John Henry, Chaim Bloom booed at uncomfortable Red Sox Winter Weekend event

SPRINGFIELD, Mass. — The boos rained down as Red Sox owner John Henry, CEO Sam Kennedy, chief baseball officer Chaim Bloom and manager Alex Cora took the stage at Red Sox Winter Weekend at the Mass Mutual Center in Springfield on Friday night.

What the Red Sox hoped would be a joyful event in anticipation of spring training approaching quickly went off the rails as fans let their frustrations be heard, disappointed with the direction of the team.

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It was the first Red Sox Winter Weekend fan event since January 2020, an event that came just weeks before the Mookie Betts trade and just days after the Red Sox had fired Alex Cora in the wake of the Houston sign-stealing scandal.

Pent-up frustration from the fan base dating back to the Betts trade and more recently to a confounding 2022 trade deadline, followed by another last-place finish and the inability to sign Xander Bogaerts this past winter, as well as the general malaise of the team, boiled over.

Throughout the Q&A session Henry, Kennedy and Bloom had to pause multiple times as fans shouted at them from the arena seats. There were plenty who voiced support and cheered, but it hardly masked the vitriol from the portion of the fan base fed up with the club, and they didn’t hold back.

John Henry met with tons of boos from Red Sox Nation. pic.twitter.com/1lyXVMQNFa

— Chris Henrique (@ChrisHenrique) January 20, 2023

Early in the event, Bloom tried to explain why the club signed Rafael Devers to a 10-year, $313.5 million deal this month but didn’t manage to reach a deal with Betts three years prior.

In a roughly four-minute explanation, in which he had to stop several times, Bloom explained — from the front office perspective — that the Red Sox weren’t in a position to win over the course of a Betts deal. The young talent in the system was years away from contributing, and signing a long-term deal for a player without talent around him didn’t feel like a responsible move.

“Where was the organization three years ago?” Bloom said. “The organization was coming off an 84-win season. That team had shown in 2019 it had good players, but the team wasn’t good enough, there wasn’t a whole heck of a lot coming.

“So we could keep going and drive right off that cliff,” he continued. “You’ve seen big-market teams do it before and end up rebuilding for half a decade. That’s not acceptable, that’s not acceptable to you guys, and it can’t happen in Boston. So what we had to do was find a way to turn that car around before it drove off the cliff. It’s hard to do if you want to win at the same time.

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“At that time three years ago, we were faced with a similar choice with a superstar player one year from free agency,” Bloom said, referencing Betts as the boos echoed in the arena. “We didn’t sign him, and I want to explain why, because it relates to where we’re going. We didn’t sign him because when you make those bets, they’re big bets and … those bets — hang with me here,” he said as the chorus of anger rose. “Those bets, you all know it and are smart — they are much better up front than on the back end. We know that and every team knows that, but if you want to make that type of bet, you better be ready to back it up and surround that with a whole lot of talent, a whole lot of young talent, or you’re not going to win. You see it all the time in this game. I don’t think anybody would disagree where the organization was, we just weren’t ready to back up that bet.”

Bloom outlined the Betts trade, in which the team got Alex Verdugo, Connor Wong and Jeter Downs (who has since been designated for assignment) in return from the Dodgers, moves made in an effort to bolster the farm system and young talent pool but have since left more to be desired. And while the moves the front office made in 2021 did bring the team within two games of the World Series, 2022 marked a step backward.

Nevertheless, Bloom felt the team was in a better position this winter to make a long-term commitment to Devers, knowing so many young players would be on the way.

“Here we are in a similar crossroads with a superstar player a year from free agency and we did something different,” Bloom said. “We made the bet. Why? Because we’re going to be ready to back up that bet, we’re going to be ready with the talent we have coming and those guys here on stage to surround him the right way, so we can get back to winning the right way so we never have to go through what we just went through again. We made that bet because as an organization we’re going to be ready to back that up.”

Bloom’s attempt to explain the trade and the Red Sox’s situation did little to appease the frustrated fans in attendance.

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Bloom took much of the ire on the night and let the fans have their moment, telling the crowd that as a Philadelphia native, he welcomes the intense passion, noting that when things are going well, the Red Sox fan enthusiasm is “the wind in our sails.”

Later in the night, Henry, who rarely speaks publicly, noted that he’s fully invested in and committed to the Red Sox after a question was raised about his investment in other teams and sports.

“We’re fully invested, not just monetarily, we’re fully invested in wanting to win championships,” Henry said.

But many of the fans felt his words rang hollow watching Bogaerts depart just over a month ago. Henry didn’t help his case by noting that the team’s high ticket prices help field the team’s payroll.

All in all, day one of an event the Red Sox hosted to celebrate their appreciation for the fans ended with about as uncomfortable an atmosphere as possible. Front office members, coaches and players will be milling around and mingling with fans Saturday at the Mass Mutual Center for photos, autograph sessions and panel discussions, but the rough tone for the weekend was already set Friday night.

(Photo of John Henry: Billie Weiss / Boston Red Sox / Getty Images)

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