Red Sox Offseason Outlook Series Part I: Assessing the Front Office Situation

A first look at the Red Sox offseason in a series of posts over the next few weeks.

AP Photo/Charles Krupa

Last year on my Medium I wrote a number of posts assessing the Boston Red Sox and what they needed to do heading into the 2023 season.

As the Red Sox end the 2023 season with the exact same 78-84 record they had in 2022, I’m bringing my outlook series over to Beyond the Monster.

The team heads into a critical offseason with a high degree of uncertainty. Chaim Bloom was fired in mid-September and there may not be a replacement for several more weeks. 

Despite the Red Sox not getting the best play out of their players all year, and the club cratering with their worst September in over a decade, Alex Cora is guaranteed to be manager in 2024 and signs are showing that his power in the organization has never been greater than it is right now.

The club's on-field needs are clear: in order to get back to the postseason the Red Sox must add dependable arms to their starting rotation, improve their team defensive play, and they’ll likely need to add at least one right-handed power bat to the middle of their lineup.

How they can address these areas will be something I’ll cover in future posts. But for now, the Red Sox need someone to lead the front office, and that’s where I’ll start.

Head of Baseball Operations Search

Despite whispers in the media about big plans for the 2023-24 offseason for the Red Sox, it’s really hard to pin down anything they might do since they don’t have a chief baseball operations executive in place—and it’s unclear when they will have one.

Bloom, for all his failures, left a solid situation for whoever comes in to replace him. The farm system is in a great spot, the baseball operation has been modernized with analytics and player development hires to help bring them in line with leading organizations, and many players took steps forward on the MLB roster this year.

Yet, the search for a new leader got off to an inauspicious start. It didn’t kick off until a week after Bloom was fired because, according to the Athletic, Red Sox brass had to do damage control internally over the firing and they needed to work out a new title for former GM Brian O’Halloran. 

Team president Sam Kennedy said Monday they still haven’t done any interviews and won’t until probably later this week. That seems not great for a team that needs to have a huge offseason.

We don’t know if the team will hire one person to oversee all baseball operations or if it will be a power-sharing situation. We don’t know what the title will be for the top baseball operations role, or if it will be like it was with Bloom where he had a GM working under him. 

We do know, based on Kennedy’s Monday comments, that the organization will interview both internal and external candidates, that they’ve already sought permission to interview external candidates, and the process will be more drawn out and deliberate than the 2019 process when Bloom was the only candidate interviewed.

There’s been smoke around a few outside names, including Marlins GM Kim Ng, Dodgers GM Brandon Gomes, Phillies GM Sam Fuld, Dodgers SVP Josh Byrnes and DBacks assistant GM Amiel Sawdaye among others. Ng and Byrnes both have experience as the final decision-maker in MLB front offices—the others don’t.

Internally, the two likeliest candidates to be considered for a role atop the Red Sox baseball operations infrastructure are longtime assistant GMs Raquel Ferreira and Eddie Romero. 

Romero has been the de facto GM since Bloom was fired and O’Halloran was reassigned. He has rightly earned the trust of the entire organization, as his work in signing international free agents and helping develop many of them into stars speaks for itself. He’s watched numerous heads of baseball operations work in Boston, from Epstein to Cherington to Dombrowski to Bloom. He’s ready for the job, if he and the team are willing. 

O’Halloran, Ferreira and Romero will all be under contract for next year, per the Athletic, so the next head of baseball operations will be required to work alongside them.

Additionally, there’s been a lot of talk about big plans for this Red Sox offseason already—be they going after big name pitchers or the biggest fish in the free agent pond possibly ever in Shohei Ohtani. 

But don’t the whispers about the Red Sox having big plans for the offseason, or even something as small as talk about extensions for Brayan Bello and Nick Pivetta, seem really odd when you consider the team hasn’t actually hired the person who would ostensibly make those decisions?  

And yet, one would think if Romero, or Ferreira for that matter, was getting the job it would’ve already happened. 

Where Alex Cora Stands

Looming over all this is the outsized influence Cora has over the Red Sox organization. Clearly, ownership is enamored with Cora. He has a close, long-standing relationship with Kennedy, who is running the search and hiring process for the new head of baseball operations.

Cora has expressed interest in one day working in an MLB front office, and has said he doesn’t want to be like his mentor Terry Francona as an MLB managerial lifer. Naturally, once Bloom was let go, questions started to rise about Cora possibly ascending to a front office role.

On Sunday, Cora told the Red Sox media he specifically informed ownership he wasn’t ready to be considered for a front office role. He also said he’d been assured he would be back as manager and, most incredibly, he’ll be involved in the search process for the next head of baseball operations.

One way the last month of happenings within the Red Sox could be viewed is that Cora won a power struggle over Bloom and, as such, he is being given more power within the organization. It’s hard to say if that’s exactly the case, but it’s easy to see Cora will play a big role in how the team will be shaped going forward.

It’s worth noting Cora was the manager of two back-to-back 78-win teams, both of whom can be reasonably argued were teams with talent that underachieved. In 2023 the Red Sox entered September four games above .500 and within striking distance of a playoff spot. They proceeded to go 9-18 the rest of the way, their worst season-ending mark since the back-to-back disappointments of 2011 and 2012—both of which resulted in managers getting fired.

Meanwhile, Cora is being entrusted with seemingly more power than a normal manager. He also said Monday that while final decisions haven’t been made on the 2024 coaching staff, he doesn’t necessarily think changes need to be made there for the team to get better, a truly unbelievable statement given how poor Red Sox pitching, defense and situational hitting was for most of 2023.

It was at least nice to hear Cora say that both the coaching staff and he himself have to be better at their jobs in 2024. But talk and action are two different things.

There’s also the strange dynamic that Cora doesn’t have a contract beyond 2024, which is a very tenuous situation for someone being given this much power in an organization.

So, the next head of baseball operations won’t be able to hire their own manager, who also seems unwilling to move on from current coaches. They will have to work with an array of lieutenants who are firmly entrenched in the organization and have longstanding relationships with the club president for upwards of two decades. And Kennedy will not directly commit publicly to spending over the Collective Bargaining Tax or, at least, having a top payroll relative to other MLB teams like when Dave Dombrowski was in charge.

All of this should be troubling to Red Sox fans. The only thing we know ownership doesn’t want is more losing. But they seem unwilling to make systemic changes so the team can compete with the best organizations in MLB, like the Dodgers, Braves, Astros, Rays and Orioles among others.

The message from the Red Sox entire organization—including comments from players like Kenley Jansen—to fans and media has been crystal clear the last few weeks:

The failures of the last two years are on Chaim Bloom. They got rid of him, and you should trust them to get it right going forward. This time, it’ll be different.

Four rings the last two decades from Fenway Sports Group buys a lot of trust. But at what point do we wonder if FSG is the problem here?

I’ll have more to say on all these topics as the offseason unfolds.

If you’re interested in more on the Red Sox minor league system, I’m joined each week on The Pesky Report by Derrik Maguire and Hunter Noll to talk all things Red Sox prospects. Listen and subscribe to The Pesky Report here.

Follow Jake on Twitter @JakeTODonnell.

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