What’s next for the Red Sox following Bregman's surprising deal with the Cubs?
BOSTON -- For the second consecutive winter, Alex Bregman has been a prominent subject of discussion at Fenway Fest, even though he wasn’t physically present this time.
As the annual event wrapped up on Saturday, it became clear that Bregman’s next appearance at Fenway Park will be during the final series of the 2026 regular season when the Red Sox are set to host the Chicago Cubs, which is a matchup that fans are already looking forward to.
Indeed, the Cubs.
After a day filled with optimism from chief baseball officer Craig Breslow, manager Alex Cora, and various players, all hoping for Bregman's return to Boston, news broke that he had instead chosen to sign a five-year, $175 million contract with the Cubs, as reported by MLB.com’s Mark Feinsand.
Now, the Red Sox find themselves needing to reassess their strategy. Earlier in the offseason, they managed to acquire first baseman Willson Contreras just before Christmas, but they were still in pursuit of another impactful right-handed bat to complement their lineup. With Bregman now off the market, they must quickly adapt.
One potential target is infielder Bo Bichette, who is currently the top free agent available. However, interest in him has been on the rise lately, with the Philadelphia Phillies being the latest team linked to him.
Could the Red Sox consider making a more substantial offer to the 27-year-old Bichette compared to the reportedly “aggressive offer” they previously extended to the 31-year-old Bregman? Under the ownership of John Henry, the Red Sox have typically been cautious about committing significant funds to players who are in their thirties.
Interestingly, Bichette, primarily a shortstop, has indicated he would be open to transitioning to second base. This position would suit the Red Sox well, as Trevor Story is already locked in at shortstop for the next two years.
With Bregman’s departure, there now lies an opportunity for Marcelo Mayer, the fourth overall pick in the 2021 draft, who made his Red Sox debut last season but ended his campaign early due to a right wrist injury. Mayer expressed on Saturday that he is preparing himself mentally and physically to play either second or third base, depending on how the rest of the roster shapes up.
Bo Bichette's father, Dante, concluded his own noteworthy career with the Red Sox in the 2000-01 seasons. In fact, Bo’s parents met at a Gold’s Gym located just behind the iconic Green Monster. If the Red Sox secure Bichette, he could potentially take aim at that famous wall for the years to come.
In terms of performance, Bichette has played 35 games at Fenway, boasting an impressive batting average of .329, with a .382 on-base percentage and .524 slugging percentage, along with six home runs and 30 RBIs.
Another option on the free-agent market is third baseman Eugenio Suárez, who profiles as a raw power hitter, showcasing a batting average of .228, with 49 home runs and 118 RBIs last season.
Alternatively, the Red Sox might look to acquire a player who excels more as a contact hitter rather than solely focusing on power. Two trade candidates that could fit this description include Brendan Donovan from the Cardinals and Nico Hoerner from the Cubs. Donovan is a left-handed hitter, whereas Hoerner swings from the right side, which could help balance a Red Sox lineup that currently leans heavily towards left-handed bats.
Before news of Bregman’s signing broke, Breslow stated that he preferred to explore free agency to finalize the lineup, having already executed several trades over the past two winters while being mindful of the team's organizational depth. Yet, true to his nature, he did not dismiss other possibilities.
"It’s really difficult to predict how other teams will act. There are still quality players on rosters that are likely to be traded," Breslow remarked.
As for the relationship between Boston and Bregman, this chapter closes a lengthy saga that began last offseason when the club spent considerable time tracking his free-agent status, ultimately signing him to a three-year, $120 million deal (including deferred payments) that featured two opt-out clauses just days before Spring Training commenced.
Following a strong performance during his time with the Red Sox, Bregman quickly opted out in November. With no qualifying offer attached to him this offseason, Bregman’s agent, Scott Boras, felt optimistic that his client would land a long-term contract, a feat that eluded him the previous winter. The Cubs, who had also shown interest in Bregman last offseason, successfully secured him this time around.
The Red Sox recently submitted an offer they believed could close the deal.
"The ball is in his court," Cora commented earlier on Saturday. "We’ve been collaborating to see what unfolds, but this offseason feels distinctly different for Alex."
After a successful 2025 season where the Red Sox made a return to the postseason for the first time since 2021, only to be ousted by the Yankees in Game 3 of the American League Wild Card Series, the team’s objective remains a deep playoff run. Adding one more solid bat could be crucial in achieving that goal.
“Our fans ultimately desire exactly what we desire,” stated Sam Kennedy, president/CEO of the Red Sox. “We are obligated to deliver that, which means reaching the playoffs and succeeding in October. Nobody celebrates merely reaching a Wild Card Series.”
Cora urged fans to remain patient.
"The offseason is far from over—based on my experience," Cora remarked. "J.D. Martinez joined us a week into camp in 2018 and made a significant impact. Alex arrived last year on the final day before reporting and was a game-changer. So we’ll see how things unfold in the upcoming weeks."
Breslow is at the forefront of finalizing what is shaping up to be a formidable roster.
"As evidenced by the fact that it’s January 10 and many talented free agents are still available, it appears the market is progressing slowly and thoughtfully," Breslow noted. "At this juncture, we remain engaged. As I have consistently stated: We will do everything possible to enhance our roster."
This situation raises important questions: How do you feel about the Red Sox's decision-making process regarding player acquisitions? Do you think they should pursue Bichette aggressively, or explore trade options instead? Let your thoughts be known in the comments!
