The Continued Enshittification of the Boston Red Sox

Hey, Fenway Sports Group, stop telling me to be patient.

Photo by Osman Rana on Unsplash

Last year the hard-working staff here at Drezner’s World vented its considerable frustration with the ownership group and management team of the Boston Red Sox. I suggested that everything ownership had done since winning the 2018 World Series seemed to embody Cory Doctorow’s enshittification thesis. I concluded, “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.”

The 2024 season and the first two months of the 2025 season seemed to bolster my thesis. The 2024 team finished 81-81, the epitome of mediocrity.

During the last offseason, it seemed that management had gotten the message. Chief Baseball Officer Craig Breslow traded for ace Garrett Crochet and signed Alex Bregman, Walker Beuhler, and Aroldis Chapman as free agents. A crop of young talent — including Kristian Campbell, Marcelo Meyer, and Roman Anthony — were on the cusp of joining the major league franchise. One could see a promising future. But a rash of pitcher and position player injuries gutted the roster, leading to the team being five games under .500 in May.

Still, credit where due, the team bounced back this month, winning two series against the Yankees and one against the Rays. The team’s bad luck in one-run games suggested a record that was not indicative of the talent on the roster. Maybe, just maybe, the team was poised to make a postseason run.

That run might still happen — but it would have to be in spite of management accelerating the enshittification process.

On Sunday, after a sweep of the Yankees, the Red Sox pulled the trigger on the most shocking sports trade since the Dallas Mavericks gifted Luka Dončić to the Los Angeles Lakers. According to MLB Trade Rumors’ Nick Deeds:

In a shocking mid-June blockbuster, the Giants have acquired star slugger Rafael Devers from the Red Sox in exchange for right-hander Jordan Hicks, left-hander Kyle Harrison, outfield/first base prospect James Tibbs and right-handed pitching prospect Jose Bello. The teams subsequently announced the trade, and the Red Sox optioned Harrison to Triple-A Worcester. The Giants will absorb the remainder of Devers’s contract in its entirety as part of the deal.

It’s a stunning move that will have massive implications for both franchises as they both pursue their first playoff appearances since 2021 this year. The Red Sox, 37-36 after sweeping the division-leading Yankees this weekend, part with a player they signed to be the next face of their franchise just two years ago. The relationship between the two sides broke down quite publicly over the past few months, however. Devers has long made clear that he wants to play third base on a regular basis, but the Red Sox clearly had other plans this offseason as they sought to add a big right-handed bat to their lineup. After discussing a deal that would’ve sent Nolan Arenado to Boston with the Cardinals earlier in the winter, they ultimately pivoted and signed Alex Bregman to a three-year, $120MM pact that affords him the opportunity to opt out following the 2025 and ’26 seasons.

That proved to be the end of Devers’ time at third base, and though he initially resisted the move he eventually took up his new role as Boston’s regular DH. That seemed to settle the controversy at first despite reports that indicated Devers considered asking for a trade after the Bregman deal, but tensions erupted once again when Triston Casas was sidelined by knee surgery that will likely end his 2025 season. At that time, Chief Baseball Officer Craig Breslow asked Devers to move to first base to cover for the loss of Casas, a move that would have opened up DH at-bats for another player such as top prospect Roman Anthony. Devers refused and expressed frustration with team leadership for asking him to move to an unfamiliar position in the middle of the season, ultimately leading to a private meeting between Devers, manager Alex Cora, and club owner John Henry last month.

In evaluating the trade, Deeds notes, “it’s unclear how [the Red Sox] will replace Devers in their lineup in the short-term.” That sentence is a variation on a larger theme: baseball observers grading this trade poorly for the Red Sox. Consider the following assessments:

• ESPN’s David Schoenfield: “The Red Sox have been hard to understand for years now, since the Betts trade, operating more like a mid-major market than the team that had the highest payroll in the majors in 2018 and 2019…. when you're looking to trade a player because of a broken relationship, it's hard to get fair value in return -- and it seems as if the Red Sox came up short here. Maybe this will prove to be the best move for the organization in the long run, but Boston's playoff hopes for 2025 take a hit.”

• The Athletic’s Keith Law: “The Red Sox get some value back, certainly, but nowhere near enough to justify offloading Devers’ contract while the team is ostensibly trying to contend this year…. I don’t think this deal adequately addresses their run-prevention issues. They’re already on the fringes of contention as it is; this could push them out of it entirely.”

• SBNation’s Mark Schoefield: “If [Red Sox fans] seem a little scarred, can you blame them? Just a few years after seeing the organization trade away Mookie Betts, the Red Sox fan in your life has now seen Boston ship off Devers, the latest big-ticket bat in the middle of their lineup.

• The Ringer’s Ben Lindbergh: “Once again, the Sox seem to be testing how many faces a franchise can shed before it destroys its identity…. few franchises have squandered long-standing success and goodwill as thoroughly as [John] Henry’s has since 2018.”

• The Athletic’s Ken Rosenthal: “The only question that matters, in the wake of the Boston Red Sox showing Rafael Devers who’s the boss, is this: Are the Sox a better team? For 2025, it’s difficult to imagine the answer is yes.”

To be fair, a healthy number of baseball execs told The Athletic’s Brittany Ghiroli that they could understand the deal from the perspective of the Red Sox. Boston unloaded a massive contract of an aggrieved player with minimal defensive value who was making it hard for them to play their young talent. They got something of value in return.

And yet, hearing Craig Breslow struggle to explain management’s thinking in pulling the trigger on this trade was painful. He acknowledged, “The timing was absolutely not great” and then had some difficulty answering the question of whether the trade would make the Red Sox a better team this year:

Yeah, it's a good question, and I understand why the initial reaction would be that. It’d be tough to sit here and say when you move a player of Raffy’s caliber, when you take that bat out of the lineup, how could I sit here and say that we're a better team?

I acknowledge that on paper, we’re not going to have the same lineup that we did. But this isn't about the game that is played on paper. This is about the game that's played on the field, and ultimately about winning the most games that we can. In order to do that, we are trying to put together the most functional and complete team that we can.

In isolation, maybe Breslow could have been more persuasive. Showing some patience as the Red Sox’s younger talent starts to blossom might make long-term sense. I might have been willing to go along if this was about the team maintaining its long-term competitiveness.

But the Fenway Sports Group burned through their goodwill a long time ago. In the seven years since winning their last World Series, the Red Sox have only made the playoffs once while losing the core of that team — Mookie Betts, Xander Bogaerts, and now Devers — to National League West teams. Devers felt aggrieved in no small part because Breslow and company dicked him around this offseason, eventually signing someone to replace him at third base. Breslow acknowledged at the press conference that his communication with Devers had been suboptimal during the offseason.

In other words, it was the Red Sox management team that degraded Devers’ value to the point where they were selling a bit low. That seems like the opposite of Moneyball to me. It makes it hard to give the Red Sox the benefit of the doubt.

I hope I am proven wrong and that the Red Sox continue their recent winning ways. It would be nice to watch the Red Sox play meaningful games in September and October. Their recent track record, however, suggests a team more concerned with minimizing its budget than maximizing its talent on the field.

So excuse me if I watch this video of Raffy Devers’ career highlights with the Red Sox — it will remind me of better times.¹

1. The hardest I have ever laughed watching a baseball game was when Devers homered off of Aroldis Chapman, shocking everyone in Yankee Stadium.