Red Sox’s Chaim Bloom on losing Xander Bogaerts: ‘It got to a point we weren’t going to’

As the Winter Meetings wound down at the Manchester Grand Hyatt in San Diego on Wednesday, the lobby was buzzing with rumors that the Red Sox were getting close to re-signing star shortstop Xander Bogaerts. Reports that the sides were making progress swirled. Team executives were tight-lipped. From the outside, an agreement seemed likely if not imminent.

But that was not the case. By that point, Sox chief baseball officer Chaim Bloom said late Friday, the Red Sox already knew Bogaerts was almost certainly headed elsewhere. By the time Bloom addressed reporters for the final time around 3 pm PT on Wednesday, he knew Bogaerts’ departure was a foregone conclusion. He did not find out that reality from Jon Heyman’s tweet that Bogaerts was headed to the Padres shortly after midnight on the east coast.

“We had a good sense of where it was headed for some time before the deal was actually done,” Bloom said in a lengthy conversation Friday night. “I know what was reported, but that was definitely not what our impression was throughout the day and even the day before.”

If leaks of a Red Sox push were intended to drive San Diego’s price up, it appears they worked. Bogaerts received an 11-year, $280 million mega-deal that far exceeded expectations and what the Red Sox were willing to pay. Bloom declined to confirm the specifics of Boston’s offers (The Boston Globe reported the team went as high as $160 million over six years) but said that the sweepstakes got to a point that made it necessary for the Red Sox to bow out.

“It got to a point that we just weren’t going to get to,” said Bloom, who has not spoken to Bogaerts since the signing. “That’s not to say that, emotionally, it wasn’t hard, but I don’t think there’s any sense in beating around the bush on that. The endpoint speaks for itself. We just weren’t going to get there.”

Bowing out on Bogaerts was the latest in a serious of pragmatic yet controversial decisions for Bloom, who prides himself on separating emotions from business in even the tensest negotiations. The man who traded Mookie Betts, Andrew Benintendi and Christian Vázquez accepted the reality that perhaps Boston’s most beloved homegrown star of the last decade would be leaving the organization at some point Wednesday.

“It’s really hard and it’s really important (to draw a line somewhere),” Bloom said. “I also fundamentally believe that building around homegrown talent is also something that’s really important to the organization. A lot of those things go beyond anything you can put on paper. They go beyond numbers or production so there’s a lot of different things to balance there. But we do ultimately have to make sound business and baseball decisions. Sometimes that perfectly aligns with where your heart is and sometimes it doesn’t.

“He’s a really important person to everyone here and he’s important to the organization. From that standpoint, the fact he’s not going to be here anymore is hard,” Bloom said. “And that’s sad. I think anyone who sugarcoats that is being dishonest. Just because there are business decisions everyone has to make doesn’t mean that the emotional side or the personal side is any less.”

Bloom said the Red Sox truly considered Bogaerts his top priority for the last few weeks and tried to back it up with actions, even if the final offer came well short of what the shortstop took from San Diego.

“We wouldn’t have said that if we didn’t mean it,” Bloom said. “I think it became clear to us as things went on that this was going to go to a point that we just weren’t, regardless of how we prioritize things, it just wasn’t something that we should do. It’s hard because of how much we love him. But it’s just the reality of the situation.”

In a recent interview with the Globe, team president/CEO Sam Kennedy said he regretted that the team was not more aggressive in its attempts to sign Betts to an extension earlier in his career. Bloom, who was not yet with the team when those talks happened with Betts, acknowledged that the Red Sox may need to take a step back and examine how they proceed in future extension talks. He said that moving forward, he wants to be more aggressive in locking up players on pre-arbitration deals like the one the Sox did with Garrett Whitlock in April.

“I do think it’s fair to say that there are some things to think about there,” Bloom said. “Anytime you have a situation where you have a homegrown player who wants to be here and we want him here and it doesn’t happen, I think those are fair questions to ask and those are questions we certainly need to ask ourselves. We haven’t, as an organization, always found a way to come together in those situations. I think it’s something to think about and assess.”

The Red Sox believed Bogaerts’ priorities had changed between 2019, when he accepted a team-friendly extension to avoid free agency, and 2022, when he saw a potential payday coming, according to sources. The club did not begrudge him for that business-like stance. That, and Bogaerts’ disappointment about being lowballed in spring training, put the sides behind the eight ball as negotiations began.

“This is a little bit of a unique situation because he had already put off free agency once,” Bloom said. “He was at a different place in his career than what Sam was referencing with Mookie.”

Since taking over in Oct. 2019, Bloom has overseen the departures of two generational talents in Betts and Bogaerts. That, along with Boston’s roller-coaster play on the field, is his legacy through three years. He’s aware of that. And he’s hellbent on changing it.

“If I ever put (my legacy or reputation) ahead of the organization, I’m not doing my job,” Bloom said. “There are, in any of these jobs, decisions that make everybody happy and some decisions that are tougher and are going to be unpleasant. You can’t run from those. Especially the nature of this job. It doesn’t mean I’ve gotten everything right or will get everything right.

“I knew there were going to be a number of hard decisions and there were going to be some things we’d do that we’re going to take some (expletive) for,” he continued. “The bottom line is that this to me is about winning and I don’t care how much (expletive) I take if it gets the organization where it needs to go. That’s tough here when what that means is seeing a great homegrown player go sign with someone else, especially when we are trying to win. We still have to make the right decisions.”

Bloom knows the heat has been cranked up in the wake of Bogaerts’ departure

“What happened here is not super uncommon in our game, especially today,” he said. “It’s not something that should be totally unexpected. But given how he felt about the Red Sox and how everybody here felt about him, I totally get why people are asking those questions.”

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