On Sept. 30, the Boston Red Sox’s season came to an end against the New York Yankees in the Bronx. This is the second year in a row in which the Red Sox were eliminated from the post-season by their biggest rivals in enemy territory, and this time they were a lot less competitive.
In the two-game sweep, Boston’s bats went completely silent, only yielding a combined seven total hits compared to New York’s 26. The pitching was poor as well, but this can be attributed to decisions made by newly extended manager Chad Tracy, who decided to pull starting pitchers Payton Tolle and Sonny Gray early into their respective games. The bullpen, which — in fairness — had otherwise been good in the regular season, was subsequently run down by New York in both games.
The sour end to Boston’s season feels all too familiar, and not just because of last season’s results. Since the 2021 MLB playoffs, where they fell just short of a World Series appearance with a loss to the Houston Astros in the ALCS, every Red Sox season has mainly proceeded in the same way. Analyzing Baseball Almanac’s monthly game splits per year allows an effective way to visualize this.
They typically have a slow start to the season. Between the months of March, April and May, Boston averaged a winning percentage of 0.474. In the summer months of June and July the Red Sox tend to catch fire, improving their winning percentage to 0.580. For reference, this is equal to the full season winning percentage of the 2026 Atlanta Braves. In August and beyond, which is arguably the most important section of the season, the team returned to an average winning percentage of 0.482.
Clearly, for the past five years, the Boston Red Sox have put fans through a spin cycle throughout the seasons. The poor starts followed by major improvement during the summer renews feelings of hope in the franchise having a solid postseason run or even building towards something for the future. Unfortunately, the team continuously recedes to playing poorly in the final stretch of the season, leaving everyone with doubts on how to proceed.
It’s a strange way for a team to stagnate over the course of a half-decade, and it’s difficult to parse why this occurs. If Boston started slow but finished strong every season, certain conclusions regarding rookie development or mid-season adjustments could be drawn.
The oscillation in performance seen over the course of five seasons, however, is a bit inexplicable. Of course, it’s entirely possible that the past few seasons can be explained away by statistical variance that comes from things like injuries, the schedule or just the nature of the sport.
What’s stark, however, is that it’s difficult to find another team that has had a similar performance over any similarly long stretch, at least without a deep analysis of every team’s recent history. That realization dampers any explanations based on a reasonable amount of variance. The Boston Red Sox are in an incomprehensible league of their own, and not in a good way.
Instead of trying to explain the recurring shape in which the stagnation occurs, understanding why no major improvement or changes have been seen with the team since their 2021 ALCS run may be more worthwhile. In that regard, it’s rather simple to find an explanation within the team’s front office and broader Fenway Sports Group (FSG), which owns the team.
Player mismanagement has been the largest source of criticism of the Red Sox’s front office. One of the best examples of this can be seen from the handling of power hitters Rafael Devers and Alex Bregman.
It started with poor communication between Devers and management at the beginning of 2025 over his position on the team. In the middle of the same season, he was traded to the San Francisco Giants in exchange for a poor return.
Tangentially, in the aftermath of the trade, sports journalist Joon Lee revealed how dysfunctional the front office has been under chief baseball officer Craig Breslow. These problems still persist a year later, hinted at by statements made by first baseman Willson Contreras following the Wild Card sweep regarding over-use of analytics, something Breslow champions.
Though the Devers trade outraged many at the time, it could be justified given that it took the Red Sox off Dever’s contract, which made room to pay for Bregman in the offseason. It therefore was a major surprise when the Red Sox failed to get a deal done as Bregman signed with the Chicago Cubs instead. The team started 2025 with a choice of two big hitters and entered 2026 without either of them.
The whole saga illustrates just one example of failure to retain any veteran talent that comes to the club, either via the farm system or the open market, and illuminates systemic problems within the organization.
Some of this may be blamed on those directly in the front office like Breslow, but some journalists and analysts (along with many fans) place the blame squarely on team owner John Henry. Many believe he refuses to operate the Red Sox like a big market team, so the end result is continual underperformance, but not to the point that fans abandon the team.
With Henry having no intentions to sell the Red Sox, longtime FSG CEO Sam Kennedy still heading the team after an entire decade, and the upcoming CBA negotiations, it’s hard to see if this mentality will change in the future. Fans may have to come to terms with the fact that an organization that should be primed for success is otherwise stuck in a rollercoaster of inconsistent play and empty promises.