Red Sox's Biggest Offseason Needs Ranked After ALWCS Disaster

The Boston Red Sox's roster arguably is in a better place right now than at this point last year, but there is no denying the fact that there is still work to do for the organization.

When you get bounced in the wild-card round by your biggest rival in two straight seasons, that's going to be the case. For the Red Sox, one of the biggest positives is the fact that the catcher position is set. Adley Rutschman is a star and is under team control next year. In fact, the Red Sox should do everything possible to get an extension done. Even when Rutschman's bat wasn't going initially after the trade deadline, what he was able to do behind the plate was special in itself. Then, he slashed .266/.299/.547 with an .845 OPS, four homers and nine RBIs in 17 games in September. That should get the fanbase excited and should open up the checkbook as well.

So, fortunately, catcher isn't a need any longer. But Boston does have a few things to square away, starting with adding more power. Let's take a look at the most pressing needs for the club this winter.

No. 1: Adding Power

Boston Red Sox shortstop Trevor Story — Sep 20, 2026; St. Petersburg, Florida, USA; Boston Red Sox short stop Trevor Story (10) celebrates a home run during the ninth inning against Tampa Bay Rays at Tropicana Field. Mandatory Credit: Pablo Robles-Imagn Images | IMAGN IMAGES via Reuters Connect

This was Boston's biggest need last year and it remains the case right now heading into 2027. Boston finished the 2026 regular season 26th in the league with 163 long balls. Boston needs more. The Yankees finished second in the league with 223 homers in the regular season and then crushed four in the two-game wild-card series. Homers are massively important, especially in the playoffs. Boston needs more.

Some will argue that the power problem was actually an injury problem. Trevor Story had just five homers because he played 64 games. Roman Anthony had five homers in 55 games. Curtis Mead hit 17 homers with the Washington Nationals, but played just one game with Boston. Even Rutschman clearly wasn't at full strength when he was activated off the Injured List. He hit five homers with Boston in 32 games. Four of them came in September. If these guys were healthier, Boston obviously would've had more home runs. But how many times can the club simply bet on better health?

No. 2: Determining The Top Right-Handed Starter

Sep 30, 2026; Bronx, New York, USA; Boston Red Sox pitcher Sonny Gray (54) delivers a pitch in the first inning against the New York Yankees during game two of the Wildcard round for the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | IMAGN IMAGES via Reuters Connect

Sonny Gray has a mutual option that is unlikely to be picked up. Do the Red Sox find a way to keep him around beyond the 2026 season? That would be wise. Other internal options are Brayan Bello, Tanner Houck and Kutter Crawford. Boston is loaded from a left-handed perspective with Garrett Crochet, Payton Tolle, Ranger Suarez and Jake Bennett. But you can't just have a rotation of lefties. If the Red Sox were to lose Gray and opt to go external, one option they should watch is Shane Bieber, who has been on their radar multiple times at this point.

No. 3: Finally Sorting Out The Outfield Logjam

Sep 9, 2026; Boston, Massachusetts, USA; Boston Red Sox left fielder Jarren Duran (16) runs off the field during the sixth inning against the Los Angeles Angels at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | IMAGN IMAGES via Reuters Connect

Do you roll with Roman Anthony, Jarren Duran, Ceddanne Rafaela and Wilyer Abreu again? Duran specifically had the most difficult season of his career in 2026. Anthony has been significantly impacted by injuries in both 2025 and 2026. The idea of staying healthy is important here. Injuries happen and it just so happened that Boston lost an outfielder for three months, which delayed the conversation.

Arguably, the time is now to sort it out. Especially with Masataka Yoshida in the mix as well. It's been a few years at this point. It's time to rip the Band-Aid off and make a call and stick to it.

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