Just keep growing that portfolio baby!) But on another, far more important and longer lasting scale, Henry’s actions are mind boggling. Without following in Frazee’s footsteps, Henry has a chance to be known as the man whole piled up so many championships in Boston during his few decades as leader of the club that they ultimately couldn’t be caught in the battle for the team of the century. Just like they were 100 years ago, the Red Sox are leading the pack in that race right now….

Instead, he’s penning his own Flowers for Algernon story with the Red Sox as the test subject. He’s exposing himself to the ideology of a cancer cell, where nothing matters except the endless growth of his mismatched empire, where he leaves only a soulless corpse behind where the once vibrant original host stood. He’s leaving his legacy vulnerable to become Harry Effing Frazee!

Maybe being a billionaire just breaks your brain. Maybe the money consumes you with such a tight grip that you’re unable to see the importance of anything else in the world. But wow is it hard for me to conceive that anybody who’s soared to the heights Henry has in this sport would jeopardize their legacy the way he’s doing now. True madness!

The overwhelming consensus at OTM is that ownership could be doing more. But they’re just sports bloggers, right? Surely those in the know have different opinio— oh, wait, former Red Sox All-Star Dustin Pedroia agrees with them? And current closer Kenley Jansen saying, “it’s definitely frustrating watching how things go, but it’s not in our control.” And All-Star Rafael Devers pretty much saying the same thing? Never mind.

It is difficult not to conclude that the Fenway Sports Group is enshittifying the Boston Red Sox in order to increase profits. I would be willing to pay John Henry some money for him to prove me wrong. The problem is that it’s less money than he could make from enshittifying the Red Sox.