Red Sox’s Offseason ‘Biggest Regret’ Was Avoidable

The Boston Red Sox surprised a lot of people this past offseason, although there were a lot of good moves made.

Boston added guys like Willson Contreras, Caleb Durbin, Sonny Gray and Ranger Suárez, among others. It's not even like the Red Sox just made splashy moves, as well. The Johan Oviedo trade with the Pittsburgh Pirates was big and he grabbed most of the headlines, but the Red Sox also added depth with upside in Tyler Samaniego and it took him just one game to make team history.

If you just look at who came in, it's hard to say it wasn't a great offseason. But you do have to take into account that Boston lost Alex Bregman in the process as well. He's actually struggling with the Chicago Cubs to kick off the season with a .188/.278/.333 slash line, but that was a tough loss for Boston. It's important to note that the Red Sox publicly opened the offseason talking about the need for two power bats and then were seemingly in on everyone, but couldn't get deals over the finish line, outside of the Contreras trade. He's one of the bats Boston needed, but the club specifically said it wanted two big-time power bats.

The Red Sox still have one roster issue

Apr 3, 2026; Boston, Massachusetts, USA; Boston Red Sox third baseman Caleb Durbin (5) throws the ball to first base for an out against the San Diego Padres during the third inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

The offense has lacked a bit of thump this season as well. Right now, Boston is tied for 24th in the league with just nine homers through 12 games. Because of this, it's no surprise that Bleacher Report's Alex Kay called Boston's "biggest regret" of the offseason not investing in another slugger.

"Boston Red Sox: Not making major offensive free-agent investment," Kay wrote. "It's way too early to write off Ranger Suárez, though he had some red flags as a free agent, and the early returns on a five-year, $130 million deal aren't promising. Still, it's hard to shake that the Red Sox alienated Rafael Devers while giving up draft-pick compensation and international bonus pool money to sign Alex Bregman as a qualified free agent, only to allow him to leave for nothing after one year in free agency.

"It would have been one thing if the Red Sox pivoted to a free agent with more home run potential, such as Alonso, Kyle Schwarber or even Eugenio Suárez. But failing to either re-sign Bregman or add another big bat around Roman Anthony and Wilyer Abreu is perplexing. Who knows, maybe Willson Contreras and/or Caleb Durbin will heat up soon."

Power was a question hanging over the club heading into the offseason and it is still lingering now. Contreras will at least come close to replacing Bregman's production. But Boston had a power problem when Bregman was on the roster. That issue still remains. It didn't have to. Bregman was out there for the taking for a while, along with others. But, things just didn't work out.