As if the Boston Red Sox's lackluster trade deadline performance wasn't bad enough for chief baseball officer Craig Breslow, reports have emerged in an attempt to explain Boston's lack of impact moves.
On a post-trade deadline episode of the "Foul Territory" podcast, MLB insider Bob Nightengale didn't hold back. His comments didn't paint Breslow in a positive light, which is the last thing he needed after his deadline moves.
"Teams hate dealing with the Red Sox, it's very tough to deal with Breslow," Nightengale said on August 1. "...When you talk to GMs around the game, they say it's very tough to deal with the Red Sox and Craig Breslow in particular."
Nightengale's word choice was strong, but still believable for members of Red Sox Nation. Breslow has become known for his robotic delivery and overall lack of people skills, and many speculated that's how his relationship with Rafael Devers soured before Boston traded him to San Francisco. It's troublesome to hear, especially since Breslow has only been CBO for two years, and it's concerning that he's already garnered such a reputation in opposing front offices. But it's no surprise that Breslow's demeanor may hurt the Red Sox in the trade market.
MLB insider Bob Nightengale's report on Craig Breslow could be disastrous for Red Sox's offseason pursuits
Teams hate dealing with the Red Sox, says @BNightengale.
— Foul Territory (@FoulTerritoryTV) August 1, 2025
"When you talk to GMs around the game, they say it's very tough to deal with the Red Sox and Craig Breslow in particular." pic.twitter.com/X2usHWRtGv
Nightengale mentioned that he didn't think the Red Sox were close to landing star pitcher Joe Ryan from the Minnesota Twins, and hopefully, those negotiations can begin again over the offseason. But if teams don't like discussing trades with Breslow, Boston could be in some trouble. The Red Sox will be far from the only team in line to trade for Ryan, and they already extended the Twins a bunch of offers at the trade deadline, which gave them an idea of his worth on the market, and which other teams may have the capital to make a deal.
If trade negotiations with the Red Sox front office are brutal, contract negotiations could also be a disaster. Breslow has orchestrated Alex Bregman's contract with Boston, as well as the trade and subsequent extension of Garrett Crochet, but it took months of back-and-forth to land Bregman, who had a smaller market than anticipated this offseason. Top-tier free agent candidates with large enough markets could skip discussions with the Red Sox entirely if Breslow is as exhausting as Nightengale says.
Boston is already quite unsuccessful on the free agent market compared to other big market teams and it's seemingly reluctant to spend on top-tier talent in recent years. The Red Sox and their lowball offers don't need any extra deterrents in the eyes of free agents — Breslow may be a liability the club can't afford.