Boston Red Sox President Sam Kennedy, right, looks on as Craig Breslow is introduced as the team’s new chief baseball officer on Nov. 2. Charles Krupa/Associated Press

Red Sox Winter Weekend begins on Friday. The event, held in Springfield, Massachusetts, has become an annual referendum on how fans are feeling about their team. It’s safe to say those fans are feeling unsettled with spring training less than a month away. After a last-place finish and a change in baseball leadership, the Red Sox are facing many of the same needs today that they were dealing with in October.

For weeks we’ve been talking about the team’s lack of front-end starting pitchers. And right-handed power. That conversation will get louder as fans descend on western Massachusetts looking to have their voices heard.

They were heard last January when the team’s annual town hall was overshadowed by boos and catcalls from the crowd. Ownership tried to explain its vision but everyone – save Manager Alex Cora – got the message that Red Sox Nation expects more from its team.

This year, for the first time, there will be no town hall. Instead of management taking questions from fans, they will be facing the inquisitive stylings of Jonathan Papelbon as part of “The Cinco Ocho Show.” I’ll be there to try to keep things from going too far off the rails.

Fans may be disappointed that they don’t get to ask the questions this year, but chances are strong that Papelbon holds Red Sox President Sam Kennedy and Chief Baseball Officer Craig Breslow accountable for what’s happening with this team. Throughout his appearances last season Papelbon talked about the team’s culture, saying he believes it has lost its way and is no longer the same championship-driven team that he played for.

He also believes it can be fixed. Bringing in the right players will speed that process up.


The Red Sox believe they have assembled a core they can build upon. They believe strongly that Trevor Story is ready to take on a leadership role after two injury-plagued seasons in Boston. They think Rafael Devers is ready to blossom into a true superstar. They feel young players like Triston Casas, Jarren Duran and Brayan Bello are ready to become stars.

Even though the roster is unfinished, they feel the current group is ready to take a step forward and be a better team in 2024. Yet they have to answer to comments made last fall, when Chairman Tom Werner said the team will go “full throttle” this offseason and Breslow said he will be bold in his pursuit of talent.

Yet the offseason has been a disappointment. Top free agents have gone off the board. Breslow has made bold moves, acquiring Vaughn Grissom for Chris Sale in one of several trades, yet the end result is a roster that has changed some of its players rather than added to the overall level of talent.

As currently constructed, the Boston roster isn’t impressing many experts. Vegas sets the over/under for Sox wins at 80.5. That’s slightly better than last year’s 78-84 record.

At the moment the Sox seem more like a team that is continuing a long-term rebuild rather than a team that is going all-in for the coming season. Are fans OK with that? Fans in Baltimore were disillusioned as the Orioles averaged 100 losses (in full 162-game seasons) from 2017-22, but they’re on top of the world now after their first 100-win season in more than 50 years.

It will be interesting to see what Kennedy and Breslow have to say about the current state of that rebuild. Do they expect to contend for a playoff spot in 2024? How soon do they believe fans will have to wait to battle for a championship?

Those questions will be louder than the sounds of slot machines at MGM Springfield throughout this winter weekend. The answers provided might give us a better idea on what we can expect to see on the field this summer.

Tom Caron is a studio host for Red Sox broadcasts on NESN. His column appears in the Portland Press Herald on Tuesdays.

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