Craig Breslow’s biggest mistake with Red Sox? Maybe not hiring a general manager

The Red Sox sound like an organization with issues that run far deeper than a last-place record. Every day seems to bring another report, another comment, or another sign that something isn’t quite right inside the walls of Fenway Park as Craig Breslow and the front office search for answers.

Those concerns were on full display again this week. During an appearance on WEEI, ESPN’s Buster Olney reported that someone within the league told him that, “to a degree,” Red Sox ownership has been making calls to improve its roster. 

"Today I talked to someone with another team that told me that it’s to the degree that the Red Sox ownership has gotten involved," said Olney. "I have not confirmed the name of the owner, so I'm not gonna mention the name that I heard ... but an owner, one of the Red Sox ownership group, is actually calling around and trying to grease the skids to something to add a right-handed bat." 

Olney has repeatedly reported that the Red Sox are "aggressively looking" to add a right-handed power bat and have shown a willingness to take on salary to make a deal happen.

The Red Sox essentially swapped Alex Bregman for Willson Contreras to truly bolster the lineup after Bregman departed for the Cubs in free agency, but other than that, the lineup remained largely unchanged. The lack of right-handed power that plagued the club a year ago remains a glaring issue today.

What’s even more telling is the perception that ownership is now becoming involved in those efforts to find a bat to balance the lineup.

Olney’s reporting continues to point out the flaws of Breslow, each one more embarrassing in the report. 

If people above Breslow are helping identify trade targets and pushing to improve the roster, that’s not exactly a ringing endorsement of the front office’s work. Fair or not, it raises questions about how much confidence ownership has in the direction of the baseball operations department.

Despite the growing criticism, however, Breslow’s job does not appear to be in immediate danger.

According to The Boston Globe’s Tim Healey, principal owner John Henry is not considering a change atop baseball operations, even as the Red Sox continue to underperform and frustration mounts both inside and outside the organization.

For now, Breslow appears safe. The bigger question is how much longer ownership will remain patient if the losses continue to pile up and the club remains stuck in last place.

"Further, amid the team’s underperformance — and speculation that Breslow may be on the hot seat — the club’s ownership hierarchy has not even discussed making a change,” reported Healey. 

Breslow has been on the proverbial hot seat ever since the Red Sox stumbled out of the gate and he responded by firing Alex Cora and several members of his coaching staff.

When Cora was shown the door, Boston was 10-17. Under interim manager Chad Tracy, the Sox have gone 17-19, but frankly, not much has really changed. The same issues that plagued the team in April are still showing up in June, most notably an offense that can look explosive one night and completely disappear the next.

Entering Monday night’s loss to the Rays, the Red Sox ranked dead last in baseball with 48 home runs and 29th in runs scored with 249. That's just not good enough. 

That’s why the recent public support for Breslow is interesting. Some times in sports, when ownership starts going out of its way to tell everyone that someone’s job is safe, it usually gets people’s attention.

Breslow has already been criticized publicly by Theo Epstein, who has reportedly grown concerned with some of the inner workings of the Red Sox baseball operations department. 

“Theo Epstein has been disappointed by the Sox’ intense analytical direction under Breslow, multiple league sources said,” Healey wrote. “A minority owner and adviser who led the franchise to two World Series titles as GM, Epstein has long been a mentor to Breslow, hiring him to the Cubs’ front office and helping him get the Sox job.”

Speaking to MassLive’s Chris Cotillo in late May, Breslow was asked if he had any concerns over his job security.

"I worry about making sure I’m doing what I can to help the team,” Breslow told Cotillo. "That is the truth, because the second you start thinking about other things, you’re not doing the best for its organization, its players or our fans.

"The conversations I have with ownership are about ideas for helping us turn the season around and any potential opportunities that exist. Ownership is incredibly engaged and aware of our performance, our players and guys in the minor leagues that might be able to help us. That’s the content of the conversations."

While it feels like everyone is taking shots at Breslow right now, the noise around the Red Sox isn’t slowing down. A recent rumor made the rounds that the Red Sox actually traded Marcelo Mayer.

"I had somebody reach out to me and say, ‘Is it accurate to say you traded Marcelo to the Diamondbacks?'" Breslow told Alex Speier this week. "There’s some things that you see, and you’re like, ‘OK, that is not accurate, but I at least understand where it came from.’ And then there are things that are just blatantly false and don’t deserve a ton of attention, and this falls into that category."

It’s no secret that during the offseason the Red Sox and Diamondbacks discussed a trade for infielder Ketel Marte but Arizona decided to keep the slugger. Marte, 32, is a switch hitter batting .246 this season with 11 home runs and 37 RBI.

While the Sox want to add, national reporters are reporting the club could be in sell mode. 

Over the weekend, USA Today’s Bob Nightengale reported the Red Sox are expected to trade All-Star closer Aroldis Chapman. 

“Boston Red Sox closer Aroldis Chapman is expected to join his eighth different team, and potentially be in the postseason with his sixth different team,” Nightengale wrote. “He is the top reliever available on every contender’s target list, converting 28 consecutive saves dating back to last season, one shy of his career record.”

The club has reportedly told teams around the league that Chapman, Garrett Whitlock, and Justin Slaten are off-limits. At least for now. 

If the Sox traded Chapman, that would be the ultimate signaling of waving the white flag, and based off some of Breslow’s trades, can he be trusted to run another trade deadline for the Red Sox?

Last summer’s trade of Rafael Devers is a massive indication that Breslow shouldn’t be trusted in selling off pieces. The Red Sox have one player left from the Devers trade, right-handed minor league pitcher Jose Bello. He traded Kyle Harrison for Caleb Durbin in a six-player swap and the Sox are watching the left-hander have an All-Star season in Milwaukee while Durbin hasn’t been able to hit his weight. 

Because I’m a glutton for punishment, I'd be remiss to not mention the James Tibbs III and minor league outfielder in a trade for Dustin May. Boston failed to acquire Joe Ryan from the Twins last trade deadline and had no backup plan, resulting in May and Steven Matz. I don’t fault Breslow for trading Chris Sale to the Braves, as the lefty had struggled with injuries. But the return of just Vaughn Grissom and then not letting the him get a fair shake to show if he could play in Boston was a mistake. 

The Red Sox are showing very few signs that they’re actually moving forward, and because of that, the frustration directed at Breslow is understandable.

Looking back, Breslow’s biggest mistake may not have been a trade, a free-agent signing, or even the handling of Devers. It may have been not hiring an experienced baseball executive to serve as his general manager.

Paul Toboni was a candidate who made a lot of sense. Instead, he left and is now running the Nationals’ baseball operations department. Someone with a different perspective, someone who understands analytics but also has a feel for the human side of the game might have provided a valuable counterbalance inside the front office.

A strong GM isn’t there simply to agree with Breslow, they’re there to challenge ideas, offer different viewpoints, and help avoid blind spots. Who knows, maybe it wouldn’t have changed anything, the Red Sox could still be sitting in last place with someone serving as Breslow's right-hand man. But it’s fair to wonder whether another experienced voice in the room could have helped navigate some of the situations that have defined the past year.

The Devers divorce is one example. Whether the split was inevitable or not, it became increasingly clear there was a breakdown in communication between the organization and its franchise player. The Sox having someone who excels at relationship-building and communication can prevent a disagreement from becoming an organizational fracture.

It has been reported that Breslow has been a poor communicator. He's tried to change that impression quite a bit the last couple of months, but the damage may already be done. 

"Over the past month, Breslow has made a concerted effort to have more conversations with players and clubhouse-level personnel, he said," Healey wrote. "Part of the point is telling them he cares about them and winning and he is there to support them."

There’s many within the organization who think Breslow could benefit from having “an interpreter of sorts.” Hence the experienced seasoned general manager to help Breslow in difficult times.

While there's reporting defending Breslow's communication with the players, Carlos Narvaez's comments about his diminished playing time adds more fuel to the fire. 

The Sox' catcher spoke with The Athletic’s Jen McCaffrey about that lessened role. 

“It wasn’t expected, I’m not going to lie, it’s not easy,” Narvaez told The Athletic. “But I’ve just got to be ready. Last year is last year; whatever happened, happened. It’s a different year, different situation, and I’ve got to be a professional. I’ve got to be ready to play every day no matter what the situation is, just be ready.”

The 27-year-old Narvaez has hit just .209 with two home runs and three RBIs this season. Mickey Gasper has seen the bulk of playing time, giving the Sox a contact hitter in its weak lineup. 

“I haven’t talked with nobody, and nobody has talked with me,” he said. “But like I said, I get it, I’m a part of the team and I understand what’s going on, but on my end I just have to be ready. No one is telling me anything, if something changed — clearly something changed — but I don’t know, just be ready for the opportunity, and that’s it.”

This doesn’t entirely fall on Breslow’s shoulders, Tracy owns some of the blame for the communication. Players in Worcester always raved about Tracy’s communication and transparency, yet it’s really unclear as to who is at fault for the communication breakdown with Narvaez. 

The Red Sox still prefer to be buyers but the confidence in Breslow is at an all-time low. Boston’s continued search for a right-handed bat signals that Breslow and Henry are not yet ready to wave the white flag on the 2026 season. Despite sitting in last place in the American League East, Boston remains within striking distance of a wild card spot and appears intent on adding rather than subtracting. While Breslow talks trades around the league, people are taking shots at him left and right.

It’s sad that the Red Sox are a mess, and this may have all been avoided had Breslow hired someone with experience to help him out.