Red Sox acquire right-hander Dustin May from the Dodgers for two prospects as Craig Breslow tried to get ‘uncomfortably aggressive’ at the trade deadline

With the clock ticking as the trade deadline was set to expire, the Red Sox made a deal to add depth to their starting rotation, acquiring right-handed pitcher Dustin May from the Dodgers.

Boston is sending two prospects, outfielder/first baseman James Tibbs III and Zach Ehrhard, back to Los Angeles, according to MassLive’s Christopher Smith. To make room on the 40-man roster, the Sox moved Tanner Houck to the 60-day IL.

Tibbs III was initially acquired on Father’s Day in the blockbuster trade that sent Rafael Devers to the Giants. Ehrhard, an outfielder, was the Red Sox' fourth-round pick in 2024 and was playing for the Portland Sea Dogs this season.

May, who is eligible to become a free agent after the season, will turn 28 in September. This season with the Dodgers, he started 18 games and went 6-7 with a 4.85 ERA and 97 strikeouts with a 1.35 WHIP. He pitched against the Red Sox at Fenway Park last weekend when Los Angeles was in town, allowing four runs on five hits in five innings while being saddled with the loss.

He’s recorded a 5.59 ERA while giving up 30 earned runs in 48 1/3 innings over night games (eight starts) since the beginning of June.

The lanky right-hander has been hampered by injuries over the course of his career. He missed all of last season due to an issue with his esophagus, which resulted in emergency surgery. He’s also gone under the knife twice, having Tommy John surgery both times.

He has elite stuff, with his four-seam fastball sitting at 95.5 mph, and offers a sinker and sweeper. May has been ineffective at times this season, which made him a potential trade candidate. If he had not moved on Thursday, he potentially was going to be optioned to Triple-A with both Blake Snell and Emmet Sheehan coming off the injured list.

The Sox' new righty has thrown 104 innings, which is a career high. In parts of six major league seasons, May is 18-16 with a 3.71 ERA, and in the postseason, he’s 3-1 with a 3.86 ERA in nine appearances, six of them coming out of the bullpen.

May fits the backend of the Red Sox rotation but leaves Boston short of another frontline hurler to slot behind Garrett Crochet. The righty is better than Richard Fitts, but the Red Sox should have been aiming higher. All the teams competing with Boston in the wild-card hunt have made improvements.

The Yankees added tremendous bullpen depth by trading for David Bednar and Camilo Doval, the Blue Jays added pitching, the Rangers traded for Merrill Kelly, who had been linked to the Sox, the Mariners were very aggressive and traded for both of Arizona's sluggers to improve their lineup, the Rays landed reliever Griffin Jax, and the Astros, who lead the AL West, acquired Carlos Correa.

Boston comes out of the trade deadline making just two moves, acquiring left-handed pitcher Steven Matz on Wednesday night and May on Thursday. Both trades are underwhelming and do not significantly impact the club.

"The team has been playing well, one in which the playoffs are firmly in view... We pursued as much as we possibly could. Ultimately brought in Matz and May,” Craig Breslow said to the media during the post-trade deadline Zoom call.

The 34-year-old has primarily pitched out of the St. Louis’ bullpen this season and has also been a starter in his career for the Cardinals, Blue Jays, and Mets. This season, the southpaw has logged 55 innings for St. Louis, achieving a 3.44 ERA and a 2.88 FIP while striking out 47 batters and walking just nine in 32 appearances, which include two starts.

Matz will be added to the Sox bullpen, which now has five lefties in Brennan Bernardino, Justin Wilson, Chris Murphy, and Aroldis Chapman in the mix. Boston could potentially send Murphy back to the WooSox. Bernardino is another candidate to head to Polar Park. He has pitched in 47 games with a 3.09 ERA and a 1.26 WHIP and could also be sent back to the minors.

The southpaw has been tough on left-handed hitters, holding them to a .179 average and .442 OPS. Righties, however, have hit .313 off him with an OPS of .814. Breslow told reporters that Matz’s stuff “ticks up” out of the bullpen and downplayed the idea the lefty will be stretched out as a starter. It should be noted, he didn’t exactly rule it out, either.

This trade deadline reeks of disappointment as Boston failed to make a big splash and really improve their roster. The Red Sox had been heavily connected to the Twins’ Joe Ryan and it was reported by MLB Network’s Jon Morosi that they made a late push to land the righty.

Ryan would have been a perfect fit behind Crochet and fit the model of what the Red Sox were looking for coming into the deadline. Boston wanted controllable pieces, particularly pitchers.

"We pursued a number of really impact possibilities... Ultimately it takes two teams lining up for those teams to line up… Teams have to like our players in order for that to happen,” Breslow said.

Ryan has two years of control remaining, and despite seemingly trading everyone on their roster, the Twins did not move their ace. It’s safe to say that Minnesota will trade him this winter as they undergo a full rebuild. Boston may have established momentum and groundwork for a potential deal in the offseason. Breslow held talks with the White Sox last summer for Crochet and finally traded for their ace in December.

"If fans were in the office during this deadline, they would see that guys we didn’t expect to be willing to talk about going into these conversations, we made available,” Breslow said. “We tried to put the most aggressive offers we could in hopes they were going to end in deals."

Others the Red Sox were linked to were traded, including rentals in Kelly (traded from the D-Backs to the Rangers), Charlie Morton (Tigers), Shane Bieber (Blue Jays), and Adrian Houser (Rays), and position players like Eugenio Suarez (Mariners). Boston held talks with Arizona about adding Kelly but was unable to come to an agreement. Zac Gallen, who was also tied to the Sox, was not moved, and Yandy Diaz, whom many in the Red Sox front office coveted, also remained with Tampa Bay.

“A lot of the industry does appreciate the young players we have in our system,” Breslow said. “We tried to work through different combinations of guys. We didn’t approach some of these conversations as though any players were off-limits. We couldn’t line up. We were pursuing multiple impact players. On the other side, teams that were operating as sellers were trying to juggle different concepts. For whatever reason, we weren’t able to line up."

Breslow did not want to subtract from the 26-man roster despite teams' interest in his players. The Padres pushed extremely hard for Jarren Duran, and teams around the league checked in on the availability of Chapman. He shut down any thoughts of trading his All-Star closer despite the prices relievers went for through the course of the day.

"It became clear that all 26 guys on our roster were contributing to what we were doing,” Breslow stated. “We weren’t willing to take a hit to our major league team and potentially impact the 2025 season in favor of trying to repackage or repurpose in a way that might have improved the future. There weren’t really opportunities to both trade off our major league team and improve our 2025 outlook, so we felt it was best to leave that group as it was and try to use what I think is a strong and deep system to try to improve the team."

The Red Sox will assume the remainder of Matz’s $12 million salary, which is about $4 million the rest of the way. May was making $2.125 million, of which the Sox will pay around $700,000. Estimates have the Red Sox’ collective bargaining tax (CBT) projection around $252 million, which is north of the tax threshold of $241 million.

“We’re happy with the guys we brought in, with Steven and Dustin, but we also pursued real impact players that we felt like could improve our team in ‘25 and beyond. We were uncomfortably aggressive in trying to pursue them in the players we were trying to put into deals. Ultimately, it wasn’t from a lack of effort. Other teams needed to say, ‘Hey, that’s enough. That crosses the line.’ It wasn’t about an unwillingness to talk about our full system.”

Boston sent Blaze Jordan to the Cardinals to complete the Matz swap. Jordan was drafted by Chaim Bloom in the third round of the 2020 MLB draft and will be reunited with the Sox’ former front office leader in St. Louis. The corner infielder has split time with the Sea Dogs and WooSox this season. Prior to his Triple-A promotion, he owned a .928 OPS in Portland and hit .289 with six homers, 24 RBI, and an .809 OPS in 43 games for Worcester.

The 22-year-old offers tantalizing power but has failed to showcase it during games and only in batting practice. He should be added to the Cardinals' 40-man roster to protect him from the Rule 5 draft.

Tibbs III had a brief stint with the Red Sox organization. The 22-year-old batted .207/.319/.267/.586 one homer, two doubles, one triple, seven RBIs, 16 runs, 19 walks, and 39 strikeouts in 30 games for the Sea Dogs. The Georgia native was drafted by the Giants in last summer’s amateur draft in the first round.

“We obviously didn’t get to know James Tibbs as well as Blaze and Zach but feel like they are really good baseball players,” Breslow said. “They are going to go on to have successful careers. Each does something that we like whether it’s James’ contact. Zach has started to hit ball pretty hard, really good defender in the outfield. Blaze obviously has been performing really, really well in Triple A this year.

Ehrhard was ranked by MLB.com as the Red Sox’ No. 27 prospect. The right-handed hitter has played in 89 games this season between High-A Greenville and Double-A Portland, combining to bat .267 (86-for-322) with nine home runs and 45 RBI.

Breslow made it clear to reporters that not one minor leaguer or prospect was considered untouchable during trade talks. 

“I don’t think this is about an unwillingness to include guys or anything like that,” he said. “Teams have to like our players in order for that to happen. We went into this deadline feeling like, in order to accomplish what we needed to accomplish and what we hoped to accomplish, we couldn’t take some of our young minor league players off the table. We couldn’t go into this with untouchables. And we didn’t. We were willing to talk about all of our guys in the name of improving our team. It just didn’t work out.

“The team has been playing well, in a position where the playoffs are pretty firmly in view. Felt like we needed to do what we could to try and bolster the team. I think I’ve been pretty outspoken about that. We pursued as much as we possibly could. Ultimately, brought in Matz and May."

Following the Devers trade, Breslow told reporters that there was “no mandate” to offload the disgruntled slugger but that he wanted "a more functional roster." With money to spend and the cupboards filled with talented prospects, Breslow had an opportunity to back up his bold claim after dealing Devers.

"And so at the end of the season, I think we could look back and say we've won more games than we otherwise would have because of the way that this roster is now able to come together," said Breslow.

We shall see.