“We feel like we’ve got a tried and true and battle-tested starting pitcher coming from an organization that’s had a ton of postseason success, and somebody who can step into our rotation and add to our pitching group.” That’s what Craig Breslow said when the Boston Red Sox acquired the right arm from the Dodgers during the trade deadline. However, the reality is way different from the expectations.

Enter Dustin May. The ex-Dodgers pitcher, with a market value of $3.9 million per Sportarc, that Breslow talked about came to Boston in a trade for prospects James Tibbs III and Zach Ehrhard. Against the Pirates at Fenway Park on August 30, 2025, May pitched for only 5 1/3 innings, giving up 8 hits (including a home run), walking 4 batters, hitting one, and striking out only 5 batters while giving up 7 runs (6 earned). Result? A loss by 3-10.

Meanwhile, back in the BoSox dugout, the visuals weren’t great either. Tim Healey, a Red Sox insider, shared the information on X, “May sat in the dugout, alone, sweat seeping through his hat, head in his hands, barely able to believe it.… ‘I got traded over here to help,’ May said, ‘and I feel like I’ve done the opposite.'” 

The contrast between expectations and reality has been jarring. May put up decent numbers while pitching for the Dodgers in 2025, going 6–7 with a 4.85 ERA in 18 starts with 97 strikeouts. Since the trade deadline, he’s had a rough time in Boston, going 1–4 with a 5.68 ERA in five starts. His 2025 stat total is now 7–11, with a 5.01 ERA, 122 Ks, and a 1.41 WHIP. These numbers present a worrisome situation for his career.

Despite the bad play, the skipper, Alex Cora, has still shown confidence in him. In the post-game interview, he said, “He’s a guy that we trust. He’s got good stuff. We’ve just got to make sure we get him back on track.”

Well, not only Dustin May but Alex Cora his needs other pitchers to get back on track, too, if the playoffs are something the Red Sox are aiming for.

Red Sox Rotation Misfire Is Not Limited to Dustin May

Boston’s pitching problems against Pittsburgh just won’t go away, and it feels like déjà vu. Payton Tolle was amazing in his first game, pitching 5.1 innings, giving up two earned runs, and striking out eight batters. But relievers Greg Weissert and Jordan Hicks let inherited bases and a late run score, which led to a 4-2 loss.

Even so, manager Alex Cora has still shown optimism in Hicks. Cora said, “We believe in the stuff. We just gotta keep working with him.”

And he did give him another chance in Game 2. Jordan Hicks pitched 0.1 innings, giving up 2 hits, 1 earned run, with no walks or strikeouts and an ERA of 6.38. His final line: 0.1 IP, 2 H, 1 ER, 0 BB, 0 K. The rest of the arms weren’t helpful either. Reliever Brennan Bernardino took the ball and quickly fell apart, losing control and giving up five runs in just two-thirds of an inning. It was the kind of meltdown that made Fenway feel cold.

The race for the playoffs won’t wait for Boston’s pitchers to get their act together. As Wild Card places slip away as division rivals take advantage of every mistake, the Red Sox have to do something. They are currently at 3rd with a record of 75-62, just 3.5 games behind the Yankees.

With Cora’s confidence in the pitching, can the Red Sox win game 3 against the Pirates and solidify their position for the playoffs? Or will the pitching woes continue?