Craig Breslow’s tenure as chief baseball officer of the Boston Red Sox has been as polarizing as any front office run in recent memory. Savvy offseason additions like Garrett Crochet, Aroldis Chapman, and Carlos Narváez built early goodwill and suggested a clear vision for roster construction.
That momentum stalled midseason. A clubhouse fracture culminated in the shock trade of Rafael Devers, a move that sapped the power in Boston and sharply shifted fan perception of Breslow’s leadership and long-term plan.
Devers was traded for Jordan Hicks and three prospects in Kyle Harrison, Jose Bello and James Tibbs III. While the return package included several decent prospects, the move was disappointing to many in Boston, reading more like a salary dump than a fair return for one of the best players in recent franchise history.
Another move that left a sour taste all over New England was acquiring righty Dustin May from the Dodgers for prospects Zach Ehrhard and James Tibbs III — the same Tibbs from the Devers trade.
Although the Dodgers have plenty of prospects waiting to join the stacked major league roster, Dodgers Insider Fabian Ardaya says that “Tibbs and Ehrhard could be in the mix” for the 2026 season. Breslow was brought in May to be a cheap option at the back-end of the rotation. Giving up Tibbs and Ehrhard for May, who has already signed with the St. Louis Cardinals for the 2026 season, wasn't have been the most forward-thinking move.
Red Sox's overpay for Dustin May coming back to haunt them quickly with latest Dodgers prospect update
The frequently-injured May’s time in Boston was short. The 27-year-old May featured in just six games for the Red Sox, sporting a 5.40 ERA through five starts. May’s velocity on his leading four-seamer was hovering around 95 miles per hour, down from 97 in 2023. Although May’s freak injury history was clearly affecting his play, he posted 132.1 innings in 2025, his career-best.
Tibbs was a first-round pick for the Giants in the 2024 draft before being shipped to Boston, and now back to Los Angeles. The 23-year-old outfielder is currently ranked the No. 8 prospect in the Dodgers' pipeline.
Tibbs is known for his pop at the plate and his arm in the outfield. With the Dodgers, Tibbs hit .269 with the Double-A Tulsa Drillers in 2025. Although he has only reached Double-A thus far, Tibbs has plenty of potential and time to continue on his path and make Breslow regret moving him so quickly.
Ehrhard was the lesser-mentioned piece in the deal. The now 22-year-old was drafted by the Red Sox twice, first in 2021 and again in 2024, when he eventually signed as a fourth-round pick. Ehrhard reached Double-A Portland before being sent to Los Angeles, where he hit .282 for the Tulsa Drillers with a .391 OBP and has since made a name for himself as the No. 27 prospect in the Dodgers system.
As it stands, both players are climbing the farm system for the back-to-back champions in Los Angeles. While Devers continues to hit bombs at Oracle Park in the Bay Area and Dustin May cashes in with a $12.5 million deal in St. Louis, Breslow is left with little to show for all of his big moves.