The Boston Red Sox are now in full pivot mode as Alex Bregman won’t be returning to Fenway Park in 2026. It was announced on Saturday night (Jan. 10) that Bregman agreed to a five-year, $175 million contract with the Chicago Cubs. Jeff Passan was first on the news as the Red Sox lost out on another bat this offseason.
Bob Nightengale mentioned a little bit after the news dropped that the deal between Bregman and the Cubs includes a no-trade clause and no opt-outs. Furthermore, the annual average value of the contract is $35M per season.
What makes the news even worse when it comes to Bregman is that the Red Sox traded superstar infielder Rafael Devers to the San Francisco Giants following an internal strife between the player and the organization. Essentially, the Red Sox traded Devers away for a one-year rental of Bregman, and now they are without either player. Chris Cotillo of MassLive later reported that the Red Sox were willing to go to five years but weren’t willing to go to $175M as the Cubs did.
After the initial shock wears off, the next question is: what now?
Red Sox Now In for Bo Bichette?
GettyBo Bichette
Before the Bregman news was announced, chief baseball officer Craig Breslow at Fenway Fest answered some questions about Bregman, without diving into too many details. He stated, “I’m going to be very careful in how I talk about any individual pursuit. We saw the impact that Alex had last year — on the field, in the clubhouse, in the community — and he’s someone that fits our team really well. He’s still out there, which means we have a chance to sign him.”
Since they are now out to sign Bregman, what’s next for the Red Sox? The first name that comes to mind after the Red Sox lost out on Bregman is infielder Bo Bichette. It’s been mentioned multiple times that The Athletic has projected Bichette to sign for eight years, $212 million this offseason. However, if the Red Sox were out on the $175M for Bregman, are they in for over $200M for Bichette?
The only thing that helps in this scenario is that Bichette is 27 years old and is willing to move to second base. His moving to second base has to happen since the Red Sox still have Trevor Story for two more seasons at shortstop. Bichette finished the 2025 season in Toronto with a .311 average in 139 games, with a slash line of .357/.483/.840 and a 129 OPS+. Bichette had 181 hits, 44 doubles, one triple, 18 home runs, 94 RBIs, and a wins above replacement (WAR) of 3.5.
If they don’t go with Bichette, who is another option for the Red Sox to acquire another bat, following the trade for Willson Contreras from the St. Louis Cardinals?
Going Back to the Trade Well?
The other name that comes to mind is St. Louis Cardinals second baseman Brendan Donovan. Like Bichette, he’s a little older at 28 years old, but is someone who could fit in well with the Red Sox. Plus, Donovan is set to make $5.75 million in 2026 and will be a free agent heading into the 2028 season.
Unlike Bichette being a right-handed bat, which the team has mentioned needing, Donovan is a left-handed hitter. However, despite that, he could hit well within the confines of Fenway Park.
Last season with the Cardinals in 2025, Donovan had a .287 average, with 132 hits, 32 doubles, 10 home runs, 50 RBIs, three stolen bases, and 42 walks. He finished with a slashline of .353/.442/.775, along with an OPS+ of 118, and a 2.7 WAR. Breslow has already traded twice with St. Louis this offseason for Sonny Gray and Contreras. Does he go back to the well a third time?
GettyBrendan Donovan of the St. Louis Cardinals
There is another wrinkle to consider if the Red Sox pivot to Bichette or Donovan after losing Bregman. Who plays third base, and do you move on from an outfielder? There is a hole at third base if the Red Sox sign or trade for a second baseman. However, they do have Marcelo Mayer, who played third base last season when Bregman was out. He is capible if playing the position. It’s about going through the growing pains of a young player at the hot corner.
Furthermore, if they sign either of those guys, does that force the Red Sox’s hand to keep Ceddanne Rafaela at center field and trade away another outfielder? The Red Sox have mentioned how they want to play Rafaela in center field, but are willing to move him to second if they keep either Wilyer Abreu and/or Jarren Duran.
The Red Sox have put themselves in a situation where they need to get a second bat, and whether it’ll be a third baseman or a second baseman. After that, it’s about addressing the logjam in the outfield if they don’t play Rafaela at second base if Bichette or Donovan are brought into the fold for 2026. When it comes down to it, the Red Sox gave up Devers for a one-year rental of Bregman and now have to panic pivot to fill in one of two different positions as we get closer to Spring Training next month.
That said, what will the Red Sox do now?
Red Sox Forced to Pivot After Losing Out on Alex Bregman