Craig Breslow says he won’t wave the white flag on the Boston Red Sox’s last-place season, even as the team sits at 33–46 and gets closer to the August 3 trade deadline. In a Friday morning radio interview, he acknowledged the organization will have to become
For the third straight stretch that felt like a warning shot, the Boston Red Sox couldn’t make it count on the field.
They were swept by divisional opponents twice in June and were coming off an embarrassing series loss to the Colorado Rockies when Craig Breslow was asked the tough questions—about the roster he assembled last offseason. about whether he still believes in a turnaround. and about how much time is left before the front office has to act.
Breslow, the Boston Red Sox chief baseball officer, met those questions head-on in an interview on WEEI’s “The Greg Hill Show” Friday morning. He said he would not “wave the white flag” on Boston’s last-place season.
“We have to win a lot of baseball games and we don’t have a ton of time to do it. ” Breslow said of the 33–46 Red Sox. who are last place in the American League East. Boston is five games back of the A.L.’s third wild-card spot. “I believe that we’re capable of doing it. It’s going to require more consistent play on the field. But I see no reason that with the pitching that we have and the consistency of the starting pitching. with the strength of the backend of the bullpen. we can’t get ourselves in a position where we do win these games.”.
The stubborn optimism is paired with a clear acknowledgment that the calendar is moving. Breslow said the organization is constantly assessing what’s happening inside Fenway Park and on the field, as well as how the rest of the league is shaping up.
“We’re constantly assessing where we are in terms of what’s happening in Fenway Park and with our team on the field. and what’s happening around us. But we have to be realistic about where we are. and it’s true that we can believe in the roster that we have. ” he said. “We can believe in our players and know that we’re capable of playing better baseball. and also that we’re not where we expected to be. That’s incredibly frustrating and disappointing. and we’re going to have to be realistic about what is best for the organization.”.
That realism matters because there is still time before the organization has to decide whether to buy or sell at the trade deadline. The August 3 trade deadline is the marker Breslow’s comments keep circling. He said Boston has several options if it chooses to sell, including Sonny Gray and Willson Contreras.
But the clock is ticking, and the path for the front office “becomes clearer by the day,” Breslow said—selling as the direction that grows harder to ignore.
On the field, the story has stayed stubbornly similar to what it has been since April: strong starting pitching and relief outings paired with a lack of offense that ends in loss—“then rinse and repeat,” as Breslow reflected on the season’s pattern.
Breslow said he hasn’t conceded Boston’s chances yet, even with the growing consensus among fans and some in the media that the season is slipping away.
He described how the decision will eventually come—once the front office reaches a point where it can state what direction it wants to take and why.
“The conversations are pretty regular and fluid. and we’re constantly assessing where we are relative to the rest of the league. ” he said. “But in terms of a direction. I will make a recommendation. the one that I think is best for the organization. and sit down with Sam [Kennedy]. John [Henry]. Tom [Werner]. [Fenway Sports Group president] Mike Gordon. [FSG part owner] Theo [Epstein]. and kind of state the case for why I think one direction is the right one for us.”.
The steps he pointed to for a postseason push in 2026 were specific: continuing to pitch quality starts, driving in runners in scoring position, and properly working counts.
Still, he also admitted that, in hindsight, he might not have assembled the best possible team going into the season. During a moment of reflection amid a dismal first half, Breslow said Boston improved its roster compared with the team that finished the 2025 season.
“I think we improved our roster relative to the team that finished the season in 2025,” Breslow said. “Again, this comes down to what happens on the field. This is the big leagues and we’re measured by the success that we have on the field. And right now, we’re falling short.”
Breslow didn’t try to soften that conclusion.
“We can believe in the players, we can believe in the roster, but ultimately we have to look back at the decisions we made and question where we might have been able to do things better,” he said.
On the question of his own job security—an issue that has been hanging over the season despite public backing by team president Sam Kennedy earlier this month—Breslow was direct. He was asked whether he talks to owner John Henry about the safety of his role in the organization. Breslow said he does not.
“I don’t have conversations with John [Henry] about my job,” Breslow said. “My focus is on doing the things that I was brought in here to do. Things like built a strong internal pitching development pipeline. to try and work through the defensive struggles that we’ve had … to modernize the front office and make sure that we can compete with 29 other teams. and doing everything we can to put our players in a position to win Major League Baseball games.”.
That theme—responsibility, not resignation—ran through the end of the interview. Even as he acknowledged the urgency of turning things around, Breslow pushed back on the idea that Boston can’t improve over the next month.
“I think things can change. We’ve seen that things can change,” he said. “I think more than that, though, is that we’ve got a group of players and coaches that are committed to doing what we can to give ourselves a chance for that to change.”
He said the mindset is visible in the clubhouse and coaches’ room.
“If you walk through the clubhouse or through the coaches’ room, that’s what you see. It’s guys who feel like it’s an honor and a privilege to put on a Red Sox uniform, who want to go out and compete at a level that makes the fanbase proud, and that’s something I share with them.”
In a season defined by losses and swept series, Breslow’s message isn’t that the deadline is far away. It’s that the front office is watching the same numbers everyone else is—and that when the time comes, he’s prepared to make the recommendation he believes is best for the organization.
Craig Breslow Boston Red Sox WEEI The Greg Hill Show Sam Kennedy John Henry trade deadline August 3 Sonny Gray Willson Contreras AL East wild card