Thousands of fans descended on western Massachusetts late last week for the annual hot stove gathering known as Red Sox Winter Weekend. There were games, autograph sessions and panel discussions with management, players and legends.

There were also boos. Plenty of them. For the second straight year, fans made it clear they were unhappy with a team that finished in last place.

“I want you to know the boos, the anger, the hate we see on social media … we get it,” Red Sox President Sam Kennedy said in an appearance on The Cinco Ocho Show with Jonathan Papelbon, a late-night talk show style event I got to co-host at the Winter Weekend. “It is our job to turn things around to make you proud. There’s only one way to turn the boos into applause. And that’s by winning baseball games.”

This came minutes after Kennedy told writers that the 2024 team will probably have a lower payroll than last year’s sub-.500 team.

On Saturday, Red Sox Chairman Tom Werner was quick to dismiss any suggestion that Fenway Sports Group was thinking about selling the team. He also said he and principal owner John Henry were “in lockstep” in their vision for the team. That vision has been handed down to new Chief Baseball Officer Craig Breslow, brought in to replace Chaim Bloom after his four years at the helm of baseball operations.

When Breslow took the stage Friday night, a fan in the crowd yelled “You’re Chaim Bloom 2.0.” The comment crystallized fan sentiment that the team has not done enough to change the downward trajectory of the past two years.


“I don’t think we’re far away,” Breslow said on stage. “I don’t think we’re talking about years and years and years.”

Yet it’s been years and years and years — three of the last four, to be exact — in which the Sox have finished last in the American League East. And most experts are predicting they will be right back there in the coming season.

“If we’re having this conversation next year, we’ve failed,” added Breslow. “We need to take a step forward.”

On Saturday, Kennedy told me the team will spend — and spend big — again. He made it clear they were not willing to overspend on one player who may not make enough of an impact on this year’s team but could hamstring efforts to build a contender in future years as prospects such as Marcelo Mayer and Roman Anthony make it to the big leagues.

“Sometimes you don’t have a particularly exciting offseason when you stay disciplined,” said Kennedy. “There will be a time when we match up on free agency. It just hasn’t happened this offseason. And we understand that that can be disappointing for fans. But hold us accountable. Let’s see where we are in six months, 12 months, 18 months, 24 months. Fans held us accountable last night. We know they will in the future.”

How far away is that future? Is it six months? Twenty-four? That was the question most fans still had as they left Springfield. We also couldn’t help but think about the remaining free agents on the market, notably pitchers Jordan Montgomery and Blake Snell. Either would dramatically upgrade Boston’s depth and increase their expected win total for the season.

For now, the Sox haven’t offered what it will take to bring either to Boston. They have remained disciplined, even if it means hearing boos from an angry crowd.

Tom Caron is a studio host for the Red Sox broadcast on NESN.

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