Offseason Outlook: Boston Red Sox

The Red Sox finally made it back to the postseason this year, though their third place finish in the AL East and a quick exit in the Wild Card Series at the hands of the Yankees leaves fans hoping for more in 2026.

Guaranteed Contracts

• Garrett Crochet, LHP: $166MM through 2031 (deal includes conditional $15MM club option for 2032; can opt out after 2030)
• Roman Anthony, OF: $125MM through 2033 (deal includes $30MM club option for 2034)
• Brayan Bello, RHP: $50.5MM through 2029 (includes $1MM buyout on $21MM club option for 2030)
• Kristian Campbell, 2B/OF: $47MM through 2032 (includes $4MM buyout on $19MM club option for 2033, deal includes $21MM club option for 2034)
• Ceddanne Rafaela, OF/2B: $46MM through 2031 (includes $4MM buyout on $16MM club option for 2032)
• Masataka Yoshida, DH: $36MM through 2027
• Jordan Hicks, RHP: $24MM through 2027
• Aroldis Chapman, LHP: $13.3MM through 2026 (includes $300K buyout on $13MM vesting option for 2027)
• Patrick Sandoval, LHP: $12.75MM through 2026
• Garrett Whitlock, RHP: $8.25MM through 2026 (includes $1MM buyout on $8.25MM club option for 2027, deal includes $10.5MM club option for 2028)

Option Decisions:

• Alex Bregman, 3B: Will opt out of $80MM through 2027 ($40MM deferred)
• Trevor Story, SS: Can opt out of final $50MM through 2027. If opt out exercised, Red Sox can either void it by exercising $25MM club option or pay Story a $5MM buyout.
• Lucas Giolito, RHP: $19MM mutual option with $1.5MM buyout.
• Liam Hendriks, RHP: $12MM mutual option with $2MM buyout.
• Jarren Duran, OF: $8MM club option with $100K buyout. Eligible for arbitration if option is declined.

Total 2026 commitments: $168.9MM
Total future commitments: $662.4MM

Arbitration-Eligible Players (service time in parentheses; salary projections via MLBTR contributor Matt Swartz)

• Nathaniel Lowe (5.145): $13.5MM
• Tanner Houck (4.100): $3.95MM
• Jarren Duran (3.155): $8.4MM (if club option declined)
• Kutter Crawford (3.136): $2.75MM
• Romy Gonzalez (3.083): $1.8MM
• Connor Wong (3.079): $1.6MM
• Triston Casas (3.032): $1.7MM
• Josh Winckowski: (3.003): $800K
• Brennan Bernardino (2.150): $1.1MM
• Non-tender candidates: Lowe, Houck, Wong, Winckowski

Free Agents

• Alex Bregman, Lucas Giolito, Steven Matz, Liam Hendriks, Dustin May, Rob Refsnyder, Justin Wilson

Much of Boston’s offseason will be dictated by the opt out decisions made by the left side of the club’s infield. Alex Bregman is already expected to opt out of his contract and return to the open market, but it’s not yet clear whether or not Trevor Story will follow in those footsteps. With no locked in starter at second base and chief baseball officer Craig Breslow unwilling to commit to Triston Casas at first base for next year, it’s not impossible to imagine a scenario where the Red Sox are looking to reshape their entire infield as they look for defensive upgrades.

At the very least, they’ll need to either re-sign or replace Bregman. Re-signing the veteran coming off his third career All-Star appearance may prove to be the most sensible course of action. While he’ll be seeking a true long-term deal this winter as he heads into his age-32 campaign, it would be difficult to find the sort of production Bregman offers elsewhere. Just three third basemen (Jose Ramirez, Junior Caminero, and Isaac Paredes) posted a higher wRC+ than Bregman’s 125 this year, and Fangraphs’ Def metric pegs Bregman as the seventh-most valuable defensive third baseman in baseball this year despite a quad injury limiting him to just 114 games.