
USA Today via Reuters
MLB, Baseball Herren, USA Spring Training- Chicago Cubs-Workouts, Mar 12, 2022 Mesa, AZ, USA Chicago Cubs assistant general manager Craig Breslow arrives during a spring training workout at Sloan Park. Mandatory Credit: Joe Camporeale-USA TODAY Sports, 12.03.2022 09:02:29, 17880202, MLB, NPStrans, Craig Breslow, Sloan Park, Chicago Cubs PUBLICATIONxINxGERxSUIxAUTxONLY Copyright: xJoexCamporealex 17880202

USA Today via Reuters
MLB, Baseball Herren, USA Spring Training- Chicago Cubs-Workouts, Mar 12, 2022 Mesa, AZ, USA Chicago Cubs assistant general manager Craig Breslow arrives during a spring training workout at Sloan Park. Mandatory Credit: Joe Camporeale-USA TODAY Sports, 12.03.2022 09:02:29, 17880202, MLB, NPStrans, Craig Breslow, Sloan Park, Chicago Cubs PUBLICATIONxINxGERxSUIxAUTxONLY Copyright: xJoexCamporealex 17880202
In Boston, it feels like déjà vu. Just as in 2023, the Red Sox entered this year’s MLB trade deadline in the thick of the Wild Card race. And just as in 2023, the front office let the clock run out without making the kind of splash that could shift the team from hopeful pretender to legitimate contender. Fans really bet on their cautious optimism that Thursday’s deadline might bring an aggressive move or two to jolt the roster forward. Instead, the only arrivals were low-expectation veteran arms Dustin May and Steven Matz.
That’s unlike the headline-grabbing reinforcements fans were hoping for.
So why the hesitation? On the surface, the Red Sox’s passivity could be blamed on financial caution or roster calculus. But insiders suggest something deeper is at play. Around the league, CBO Craig Breslow and the Red Sox have developed a reputation that may be shaping how other teams engage with them. And ultimately, why Boston stood pat yet again. And if that is the case, the Red Sox’s slower pace of reinforcing their lineup is here to stay. So, brace up to witness the same scenes further.
“
Yeah, teams hate dealing with the Red Sox. They said just very tough to deal with Breslow. The Diamondbacks had some momentum going with Merrill Kelly, and that fell apart at the end. I don’t think they were ever really in on Joe Ryan. I’m not sure they even had conversations, but when you talk to GMs around the game said just very tough to deal with the Red Sox and Craig Breslow in particular,” MLB insider Bob Nightengale was vocal on an episode of Foul Territory about what could have gone wrong for the Red Sox.Teams hate dealing with the Red Sox, says @BNightengale.
"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
— Foul Territory (@FoulTerritoryTV) August 1, 2025
Well, it’s not exactly a great sign when other teams don’t enjoy dealing with the Boston front office. Sure, every franchise wants to win a trade and drive a hard bargain. But having a solid reputation and good relationships can be the difference when it comes to pulling off game-changing moves. And the fact that the Red Sox haven’t made many big acquisitions, outside of Garrett Crochet, over the last couple of years, backs up the idea that rival clubs would rather trade with someone else.
Yes, Craig Breslow is a hard nut to crack, but Boston still had a pretty quiet trade deadline for a team chasing a playoff spot in the AL. The Red Sox were on the verge of making a few good moves. They reportedly talked with the Twins about All-Star starter Joe Ryan, but those talks fizzled out. They also had their eyes on Merrill Kelly, only to see him shipped to the Rangers by the Diamondbacks.
So yeah, the problem seems to be in how the Red Sox are dealing with others.
The Red Sox might just be letting the Rangers race ahead
“I think if they didn’t do anything, they may be sitting home, and the Texas Rangers take their place as a wild card team,” Nightengale further added.
Well, the Red Sox are currently sitting at 59–51 and holding onto a Wild Card spot. But the Rangers aren’t far behind at 57–53, just one game out. And if the trend continues, Texas might leapfrog Boston soon. How?
The Rangers already boast the best starting rotation ERA in baseball at 3.22, and they just got even stronger. On Thursday, they reportedly landed veteran starter Merrill Kelly from the Diamondbacks. And that too by just sending pitchers Kohl Drake, David Hagaman, and Mitch Bratt to Arizona. For the unversed, Kelly, 36, has been sharp this season. He posted a 3.22 ERA with 121 strikeouts over 128.2 innings in 22 starts. And interestingly, Boston was also in the mix for Kelly before Texas closed the deal.
Now, on top of that, the Rangers added relievers Phil Maton and Danny Coulombe to reinforce their bullpen. And with pitching this deep, it wouldn’t be a shock if Texas passed the Sox in the Wild Card race before long.
So, even though Breslow admitted that the Red Sox were uncomfortably aggressive at the deadline, it is teams like the Rangers and Mariners that showed what it means to be aggressive in trade.
And for the Red Sox fans, your bet would now be on Dustin May. Just hope that the reinforced pitching lineup of the Rangers doesn’t come in between the Red Sox’s wild card race.
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Is Craig Breslow's tough negotiation style hurting the Red Sox's playoff chances?