The first major move of the offseason has been executed by the Boston Red Sox. That's somewhat shocking on its own, because the Red Sox have been hesitant to make key free-agent moves in recent seasons.
The signing of Jake Bauers away from the World Series champion Milwaukee Brewers is the first of what should be multiple moves by the Red Sox. If they want to compete with the Tampa Bay Rays and the New York Yankees for first place in the American League East and a potentially dominant position in the American League, team president Craig Breslow is going to have to sign additional players to improve the lineup.
There's also the question of the starting pitching staff. Sonny Gray was the best pitcher on the Red Sox starting staff and one of the three best starters in the American League, but there is a feeling that the Red Sox are willing to pass on the 37-year-old right hander unless he is willing to sign a deal that fits the Red Sox budget.
But the pitching staff appears to be secondary to the lineup, and the addition of Bauers means the Red Sox have to figure out how they are going to configure their batting order and also decide who plays in the field, who serves as the designated hitter, which players are shunted to the bench and which players are moved out of the organization.
Bauers and Contreras should split time between first base and DH
Bauers is primarily a first baseman, and that's the same position occupied by Willson Contreras. The Red Sox got excellent production from Contreras and he was the team's best power hitter with 27 home runs in 2026.
It appears that Contreras and Bauers can alternate between first base and designated hitter. Contreras slowed down in the final six weeks of the regular season and he may have more left in the tank if he is not in the field every day. Contreras also crowds the plate when he is at bat, and he got hit by 24 pitches last year. This is a regular occurrence for the slugger, because he was hit 23 times in 2025 while playing for the St. Louis Cardinals.
Both men will be in the lineup. The Red Sox are depending on the right-handed hitting Contreras and the left-handed hitting Bauers to supply a good chunk of the power for the 2027 Olde Towne Team.
Red Sox have to decide how to resolve LF issue
One of the major questions facing the Red Sox is the crowded house in the outfield. Right fielder Wilyer Abreu and centerfielder Ceddanne Rafaella both are coming off Gold Glove seasons for the Red Sox. Both are important aspects of the excellent team defense the Red Sox played this season and both are key offensive contributors. Neither player is getting traded unless the Red Sox got blown away by an unexpected offer.
However, Jarren Duran may be on the move from his perch in left field. Duran has been a vital piece of the Red Sox lineup in recent years. However, he is coming off a brutal season that saw him slash .207/.266/.361 after three much more accomplished seasons from 2023 through 2025.
Duran did manage to his 20 home runs and drive in 69 runs, so the season wasn't a complete disaster. However, he did not resemble the player who won the MVP Award in the 2024 All-Star Game. In addition to hitting the game-winning home run in that classic, Duran led the majors with 48 doubles and 14 triples while hitting .285 and stealing 34 bases in 2024.
While Duran could bounce back, his position will likely go to Roman Anthony. The Red Sox see Anthony as a potential superstar who can get on base at a dynamic pace and also become one of the team's best power hitters. The Red Sox believe he will be an asset for years, but he has been plagued by injuries each of the past two seasons.
Red Sox will be making a mistake by playing it casual with Gray
The Red Sox went into the 2026 season with the belief that left-handed power pitcher Garrett Crochet would follow up his brilliant season in 2025 with another great year. However, that theory flew out the window when Crochet was injured and didn't pitch again until the postseason.
The belief is that Crochet should be able to regain his position at the top of the rotation and that the Red Sox also have Payton Tolle and Ranger Suarez as two of their key starters.
However, they appear to be in a take-it-or-leave-it position with Gray. All he did last year was put together an 18-5 season with a 2.72 earned run average while pitching 169.0 innings.
The Red Sox would be making a mistake to let Gray go to another team. They appear to be following the same path they took last year with Alex Bregman. When the Chicago Cubs offered a bit more than the Red Sox were willing to pay, they lost one of their best players.
Now they may lose one of their best pitchers, and that would be a huge mistake.