Boston Red Sox
The Red Sox could use former players like Kyle Harrison and Kyle Schwarber this season.
Kyle Harrison has been a difference-maker for the Brewers. AP Photo/Eric S. Lesser
There may still be more than 80 games remaining in the 2026 season for the Red Sox, but the writing on the wall suggests it will be another lost summer at Fenway Park.
For all the promise initially rooted in this offseason, Boston still sat in last place in the AL East on Sunday night with a 31-44 record.
Key players like Roman Anthony and Garrett Crochet have been hampered by injury, while other key players like Jaren Duran, Trevor Story, Marcelo Mayer and Caleb Durbin have underperformed.
To add to the change, several former Red Sox players have expressed their admiration for their clubs in 2026 — putting an even greater spotlight on a Boston club that has allowed a lot of talent to leave Fenway over the past few years.
Here’s a quick recap of several former Red Sox players and how they’ve held up across the MLB so far this summer:
Kyle Harrison, LHP
Harrison — who was acquired by Boston as one of the top returns in the Rafael Devers trade with San Francisco — only played 12 innings with the Red Sox last season before being traded to Milwaukee over the winter.
While Caleb Durbin has at times served as Boston’s third baseman, Harrison has flourished as another elite outfielder thus far with the Brewers.
The 24-year-old southpaw is 8-1 so far this season in Milwaukee with a 2.50 ERA, striking out 87 batters over 72 innings of work and owning a WHIP of 1.06.
The Red Sox’ starting rotation has been far from the club’s most pressing issue this season. But moving on from another promising young left-hander like Harrison already seems like a huge whiff.
Dustin May, RHP
A newbie like Dustin May represents a rough case of asset management for Craig Breslow and his staff.
With Boston needing reinforcements in their rotation last season, the Red Sox dumped prospects James Thibbs III (acquired just over a month ago in the Devers trade) and Zach Erhard to acquire Maye from the Dodgers. The righty was a failure in Boston – appearing in just six games (five starts) and posting a 5.40 ERA.
Giving up a talented Tibbs prospect for a one-year rental like Maye is already painful, but the starter has also been a solid option this season with the Cardinals.
After signing a one-year contract in St. Louis last winter, May is 5-6 this year with a 4.30 ERA — headlined by a one-hit, all-game shutout last week against San Diego.
And for those keeping track, Tibbs has suffered a drop in Triple-A so far this season — batting .294 with 20 home runs and 62 RBI over 71 games as one of the Dodgers’ top prospects.
Walker Buehler, RHP
Walker Buehler, a two-time World Series champion, had a disappointing season with Boston in 2025, pitching to a 5.45 ERA across 23 outings before the team released him. He bounced back with the Phillies during a short stint in the fall (3-0, 0.66 ERA) before signing a minor league contract with the Padres.
He never recaptured his form as a former standout with the Padres, but Buehler was serviceable in San Diego with a 4-3 record and 3.96 ERA across 15 starts. Since the start of June, the 31-year-old Buehler is 1-0 with a 1.71 ERA.
Chris Sale, LHP
Chris Sale dominated his first two seasons with the Red Sox, playing a key role in Boston’s 2018 World Series. However, the All-Star lefty had a miserable end to his tenure in Boston, making just 56 appearances and posting a 4.16 ERA over his final five seasons with the club from 2019-23.
Sale has regained his form as one of the best pitchers in MLB since Breslow traded him to the Braves in exchange for outfielder Vaughn Grissom.
Despite seemingly entering the “twilight” of his career upon his arrival in Atlanta, Sale went on to win the NL Cy Young Award in his first season with the Braves, and now sports a 2.14 ERA through 14 starts so far in 2026.
In three seasons so far with the Braves, Sale is 33-13 with a 2.43 ERA with 482 strikeouts over 381.1 innings of work.
Meanwhile, Grissom — who has appeared in just 31 total games with Boston — is batting .231 with four home runs and 27 RBI across 44 games with the Angels in 2026.
Chase Medroth, 2B
Chase Meidroth wasn’t the headline in the blockbuster Garrett Crochet deal with the White Sox, as Chicago mostly coveted a pair of prospects in Kyle Till and Braden Montgomery as part of that swap.
But the 24-year-old Medroth is building a solid big-league career as a balanced, right-handed bat who can grind bats — similar to what the Red Sox envisioned when they parted with valuable draft capital to acquire Durbin.
So far this season with Chicago, Medroth is batting .271 with 14 doubles, six home runs and 25 RBI.
Kyle Schwarber, DH
A Red Sox team lacking a proven pop at the plate should be kicking themselves for letting Kyle Schwarber walk in free agency after Boston’s unexpected trip to the ALCS in 2021.
Since Schwarber left Boston in free agency to sign with the Phillies, he has hit 216 home runs in 701 games in Philadelphia, averaging nearly 50 home runs per season with his new club.
He may be a flawed player when it comes to his rate and defensive limitations. But the Red Sox would welcome a fearsome power hitter like Schwarber anchoring the middle of the lineup.
In the same season that Schwarber signed with Philly, the Red Sox turned around and signed Masataka Yoshida, who had only hit 31 home runs over four seasons with Boston.
Xander Bogaerts, SS
The Padres already regret handing Xander Bogaerts an 11-year, $280 million contract in December 2022.
The 33-year-old shortstop has flopped in San Diego, batting .229 with eight home runs and 28 RBI across 72 games.
However, it could be argued that the Red Sox should not have allowed Bogaerts to hit the open market after the 2022 season, with Boston sorely missing Bogaerts’ veteran leadership and coming off the right side of the plate.
Alex Bregman, 3B
There are two things that could be true. The Red Sox sorely miss veteran Alex Bregman’s presence and talent in the Green Monster offense.
But handing him the same five-year, $175 million deal he ordered from the Cubs in January would also have been a miss — given that Bregman is batting .250 with six home runs and 25 RBI in an up-and-down Chicago team.
One could argue that a full season at Fenway would have boosted those numbers for Bregman, while the optics of losing Bregman just one year after his arrival — which sparked controversy that led to the Devers trade — represents some asset mismanagement on Boston’s part.
Nathan Eovaldi, RHP
The Red Sox’ decision not to trade Nathan Eovaldi during the lost 2022 season and then opting to let him walk for nothing the following season was another huge mistake.
The 2018 playoff champion was already a reliable starter for the Red Sox, and that trend carried over into his time with the Rangers.
While injuries hampered him at times with the Texans, Eovaldi is 41-23 with a 3.32 ERA over the past four seasons with the Rangers — headlined by a 2025 campaign in which he went 11-3 with a 1.73 ERA across 22 outings.
This year, Eovaldi is 7-7 with a 4.24 ERA with the Rangers.
Michael Wacha, RHP
Similar to Eovaldi, Michael Wacha is another starter who could have solved a lot of problems in Boston’s rotation had the Red Sox decided to keep him in free agency a few years ago.
One of the few bright spots for the 2022 Red Sox (11-2, 3.32 ERA), Wacha has continued to serve as a dependable starter for the Padres and Royals over the past four years — accumulating 10.5 WAR over that stretch with a 3.52 ERA.
This year with the Royals, the 34-year-old Wacha is 4-5 with a 3.64 ERA across 94 innings of work.
Rafael Devers, DH/1B
The Rafael Devers trade appears to have been a loss for both the Red Sox and Giants over the past year.
The Giants — who received the remaining $255 million in Devers’ deal last June — are well below .500 at 31-46 this season, with Devers far from the game-changer in the offense he was expected to be.
So far this season, Devers is batting .238 with 11 home runs and 36 RBI with just a .302 on-base percentage. The optics of Devers brandishing a runner in the ninth inning of Sunday’s loss to Miami were also a terrible look.
The Red Sox certainly didn’t exactly benefit from moving Devers, especially when it came to squandering several assets they grabbed from the Giants in the first place, like Harrison and Tibbs.
Despite the headaches Devers had last season, Boston still lacks the assured production he achieved, year after year, over eight years with the Red Sox.
Mookie Betts, SS
Truth be told, Mookie Betts is actually in the midst of the worst season of his distinguished career — batting .218 with eight homers and 19 RBI across 43 games with the Dodgers.
This potential drop from the 33-year-old superstar could validate some of Boston’s fears when they traded him to Los Angeles ahead of an expected seismic payday (12-year, $365 million extension with the Dodgers).
But, even if this contract turns out to be a bad one, the Dodgers likely have no regrets about bringing in Betts, who helped them win three World Series titles while being considered one of the best players of his generation.
In his six seasons with Los Angeles, Betts earned four All-Star nods and finished runner-up for the NL MVP award on two different occasions — to go along with his October hardware.
Subscribe to our newsletter today
Get everything you need to know to start your day, delivered straight to your inbox every morning.