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With massive financial flexibility, how will the Red Sox approach a crucial offseason?

Chaim Bloom (center) has been the Red Sox' chief baseball officer since 2019.Jonathan Wiggs/Globe Staff

Who are the Boston Red Sox? How do they operate? What does it mean to be a near-top-of-the-market team chasing sustainable competitiveness?

Those questions have floated throughout the baseball industry for the last three years, ever since the team fired president of baseball operations Dave Dombrowski in September 2019 and hired chief baseball officer Chaim Bloom one month later. Now, with the offseason officially underway following the conclusion of the World Series between the Astros and Phillies, the answers to those curiosities will come to light more clearly than at any point in Bloom’s tenure.

When Bloom came to Boston, he inherited a team with several established stars but a payroll that was maxed out with a number of players on pricey long-term deals and a farm system that didn’t have any impact major-league ready prospects. Over three wildly inconsistent years – a surprising ALCS run bookended by last-place finishes in 2020 and 2022 – most of the team’s moves have been framed by self-imposed constraints while trying to gain payroll flexibility and improve a farm system to allow a steady supply of cornerstone big league contributors.

Now, for the first time under Bloom, the Red Sox enter an offseason with a massive amount of financial flexibility – more than $120 million in commitments from last year’s roster is off the books – and a farm system that has Brayan Bello and Triston Casas in the big leagues and others (Ceddanne Rafaela, Brayan Mata, Marcelo Mayer, among others) poised to join them in coming years. They also face the potential departure of a franchise cornerstone in Xander Bogaerts, who opted out of the remaining three years of his six-year, $120 million deal on Monday, as well as J.D. Martinez and Nate Eovaldi.


Bloom and the Red Sox front office have the freedom to pursue very different deals than they have over the past three years.


“A lot of it basically comes down to us not feeling like we are backed into a corner, so to speak, that we were after 2019,” said Bloom, referencing the organization’s sense that it needed to trade Mookie Betts (in a package with David Price) for Alex Verdugo and prospects Jeter Downs and Connor Wong in an effort to free payroll and start building the team’s young talent base. “Obviously, not everything has gone perfectly, as the 2022 season shows. But we have a lot of different avenues that you can look at ahead and see us playing winning baseball for a long time. And we have the ability to go out and enhance that group that we have.”

The Red Sox face an offseason of far-reaching needs. With Bogaerts expected to opt out, they don’t have a shortstop for next year. Their outfield production in 2022 was woeful. The team’s two primary catchers at the end of the season – Connor Wong and Reese McGuire – both profile as backups, leaving the team in need of a starter. And, of course, the club’s pitching staff fell well short of adequate last year, creating a need to add multiple arms to both the rotation and bullpen.

The length of that checklist is daunting and certainly will frame what the team does this winter. But at the least, the team sees itself as having greater freedom to pursue a wider range of transactions – whether deploying some of the growing number of prospects to trade for big leaguers or pursuing true top-of-the-market deals for elite talent.


“We’re entering an offseason where we will have more options in front of us,” said Bloom. “Some of that is due to the increased strength of the talent base of the organization. Some of that’s due to having a little more financial flexibility than we’ve had in the past. Now, with that obviously comes a lot of needs and a lot of to-dos. It all goes hand-in-hand. But I think there’s a lot more options that we’ll be able to consider and that we’ll need to consider.”

It is, however, one thing to “consider” a wider array of options, and quite another to order from a different menu than the generally budget-conscious, low-calorie one that has (outside of the six-year, $140 million deal for Trevor Story) been the primary one utilized by the Sox under Bloom.

The team has traded away just one prospect in its top 30 (Aldo Ramirez, who went to the Nationals in the Kyle Schwarber trade deadline move in 2021 and who threw 7 2/3 innings in the Nats system before tearing his ulnar collateral ligament and requiring Tommy John surgery) and none in its top 10 since Bloom came to Boston. Story is the only player the team has signed to a guaranteed deal of more than $20 million.


It has been a cautious approach, focused on a notion of long-term building toward sustainability. In general, the Sox have worked (not entirely effectively, as the 2022 season demonstrated) to raise their organizational floor, but they have made few moves to improve their ceiling.

To those outside of the organization – particularly agents who were used to having the Sox under Dombrowski pursuing top names on the market – it’s been a puzzling departure.

“This isn’t manufacturing and efficiency. It’s got to be more than that,” said one agent. “At the end of the day, they need to look and say, ‘We’re the Red Sox.’ They should operate as if they’re the Red Sox – period. You make big decisions. You’re the Red Sox.”

What does that mean? Will they behave in a way this winter in which their expression of interest in retaining Bogaerts proves to be more than lip service, in which their vow to explore the higher-end of the starting pitching market results in an established mid-rotation (or better) starter, when they move aggressively in the trade market to address deficiencies?

The Red Sox now have the opportunity to start answering those questions in an offseason that will prove a pivotal one in Bloom’s Red Sox tenure.

Alex Speier can be reached at Follow him @alexspeier.