Red Sox in last place as ex-stars rise

With the Boston Red Sox sitting last in the AL East at 31-44, several former players are thriving elsewhere in 2026—turning the franchise’s recent roster decisions into a louder debate about what got away and why.

For the third straight day of frustration at Fenway, the feeling isn’t subtle. With more than 80 games still on the calendar, the writing is already showing on the wall: this looks like another summer the Red Sox will be watching from the edge of the standings.

On Sunday evening, Boston sits in last place in the AL East with a record of 31-44. The season was supposed to carry early promise. but key players have been slowed by injury—Roman Anthony and Garrett Crochet among them. Other regulars, including Jarren Duran, Trevor Story, Marcelo Mayer, and Caleb Durbin, have struggled to meet expectations.

And then there’s the other storyline, the one that follows the team out of the ballpark every time a former Red Sox name plays with confidence on someone else’s roster.

Kyle Harrison. the 24-year-old left-hander Boston acquired as one of the top returns in the Rafael Devers trade with San Francisco. has been a difference-maker with Milwaukee. Harrison only pitched 12 innings with the Red Sox last season before being flipped to the Brewers during the winter. In Milwaukee in 2026, he’s gone 8-1 with a 2.50 ERA, striking out 87 batters over 72 innings and posting a 1.06 WHIP.

Boston isn’t just missing contributions elsewhere in the abstract. The Harrison case lands because it wasn’t long ago that he was one of the young pieces the club expected to grow with.

The same kind of sting shows up farther back in Boston’s recent decisions. Dustin May stands out as a cautionary tale about asset management for Craig Breslow and his staff. Last season. the Red Sox were in need of reinforcements in their rotation. and they dealt away prospects James Tibbs III—acquired a little over a month earlier in the Devers trade—and Zach Ehrhard to acquire May from the Dodgers. May was a bust in Boston, appearing in just six games (five starts) and posting a 5.40 ERA.

The right-hander did not stay in the Red Sox long enough for the investment to pay off. After the team let him go, May signed a one-year deal with the Cardinals in the past winter. In 2026. he’s 5-6 with a 4.30 ERA. and his season has included a one-hit. complete game shutout last week against San Diego.

Even if May’s turnaround was its own story, Tibbs has been the part that keeps resurfacing. In Triple-A this season, Tibbs is batting .294 with 20 home runs and 62 RBI over 71 games, and he’s doing it as one of the Dodgers’ top prospects.

Not every former Red Sox has carried momentum in a straight line. but several have helped make the contrast feel sharper. Walker Buehler. a two-time World Series champion. had an underwhelming 2025 with Boston. posting a 5.45 ERA across 23 outings before being released by the team. He bounced back with the Phillies over a short stint in the fall. going 3-0 with a 0.66 ERA. and then signed a minor-league deal with the Padres.

In 2026, Buehler hasn’t returned to the kind of form that made him a standout, but he has been serviceable. He’s 4-3 with a 3.96 ERA across 15 starts for San Diego. Since the start of June, the 31-year-old is 1-0 with a 1.71 ERA.

Chris Sale, too, has been steady enough to raise eyebrows about what Boston gave up and what it got back. Sale dominated in his first two seasons with the Red Sox. including a key role in Boston’s 2018 World Series run. But he had a miserable end to his tenure in Boston. making just 56 starts and posting a 4.16 ERA over his final five seasons with the club from 2019-23.

Now he’s back among the league’s most formidable pitchers. Sale was traded to the Braves in exchange for infielder Vaughn Grissom, and after arriving in Atlanta, he went on to win the NL Cy Young Award in his first season there. Through 14 starts in 2026, Sale is sporting a 2.14 ERA.

The bigger picture with Sale is that he’s not just holding on. In three seasons with the Braves, he’s gone 33-13 with a 2.43 ERA and 482 strikeouts over 381.1 innings.

Grissom’s results with the Angels in 2026 have been more modest. He appeared in only 31 total games with Boston, and in 2026 with the Angels he’s batting .231 with four home runs and 27 RBI across 44 games.

Boston’s roster churn has affected more than just pitchers and headline stars. Chase Meidroth. acquired in a Garrett Crochet blockbuster deal with the White Sox that placed Chicago’s focus on Kyle Teel and Braden Montgomery. has been quietly building a big-league career. Meidroth, a 24-year-old right-handed bat, is batting .271 with 14 doubles, six home runs, and 25 RBI so far this season with Chicago.

There’s also the power bat Boston let walk—Kyle Schwarber. After Boston’s unexpected run to the ALCS in 2021. the Red Sox had the rare opportunity to keep a middle-of-the-order weapon. Instead, Schwarber left in free agency and signed with the Phillies. In Philadelphia, he’s clubbed 216 home runs in 701 games, averaging nearly 50 dingers per season.

Schwarber’s game comes with flaws. including a whiff rate and defensive limitations. but the point remains simple: the Red Sox have reasons to remember what it looked like when he was a feared presence. The offseason Schwarber signed with Philly. Boston pivoted and signed Masataka Yoshida. who has hit 31 homers across four seasons with the Red Sox.

Even the deals that once looked like forward progress can become complicated when the numbers land elsewhere. Xander Bogaerts, signed by the Padres to an 11-year, $280 million contract in December 2022, has underwhelmed in San Diego. The 33-year-old shortstop is batting .229 with eight home runs and 28 RBI across 72 games.

Boston’s supporters have argued the club shouldn’t have waited to let Bogaerts reach the open market after the 2022 season, when Boston desperately needed his veteran leadership and right-handed pop.

Alex Bregman brings another kind of debate—one that sits in the same uncomfortable space as the team’s current struggles. The Red Sox miss his veteran presence and the way he can pepper the Green Monster. But giving him the same five-year. $175 million deal he commanded from the Cubs in January also would have been a misstep. based on his current production on a fluctuating Chicago roster. In 2026, Bregman is batting .250 with six home runs and 25 RBI.

One could argue a full season at Fenway might have boosted those totals. The optics. though. are already part of the conversation: losing Bregman just a year after his arrival. in a situation surrounded by controversy that led to the Devers trade. is often framed as poor asset management on Boston’s side.

There are also the cases where Boston chose not to trade a dependable arm—or simply didn’t keep one when it mattered. Nathan Eovaldi’s situation is tied directly to decisions from the club’s lost 2022 season. The Red Sox did not trade Eovaldi during that stretch, then let him walk for nothing the next offseason. Eovaldi was a 2018 playoff hero and remained dependable as a starter for Boston.

Now with the Rangers, his record continues to hold up. Over the last four seasons with Texas, Eovaldi is 41-23 with a 3.32 ERA, including a 2025 campaign in which he went 11-3 with a 1.73 ERA across 22 outings. This year with the Rangers he’s 7-7 with a 4.24 ERA.

Michael Wacha has been similar—one of those players Boston could have kept in the rotation conversation a few years back. but didn’t. One of the few bright spots in the 2022 Red Sox was Wacha, going 11-2 with a 3.32 ERA. Since then. he’s been a dependable starter for the Padres and Royals over the last four years. compiling 10.5 WAR with a 3.52 ERA.

In 2026 with the Royals, the 34-year-old is 4-5 with a 3.64 ERA across 94 innings.

And then there’s Rafael Devers. the centerpiece of the trade that already helped send players out of Boston in greater numbers than the Red Sox may have expected to survive. The Devers trade has turned into a lose-lose for both the Red Sox and Giants. at least through the first sweep of the deal’s impact. The Giants took on all of $255 million left on Devers’ deal last June. and they are well below .500 at 31-46 this season.

Devers’ offense has also fallen short of projection. So far this season, he’s batting .238 with 11 home runs and 36 RBI, with a .302 on-base percentage. His optics have been a sticking point too—Boston fans will remember how damaging even small moments can feel in the wake of a major franchise shift. On Sunday’s loss to Miami, Devers waved off a pinch-runner in the ninth inning.

Boston’s criticism is sharpened by the fact that it didn’t maximize what it received. The Red Sox haven’t exactly taken advantage of moving Devers, and they’ve also squandered several of the assets they grabbed from the Giants, including Harrison and Tibbs.

Still, the way the season is going in Boston can’t be blamed on trade history alone. Even with Devers as an example of what has gone wrong elsewhere, Boston is missing the assured, year-in-and-year-out production that he generated over his eight-plus years with the Red Sox.

Mookie Betts is the latest name that turns every offseason debate into something more personal. Betts is in the midst of the worst season of his standout career so far. batting .218 with eight homers and 19 RBI across 43 games with the Dodgers. For a franchise that traded him ahead of an expected seismic pay day—an extension of 12 years and $365 million—this kind of decline could confirm fears.

But the Dodgers’ response has been the kind that makes hope complicated. Over the last seven games, Betts is hitting .357/.379/.643. He also hit a bottom of the ninth inning home run, and on the night of the cited performance he went 3-for-5.

Betts’ long-term value is still there, too. In his six seasons with Los Angeles, he has earned four All-Star nods and finished runner-up for NL MVP on two different occasions, along with winning three World Series titles.

The sequence of player departures and outcomes doesn’t have to be argued in theory when the standings tell a different story from what was once promised in Boston. While the Red Sox sit in last place at 31-44. former names—Harrison. Tibbs. May. Sale. Buehler. Meidroth. Schwarber. Wacha. Eovaldi. and others—have filled out the ledger in other uniforms.

For a team still carrying more than 80 games of the season, the question isn’t whether talent can be replaced. It’s whether the cost of decisions already made has become too expensive to ignore.

Boston Red Sox AL East Rafael Devers trade Kyle Harrison Dustin May James Tibbs III Chris Sale Kyle Schwarber Mookie Betts Walker Buehler Alex Bregman Xander Bogaerts