The Red Sox have snagged playoff spots in two straight years but have been quickly dispatched both times. In 2027, they will need several players to bounce back from injury, but will also have to make plenty of decisions before then.

Guaranteed Contracts

Garrett Crochet, LHP: $142MM through 2031 (deal includes club option for 2032)
Roman Anthony, OF: $123MM through 2033 (deal includes club option for 2034)
Ranger Suarez, LHP: $120MM through 2030 (including buyout of 2031 mutual option)
Kristian Campbell, OF: $55MM through 2032 (including buyout of 2033 club option)
Brayan Bello, RHP: $44.5MM through 2029 (including buyout of 2030 club option)
Ceddanne Rafaela, OF: $44MM through 2031 (including buyout of 2032 club option)
Trevor Story, SS: $30MM through 2027 (including buyout of 2028 club option)
Willson Contreras, 1B: $24.5MM through 2027 (including buyout of 2028 club option)
Masataka Yoshida, OF/DH: $18MM through 2027
Aroldis Chapman, LHP: $13MM through 2027 (salary could increase by up to $1MM based on Reliever of the Year vote)

Option Decisions

Sonny Gray, RHP: $30MM mutual option with $10MM buyout
Garrett Whitlock, RHP: $8.25MM club option with $1MM buyout (deal also contains 2028 club option)

2027 financial commitments: $158.5MM
Total future commitments: $625MM

Arbitration-Eligible Players (service time in parentheses; projected salaries courtesy of MLBTR contributor Matt Swartz)

Non-tender candidates: Houck, Oviedo, White, Crawford, Wong, González, Casas, Monasterio, Kelly, Jones

Free Agents

In a sense, the 2026 season was a bit of a letdown for the Red Sox. They made the postseason in 2025. Garrett Crochet established himself as an ace. Youngsters Roman Anthony, Payton Tolle and Connelly Early made their debuts and gave the club an exciting wave of young talent. The Sox had an aggressive offseason heading into 2026, hoping to move up to the next level. They gave a nine-figure deal to Ranger Suarez. They acquired Sonny Gray and Willson Contreras from the Cardinals.

Unfortunately, they didn’t end up making any progress. Their win total dropped by two, going from 89 to 87. They still made the playoffs but with essentially the same disappointing result. In 2025, they had at least pushed their Wild Card matchup with the Yankees to three games. In 2026, they were handily dismissed. They again faced the Yankees but were swept this time, losing the two games by a combined 18-2 score.

It was a deflating result. If one wanted to be optimistic, they could point out that the Sox worked around a large number of injuries. Crochet made only six starts due to shoulder issues. A hand/wrist situation limited Anthony to just 55 games. Contreras was on the injured list for half of September due to a hamstring strain. He was off the IL for the second half but got hit on the hand by a pitch and missed more than a week. Trevor Story had a nice bounceback season in 2025 but hernia surgery limited him to 64 games of limp production in 2026.

Even the midseason reinforcements got hurt. Curtis Mead was picked up at the deadline but was hit by a pitch and broke his wrist in his first game for Boston. Catcher Adley Rutschman was on the IL with wrist inflammation when he was acquired. He came off the IL but had to manage a hyperextended elbow down the stretch.

In a sense, it’s somewhat encouraging that the Sox managed to win 87 games while missing so many key contributors. But in 2027, they will need to get those guys back. On top of that, they will need to bolster the roster around the guys who are staying.

This offseason, the oft-discussed outfield shake-up might be finally coming. For a while now, the Sox have been trying to find playing time for Anthony, Ceddanne Rafaela, Wilyer Abreu, Jarren Duran and Masataka Yoshida. That logjam was mostly a non-issue in 2026 as Anthony’s injury opened things up but it’s still a crowded picture on paper.

There are some pressure points squeezing Duran at the moment. He has shown huge upside in the past but is coming off an awful season. It feels a bit strange to say that about a 20-20 campaign but it’s somehow true. His 6.7% walk rate was a drop of almost two points compared to last year. His 27.1% strikeout rate was his worst in a full season.

He finished the campaign with a .207/.266/.361 line and 69 wRC+, indicating he was 31% worse than the league average hitter. His .252 batting average on balls in play was well south of average and his previous seasons. That can sometimes indicate bad luck but Duran’s batted ball data all moved in the wrong direction. His hard hit rate went from 46.8% in 2025 to 39.9% this year. His average exit velocity dropped from 91.8 miles per hour to 89.6.

As a Super Two guy, he has already had two arbitration seasons and can be retained for two more. But he already pushed his salary to $7.7MM in 2026. The arb process has historically focused on more traditional stats than advanced ones, so he’s projected for a healthy raise to $11.1MM in 2027. That’s a lot of money for a guy who is coming off a down season and battling for playing time with several other outfielders.


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