Red Sox May Trade Top Pitchers to Fill Alex Bregman Void

The Boston Red Sox face a pressing challenge as they seek to replace Alex Bregman, who recently signed with the Chicago Cubs on a lucrative five-year, $175 million contract. With Bregman gone and Eugenio Suarez lost to the Cincinnati Reds via a one-year $15 million deal, the Red Sox are exploring options to fill the third base position before the 2026 season begins. Their interest in Cubs infielder Matt Shaw may lead to significant moves involving some of Boston’s top pitching prospects.

Potential Trade Talks with Chicago Cubs for Matt Shaw

The Red Sox are considering a trade involving pitching prospects Payton Tolle and Connelly Early to acquire Matt Shaw, a utility infielder from the Cubs. Robbie Hyde explained the Cubs’ internal dilemma:

“They have a bit of a conundrum there in Chicago, depending on how you look at it. You got Bregman at 3rd base, you got Hoerner at 2nd base, and then you got Matt Shaw, who had some ups and downs last year. Looked really good at times. Had to make some adjustments along the way. Has made some adjustments this past offseason as well. But with Shaw very up and down year, last year, but more so right now, looking at a utility role unless someone goes down, with an injury or whatever it may be.”

Hyde also noted the Cubs might retain both Hoerner and Shaw but considered Shaw likely to fit best in a backup or utility role given the presence of Bregman and Hoerner.

Shaw’s inconsistent performance last season—beginning with a .172 batting average in his first 18 games—resulted in a demotion to Triple-A. Although he improved during the latter half of the season through adjustments in his mechanics and defensive approach, the Cubs appear uncertain about his role in their future lineup. This uncertainty makes Shaw a possible trade candidate for Boston, especially as the Red Sox seek capable players for their third base vacancy.

Alex Bregman
Image of: Alex Bregman

Chicago Cubs’ Infield Strength and Player Value

Chicago’s infield features two exceptional defenders: Nico Hoerner at second base and Alex Bregman at third. Hoerner delivered a memorable defensive play last October during the NLDS Game 3 against the Milwaukee Brewers, snagging a 107.3 mph line drive from Christian Yelich to preserve crucial outs. Offensively, Hoerner has demonstrated consistent ability, highlighted by a three-run homer off Carson Wisenhunt and a strong overall performance that earned him a second Gold Glove Award last season. Hyde emphasized Hoerner’s value:

“Now, Hoerner, you’d have to give up a pretty good amount for him. Even though it’s only a one-year rental, he was in the top 20 when it came to Fangraphs’ wins over replacement last-year. Had a 4.8 WAR overall, hit .297, .345 on base, .394 on the slugging. A guy who’s going to give you more contact, but very good defense over at 2nd base. One of the top defenders in the game. Good speed as well. Right around 30 stolen bases last year. So, a guy that I could see fitting very well with the Red Sox.”

Despite Hoerner’s appeal, Hyde expressed doubt that the Cubs would be willing to trade him:

“But from the Cubs’ point of view, I don’t know if they’d want to give him up, man. I mean, I think you could say he was their MVP last year. So, in the end, I don’t know. I have a hard time seeing the Cubs moving on from him.”

The potential loss of Hoerner, a free agent next year, adds complexity to Chicago’s decisions regarding their infield personnel.

Matt Shaw’s Role and Fit for the Red Sox

Matt Shaw is primarily a third baseman but took on more of a utility role with Chicago. In 126 games last season, Shaw made defensive highlights, notably a barehand stop and throw in a key play against the Milwaukee Brewers in August. He posted solid offensive numbers with 13 home runs and 44 RBIs, making him an attractive option for Boston’s struggling third base slot.

With the Red Sox, Shaw could join an evolving infield roster including Nate Eaton, Nick Sogard, and Marcelo Mayer. There is also speculation that Shaw might be shifted to second base to complement Mayer at third base. This flexibility increases his value for Boston as they search for viable replacements.

Pitching Assets Boston May Offer in Trade

The potential trade for Matt Shaw could involve prospect pitchers Payton Tolle and Connelly Early. Tolle displayed impressive strikeout ability in his MLB debut last August, fanning eight batters while allowing only two runs and accumulating 19 strikeouts over seven games. Early made a historic major league debut by striking out 11 batters in five innings and ended the season with a 2.22 ERA and 29 strikeouts across four games.

Both Tolle and Early represent promising additions to the Cubs’ pitching staff, which already includes starters like Edward Cabrera, Shota Imanaga, Justin Steele, and Cade Horton. These pitching prospects could help strengthen Chicago’s rotation, aligning with their organizational focus on pitching depth.

Exploring Additional Moves: Potential Deal with San Diego Padres for Second Base

The Red Sox are also reportedly targeting Jake Cronenworth from the San Diego Padres to solidify their second base position in 2026. They may offer Brayan Bello in return. Cronenworth impressed defensively last July against the New York Mets with an athletic diving catch and contributed offensively with 11 home runs and 59 RBIs in 135 games last season. His addition would bolster Boston’s infield, providing experience and stability alongside David Hamilton, Romy Gonzalez, Mickey Gaspar, and Ceddane Rafaela.

Brayan Bello, a back-end rotation pitcher for the Red Sox, had a solid season with 124 strikeouts and a 3.35 ERA across 29 games. He demonstrated his potential with a seven-strikeout outing over 5 2/3 innings. For the Padres, Bello could provide effective pitching depth in a staff including Randy Vasquez, Matt Waldron, JP Sears, Joe Musgrove, and Nick Pivetta.

Urgent Decisions Ahead of Spring Training

With Spring Training scheduled to begin on February 20, 2026, the Red Sox must finalize their moves swiftly to field a competitive team. Addressing the third base vacancy caused by Bregman’s departure is critical, as is shoring up second base with possible trades involving top prospects and existing players. The organization’s readiness to part with high-potential pitchers such as Tolle and Early reflects the urgency and complexity of filling the voids left by recent departures.

These potential trade activities underscore the Red Sox’s determined effort to rebuild a solid infield lineup for the upcoming season, despite the risks to their pitching pipeline. How these moves unfold will significantly influence Boston’s competitiveness and roster balance in 2026 and beyond.

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