CHAIM BLOOM HAS been reliving the negotiations with Xander Bogaerts in his head.

“There are a couple of regrets,” the chief baseball officer of the Boston Red Sox told ESPN a week after Bogaerts signed with the San Diego Padres.

When Bogaerts landed an 11-year, $280 million deal this month, the question among baseball executives and agents wasn’t whether Boston should have matched San Diego to re-sign its star shortstop, but why Bogaerts even got to free agency in the first place.

When Bloom signed Trevor Story to a six-year, $140 million contract before spring training last year, Bogaerts felt hopeful that an extension on his own contract might follow. One source close to Bogaerts said he would have seriously considered an extension similar to Story’s deal. Instead, the Red Sox offered Bogaerts an additional year and $30 million on top of the three years and $60 million left on his deal. For a player who helped bring championships to Boston in 2013 and 2018 and had grown into the team’s de facto captain, the offer felt like “a slap” according to a source close to Bogaerts.

Bloom and the Red Sox did not want to sign Bogaerts, who would turn 30 before the end of the season, to a contract that would take him into his late 30s and early 40s. But then Bogaerts posted the best season of his career in 2022 by bWAR — his 5.7 the best among all shortstops in baseball — while hitting .307/.377/.456 with 15 homers in 150 games. And when Trea Turner (4.9 bWAR in 2022) signed an 11-year, $300 million deal with the Philadelphia Phillies, the market for shortstops ballooned. Overnight, the price for Bogaerts doubled — and in the end, for what felt like the dozenth time this offseason, the Red Sox were outbid on a player they were pursuing, this one a beloved homegrown star.

Even with the signings of Masataka Yoshida and Justin Turner so far this offseason, two-last place finishes in three years (a span that also includes one American League Championship Series appearance) have elicited questions from fans who want answers not only about the team’s plan to win, but how a front office that preaches building around in-house talent could let go of two of the most accomplished homegrown stars in franchise history — Bogaerts and Mookie Betts, whom Bloom traded to the Los Angeles Dodgers in 2020.

But when asked if there was anything in particular he regrets about the handling of Bogaerts, Bloom declined to share.

“I don’t want to elaborate,” Bloom said. “It’s more private. I don’t want to get into it.”

RED SOX PRESIDENT Sam Kennedy understands why fans are questioning the ownership group’s commitment to winning. As someone who grew up a few subway stops from Fenway Park, Kennedy constantly hears from his parents and the friends of his children about the team’s struggles in 2022.

“You want that passion,” Kennedy said. “You want the talk radio lines lit up.”

Since John Henry led Fenway Sports Group (then known as New England Sports Ventures) in 2001 to buy the Red Sox, the investment firm has grown into an international sports conglomerate that now owns Liverpool FC in the Premier League and the Pittsburgh Penguins of the NHL, with reports indicating Henry’s potential interest in bidding for the Washington Commanders, in addition to FSG partner LeBron James publicly indicating he wants an NBA team in Las Vegas. Kennedy said FSG targets sports teams tied to communities with deep emotional investments in their franchises — and that they spend to win.

But after missing out on Bogaerts, and finishing in second place in many other free agency sweepstakes, Red Sox fans are questioning the owners’ commitment to the team. In truth, those frustrations go all the way back to David Ortiz, who went year-to-year with the Red Sox during the last seasons of his career, and Jon Lester, who received a below-market extension offer in 2014 before being traded to the Oakland A’s.

Four years after trading Lester, Boston would win a World Series in 2018 after signing David Price to a seven-year, $217 million contract, trading a haul of top prospects for Chris Sale and Craig Kimbrel and locking up J.D. Martinez to a five-year, $110 million contract. And that, Kennedy believes, is the real difference in the fans’ responses to the departures of Betts and Bogaerts: the team’s last-place finish in the AL East in 2022.

“It gets frustrating and irritating when you hear [questions] about your commitment to winning,” Kennedy said. “All of our decisions we make are geared towards trying to win a World Series championship. We don’t get those questions when we’re winning.”

After their last World Series win, former president of baseball operations Dave Dombrowski spent big to keep Sale, Martinez and Eovaldi, pushing Boston over the luxury tax threshold. When Betts then asked for a contract valued at $400 million, the Red Sox were unwilling to commit that amount of money, according to multiple league sources. Betts made it clear that he wanted to stay in Boston — he just would not give the team a hometown discount.

The ownership group fired Dombrowski before the end of the 2019 season, less than a year after winning the World Series, and mandated the team cut salary in order to reset the luxury tax penalties. In came Bloom — whom Boston hired from the Tampa Bay Rays — with a vision of creating a Dodgers-style of sustained success, spending big money on star players while consistently developing top prospects to fill out the lineup.

According to multiple sources, Boston’s ownership group did not mandate that Bloom trade Betts to get under the luxury tax. But that is what Bloom ultimately decided to do, with an eye toward increasing the Red Sox’s options in the future. The team traded Betts and Price to Los Angeles for Alex Verdugo, Jeter Downs and Connor Wong. And Betts eventually signed a 12-year, $365 million contract with the Dodgers — a deal he told ESPN in August that he would have accepted in Boston.

Just last week, the Red Sox designated Downs for assignment, admitting defeat on the prospect centerpiece of the Betts deal.

“Have we made wrong decisions in the past? Lots of them,” Kennedy said. “You can’t sit around regretting mistakes of the past. That’s not a good recipe. We respect Mookie and it’s a hard decision, but we’ve moved on.”

But for fans who were told that trading Betts was to create financial flexibility for the future, watching the team get outbid on Bogaerts was the last straw.

With Bogaerts’ production exceeding the team-friendly extension he signed in 2019, the All-Star shortstop planned to exercise the opt-out in his contract after the 2022 season, but he had hoped to play the rest of his career in Boston. He privately expressed to those close to him that he would be willing to eventually move to second or third base if necessary, but he was determined not to accept another team-friendly contract. Like Betts before him, Bogaerts wanted a deal more in line with his perceived value across the sport.

On last season’s Opening Day, Bogaerts expressed his disappointment in not getting an extension done with the Red Sox, and he played out the season knowing he would be a free agent at the end of it.

Bogaerts excelled in 2022, providing one of the few bright spots for a Red Sox team that finished 78-84 and at the bottom of an extremely competitive division. By the end of the season, both Bloom and Kennedy had publicly said signing Bogaerts was their top priority.

Before signing his first extension, Bogaerts told his agent, Scott Boras, that he wanted to stay in Boston. This time, though, he expressed a desire to explore free agency.

“I understand myself better,” Bogaerts told Boras. “I have more of a view of free agency. I want to look into it and see what’s available for me. I want to win, and I want to win now.”

San Diego significantly outbid Boston, and at Bogaerts’ introductory press conference on Dec. 9, he thanked the Padres for being “very straightforward” with him during negotiations.

Boras said Boston’s unwillingness to match the offer from the Padres stemmed from the organization’s evaluation of Bogaerts.

“I can only say that the market for Xander was very different from what their models said,” Boras told ESPN. “But that’s happened before.”

Executives around the sport see the same pattern emerging with Red Sox star third baseman Rafael Devers, who will be 26 at the start of the 2023 season, his last before he becomes an unrestricted free agent in 2024. According to multiple league sources, the Red Sox and Devers are “galaxies apart” in their contract negotiations. The current expectation from Devers and his camp is that the third baseman will be a free agent at the end of 2023, given the current state of contract talks.

Bloom said Boston will make every effort to keep Devers.

“We will probably, I think, go beyond reason to try to get this done,” Bloom said. “Hopefully we can get this done. There are always going to be limitations, like people can just put something plain out of reach. Some people love to bet on themselves and I hope he hits 63 homers if he does that.”

WHILE BOSTON DIDN’T break the bank to sign Bogaerts, the team has given out some large contracts this offseason, signing Japanese outfielder Yoshida to a five-year, $90 million contract while adding Kenley Jansen, Joely Rodriguez and Chris Martin to the bullpen. On Sunday night, the Red Sox also added Turner, a 38-year-old third baseman, on a two-year, $22 million deal. Bloom said the team aimed to add seven to nine players this offseason, and the Red Sox are continuing to explore trades. Additionally, the team is trying to sign players to contract extensions before they hit arbitration, similar to the four-year, $18.75 million contract they gave Garrett Whitlock in April.

If Kennedy is right, and a change in the team’s on-field fortunes will help the fan perception, Boston will need many things to go right that did not in 2022. Ace Chris Sale and center fielder Enrique Hernandez will need to stay healthy. Yoshida will need to produce immediately. Story will need to be more consistent at the plate. The Red Sox will need more contributions from players like Verdugo and Triston Casas, while the rotation will need to lean on Nick Pivetta, Whitlock, Tanner Houck, Brayan Bello and James Paxton, unless Boston adds another starting pitcher. The Red Sox will need to replace the offensive production of Bogaerts in the lineup and his clubhouse presence as a player who spoke both Spanish and English.

As the team builds the roster for 2023, some within the Red Sox front office have questioned Bloom’s decision-making process, team sources told ESPN. One front-office official said Bloom’s deliberate process toward making moves — asking many people for their input before making a decision — can put the Red Sox in a position to fall behind, reacting to other teams versus setting the market.

“I think we have a culture where people can and do express directly to me when they disagree with something,” Bloom said. “We have a lot of people in the loop on transactions that we make and we have a lot of really good debate. We have a place where people can share their opinion and have it be heard.”

Boras said during the negotiations on both Bogaerts and Yoshida that Bloom was “forthright and prepared.”

“Chaim has very defined structure and models that he does for player evaluation,” Boras said.

Executives from other teams question if Bloom can be decisive enough to make big moves to satisfy a rabid, impatient fan base, and whether the approach he built in Tampa will be aggressive enough for a market like Boston.

“I’m not sure how to respond to that,” Bloom said. “I certainly think we’ve made some large commitments in the time I’ve been here. For people who would’ve liked to have seen more, that’s their right. I think a lot of circumstances under which I joined the organization really precluded that for a period of time. I would argue we would’ve been worse off certainly prior to 2021 had we listened to people who wanted to see us make a splash instead of building a good baseball team.”

Boras said Bloom’s aggressiveness varied between Bogaerts and Yoshida.

“For Yoshida, they were very aggressive,” Boras said. “With Xander, they certainly did not meet the standards of what we expected them to do.”

Bloom hears the criticism from the fans, too. When asked about his job status, though, Bloom did not entertain the speculation, saying, “I don’t really worry about that.”

The pressure is on Boston to succeed, but both Bloom and Kennedy know one thing can change the minds of Red Sox fans and earn back their trust: winning.

“There was a lot of talk about our spending in 2022, there was not a lot of talk about our spending in 2021, which was about the same,” Kennedy said. “I think it goes with the wind. If you make the postseason, you’re not going to hear a lot about the spending. If we don’t win, it’s going to be we need to spend, we need to fix things, we need to get better. Winning solves everything.”