The Boston Red Sox finally returned to the postseason in 2025 after some excellent offseason moves by Craig Breslow and stunning top prospect debuts. Boston's strengths were not enough to best the New York Yankees, however, and it was eliminated after a demoralizing Wild Card Game 3 loss.
Now, the front office will turn its attention to a new round of offseason pursuits to fare better next year. The Red Sox are a rather young team without many impending free agents, so they likely won't have many pure vacancies to fill this winter, but they'll have to decide whether to pursue reunions with the players hitting the open market.
There could be multiple reasons not to reunite with their soon-to-be free agents, from underperformance to high contract price demands to there being better options elsehwere. Here are four 2025 Red Sox who we think won't be back in 2026 and why.
4 Red Sox who won't be back in 2026 after Yankees send them home
Lucas Giolito
Lucas Giolito was the rebound player the Red Sox hoped he'd be, just a year late. Boston signed him before the 2024 season hoping to reinvigorate his career, but an elbow injury delayed his resurgence by a year. Giolito's 2025 campaign started poorly with a few rough outings, but he found his prime form early in the summer and finished the season with a 3.41 ERA, 121 strikeouts and 46 walks over 145 innings.
Giolito sustained another elbow injury in late September and couldn't participate in the postseason. Scans revealed no structural damage in his elbow, but two such injuries in as many years are a troubling sign for an impending free agent.
The Red Sox have a litany of homegrown pitchers who will need spots in the big leagues next year. Hunter Dobbins, Connelly Early, Payton Tolle, David Sandlin and possibly Luis Perales are just a few of them. Kutter Crawford and Patrick Sandoval will also be healthy. Still, none of those players can reliably fill the No. 2 spot in the rotation behind Garrett Crochet, and finding a clear No. 2 starter should be Boston's highest offseason priority. Trade deadline target and 2025 All-Star Joe Ryan could be an option, but Giolito should not be.
Dustin May
The Red Sox traded for Dustin May from the Dodgers at the 2025 trade deadline, and the deal was a disaster from the jump. Los Angeles was looking for a way to get May out of its rotation so it could activate Blake Snell from the injured list, and it somehow convinced Breslow to give up a top prospect from the Rafael Devers trade for a clear DFA candidate.
May clocked a 5.40 ERA with 26 strikeouts and 13 walks over 28.1 innings after his trade to Boston. He posted a career-high 132.1 innings this season, but he's never approached 100 any other time in his six year career, and he fell injured before the season was over. May isn't reliable enough to take up the final spot in the Red Sox's rotation, and they could find a better suitor elsewhere on the free agent or trade market.
Liam Hendriks
Like Giolito, the Red Sox signed Liam Hendriks as a rebound candidate after he underwent Tommy John surgery. Recovery and another injury setback kept him sidelined for all of the 2024 season, and Hendriks only pitched 13.2 innings for the big league squad in 2025.
Hendriks allowed 11 runs on 12 hits over his 14 appearances for the Red Sox this season, and with as many pitchers as they have in their organization, that won't cut it for a reunion. Hendriks' recent injury history is also a concern, as he had elbow and hip inflammation, as well as ulnar nerve transposition surgery in 2025.
Steven Matz
Boston acquired Steven Matz at the trade deadline to shore up its bullpen, and he performed well as a reliever. Matz spent 10 seasons of his 11-year career as mostly a starter, and his full-time transition to the bullpen was another pitching success story by Breslow. Matz posted a 2.08 ERA over 21.2 innings with the Sox.
As mentioned before, the Red Sox have many homegrown pitchers they need to find homes for on the big league squad, and not all of them can be starters. Matz's next will be his age-35 season, and despite his recent success, signing him again could be a risk. There are more experienced relief options on the free agent market who are better suited to Boston's needs.