NEW YORK — All significant Red Sox transactions reach ownership level eventually.
Fitting, then, that Red Sox CEO and president Sam Kennedy chose to elaborate on the critical topics of Xander Bogaerts, Rafael Devers, and a team at a crossroads at Wednesday’s MLB owners meetings.
Yes, said Kennedy, the Red Sox sweetened their offer recently to free agent Bogaerts and yes, they made an extension offer to Devers, one year from free agency, not long after the season ended.
While cautious at times about what he should say, Kennedy at other times was blunt about the club being in the doghouse for its awful 2022 season.
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The Sox are trying to learn from some of their mistakes — they waited too long to aggressively engage Mookie Betts early in his career, Kennedy conceded — in order to build a team the right way this time around.
“Coming out of [last week’s] GM meetings, I can tell you that we have been very proactive,” said Kennedy, “though I know people don’t want to hear about how aggressive we’ve been, because it doesn’t mean anything until there’s something to announce.
“But I can tell you that we’ve made offers to several players, including our own players. And we’re cautiously optimistic that things are going to start moving here.”
The club has made at least two offers to Bogaerts since the season ended, once during its period of exclusivity before the shortstop filed for free agency, and a sweetened offer since he became a free agent earlier this month.
“We’ve been engaged with Xander since the end of this season, and Scott [Boras], his agent, and I’ll leave it at that,” said Kennedy. “But we’ve had productive conversations.”
As for Devers, the 26-year-old third baseman, Kennedy said the club’s engagement with him and his agent since the end of the season has included one offer.
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A brief discussion about Devers led to one about the premium value players such as Bogaerts and Betts command by virtue of a proven track record of elite performance in the pressure-cooker atmosphere that envelops Red Sox baseball in New England.
“You have to factor that into the calculus,” said Kennedy. “It’s not for everybody. It’s intense. There’s a lot of scrutiny.”
The absence of Betts — the MVP who got away when the Red Sox traded him before his walk year in 2020 — hovers over every step the Red Sox take this offseason.
“We have not always been able to sign our own homegrown players long-term, I fully acknowledge that,” said Kennedy, “and when that doesn’t happen, it’s disappointing for the fans, and it’s disappointing for us on a personal level. But we get paid to make very, very difficult decisions, and we’ll see how those decisions work out.”
When asked if the Red Sox learned anything from the Betts experience that will be relevant in how they approach Devers, Kennedy took a while to choose his words.
“I think so,” he said. “I think engaging with your players earlier — early and often — about arrangements that are mutually beneficial is something that really well-run teams do and are doing. We just did that with [pitcher] Garrett Whitlock. We’ve had extensions for younger players in the past, and that’s certainly a lesson learned.
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“With Mookie, we could have engaged more effectively earlier on in his career,” said Kennedy, though he added that it was “unknowable” as to whether earlier engagement would have avoided the fate of trading Betts to the Dodgers, who signed him to a 12-year, $365 million contract. “From where I sit, it is certainly difficult when you move on from homegrown players.”
When it comes to non-Red Sox free agents, Kennedy was asked about Yankees slugger Aaron Judge and Astros ace Justin Verlander.
“It’s safe to say that Chaim [Bloom] and BOH [general manager Brian O’Halloran] are leaving no stone unturned,” he said. “They are being very diligent and aggressive in their examination of ways to improve a team at the major league level.”
Kennedy had a lengthy cackle when asked to simply deny that the Red Sox had interest in Judge and Verlander.
“We have a responsibility to look at any and all opportunities to improve the major league team, including free agents — all free agents,” he said. “Don’t want to talk about those two.”
With the Fenway Sports Group multitasking on numerous fronts — a possible sale of Liverpool Football Club, the Winter Classic, ownership of the NHL’s Pittsburgh Penguins, the Fenway Bowl, Fenway Music Hall, real estate ventures, and interest in owning an NBA franchise — Kennedy was asked about the perception that Red Sox ownership has too much on its plate.
“This discussion of lack of focus or distraction comes up when we underperform at the major league level, and that is 100 percent on us,” he said. “It is absolutely understandable that when we don’t perform at the major league level, we would get questioned on everything, so we deserve that criticism.
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“But I can assure you, from me, to Chaim, to BOH, to [manager] Alex Cora, it’s 24/7 worrying about the 2023 Boston Red Sox. We’re entirely focused on improving, we feel the sense of urgency, we feel the need to improve this club and be better.”
As to the age-old question of whether ownership is committed to spending enough on payroll to field a winning team, Kennedy said, “It’s an unknowable concept, because our job is to win enough games to get to the postseason and have a chance to win the World Series, and we didn’t do that.
“In 2021, when we were two games from the World Series, there was no discussion about how much money we invested in the team or if we’re focused on Liverpool or if we’re focused on other Fenway Sports Group activities — none, no discussion.
“When we fall short in Boston at the major league level, we open ourselves up for criticism and we understand that.”
Michael Silverman can be reached at michael.silverman@globe.com.