Four big moves Red Sox must make before 2026 season originally appeared on NBC Sports Boston
The Boston Red Sox have made a handful of noteworthy moves this offseason, but there’s still plenty of work to be done before the 2026 MLB season begins.
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There are glaring question marks all over the current roster. Chief baseball officer Craig Breslow said it himself: the roster remains “incomplete” after the club’s trades for right-hander Sonny Gray and first baseman Willson Contreras.
So, what moves still must be made for Boston to stay competitive in 2026? Here are four big moves the Red Sox must make before Opening Day.
Re-sign Alex Bregman
Bringing Bregman back was reportedly Boston’s top priority heading into the offseason. Yet, the veteran third baseman is still on the market as we begin the new year.
The Red Sox shouldn’t let the Bregman negotiations drag out much longer. His departure would leave a giant question mark at the hot corner and make the Rafael Devers trade look like an even bigger disaster. And outside of fellow free agent Bo Bichette, there aren’t many enticing fallback options if Bregman signs elsewhere.
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Bregman, who turns 32 in March, is projected to receive a five- or six-year contract worth somewhere in the $150-$170 million range. The Red Sox have been notoriously reluctant to offer such a deal to position players in their 30s, but they should make an exception, as Bregman was key to the club’s success in 2025.
Sign or trade for a second baseman
The second base position has been a revolving door for the Red Sox in recent years. It’s time to stabilize the position with an upgrade that can help fix the less-than-stellar infield defense.
Boston has been linked to Arizona Diamondbacks star Ketel Marte in trade rumors, and he’d be a tremendous addition as both a big bat and a solid defender. Unfortunately, it no longer appears that Arizona plans to deal Marte this offseason. So, how should the Red Sox pivot?
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There are limited options in free agency. Bichette is expected to move from shortstop to second or third base next season, and he’s undoubtedly the most intriguing option. After him, you’re looking at names like Isiah Kiner-Falefa, Luis Arraez, and Willi Castro. Not exactly needle-movers.
If Bichette is off the table, Boston’s best bet is to dip back into the trade market. Perhaps Breslow could land his new second baseman by pulling off yet another deal with his favorite trade partner: the St. Louis Cardinals.
Cardinals utility man Brendan Donovan would be a perfect fit for Boston, but he’d likely cost multiple talented young pitchers.
After acquiring Gray and Contreras in separate deals with St. Louis, the Red Sox could look to pry utility man Brendan Donovan from old friend Chaim Bloom. Donovan is a solid defender with MLB experience at all four infield spots and both corner outfield spots. The 29-year-old is coming off his first All-Star campaign, in which he slashed .287/.353/.422 with 10 homers and 50 RBI.
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Katie Woo of The Athletic recently reported that the Red Sox and Cardinals have discussed a Donovan trade, though no deal was close at the time. Boston would likely have to send more talented young arms to St. Louis, such as left-handed pitching prospects Connelly Early or Payton Tolle. If that’s the asking price, it may be too steep for Breslow and Co.
David Hamilton, Romy Gonzalez, Ceddanne Rafaela, Nick Sogard, and Marcelo Mayer are among the second base options already on the Red Sox’ roster.
Add a left-handed reliever
Veteran closer Aroldis Chapman is currently the only reliable left-handed relief option on the Red Sox’ 40-man roster. With Brennan Bernardino, Steven Matz, Justin Wilson, and Chris Murphy no longer in the mix, adding a southpaw or two to the bullpen should be among Breslow’s priorities.
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Taylor Rogers, Danny Coulombe, Jalen Beeks, and Andrew Chafin are among the top free-agent options still out there. Wilson also remains on the market after a better-than-expected debut season in Boston.
Jovani Moran and Shane Drohan could step up as the Red Sox’ go-to left-handed middle-relief options in 2026, but relying on them without bringing in reinforcements would be far too risky.
Find a solution to the outfield logjam
The Red Sox’ crowded outfield should have been sorted out last offseason, but it’s still an issue as we begin 2026. With Jarren Duran, Wilyer Abreu, Ceddanne Rafaela, and Roman Anthony, Boston has four everyday outfielders on the roster. Masataka Yoshida also factors into the equation as a left fielder/designated hitter.
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Moving Rafaela to second base is a potential solution, though the defense would suffer without his elite glove in center field. Another possible fix is putting Anthony in left, Rafaela in center, and Abreu in right with Duran as the DH, but Yoshida’s presence complicates things.
Given the outfield surplus, Duran and Abreu entered this offseason as obvious trade candidates. Either one could still be moved in a blockbuster deal — Kansas City Royals ace Cole Ragans was a rumored target earlier this winter — but Breslow seems comfortable rolling into the 2026 campaign with his current outfield. That would be a mistake.
