The 2026 trade deadline sent a few familiar names out to contenders, and for Red Sox fans, the interesting part is how many of those names trace back to Craig Breslow deals that never quite worked out in Boston.
Dustin May is the one that still sticks in the memory. Less than an hour before the 2025 deadline, a wave of mistaken reports had Sox fans believing Boston had pulled off a Joe Ryan deal with the Minnesota Twins.
Instead, the Red Sox wound up with May, who was viewed as a near-certain DFA candidate by the Los Angeles Dodgers. He lasted 28.1 innings in Boston, posting a 5.40 ERA before getting injured.
Over the offseason, May signed with the St. Louis Cardinals and turned in a 4.38 ERA with 106 strikeouts across 109 innings.
St. Louis then shipped him to the Milwaukee Brewers, who needed a consolation prize after missing out on Tarik Skubal.
Nathaniel Lowe’s Boston stop came later, after the Red Sox picked him up on waivers from the Washington Nationals. He opened his stint with a jolt, piling up three extra-base hits - a home run and two doubles - in his first three games.
By the end of September, he had hit .280/.370/.420 over 34 games. Lowe later signed a minor league deal with the Cincinnati Reds just before spring training in 2026, then put together a .266/.341/.480 line with 17 doubles and 12 home runs in 83 games.
Cincinnati eventually dealt him to the Cleveland Guardians, where he is tied with rookie phenom Chase DeLauter and Kyle Manzardo for second on the club’s home run list.
Ryan Zeferjahn was another former Red Sox piece moved at the deadline, and his path also runs through a Breslow trade that didn’t pay off in Boston. The Red Sox drafted Zeferjahn in the third round of the 2019 MLB Draft as a starting pitcher, then sent him and three other prospects to the Los Angeles Angels for reliever Luis Garcia.
Zeferjahn reached the majors with the Angels soon after the trade and put up a 2.12 ERA and 0.76 WHIP over 17 innings. Two years later, Anaheim flipped the flamethrowing right-hander to the Chicago Cubs, who were desperate for bullpen help after deadline day with 14 pitchers on the injured list.
In Other News...
Red Sox Fans Will Care About What Boston Got Back For Mayer
With Marcelo Mayer headed to San Francisco, the Red Sox did not simply clear a name from their infield depth chart, they brought back pieces that fit two different kinds of roster needs. Bostons return centers on a left-handed reliever in Erik Miller, a power arm with obvious control questions but some real upside, and a young outfielder in Carlos Gutierrez, whose profile is built more on athleticism and feel than on loud power numbers.
Miller gives Boston a chance to chase swing-and-miss from the left side, even if the command has to come with it, while Gutierrez adds another developmental outfield option to a system that always needs more of them. For a club that has spent plenty of time sorting through infield depth and long-term fit, the interesting part of this swap is not just what Mayer meant going out, but how the Red Sox chose to spread that value back across the roster. [Read more 🡒]
Red Sox Suddenly Have A Bigger Adley Rutschman Decision Ahead
Adley Rutschmans arrival gave the Red Sox something they had lacked for stretches this season: a catcher whose production had already outpaced the group Boston had been using behind the plate. The three-time All-Star is still on the Injured List, but the encouraging sign for the Red Sox is that he has started batting again after coming over from Baltimore, which at least puts him on a track back toward giving this lineup and pitching staff a more stable everyday option.
The bigger question now is no longer just when Rutschman returns, but how long Boston can keep him in place. Reports have indicated the Red Sox have a chance to work on a contract extension with him, and while no deal is in place yet, the timing adds a layer to a move that already reshaped the catching picture. For a team that values certainty at a premium position, the next step may matter almost as much as the trade itself. [Read more 🡒]
Adley Rutschmans Recovery Just Became A Bigger Red Sox Question
Adley Rutschmans return has become one of the more closely watched injury storylines around the Red Sox, with the catcher still on the injured list after going down July 20 because of a wrist injury. The encouraging sign is that he says the wrist has been feeling good, and he remains in contact with the medical staff as the club weighs the next steps.
The bigger question now is how Boston handles the ramp-up from here. Before he is back behind the plate for good, the Red Sox could choose to send Rutschman out on a rehab assignment, a move that would give them a better read on where he stands while keeping his return on a cautious track. [Read more 🡒]