The Boston Red Sox managed to put together a strong and resilient campaign this past season, even though they were forced to deal with injuries, inconsistency, and stretches of tough luck. One of the biggest reasons they stayed afloat and ultimately performed at a high level was the presence of Alex Bregman. Now that he has officially entered free agency, the Red Sox find themselves at a crossroads. Of all the decisions they need to make this winter, bringing Bregman back might sit at the very top of the list.
Last offseason, Bregman agreed to a three-year, $120 million contract that included an opt-out clause. After turning in his first All-Star appearance since 2019, he chose to exercise that option and re-enter the market. Although Bregman was consistently productive from 2019 through the end of this season, he was not always the same player who once appeared to be on a superstar trajectory in Houston.
During the 2018 and 2019 seasons—his back-to-back All-Star years with the Astros—Bregman posted a remarkable .970 OPS and was widely considered one of the most dangerous hitters in the American League. Over the following five seasons, however, that OPS dipped to .795, a number that reflected a good hitter but not the elite-level threat he once appeared to be.
This past year represented something of a resurgence. His .821 OPS was not quite at the level of his Houston peak but was a clear improvement compared to his middle-years numbers. It showed that even as he moves into his thirties, Bregman still possesses a strong bat, a polished approach at the plate, and the ability to be a key presence in the heart of the lineup.
That rebound season should help him secure a sizable contract, even if his next deal may not match the annual value he earned under his previous agreement. He may not land the same $40 million per year he just made, but a longer-term deal with a high-total value is well within reach.
In fact, Just Baseball’s most recent free-agent projections—written by Ryan Finkelstein—predicted that Bregman would receive a five-year, $155 million contract from Boston. That projected deal would place him among the highest-paid third basemen in baseball, ranking sixth in overall guaranteed money and fifth in annual salary. It’s a sizable commitment, but if the Red Sox want to stay competitive in the brutal American League East, signing Bregman long-term just might be a necessity.
What makes Bregman so valuable to Boston is not just the middle-of-the-order production. Last season, his leadership left a major impression on both the roster and the organization. He quickly became a cultural anchor, especially for the younger members of the team. According to teammates, Bregman acted almost like a second coach—someone who understood the game at an incredibly advanced level and was willing to share that insight freely.
Red Sox rookie shortstop Marcelo Mayer expressed this sentiment in an interview with The Athletic back in July. Mayer described Bregman as someone who fundamentally changed the way many players prepared on a daily basis. “He’s like a coach, really,” Mayer said. “I can’t really say enough about how much he’s helped not only me and Roman (Anthony), but the whole team. He has people coming in early and watching film, whether that’s me, (Jarren) Duran or whoever it may be. And I think he just sees the game at a super advanced level compared to most people.” Comments like these underscore just how deeply respected Bregman is, not only for his playing ability but also for the intellectual side of his game, which has long been one of his trademarks.
Even though Bregman will turn 32 by the time next season begins, he has demonstrated that he can still perform at a high level. His swing remains compact and powerful, he continues to manage the strike zone well, and he brings an experienced, steady voice into the clubhouse. In a free-agent class with several big names, Bregman stands among the best overall players available—and at a premium position.
Because of that, the Red Sox are unlikely to be the only team interested. Clubs that need infield stability, veteran leadership, or a reliable offensive cornerstone could all enter the bidding. That means Boston may have to defend its turf aggressively if it wants to retain him.
The Red Sox also have to consider the broader landscape of their division. The American League East is loaded with elite players and aggressive front offices. The New York Yankees and Toronto Blue Jays, in particular, have shown a consistent willingness to add stars and spend big when necessary.
Those clubs already have established talent cores and will continue building around them. If the Red Sox hope to keep pace, losing a player of Bregman’s caliber would put them at a clear disadvantage—both on the field and in terms of clubhouse culture.
Keeping Bregman means the Red Sox maintain a high-quality defensive third baseman, a steady and dangerous hitter, and a mentor who lifts the performance of the younger generation. Letting him walk means leaving a significant hole in several areas at once: offense, leadership, and long-term stability. Boston would then have to replace not only his statistical performance but also the intangible leadership qualities he brought—a near-impossible combination to replicate in a single player.
This past season proved that a team can overachieve when it has the right mix of talent and guidance, and Bregman was a key part of that mixture. He represented more than just numbers on a stat sheet. He brought accountability, intensity, and an understanding of winning baseball that permeated the entire roster.
Boston’s front office undoubtedly took note of how the younger players improved around him and how much he elevated the team’s preparation habits. When a player influences the culture that deeply, it becomes extremely difficult to imagine the organization willingly letting him leave.
As the Red Sox prepare for an offseason full of decisions—bolstering the rotation, improving depth, and evaluating long-term extensions—retaining Bregman may be the clearest and most impactful move they can make. He fits the team’s competitive window. He fits the clubhouse environment they are trying to cultivate. And he fits the needs of a club trying to build sustainable success while keeping pace with two big-budget rivals in New York and Toronto.
There is no denying that the next few seasons in the AL East will be fiercely competitive. Every team in the division is seeking upgrades. Every team is scouting free agents carefully. Every team is evaluating how to maximize its roster.
In that environment, losing cornerstone players is risky, and adding new stars is often the difference between contending and falling behind. The Red Sox, having watched firsthand how Bregman impacted their season, should recognize the value of retaining that stability.
In the end, bringing Bregman back is about more than rewarding a productive season. It’s about investing in leadership, in continuity, and in a player whose presence directly improves those around him. For a franchise looking to reestablish itself among baseball’s elite, keeping someone like Bregman is not just a luxury—it may be a necessity.
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