Five Boston Red Sox Players Who Won’t Be Back in 2027

With the World Series between the Milwaukee Brewers and Tampa Bay Rays well underway, we are officially on the doorstep of the offseason. After back-to-back seasons of losing to the New York Yankees in the Wild Card round, it will be a crucial offseason for the Boston Red Sox as they look to build a team that is capable of getting over the hump that is their arch-rivals and capable of competing for a World Series. 

As Chief Baseball Officer Craig Breslow builds the 2027 Red Sox, these members of the 2026 team will not be part of the team, at least in our estimation.

The outfield logjam is a problem that just won’t seem to go away for the Red Sox, but after two seasons of dealing with four starting-caliber outfielders, Breslow finally makes a move to alleviate the jam. 

The 30-year-old Duran has seemed like the odd man out for a while. He is the oldest in the group, and his best tool, speed, declines much faster with age, and the team has shopped him repeatedly since the 2025 trade deadline. That said, Breslow would certainly be selling low on Duran, who finished top 10 in MVP voting in 2024. 

In 151 games, Duran hit .207/.266/.361/.627 with 20 home runs, 15 doubles, and five triples, stole 21 bases, and drove in 69 runs. Among 135 qualified hitters, Duran finished the year in the bottom five in batting average (.207, 132nd), on-base percentage (.266, 134th), and weighted runs created plus (69, 134th). 

While poor performance dragged Duran’s trade value down significantly, a hefty arbitration estimate of $11.1 million further dampens it. However, with $268 million already committed to the 2027 roster, moving on from Duran, even for a diminished return, offers Breslow some financial relief and clears the logjam in one move. 

While the 36-year-old right-hander hasn’t officially declined his side of the $30-million mutual option, it’s widely assumed that he will collect his $10 million buyout and hit the open market. 

While Gray didn’t rule out a return to Boston in a text sent to Alex Speier of the Boston Globe when he announced he would play in 2027, things didn’t necessarily end on a great note between Gray and the team. The 14-year veteran was very vocal about his displeasure with being lifted after just 4.2 innings in Boston’s season-ending loss. 

While that may not be enough to ensure Gray’s departure in free agency, the soon-to-be 37-year-old was Boston’s best starter for much of the season, posting a 2.72 ERA in 29 starts, racking up a league-high 18 wins. Gray figures to have a healthy market in free agency. With so much money already committed to the roster and a pitching staff that could still be one of the best in baseball with or without Gray, Breslow is unlikely to be willing to meet the market price to retain him. 

After signing a two-year, $18.5 million deal with Boston ahead of the 2025 season while recovering from Tommy John surgery, Sandoval made his long-awaited Red Sox debut in July and is now set to hit free agency. 

In 15 appearances (13 starts), serving primarily as Boston’s fifth starter, Sandoval posted a 1-7 record with a 5.12 ERA over 70.1 innings, striking out 9.3 batters per nine innings and walking 4.1 per nine. While his ERA doesn’t jump off the page, a fielding-independent pitching (FIP) of 3.77 suggests he was the victim of some bad luck. 

For a fifth starter, Sandoval performed well in his role, eating innings, saving a banged-up bullpen down the stretch, while keeping the team in games for the most part. However, with Johan Oviedo, Kutter Crawford, and Tanner Houck returning to full health and Brayan Bello still under contract for three more seasons, the back end of the rotation looks crowded for 2027.

The 31-year-old utility man signed a one-year, $6-million deal to join the Red Sox ahead of the season. In an injury-shortened 2026 season, Kiner-Falefa hit .244/.322/.311/.633 in 66 games. 

With Nick Sogard, Andruw Monasterio, Romy Gonzalez, and Anthony Seigler all under team control for 2027, the group is crowded, with four players fighting for one or two bench spots. 

The 30-year-old backup catcher had a second straight underwhelming season. In 77 games, Wong hit .233/.308/.348/.655. Wong is also a poor defensive option behind the plate, ranking in the 23rd percentile in caught steals above average, pop time, and framing skills that ranked in the fourth percentile. 

For a team built on strong pitching and defense, it makes sense for the Red Sox to target a stronger defensive option to back up All-Star catcher Adley Rutschman. While signing catcher Riley Adams to a minor league deal with an invite to major league spring training may be nothing more than adding depth behind the plate, it wouldn't be a shock to see the Red Sox keep adding at the position and move on from Wong in the process.