Craig Breslow has dabbled in the extremes on the trade market since he took over as chief baseball officer of the Boston Red Sox. On the one hand, he landed Garrett Crochet from the Chicago White Sox, but he also sent Rafael Devers to the San Francisco Giants for the equivalent of a bag of balls.
Trade deadlines, in particular haven't been Breslow's strong suit, but the 2025 deadline was a complete disaster. Red Sox fans were briefly under the impression they'd landed Joe Ryan to bolster their rotation, but they actually ended up with Dustin May.
At the time of the May trade, Blake Snell was nearing his return from injury and May had performed like a clear DFA candidate last season. Instead of letting the Dodgers part with him and then claiming him off waivers, Breslow, in an act of desperation, traded prospects James Tibbs III and Zach Ehrhard for him.
Not only did May struggle with the Red Sox then fall injured quickly, Tibbs has settled in incredibly well with the Dodgers. He batted .269/.407/.493 with a .900 OPS over 36 games with Double-A Tulsa.
Former Red Sox prospect and return in Rafael Devers trade, James Tibbs III, is going off for Dodgers in spring training
Tibbs has continued his dominance into spring training as a non-roster invitee to big league practices. He's logged seven hits, including two home runs, three runs, five RBI, nine strikeouts and three walks over 11 appearances so far.
Tibbs was part of Boston's return in the Devers trade and it was a shame to see him moved for such a disappointing return. May and Ehrhard were both top prospects when Breslow dealt them to LA and May was hardly worth one of them, let alone both. This still would've been the case even if he'd stayed healthy — he clocked a 4.96 ERA and 1.42 WHIP over a career-high 132.1 innings last season and showed few to no signs of improvement with the Sox.
There's no clear place for Tibbs in the Red Sox's plans moving forward, since he's an outfielder and they have Roman Anthony, Ceddanne Rafaela and Wilyer Abreu under contract for the foreseeable future and Jarren Duran in the mix currently. Still, Boston could've used him as part of a larger trade this offseason instead of sending promising pitching prospects and depth arms all over the place.
Hopefully, the May trade taught Breslow a little something about trading with the Dodgers. He wasn't the orchestrator of the Mookie Betts trade, but everyone knows by now that LA has Boston's number, seemingly winning every trade they make by a landslide.