When a sports team is sold, fans usually have many questions. Three of these questions are usually “will the new owner invest in the team?”, “will the team be relocated?”, and “will the team finally make the playoffs?”. There isn’t always a clear and immediate answer to these questions either. When the Oakland Athletics were sold, fans were hopeful that the proposed stadium at Howard Terminal would be built. However, the new owners decided on a more controversial option, temporarily relocating the team to the home of their Triple-A affiliate in Sacramento for three years while constructing a brand new stadium that will eventually become home to the team upon their final move to Las Vegas. This sounds like a lot, and relocation and loss of a team’s identity are genuine fears amongst any loyal fanbase. Despite this, I believe the Boston Red Sox should be sold.
When a team wins four World Series in the span of fifteen years, ownership is typically considered successful. Sure, the Red Sox won in 2004, 2007, 2013, and 2018, but these did not come without challenges. Only two of these teams had the same manager, a struggle Red Sox fans know all too well. There were also significant shakeups in terms of rosters. In 2007, only seven of the players from the 2004 team remained on the Red Sox. Likewise, only four from the 2007 team were also on the 2013 team, and six from the 2013 team were on the 2018 team. A lack of commitment to the team’s star players has exhausted the fanbase. The 2020 trade that sent Mookie Betts and David Price to the Los Angeles Dodgers was widely viewed as the beginning of the end of an era in Boston, with the definitive end of that era coming in the 2025 trade that sent Rafael Devers to the San Francisco Giants. In 2026, there were no players on the team who were on the World Series-winning team in 2018.
In the years since 2018, the Red Sox have also had trouble even making the playoffs, let alone winning games. They missed the playoffs in 2019 and 2020, then made the playoffs in 2021, only to be eliminated in the ALCS by the Houston Astros.
The Red Sox then missed the playoffs every year from 2022 to 2024, and then made the Wild Card series back to back in 2025 and 2026, only to lose to their direct rivals, the New York Yankees, both times.
Is this an ownership failure? I believe so. As beloved as John Henry and his Chief Baseball Officer, Craig Breslow, are in Boston, it’s time for them both to go.
Henry and Fenway Sports Group have shown that they don’t exactly care about anything other than cutting payroll.
That’s not the mindset you want an owner to have. Yes, promoting players from the farm system saves money, but if they’re not playing well in the big leagues, then the team should be spending money and actually fighting to bring in reinforcements in free agency.
The lack of aggression in free agency is a big issue in particular. In the 2023-24 offseason, the Red Sox had an opportunity to sign superstar two-way player Shohei Ohtani, as well as Yoshinobu Yamamoto, a star pitcher in Japan’s professional league, Nippon Professional Baseball. While taking a chance on a player coming from a foreign league is always a gamble, Yamamoto was always expected to be a star pitcher in the MLB. As for Ohtani, he does have an injury history, but his stats and willingness to play through anything plaguing him proved that he would’ve been worth the money. Instead, the Red Sox made relatively uncompetitive offers, leading both players to go to the Dodgers instead.
In the 2024-25 offseason, the Red Sox made another mistake. The team had an opportunity to sign star pitcher Roki Sasaki, a pitcher so dominant in the NPB that he was given the nickname “The Monster of the Reiwa Era.” In 2022, at the age of 20, Sasaki had gained worldwide attention for throwing a 19-strikeout perfect game, widely considered the best game thrown by a pitcher in the history of professional baseball. The Red Sox failed to make a competitive offer, and Sasaki signed with the Dodgers.
This offseason, the Red Sox have the opportunity to sign numerous top tier free agents, although none of them come without a high price tag, which, in all likelihood, means the team won’t succeed in signing any of them. Tarik Skubal, Randy Arozarena, Jazz Chisholm Jr., and Trent Grisham are among those names, as are Japanese star third baseman Teruaki Sato and Japanese star pitcher Hiromi Itoh, who could make the jump from the NPB to the MLB via the posting system, but there is serious doubt the Red Sox will make offers to any of these players at all, let alone decent ones, given their payroll cuts and lack of commitment to winning.
One theory as to why the Red Sox are cutting payroll is John Henry’s ownership of other pro sports teams. He and Fenway Sports Group own Liverpool F.C., a club in the Premier League, England’s top tier soccer league. Additionally, he and FSG are co-owners of RFK Racing, a NASCAR team that has historically been dominant, but has seen a decline in recent years. With NASCAR seeing a resurgence in the fanbase and the Premier League being the most popular sports league in England, it’s understandable why Henry would want to invest in those more than he has in the past. However, in doing so, he has made an absolute mockery of the team.
In the opinions of fans and critics alike, including myself, John Henry has downplayed the Red Sox’ annual championship expectations, traded star talent and let more walk in free agency, and, to put it lightly, has had a detached ownership style, treating the team more like a financial asset or a corporate spreadsheet and less like what it is: a professional ballclub with a diehard fanbase.
This has irritated many fans, including Boston’s most loyal. As a Sox fan, I am also very irritated with Henry’s ownership.
While I’m trying to remain optimistic about both the short and long-term outlooks of the team, I find it draining to get my hopes up anytime an offer is made in free agency, as it usually ends up falling short. I can’t keep acting like everything is okay with this team, because it isn’t. Something has got to give.
I truly think new ownership would change everything for the better.
Henry has openly stated he won’t sell the team, but I do hope someone can come along and convince him to sell. In the meantime, I say this to the fans: grab your coats and buckle your seatbelts, this offseason’s probably going to be another cold, long, dreadful, and bumpy ride.