The Boston Red Sox should have another big offseason ahead after making it to the playoffs for the second straight season in 2026.

Boston missed the playoffs in three straight seasons from 2022 through 2024. In 2025, the Red Sox got back into the postseason, but were knocked out early by the New York Yankees. That was the case once again in 2026. But don't let that get you down, Red Sox fans. This team is in a significantly better position right now than at this point last year.

This was the Red Sox's Game 1 lineup in the wild-card round against the Yankees in 2025.

1. Rob Refsnyder, DH
2. Trevor Story, SS
3. Alex Bregman, 3B
4. Romy Gonzalez, 1B
5. Carlos Narvaez, C
6. Nate Eaton, RF
7. Jarren Duran, LF
8. Ceddanne Rafaela, CF
9. Nick Sogard, 2B

1. Roman Anthony, DH
2. Adley Rutschman, C
3. Willson Contreras, 1B
4. Wilyer Abreu, RF
5. Ceddanne Rafaela, CF
6. Nick Sogard, 2B
7. Jarren Duran, LF
8. Trevor Story, SS
9. Caleb Durbin, 3B

The 2027 Opening Day lineup should look very similar, aside from Curtis Mead being added either at second base or designated hitter. Boston doesn't need to do much this offseason because the vast majority of the roster is under control for 2027. Adding power would be the best way forward if Boston adds. That could easily be done at designated hitter, especially if Boston trades away an outfielder. If Jarren Duran were moved, Boston could simply slot a slugger in at DH, put Anthony in left field and Mead at second base.

There is some work to do and decisions to be made, like with Sonny Gray, but Boston is built for 2027 success. Here are some things to watch this winter.

Free Agents

There aren't a lot of internal free agents for Boston to think about. Gray has a mutual option that likely will be declined. He'll then be the most interesting Boston free agent. Patrick Sandoval and Isiah Kiner-Falefa are pending unrestricted free agents. Garrett Whitlock technically has a club option, but it will be a massive shock if it isn't picked up.

Free Agent Targets

Again, power is the biggest way Boston could improve this winter. The vast majority of the roster is in a good place. It wouldn't hurt to add a cheap starter or reliever, but power should be the priority. A few free agents to watch arguably are Eugenio Suarez, Teruaki Sato, Randy Arozarena and Seiya Suzuki.

Trade Targets

Arguably, the trade market is more interesting than free agency. It is a weak free agent class this offseason. Someone like Bryce Harper or Ronald Acuna Jr. would be pipe dream targets. Infielders like Zach Neto or CJ Abrams would be intriguing fits, depending on how Boston views Franklin Arias. On the pitching side, someone like Joe Ryan or Spencer Strider should be considered.

Decisions

Gray is the guy to watch. Mutual options almost never get picked up. So, he'll likely go to free agency. Will Boston re-sign him? That would certainly help. If not, which righties will be in Boston's rotation? Brayan Bello and Tanner Houck would be two obvious options.