Boston Red Sox Principal Owner John Henry reacts during pre-game ceremonies before a game against the Detroit Tigers
The 2026 Red Sox continue to find themselves in an excessively bizarre situation. On one hand, they’ve looked like a trainwreck on the field; particularly their home field, where they still haven’t won a game at Fenway Park with Chad Tracy at the helm in which the opponent has scored more than one run. Every day, they reach a new depth of futility and do something that hasn’t been done by a Red Sox team since before the television was invented. In short, there’s a large contingent of fans who (probably rightfully) believe the club needs a giant enema.
But I don’t think they’re going to get it, because even after all the toxic waves that have battered the ship, the Red Sox still find themselves a mere 3.5 games out of a playoff spot thanks to the combination of that ridiculous third Wild Card spot, and a historically ghastly American League, where just five teams currently reside over .500. Even crazier, Fangraphs expects that number to drop between now and the end of September, with only four teams (the Yankees, Rays, Guardians and Mariners) projected to finish north of 81 wins.
Combine this landscape with the current temperature inside the walls of Fenway, and some have concluded that Craig Breslow is going to make the Red Sox buyers over the next eight weeks to save his own skin, particularly after John Henry sided with him and dumped Alex Cora at the end of April.
Those thoughts were only further amplified yesterday afternoon when Buster Olney reported on The Just Baseball podcast that the Red Sox were aggressively looking to add a right handed bat. Here’s Tyler Milliken with the quote and the clip:
If it were just Craig Breslow making this push, that would be one thing, but when I hear that the Red Sox are “aggressively” pursuing a right handed hitter and they’re “willing to take on money” to get it done, that has John Henry’s fingerprints all over it. Craig Breslow can mortgage the farm system in a quest to save his own job, but he can’t loosen the purse strings. Only the top dog can change the budget.
So the obvious question is “Why now?”
Well, if I had to guess, I’d say it has everything to do with the enormous Fenway Corners Real Estate project that’s about to get underway in the neighborhood(s) surrounding Fenway Park. (They’ve already started moving the Citgo sign.)
Directly from that link, this project is going to include:
2 million square feet of commercial, residential, retail uses
2 acres of new/improved public open space
1 acre of public open space at the front door to Fenway park through the pedestrianization of Jersey Street
The health of this project is going to be at or near the top of John Henry’s priority list for the foreseeable future, and one of the single biggest things he can do to bolster its success and raise the value of every square foot that’s being developed is to aggressively ensure Red Sox are putting a competitive product on the field.
Think about it: Henry can’t afford to have the Red Sox be the laughing stock they’ve become for most of the post Mookie Betts era if he wants people to pay top dollar for Fenway Corners. The project is categorically more lucrative if the Red Sox are playing good baseball and there are postseason games being played at Fenway Park.
And on that note, there hasn’t been a postseason game at Fenway Park since October of 2021. Couple that with the looming lockout this winter, and there’s a chance that if the Red Sox don’t find a way to get postseason baseball back to Fenway this October, we might not see it again until at least 2028. That is way, way too long to fit into the Fenway Corners timeline, which is supposed to be nearing completion in the fall of that year.
In other words, based on the shots publicly fired in recent days between the MLBPA and the owners, Henry might need the 2026 Red Sox to make a serious run at October. If they do, you can sell it as “we made the playoffs in 2025, then we came back and did it again after a rough start in 2026, and in general were on the up and up.” If the current disaster continues though, then 2025 becomes the anomaly, and the Red Sox could be headed for their longest stretch without a playoff baseball game played at Fenway Park in decades.
Knowing this, it’s also a good time to review John Henry’s history, because when he puts his focus on something, he generally gets results. He did it with soybean futures to make his fortune, he did it in his early days in Boston winning multiple World Series titles, he’s done it with Liverpool in recent years (including a UEFA Champions League title and two Premier League titles since the Red Sox last won it all in 2018), and, most recently, he successfully backed the PGA tour in their war with LIV Golf, which they won.
That last one is important, because not only was it something that had Henry flying all around the world in 2024 to establish a foothold, but it also marks the last time he gave a really informative public quote about where Fenway Sports Group (FSG) is going. And so far, it appears he was telling the truth. Here’s what I consider to be the money passage from a story in the Boston Globe about Henry’s PGA investments from 2024:
Asked how FSG’s investment in the PGA Tour, its first in a sports league, fits within FSG’s growth strategy, Henry initially indicated it could mark the final asset addition.
“It means that we’re not looking to grow at this point,” Henry said. “I hate to say that on the record, but we’ve got our hands full with Boston, Liverpool, this, Pittsburgh [Penguins], NASCAR, real estate.”
Asked how FSG’s investment in the PGA Tour, its first in a sports league, fits within FSG’s growth strategy, Henry initially indicated it could mark the final asset addition.
“It means that we’re not looking to grow at this point,” Henry said. “I hate to say that on the record, but we’ve got our hands full with Boston, Liverpool, this, Pittsburgh [Penguins], NASCAR, real estate.”
Not only has that proven accurate over the last two years (most notably, FSG didn’t pursue the Celtics or another NBA franchise), but they’re also selling the Pittsburgh Penguins for about double the value from when they acquired them in 2021. (That transition of ownership is expected to occur later this month.)
Not only does that give John Henry more cash to play with in the shot-term, but it also means that for the first time in a long time, his primary focus appears to be in Boston. The physical signs are also there: He’s been at just about every Red Sox home game this season, he’s been signing autographs for fans, and he even logged back on to Twitter in the spring to troll Dan Shaughnessy.
In the macro, this is a positive, because one of the worst things to happen to the Red Sox in recent years was them becoming just another line item in John Henry’s portfolio. The pattern is pretty clear: When you’re John Henry’s primary focus, you get his full attention, and you’re usually successful. When you’re just part of John Henry’s empire, you blend into the background and wilt into decay.
Based on recent evidence, it seems the Red Sox are moving back into the foreground due to their obvious role in Fenway Corners, and if you view Buster Olney’s comments through that lens, it’s hard to envision the Red Sox being sellers at this deadline.
You can argue Henry won’t be successful this time, but it’s becoming harder to argue he’s not going to at least try to save the 2026 season.
