The Boston Red Sox have been active on the trade market this offseason, acquiring right-handers Sonny Gray and Johan Oviedo. At the same time, with Boston coming off a Wild Card Series loss to the New York Yankees – in what was its first appearance in the playoffs since 2021 – there's still boxes for the Red Sox to check across the board.
Here are three MLB free agents Boston should sign.
LHP Andrew Chafin
Andrew Chafin has pitched for eight teams over his 12-year MLB career. (Photo by Ric Tapia/Getty Images)
2025 Stats: 2.41 ERA, 1.43 WHIP, 36 strikeouts, 177 ERA+, 0.8 wins above replacement (33.2 innings pitched)
Yes, Boston's bullpen was second in MLB with a collective 3.41 ERA last season, but with veteran Justin Wilson (3.35 ERA in 61 appearances in 2025) on the open market, the Red Sox could use another left-hander. Enter Chafin.
Despite constantly changing teams – Chafin has been with eight clubs in the last six years – the 35-year-old continues to survive in the big leagues. He posts strikeouts at a high clip, can put away hitters and evades damage. Chafin does so with a consistent three-pitch arsenal: sinker, slider and four-seamer.
Joining forces with closer Aroldis Chapman, Greg Weissert and Garrett Whitlock, Chafin would solidify the back end of Boston's bullpen, which would be a unit that could rival any in the sport. Plus, Chafin should be attainable at a low rate on a one-to-two-year deal.
Chafin adds veteran pedigree and a pitcher who's still among the best left-handed relievers in the sport to any bullpen he joins. What team wouldn't want that, especially an aspiring contender like a Red Sox?
RHP Zac Gallen
Zac Gallen helped the Diamondbacks reach the World Series for the first time in 22 years in 2023. (Photo by Norm Hall/Getty Images)
2025 Stats: 4.83 ERA, 1.26 WHIP, 175 strikeouts, 89 ERA+, 1.1 wins above replacement (192 innings pitched)
The Red Sox held their own on the starting pitching front in 2025, posting a 3.92 ERA (12th in MLB), and the additions of both Gray and Oviedo are promising ones. That said, these acquisitions, by no means, preclude Boston from adding another starting pitcher – and signing Gallen would be a haymaker swing.
Sure, Gallen is coming off arguably the worst season of his career, as the right-hander posted a career-high 4.83 ERA. At the same time, this is a top-of-the-rotation force in the prime of his career. The 30-year-old Gallen, who leans on his four-seamer while traditionally mixing in a knuckle curve and changeup, pitches deep into games, gets hitters to bite at his low-to-mid-90s offerings and has been the backbone of the Arizona Diamondbacks' pitching staff since his 2019 arrival. From 2022-24, Gallen recorded a combined 3.20 ERA, 1.09 WHIP and 4.1 wins above replacement per season across 93 regular-season starts, highlighted by helping Arizona reach the 2023 World Series.
Garrett Crochet (2.59 ERA, 1.03 WHIP and AL-high 255 strikeouts in 205.1 innings pitched in 2025) was a force to be reckoned with and the runner-up for the 2025 AL Cy Young Award, and Brayan Bello (3.35 ERA in 2025) has come into his own. Despite this, Boston's rotation was still 20th in MLB in WHIP (1.31) and tied for 21st in opponent batting average (.252), while Lucas Giolito is a free agent (3.41 ERA in 26 starts in 2025); there's room for another proven starting pitcher.
Gallen would move Boston's rotation into the upper echelon of the AL, if not MLB as a whole.
3B Alex Bregman
Alex Bregman won two World Series with the Astros across his nine seasons with the franchise (2017 and 2022) before signing with the Red Sox last offseason. (Photo by Matt Dirksen/Getty Images)
2025 Stats: 18 home runs, 62 RBIs, 128 OPS+, 3.5 wins above replacement, .273/.360/.462 slash line (433 at-bats)
Yes, Boston could let Bregman walk and make esteemed infielder Marcelo Mayer its everyday third baseman. Or, it could retain Bregman on a short-term deal and have Mayer start at either second base or shortstop – which would move Trevor Story to second base – or serve as Boston's first infielder off the bench. Having Bregman back gives the Red Sox the best chance to contend for the AL pennant.
Bregman's 2025 campaign with the Red Sox was limited to 114 games due to a quad injury and muddled in the drama that surrounded which position star third baseman Rafael Devers was playing, which ended with the homegrown star being traded to the San Francisco Giants.
Bregman, a 2024 Gold Glover, is a rock at third base who could serve as a veteran complement, both at the hot corner and in Alex Cora's everyday lineup, to an emerging young nucleus for the Red Sox that includes Mayer and outfielder Roman Anthony, among others. While the Red Sox sport a productive offensive unit, they also lacked a bit in the power department last season, as they were just 15th in MLB in home runs (186). Wouldn't losing a proven slugger who's an extra-base hitting machine like Bregman only worsen them in that regard? Plus, Bregman, who previously won two World Series with the Houston Astros, has been in the playoffs in each of the last nine seasons.
Bregman is an impact hitter with a crisp, level swing from the right side who's accustomed to postseason play. He improved Boston's infield defense and is arguably its best all-around position player. The two sides are better together than apart.
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