It’s no secret that Craig Breslow knows a thing or two about pitching. He was a member of the Boston Red Sox’s 2013 World Series winning roster, and played for 12 seasons, eventually hanging it up at 36. He has drafted pitchers at a significant rate during his two years at the helm in Boston, and those selections have yielded players like Payton Tolle, a hulking lefty banging down the door at the big league level after just a year in the organization.
It seems that Breslow isn’t content to overhaul the pitching program via only the draft any longer, though. He’s been an active shopper when it comes to arms throughout his tenure, with a few duds coming into the team as well as some serious firepower (Walker Buheler versus Aroldis Chapman, for one).
This winter, Breslow has been aggressive in his dealmaking, parting ways with six pitchers in December alone. His trade for Willson Contreras — shipping off prospects Yhoiker Fajardo and Blake Aita alongside Hunter Dobbins — signals a potentially important shift.
This isn’t the first trade Breslow has made this winter to bring in major league talent with cash attached to the deal. Boston has been infamous in its spending disparity as of late, raking in top of the league profits while sitting outside the top 10 in spending. This is a frustration for fans, to be sure, but it’s a reality we apparently have to live with.
Don’t think it’s a coincidence that the three pitchers the Red Sox dealt for Wilson Contreras all have fastballs that struggle to miss bats consistently. The highest whiff rate of the trio was 16%. MLB average was 21-22%.
— Ian Cundall (@IanCundall) December 22, 2025
Hunter Dobbins 11.9%
Yhoiker Fajardo 12.9%
Blake Aita 16%
The Willson Contreras trade sees Red Sox parting ways with low whiff rate hurlers
Clearing cash flow issues by sending additional prospect talent for the roster moves Breslow is making may be a way of appeasing ownership before swinging a big signing like that of Alex Bregman (The Athletic has projetced a $171 million, six-year investment to win his services), Bo Bichette, or yet another pitcher like Ranger Suárez, Zac Gallen, or Seranthony Domínguez.
Much has been made about Breslow’s interest in building a pitching core with great extension. His interest in the minute details and advanced metrics appears to go beyond just that one feature of a pitcher’s delivery, though. Ian Cundall of SoxProspects posted after the latest roster move that all three pitchers dealt for Contreras sported paltry whiff rates. Dobbins was an important cog in the Boston roster in 2025, but his stat is the worst of the three at 11.9%, a full 10 points lower than league average. Fajardo tossed to as 12.9% and Aita led the pack with just 16% of balls missing bats in 2025.
In contrast, Sonny Gray’s Baseball Savant page lists his whiff % at 27.5, while Johan Oviedo’s sample size wasn’t large enough for a percentile, his figure stood at 29.9% (with a 98th percentile extension, FYI!). It might come as something of a hot take, but another pitcher with a pedestrian whiff rate on Boston’s roster is Brayan Bello, with a 20.1% figure that was good for a 13th percentile finish last season (below Dobbin’s 22nd percentile rating).
With Bello’s team friendly contract extending out to 2030 (with the next two years coming in below $10 million per season), he may be an enticing candidate to bundle up in a blockbuster trade for a genuine game changer return (here’s hoping it’s a guy like Tarik Skubal to create a masterful dream rotation for 2026).