After weeks of smoke, the Red Sox finally struck a deal for an impact bat on Sunday, acquiring first baseman Willson Contreras from the Cardinals.
Hunter Dobbins headlines the return to St. Louis, along with prospects Yhoiker Fajardo and Blake Aita in the package. Fajardo checked in as Boston’s No. 23 prospect, per MLB.com.
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It marks the second trade of the offseason between these two clubs, after the Red Sox previously landed Sonny Gray from St. Louis in exchange for Richard Fitts and Brandon Clarke.
At 33, Contreras remains one of the steadier offensive bats at his position.
Across a 10-year career with the Cubs and Cardinals, Contreras owns a .258 average to go along with 172 home runs, earning three All-Star selections along the way. He was a key piece of Chicago’s 2016 World Series title and has posted an above-average OPS+ in every season but one (2018).
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Contreras is under contract for two more years at $41 million, with a club option for 2028. And since we know saving money is always important for Boston, it should be noted that St. Louis is also sending $8 million to the Red Sox as part of the deal.
Adding Contreras to this roster solves a massive problem for Boston at first base – a position the team had problems finding consistency at throughout most of 2025, even before Triston Casas was lost for the season in May with a ruptured patellar tendon in his left knee. They now get a veteran who has only played less than 105 games in a season three times in his career, not to mention posting 135 times in 2025 – the second-highest single season total he’s had since getting called up to the majors in 2016.
He’s durable, he’s got power, he’s got championship mettle, and he’s affordable.
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That’s all music to Boston ownership’s ears.
Apr 6, 2025; Boston, Massachusetts, USA; St. Louis Cardinals first baseman Willson Contreras (40) makes a catch for an out against the Boston Red Sox during the fifth inning at Fenway Park. (Eric Canha/Imagn Images)
…but now what?
There’s still another bat to be added for Red Sox fans to feel good about their opening day roster in 2026. And for me, I think it now comes down to one guy:
Alex Bregman.
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We all know the story at this point – big free agent signing during spring training last year, was the reason Rafael Devers was asked to change positions, Devers’ pushback eventually led to him being dealt to the Giants, Bregman emerged as the unquestioned leader of the clubhouse, and despite missing a chunk of the season due to a quad injury was still among the best hitters in baseball at his position and was able to help deliver Boston’s first postseason berth since 2021. With all of that said, he still decided to opt out after his first season of a three-year deal, leaving $80 million on the table in search of a contract that will carry him to the end of his career.
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While Boston has routinely been reported as being in the pole position for Bregman all hot stove season, recent rumors from prominent baseball podcaster Jared Carrabis have now raised doubt around the idea of the two-time World Series champion returning to the Red Sox to chase his third career ring.
“I don’t feel super great about Bregman coming back, but these things are always subject to change,” he wrote on X last week. “Bogaerts was pretty much a done deal to return until the Padres swooped in with a crazy offer. These situations are fluid. But, yeah. Doesn’t sound promising at the moment.”
May 16, 2025; Boston, Massachusetts, USA; Boston Red Sox third baseman Alex Bregman (2) runs out of the dugout before the start of a game against the Atlanta Braves at Fenway Park. (Eric Canha/Imagn Images)
Despite these whispers being floated by Carrabis, my gut tells me Bregman is back in Boston for 2026. With the team loudly swinging and missing on the likes of both Pete Alonso and Kyle Schwarber, there’s plenty of money to go around still. And if Boston shows up to opening day 2026 with Roman Anthony and Garrett Crochet as the only names worthy of the marquee (because let’s face it, Contreras is an undercard), there might be paper bags over the heads of fans in the stands at Fenway Park.
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I wish that was hyperbole – Red Sox fans are nuts.
They cannot miss here on Bregman. If they need to overpay, so be it. That’s how this whole thing works.
Securing your two corner infield spots this offseason would go a long way towards Boston having a real chance to compete for a World Series next season.
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Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He’s a senior digital content producer for WEEI.com, and a native of Lincoln, RI.