Why not signing Alex Bregman will be Red Sox biggest offseason regret

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Why not signing Alex Bregman will be Red Sox biggest offseason regret

Steve Silverman, ClutchPoints · ClutchPoints

Thu, Feb 5, 2026 ·

5 min read

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Why not signing Alex Bregman will be Red Sox biggest offseason regret appeared first on ClutchPoints . Add ClutchPoints as a Preferred Source by clicking here .

The Boston Red Sox offseason has been filled with regret. They could have signed slugging 1st baseman Pete Alonso at the start of free agency but they stood idly by as the division rival Baltimore Orioles deemed him more important to their team than the Red Sox did. The Red Sox let Alex Bregman find a deal with the Chicago Cubs that was better than the one they offered. They said goodbye to Bregman after one season at Fenway Park. They watched Toronto star Bo Bichette leave Canada and sign with the New York Mets even though the Red Sox need infielders.

All of those signings lead to Red Sox regret . However, the biggest regret is not bringing back Bregman to play 3rd base and serve as the clubhouse leader of a team that views itself as a serious contender for the American League East title.

The Red Sox screwed up their situation at 3rd base when they signed Bregman prior to the start of spring training a year ago. That's because they used his signing to insult incumbent 3rd baseman Rafael Devers , telling him he could "throw away his glove." Bregman was a far superior fielder to Devers, but there should have been a better way for the Red Sox to handle the situation. Devers was their best player and top hitter by a wide margin, and he was upset from the moment Bregman was signed.

When sluggish 1st baseman Triston Casas went down with an Achilles injury, they asked Devers to pick up a 1st baseman's mitt and play the position. He had no intention of playing a position he had never attempted, especially after the team had insulted him. The Red Sox traded their recalcitrant slugger to the San Francisco Giants and received a pittance in return.

Bregman leaves Green Monster for the ivy-covered walls of Wrigley

While that was happening, Bregman injured a quad muscle and missed about 25 percent of the season. However, when Bregman was in the lineup, the Red Sox had a brilliant fielder, a true leader in the clubhouse and an excellent clutch hitter. His right-handed swing was built for Fenway Park and he appeared to love playing in Boston.

However, the Red Sox gave Bregman the ability to opt out of his contract, and he took advantage of that. The Red Sox did not react when the Cubs offered him a 5-year, $175 million deal. When the news broke that Bregman was leaving for the North Side of Chicago , Red Sox fans were left wondering what the team will do.

One imagines that manager Alex Cora is wondering the same thing. The Red Sox will undoubtedly attempt to fill Bregman's position with highly touted Marcelo Mayer . The Red Sox had promoted Mayer last year and he was excellent in the field while Bregman was nursing his quad injury. He also flashed his hitting skills, but he lacked consistency in that area. Now the Red Sox are counting on him to fill the role of being an every-day player who can hit the ball out of the park.

Red Sox offense has taken a hit

While Mayer has great potential, there are no guarantees that this young prospect will turn out to be consistently productive in the lineup. The Red Sox also have a hole to fill at 2nd base. If they had kept Bregman in the fold, Mayer could have moved to that position. Now it seems that Kristian Campbell , another minor-league phenom/prospect or recent signee Isiah Kiner-Falefa can play 2nd base. Kiner-Falefa is an excellent defensive player — he can handle 2nd base, shortstop or 3rd base — but his offensive capabilities are limited.

It seems the Red Sox are not going to have as good an offensive team in 2026 as they did in 2025. If the situation does not improve, they will struggle to compete against the Blue Jays and Yankees . The Red Sox have added to their pitching staff with Sonny Gray and Ranger Suarez , but the offense won't be as strong.

Failure with Alonso and Bichette

Mandatory Credit: Jim Rassol-Imagn Images

The Red Sox appeared to be the favorite to sign Alonso at the start of free agency. They needed right-handed power and they needed a 1st baseman. There was nobody available who was even close to Alonso in both categories.

The Orioles had been a playoff team in 2023 and '24, but had fallen into disrepair last seasons. They did not hesitate when it came to offering Alonso a 5-year, $155 million deal . The presence of Alonso in the Baltimore lineup should help Gunnar Henderson , Adley Rutschman and Jackson Holliday .

The Red Sox appeared to have a shot at Bichette as well, but the Toronto hero signed a 3-year, $126 million with the Mets. Bichette may not be a great defensive player, but he is one of the best offensive players in baseball and the Red Sox clearly could use his bat.

The team failed to sign any big free-agent bat, and the departure of Bregman is the biggest regret of all.

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