Boston Red Sox Eye Major Trades for the 2026 Season
The Boston Red Sox ended their three-year postseason drought in 2025, but the team’s management is well aware that sustained success will require more than just a short-term fix. Despite the significant acquisition of veteran right-hander Sonny Gray from the St. Louis Cardinals, the Red Sox’s front office, led by Chief Baseball Officer Craig Breslow, must continue to bolster the roster to be taken seriously as a World Series contender. As the 2026 Winter Meetings loom, the Red Sox have several critical needs to address, including fortifying their starting rotation and stabilizing the second base position.
Potential Trade Targets: Strengthening the Pitching Rotation
One of the most pressing needs for the Red Sox is to acquire another frontline starting pitcher to complement Sonny Gray and the existing rotation. Joe Ryan, the 29-year-old right-hander from the Minnesota Twins, is a name constantly linked to Boston in trade rumors. Ryan has been a consistent performer since his 2021 rookie season, reaching a new level in 2025 with a career-best 3.42 ERA, 1.035 WHIP, and 194 strikeouts in 31 games. His performance earned him his first All-Star nod. With the Twins potentially undergoing a rebuild, now might be the right time for the Red Sox to revisit trade talks. Adding Ryan to the rotation would require a significant trade package, but his potential as a true No. 2 starter makes him a top target for Breslow.
Another intriguing option is Cole Ragans, the left-handed ace of the Kansas City Royals. Ragans, who turns 28 this winter, was an All-Star in 2024 and finished fourth in the American League Cy Young voting that year. Despite injuries limiting him to 13 starts in 2025, his underlying numbers (2.50 FIP and 14.3 strikeouts per nine innings) suggest that his Cy Young-caliber talent remains intact. If the Royals are willing to trade Ragans for outfield help, Breslow should strongly consider offering prospects like Jarren Duran or Wilyer Abreu. Ragans is under team control through 2028, making him a long-term asset for Boston.
Affordable Options and Depth Additions
For a more affordable starting pitcher, Freddy Peralta of the Milwaukee Brewers could be an attractive option. Peralta, also 29, enters his contract year and has been a trusted arm in Milwaukee’s rotation since 2018. He had his best season in 2025, posting a 2.70 ERA and 1.075 WHIP with 204 strikeouts in 33 starts. Peralta earned his second All-Star nod and finished fifth in the National League Cy Young race. While he might not command as high a price as Ryan or Ragans, his performance and experience would provide a solid addition to the Red Sox’s rotation.
Stabilizing the Second Base Position
The Red Sox have struggled to find a reliable everyday second baseman, with six players filling the position in 2025 and 11 in 2024. Ketel Marte of the Arizona Diamondbacks stands out as a potential solution. Marte, 32, has been one of the game’s best hitters over the past three years, including two All-Star seasons in 2024 and 2025. Last year, he slashed .283/.376/.517 with 28 homers and 72 RBI. While acquiring Marte would require a significant trade package, his production and consistency make him a worthwhile target. The Diamondbacks, looking to trade Marte for young pitching, present an opportunity for Boston to secure a cornerstone player.
Versatile Options and Depth
A more realistic and affordable alternative to Marte is Brendan Donovan of the St. Louis Cardinals. Donovan, who turns 29 next month, has been a model of consistency since entering the league in 2022. He provides the Red Sox with a super utility man capable of playing second base, other infield positions, and both corner outfield spots. Donovan can be expected to contribute 10 to 15 home runs with an OPS in the high 700s, along with solid defense. With the Cardinals likely to deal Donovan as ex-Red Sox CBO Chaim Bloom continues to retool the roster, Breslow should inquire about making his second significant trade with St. Louis this offseason.
Final Thoughts: Preparing for the Winter Meetings
As the Red Sox prepare for the 2026 Winter Meetings, the organization has a clear set of priorities: strengthening the starting rotation and stabilizing the second base position. With several intriguing trade targets available, the front office must be aggressive in pursuing deals that will position the Red Sox for sustained success in the coming years. Whether it’s landing a frontline starter like Joe Ryan or securing a versatile player like Brendan Donovan, the Red Sox have the opportunity to make impactful moves this winter. The success of these trades could very well determine whether the Red Sox are merely competitive or true World Series contenders.
