Grading Red Sox 2025 trade deadline: Craig Breslow, John Henry fail fanbase yet again

Minnesota Twins v Boston Red Sox
Minnesota Twins v Boston Red Sox | Billie Weiss/Boston Red Sox/GettyImages

Another MLB trade deadline has passed, and the Boston Red Sox underwhelmed yet again. After the Rafael Devers trade, the front office said it would buy into the team and by no means had they thrown in the towel. When Boston carried a 10-game winning streak into the All-Star break just one month later, big additions at the deadline seemed imminent.

That isn't what the Red Sox got. Chief baseball officer Craig Breslow brought in two pitchers, but no offensive or defensive reinforcements. Abraham Toro and Romy Gonzalez will still platoon at first base, and Carlos Narváez didn't get any help behind the plate. Even the pitching additions Boston made are nothing to write home about.

The Red Sox and their fans feel they were promised action, but they received more of the same thing they got in recent deadlines past — budget additions to hold onto prospects and money. Here, we'll evaluate Boston's two deadline moves individually, then grade its approach as a whole.

Grading Red Sox 2025 trade deadline: Craig Breslow, John Henry fail fanbase yet again

Red Sox acquire Steven Matz from the Cardinals for Blaze Jordan

The Red Sox opened their trade deadline by trading for Steven Matz from the Cardinals late on Wednesday night. Boston will use Matz out of the bullpen, but did not rule out using him as a starter if necessary. The 34-year-old has pitched to a 3.44 ERA with 47 strikeouts and nine walks over 55 innings this season. He made two stars for St. Louis.

Boston traded corner infield prospect Blaze Jordan for Matz. Jordan, 22, batted .308/.377/.495 with 22 doubles, a triple, 12 homers and 62 RBI in 88 games between Double-A and Triple-A. Jordan will be Rule-5 Draft eligible after the 2025 season, and if the Red Sox had no plans to roster him, it was wise of them to get a return for him while they had a chance. Jordan was one of the best first base prospects in the system, and since Triston Casas won't be ready to start on Opening Day, Boston will need to find someone to play first base over the winter.

Grade: B

Red Sox acquire Dustin May from the Dodgers for James Tibbs III and Zach Ehrhard

Minutes before the 6 p.m. deadline on Thursday evening, the Red Sox traded for starter Dustin May from the Dodgers. LA hoped to trade May at the deadline, as he's an impending free agent and it expects Blake Snell back from the injured list before August is over. Boston's trade for May felt especially underwhelming after Red Sox fans were briefly led to believe the team had landed Joe Ryan from the Twins, but we won't hold that against the move.

Still, May was one of the less impressive rental pitchers on the market, and he'll become the third pitcher in the Red Sox's rotation who has rehabbed from Tommy John surgery in the last two years. He's posted a 4.85 ERA with 97 strikeouts and 43 walks in 104 innings this season.

The Red Sox managed to overpay for May minutes after being outbid for Merrill Kelly by the Rangers. James Tibbs III was one of Boston's returns in the Rafael Devers trade, and the No. 5 prospect in the system, per MLB Pipeline. Zach Ehrhard, a Double-A outfielder, was the No. 27 prospect. The Red Sox shouldn't be prospect huggers, but they should give them up under the right conditions — a top five and a top 30 prospect for two months of May in the worst season of his career so far is a laughable overpay. May deepened the rotation, which the Red Sox desperately needed, but he doesn't make it as good as it needs to be to compete in the AL East and the tight AL Wild Card race.

Grade: C-

Overall grade: D

The Red Sox need more help than they brought in at the trade deadline. Matz and May make the bullpen and rotation deeper, but not deep enough, and Boston needed a safe bet in the rotation due to Lucas Giolito and Walker Buehler's inconsistency. The Red Sox's attempt to trade for Ryan felt like a last-minute scramble, and their approach was called "feeble, at best" by MLB insider Ken Rosenthal. Boston didn't add a bat to help fix its streaky offense, and Narváez and Connor Wong remain its only catchers.

The Red Sox backed down when they saw the rest of the AL going all-in. The Blue Jays, Yankees, Rangers and Rays — all the teams currently around Boston in the Wild Card chase — all got better while the Red Sox stayed close to the same. Boston has the hardest second-half schedule in MLB, and didn't do a thing to make it easier. John Henry and Breslow's foolish self-imposed budget and prospect-hugging could cost it yet another playoff appearance, and that should have been completely off the table, given they've missed in the last three years.

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