Craig Breslow has been a shrewd dealmaker since he took over as chief baseball officer of the Boston Red Sox — he landed Garrett Crochet, Sonny Gray, Willson Contreras and more without sacrificing too many critical pieces. But trade deadlines have never been his forte.
Breslow's 2024 trade deadline adds didn't move the needle before they fell injured and the Sox proceeded to miss the playoffs. Last season, he made a great move to add Steven Matz to the bullpen, but totally blew the trade for Dustin May from the Los Angeles Dodgers in a way fans may never forget.
In 2026, Breslow has changed the narrative. He made three massive trades and one smaller one to help Boston address many of its deficiencies (though not all of them) before its upcoming playoff run. Here are grades for Breslow's individual trades and an assessment of his deadline moves, as a whole.
Complete Red Sox trade deadline grades following massive top prospect purge
Curtis Mead
Breslow's first deadline move is also his most disappointing, though it's no fault of his. Boston on July 25 traded for Mead from the Washington Nationals to bring some pop to its middle infield. But in his second at-bat with the Sox, Mead was hit by a pitch that fractured his wrist and sent him to the sidelines for at least six weeks.
Mead is slashing .253/.353/.498 and his 17 homers would be tied with Wilyer Abreu for second on the team. His wrist will be re-examined by doctors in the next few weeks and, if the Sox are lucky, he may be able to re-join the team. For now, trading Connelly Early for Mead hasn't looked perfect, but Mead has the chance to change that upon his return.
Grade: B
Adley Rutschman, Jake Rogers
The rest of Boston's moves occurred on deadline day, the Rutschman trade being the first of them. The Sox also landed former Detroit Tigers catcher Rogers in exchange for Carlos Narváez, Anthony Eyanson (No. 2 Red Sox prospect), Kyson Witherspoon (No. 4) and Enddy Azocar (No. 5).
Three top five prospects and a big league catcher are undoubtedly a huge price to pay for a player who hasn't lived up to his offensive potential in the last two seasons. But Rutschman is an offensive improvement over Narváez, a three-time All-Star and an elite defender. The division rival tax is also a factor in this deal, likely driving up the price handily.
Rutschman is also under contract for the 2027 season, though the change that it is shortened by a lockout is high. The Red Sox will have to extend Rutschman to get all they can out of this trade, but he makes them better for a playoff run and Rogers brings depth, which is the main goal of trade deadline moves, anyway. Plus, the New York Yankees were high on Rutschman and the Red Sox went above and beyond to get him for themselves.
Grade: B-
Eli White
Boston made a small trade between two massive ones, sending Triple-A pitcher Tyler Uberstine to the Atlanta Braves in exchange for White, a veteran outfielder. The Red Sox already have more outfielders than they know what to do with, but White will be just the second right-handed hitter alongside Ceddanne Rafaela — all the Sox's other outfielders are lefties.
Jarren Duran has severely underperformed this season and Wilyer Abreu is in an offensive funk that has lasted over a month, despite a few timely home runs. White may just be another right-handed platoon or pinch hit option to pair with Jahmai Jones, but Boston got him for a player who had no place on its big league roster. Overall, it's a good small deal for a righty depth bat.
Grade: A-
Erik Miller, Carlos Gutierrez
Lastly, Boston shocked fans by sending Marcelo Mayer to the San Francisco Giants in exchange for lefty reliever Miller and High-A outfield prospect Carlos Gutierrez. Mayer's short tenure in MLB hasn't gone as the Red Sox expected, so they traded him high for a dominant reliever with three more years of team control.
Gutierrez is a long way from having any major league impact but Miller should be an ideal fit in the back end of the Sox's bullpen. The deal includes a bit of strange resource allocation from Breslow — yes, he wanted to sell high on Mayer, but he could've been part of a larger package to bring in the shortstop the Red Sox reportedly sought or another long-term position player. It's sad to see Mayer go but Sox fans are glad to see Miller come in, so it's a decent swap.
Grade: B+
Overall grade: B
Breslow addressed multiple of the Red Sox's needs including a catching upgrade, a few righty bats and some fearsome bullpen depth. But the Rutschman trade is risky if there's a shortened season — or maybe no season at all — next year. Breslow also didn't add to the starting rotation, which could've used another righty to pair with Sonny Gray and an innings eater to take some pressure off rookies Payton Tolle and Jake Bennett, who already have a lot of mileage on their arms this year.
If Mead and Rutschman deliver when they come off the IL and Miller continues the season he's had with the Giants, Breslow's deadline performance will be his best yet, deserving of a solid "B" grade. But if the 2027 season is cut short and Rutschman can't improve offensively, this may be a rough one to look back on, especially if one or two of Eyanson, Witherspoon and Azocar end up the impact players they have the potential to be.
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