Red Sox could return to Cardinals trade well for third time this offseason
The Boston Red Sox and St. Louis Cardinals have already made a pair of trades this offseason. A third deal could be in the works.
According to Alex Speier of The Boston Globe, the Red Sox are still looking for a right-handed-hitting infielder. Speier further noted that the Red Sox are targeting Cardinals utility man Brendan Donovan.
The Red Sox have already raided the rebuilding Cardinals to fortify a pair of weaknesses. Pitcher Sonny Gray was acquired at the end of November to give Boston a second top-of-the-rotation starter behind ace Garrett Crochet. Willson Contreras was acquired a month later to fill the Red Sox’s void at first base.
Boston Red Sox have competition for Brendan Donovan
While Donovan is capable of filling in around the diamond, he has seen most of his action at second base or left field over the past two years. A first-time All-Star in 2025 and the winner of the 2022 NL utility man Gold Glove award, Donovan has emerged as a solid hitter in the Cardinals’ lineup. He has produced a .282/.361/.411 batting line over his 2006 plate appearances, hitting 40 homers and 97 doubles.
While the Red Sox are interested in bringing Alex Bregman back at third, they also have an opening at second base. David Hamilton, Romy Gonzalez and Kristian Campbell were not an overly productive trio at the keystone in 2025, and the Red Sox want to keep Ceddanne Rafaela in center for his defense. Adding Donovan would give the Red Sox time for Campbell to develop while providing a solid option should he return to a utility role.
The Red Sox are not the only team interested in Donovan. Katie Woo of The Athletic reported that the Giants and Mariners have emerged as the frontrunners for his services. However, given the Red Sox and Cardinals trades this offseason, it is entirely possible the two sides could team up for a third time.
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Chicago Cubs listed among favorites to land Alex Bregman, but…
The Chicago Cubs have hyper-focused on their bullpen this offseason, pushing to fill an obvious need after free agency and other roster decisions left just two of the NLDS relief corps still with the team.
The signings of Phil Maton, Hoby Milner, Jacob Webb, and Hunter Harvey, along with the re-signing of Caleb Thielbar, go a long way to stabilize an all-but-vacant bullpen.
But there are still bigger fish to fry this winter.
The Cubs are headed into 2026 with a lot of question marks involving durability when it comes to their starting rotation. There’s also a huge question mark when it comes to filling the hole left behind as right fielder Kyle Tucker drifts off into free agency.
Chicago has reportedly checked into adding a front-of-rotation arm. They’ve also explored a deal with free agent third baseman Alex Bregman to replace Tucker’s presence in the lineup and his leader-by-example role with the team.
The pursuit of Alex Bregman
Lately, it seems as though the latter may be the more earnest pursuit.
In a recent appearance on 670 The Score’s Inside the Clubhouse, MLB insider Bruce Levine affirmed the Cubs’ seriousness when it comes to engaging with Bregman.
“The Cubs have had many conversations with [agent] Scott Boras about Alex Bregman,” Levine said, before mentioning that the Cubs are among the three teams most interested in the three-time All-Star Gold Glover, along with the Toronto Blue Jays and Arizona Diamondbacks.
It’s also being reported by MassLive.com’s Chris Cotillo that Bregman is a “plan A” priority for the Boston Red Sox, who signed him to a three-year, $120 million contract last winter, but may lose him due to a contractual player opt-out stipulation in that contract.
What Bregman brings vs. what Tucker brought
In Boston last season, Bregman slashed .273/.360/.462 with 18 home runs and 62 RBIs despite missing 43 games because of a right quadriceps strain. He was also highly regarded as a clubhouse leader and fan-favorite field presence.
In a lot of ways, Bregman would be the kind of player they hoped to be getting when they traded for Tucker last offseason. Because, while Tucker shined when healthy, injuries to his thumb and calf were slow to heal and ended up resulting in extended offensive slumps that he could never quite pull through.
Exchanging Bregman for Tucker would probably represent a slight offensive downgrade, but it would add the kind of vocal leadership Tucker lacked. It would also further solidify an already-elite infield defense while possibly freeing up Matt Shaw or someone else to be packaged in a trade for a high-end starting pitcher.
The question, of course, is whether the Cubs can outbid Bregman’s other suitors. For the Cubs, given their spending history and financial preferences, that’s a huge question.
The Chicago Cubs and a willingness to spend
Last winter, amid similar media reports that the Cubs were favorites to land the free agent Bregman, reality painted a different picture. Bregman, himself, would reveal that Chicago was not even really among the finalists for his services.
The Cubs’ reported offer of four years for $115 million, with opt-outs after the 2026 and 2027 seasons, fell short of the Red Sox winning bid, as well as the deals offered by the Detroit Tigers and Houston Astros. The ownership’s refusal to cut a deal with deferred money was, reportedly, a major factor in the team falling from the Bregman race.
So, why would this present tense pursuit of Bregman be any different than last year’s?
For one, the Cubs have the financial wherewithal right now, as well as a ton of money coming off the books at the end of next season as Ian Happ, Seiya Suzuki, Nico Hoerner, Carson Kelly, Matthew Boyd, Shota Imanaga, and Jameson Taillon (among others) will all become eligible for free agency.
With so much of the team’s veteran core likely to be gone, they’ll need veteran leadership on a squad of young holdovers.
Signing Bregman would also open the possibility of the Cubs having their roster cake and eating it too, as they could go out and add their established position player while also bringing in a more economical front-of-rotation pitcher via trade.
At this point, all we know is that Bregman and the Cubs are talking. Whether talk evolves into something bigger is up to the Cubs and their willingness to, at least this one time, spend like their immediate future depends on it. Because, maybe, their immediate future DOES depend on it.
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