NEW YORK — From the moment the 2025 Red Sox season ended, the team pronounced its desired trajectory. After the hors d’oeuvre of the team’s first playoff appearance since 2021 — a vanquishing by the Yankees in a three-game Wild Card Series — the team sought an entrée in 2026.
With that in mind, Red Sox CEO and president Sam Kennedy was asked on Tuesday — prior to the start of his team’s done-in-a-blink postseason — would success in 2026 be judged by the binary measure of whether the team advanced past the Yankees or fell to them for the second straight year?
“I don’t define seasons as a success or a failure. That’s for other people to define,” Kennedy said. “But there always is disappointment when you don’t win the ultimate goal.
“If we do not advance beyond [the Wild Card Series], the next round, the round beyond that, it will always be a disappointment,” he continued. “If you don’t win that last game in October, whether you’re in the LCS or the Division Series, Wild Card Series, one-game playoff, you are by definition extremely disappointed.”
The Red Sox thus enter the offseason in a state of extreme disappointment. For some — most notably, first baseman Willson Contreras — that meant questions about the state of the organization.
Yet in terms of baseball leadership, the Red Sox had already confronted those questions and rendered judgment on them.
Chief baseball officer Craig Breslow’s job security became a constant topic during the 32-46 start, particularly after the shocking April decision to fire manager Alex Cora and six other staffers failed to yield immediate improvement. It was a time of organizational misery.
“We looked like the furthest thing from the playoffs for a while. For a long while,” said Kennedy. “It was humbling for all of us, and it was a terrible, terrible period. Our job is to not go through periods like that.”
During those months, the team’s owners scrutinized what had taken the team to the brink of a lost season. But they didn’t consider firing Breslow.
The Red Sox then experienced a historic reversal with a 32-5 run over a seven-week stretch. It convinced the organization to move aggressively at the deadline (especially in trading for catcher Adley Rutschman) while cruising towards the postseason. While some in the industry were surprised by the prospects the Red Sox sacrificed, others — including some members of the team — were excited by a willingness to make a bold bet meant to chase a title.
After the Red Sox clinched their playoff berth, the team promoted Chad Tracy from interim to full-time manager through 2029 (with a team option for 2030). Additionally, the team announced it was exercising options on Breslow’s contract for 2029 and 2030.
Breslow was told of the decision to exercise his options shortly after this year’s trade deadline. Given he was already under contract through 2028, why did the Red Sox make their decision with Breslow at that moment? Did they want their head of baseball operations to have a deal that ran beyond his manager’s? Did Breslow’s contract require a decision?
“We talked about it, [principal owner John Henry, who also owns the Globe; chairman Tom Werner; FSG president Mike Gordon] and I, throughout the course of June, July,” said Kennedy. “We just felt it was the right time to establish continuity and clarity within baseball operations, and make that commitment to Bres and his crew.
“Something we’ve been striving for is baseball operations continuity and stability. I know that sounds a little odd, given that we made a change with the manager and coaching staff [with Cora’s dismissal]. The hallmark of a good baseball organization is continuity, No. 1, at the ownership level. But with your baseball operation, we haven’t had that for some time.
“So we wanted to do that, we were proactive with that, and we informed him mid-season that we were picking up the option. There was no contractual need to do it, no mechanism. There was nothing that had to be done. We wanted to do that as a demonstration of commitment to stability and continuity.”
Of course, stability is only valuable if it keeps in place a decision-making and operational structure the Red Sox believe is sound. What brought them to such a determination with Breslow?
“Certainly preparation and research and diligence. But also, [his] conviction and willingness to make really hard decisions, which I think is required, especially in Boston. That’s really important,” said Kennedy. “And then the history and background as a player, to me, that’s one of the most underrated, least-talked-about aspect of Craig Breslow’s tenure as head of baseball operations.
“[Members of the Red Sox front office] believe strongly in what they believe in due to the work they do on players and background. It’s not just analytics,” added Kennedy. “[His relationships and experiences from playing] was the most important thing about the hire when we brought Bres in. He had all the baseball operations chops of modern general managers. But very few have played the game. I just think that was a lot of the reason we hired him, and a reason for picking up the [options].”
That decision reflected not only appreciation for what the team has done over the last two years — the first back-to-back playoff appearances for the Sox since 2016-18 — but also its outlook moving forward under Breslow.
“We’re very well-positioned for the long-term, but that didn’t make April, May, June of this year feel any better,” Kennedy said before the start of the series against the Yankees. “We have to continue to balance the now with [the future]. But I do think we are set up for hopefully a very good period.”
Alex Speier can be reached at alex.speier@globe.com. Follow him @alexspeier.