The Boston Red Sox faced a frustrating trade deadline on Thursday as they missed out on acquiring their two primary pitching targets, including Joe Ryan. Despite fervent efforts, the team was unable to secure Ryan or Merrill Kelly, leaving fans anxious and disappointed. Instead, Boston settled for acquiring pitcher Dustin May shortly before the deadline expired.
Red Sox Acquire Dustin May in Exchange for Two Top Prospects
In the final moments before the trade deadline bell, the Red Sox completed a deal for the 6-foot-6 right-hander Dustin May. Boston sent two outfield prospects, James Tibbs III and Zach Ehrhard, to Los Angeles in exchange. Tibbs, acquired as part of the Rafael Devers trade, was ranked fifth among Red Sox prospects by MLB Pipeline, while Ehrhard held the 27th spot.
May was once regarded as a rising star in pitching but saw his progress interrupted by a second Tommy John surgery during the summer of 2023. After missing the entire 2024 season, May returned to pitch in the Dodgers’ rotation this year but struggled, posting a 6-7 record with a 4.85 ERA and a 1.346 WHIP – noticeably below his previous levels from 2019 to 2023.
Injury History and Pitching Profile of Dustin May
Dustin May underwent Tommy John surgery previously in 2021, sidelining him for over a year before returning to the mound. His pitching arsenal includes four distinct pitches, with a high reliance on his sweeper and sinker, which account for 41 percent and 36 percent of his pitching mix, respectively. May throws his four-seam fastball and cutter less frequently, and he is expected to fill a role in Boston’s fifth rotation spot.
This spot has been unstable due to injuries to regular starters Tanner Houck and Hunter Dobbins, the latter having a season-ending knee injury. May’s contributions are likely to be similar to those of recently demoted Richard Fitts and injured Dobbins, rather than transformative for the team’s postseason aspirations.
Context of the American League Race and Red Sox’s Deadline Moves
The Red Sox entered the deadline holding the second wild-card position in the American League, only a game behind the New York Yankees, who sit atop the wildcard race. Meanwhile, the Seattle Mariners and Texas Rangers trailed Boston by just 1.5 games, increasing competition for playoff spots. Division leaders Toronto and Houston also made roster improvements to strengthen their chances.
Aside from Dustin May, Boston also acquired left-hander Steven Matz to add depth to their pitching staff. Matz is aimed at shoring up the bullpen, which has shown areas of weakness this season, although neither acquisition is considered a major upgrade to the team’s core strength.
Red Sox acquire Steven Matz in trade to bolster pitching depth
Failed Pursuit of Merrill Kelly and Joe Ryan Adds to Fans’ Frustration
Before the deadline closed, Red Sox executives, including Craig Breslow, made notable efforts to acquire top pitchers Merrill Kelly and Joe Ryan. Kelly, 36, is expected to enter free agency in the offseason, and despite Boston’s initial engagement, the Arizona Diamondbacks ultimately traded him to the Texas Rangers. The Rangers’ package included several highly ranked prospects, making the deal inevitable.
Jon Morosi reported that Breslow also attempted last-minute negotiations to secure Joe Ryan from the Minnesota Twins. Ryan, a 26-year-old All-Star this season under control through 2027, was viewed as the ideal addition to strengthen Boston’s starting rotation alongside Garrett Crochet.
Ryan’s acquisition would have significantly elevated the Red Sox’s championship prospects by providing a reliable frontline starter, possibly ending years of postseason drought. However, despite the Twins moving several players before the deadline, they chose to keep Ryan, disappointing Red Sox management and fans alike.
Comparisons to Previous Disappointments and Current Team Outlook
This trade deadline marks a second consecutive period of frustration under Breslow’s tenure. Last year, the Red Sox acquired James Paxton, another pitcher coming off an underwhelming period, along with backup catcher Danny Jansen and a group of relievers including Luis Garcia, Lucas Sims, and Quinn Priester. Unfortunately, these additions did little to help the team, which slid in the standings and missed the playoffs by five games.
Steven Matz may provide meaningful relief pitching support, while May’s impact is expected to mirror the inconsistent efforts from recent starters like Dobbins and Fitts. Despite the limited upgrades, Boston holds an 8-game winning record above .500 and has rekindled some fan interest after recent rough seasons.
Many fans had hoped for bolder moves from Breslow to turn the team into serious contenders for the postseason and beyond. Instead, the acquisitions signal a cautious approach that may maintain competitiveness without pushing the team significantly closer to a World Series return.