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Red Sox

At the San Diego airport, a stunned Chaim Bloom tried to process the reality of the Red Sox without Xander Bogaerts

Chaim Bloom has been the Red Sox' chief baseball officer since 2019.Charles Krupa/AP/file

SAN DIEGO — Red Sox chief baseball officer Chaim Bloom stared blankly at his iPhone late Wednesday evening.

A group of Red Sox front office personnel inside the Delta Sky Club at San Diego International Airport stared, too, trying their best to process what had just occurred.

Roughly 45 minutes before Bloom’s red-eye flight took off for Boston, capping a Winter Meetings that seemed to conclude with optimism for Bloom and the Sox, news broke that Xander Bogaerts, the kid from Aruba who warmed the souls of the Boston faithful for 10 years, had agreed to an 11-year, $280 million contract to play in the city Bloom was departing.


All Bloom could do was stare.

The group of eight or so Red Sox executives and front office staff, including assistant general manager Mike Groopman, slouched in the Sky Club’s blue leather chairs, scrolling through their phones. Bloom, the Sox’ leader, stood wearing a light green zip-up fleece along with blue pants and dark brown shoes.

Appearing out of sorts, trying to wrap his mind around the idea that Bogaerts would be a Padre, Bloom needed time to gather his thoughts. The Red Sox knew a deal with the Padres was likely, that their six-year, $160 million offer was no match for the Padres, a team that has shown a willingness to pay — or overpay — stars over the years.

“Give me a minute,” Bloom said.

The minute turned into two. Then came a brief walk to gate 37A, where Delta flight 1108 began to board.

“Give me a minute,” Bloom repeated, staring into space in isolation, no longer peering at his phone.

How could he patch this one together? How could Bloom make sense of this loss so soon after it happened? As inexplicable as it seemed at the time, the Mookie Betts trade was a move Bloom could defend. Betts was adamant about testing the free agent market. He wanted to get his fair market value and was unapologetic about it. The Red Sox were well over the luxury tax, too.


But Bogaerts was different. The Sox were under the luxury tax. They had money to spend, and at every turn Bogaerts said he wanted to remain with the Red Sox. The homegrown shortstop who exceeded expectations never wanted to leave until he was left with no choice.

“Hopefully, we figure something out,” Bogaerts said at his locker on the last day of the 2022 season.

Roughly 30 minutes before takeoff, Bloom had stared enough.

“Everybody is sad that he’s not going to be a part of the organization,” Bloom said. “We’re incredibly grateful for him. For everything he’s accomplished here and what he helped this organization accomplish.”

Bloom’s voice trembled. The Red Sox’ plan to achieve long-term sustainability has taken its lumps under Bloom, with the club finishing last in the American League East in two of the last three seasons. The Sox have now seen two cornerstone players exit over the last four offseasons.

“We make business decisions, but that doesn’t change the emotions that come with something,” Bloom said. “And even for me, who hasn’t worked with Xander as long as a lot of people around here, they’re real.”

The deal that will take Bogaerts through his age-40 season is big, but there were three or four other teams reportedly willing to go above the $200 million mark for Bogaerts.


Bloom’s biggest misstep could be traced to the spring, when the Red Sox offered Bogaerts an extension worth $90 million over four years.

Prior to Opening Day at Yankee Stadium, Bogaerts was asked if he would be open to signing an extension much like he did at the start of the 2019 season, and the shortstop offered a one-word response: “Nah.”

Bloom then had to fight with other teams in the open market for Bogaerts, a fight he lost by knockout.

“It’s a part of the game,” Bloom said, “but that doesn’t make it easier.”

The human side of Bloom’s often-shielded public persona took form inside San Diego International Airport Wednesday.

He rubbed the corner of his lips as he peered out toward nothingness. He looked shell-shocked at times.

Was he considering how he could reset so his Sox can be competitive in a daunting division? Was he considering the backlash that will undoubtedly follow from a fan base that’s already gone cold on him? Was he embarrassed?

“I expect fans will be hurt,” Bloom said. “I fully expect that, and I also expect that we’re going to put this together and deliver them winning baseball. It’s going to look a little different than it would have with Xander. But it’s going to happen and it’s on us to show them. That’s our job.”

Bloom boarded the flight at gate 37A. He took his window seat in first class. He slouched. He nodded, gazing deep into his phone again, perhaps trying to distract himself from a reality that cut deep. A truth, perhaps, too much in its infancy. Too hard to bear on a 5½-hour flight.


Bloom, despite the clammy feel on the plane, still wore his fleece.

His mind was in Boston, where it could be a cold winter.

More on the Red Sox during Winter Meetings

Julian McWilliams can be reached at julian.mcwilliams@globe.com. Follow him @byJulianMack.