The old town team is one “no thanks” away from posting a job listing on LinkedIn.

The Boston Red Sox are a historic franchise with a rich tradition, four championships since 2004, a well-stocked farm system, and a lot of money to spend in free agency this coming offseason. When taken at face value, it should be a dream job for anybody that has ever worked in the front office of a Major League Baseball team. If you don’t believe me, just ask Team President Sam Kennedy.

Yet no less then ten baseball executives have declined the open Chief Baseball Officer position that was vacated when Chaim Bloom was fired. 

Some people blame this on the Alex Cora factor.

The Red Sox manager was so beloved by ownership that they essentially took him back, no questions asked, after he served a year-long suspension in 2020 for cheating during his days as the bench coach of the trashcan gang down in Houston. Despite the industry standard of the general manager being allowed to choose his own field manager, it has been made clear that Cora will continue to be the Red Sox manager moving forward, regardless of the opinion of the next front office chief. Not only that, Cora has publicized his own desire to become a general manager once he tires of his current role.

I won’t deny that the optics of having a ready-made manager foisted upon you, one who ownership adores and may wish to poach your job someday, may feel somewhat unappealing to potential Bloom replacements. 

But I think Cora’s role is just the tip of the iceberg regarding the lack of interest in becoming the next head honcho of the Red Sox front office.

Dave Dombrowski and Chaim Bloom both fared poorly at certain aspects of their jobs. Dombrowski lived exclusively for the here and now, throwing money at established stars while utterly disregarding the pipeline to the future. Bloom, on the other hand, focused on backloading the minor league system with promising talent while failing to field a competitive team in three of his four seasons at the helm.

Dombrowski has a long and successful history as a mercenary who hands out reckless contracts that torch franchises on his way out the door. Bloom arrived in Boston with a small market pedigree based on bargain hunting and cultivating the farm.

What two traits do these polar opposite executives have in common?

  1. They both did exactly what the Red Sox hired them to do.
  2. They were both fired for it.

If I hired a seasoned contractor to build me a state-of-the-art home movie theatre with all the trimmings, I wouldn’t fire him because I couldn’t afford my mortgage the following month. In that same respect, if I hired a budding apprentice to replace that home theatre with a modest 65-inch smart TV, I wouldn’t fire him because that viewing experience didn’t feel as cinematic.

Kim Ng (Marlins), Sam Fuld (Phillies), Brandon Gomes (Dodgers), Mike Hazen (Diamondbacks), Michael Hill (Marlins), Jon Daniels (Rays), Derek Falvey (Twins), Amiel Sawdaye (Diamondbacks), and even current Red Sox employee Raquel Ferreira have declined the chance to even interview for what should be the most coveted front office opening in the sport. One of the league’s flagship franchises is looking to add a tenth ring to their trophy case, and it needs a captain to steer the ship back into history. Yet the most highly qualified people for the job won’t even sit down and chat with the Boston brass to determine if this job may be right for them.

This is not about Alex Cora. This is about a pair of eccentric taskmasters who have no idea what they want.

You’ve all worked for people like this before, regardless of the business you’re in. They’re the bosses that insist that you do a specific thing a specific way, but when a problem arises due to following their specific instructions, they blame you for not knowing any better. And when someone has to answer for the fallout? Well, it ain’t gonna be them.

Why would the top rung of Major League Baseball administrative talent ever be willing to uproot their families and bank their futures on the whims of a couple erratic PR slaves that specialize in passing the buck to their underlings?

That’s a very good question. And to be honest, I don’t have an answer.

For these reasons, Bloom’s replacement will not come from that sought-after top rung of executives. Henry and Werner will have to settle for a Chief Head President Whatever Officer of Baseball Operational Activities Esquire who has not yet established him or herself as a prominent member of the wheeling-and-dealing elite. The Red Sox will apparently spend the next three or four years hoping that some middle-of-the-pack rising star accepts their offer and endures the hair-on-fire, anxiety-inducing atmosphere that Fenway Sports Group cultivates with grace and consistency. If that unproven executive can’t meet the expectations of Henry and Werner, FSG will not hesitate to move on. If that executive is successful and actually brings another World Series trophy to 4 Jersey Street … well, FSG will still probably not hesitate to move on.

I guess it’s only appropriate that Red Sox majority owner John Henry has an operational philosophy that is so diametrically opposed to that of Yankee owner Hal Steinbrenner. Brian Cashman makes countless awful decisions every single year. He has watched four Red Sox counterparts come and go during his tenure, three of which have won World Series. Yet despite winning only one championship in the past 23 years, Cashman is still entrenched as General Manager of the Yankees with no sign of departure anytime soon. 

As ironic as it may be, John Henry is the son George Steinbrenner should have had. He may be a creepy introvert that bears a striking resemblance to Andy Warhol, but it turns out that Henry is way more of a pompous tyrant than The Boss’ own heir apparent. 

So here we are, a few days away from the World Series, and the Red Sox still without a head of baseball operations. I could do a Google search and try to give a barely-informed opinion of who I think should get the job, but I’d be wasting my time and yours if I actually tried to analyze who would be the best fit. What do any of us fans really know about the qualifications of sports executives anyway? We can’t really speak to how competent they are until we see them in action as a team’s primary decision-maker for a couple years. And it’s very possible that the person who accepts this job will be taking the reigns of an MLB team for the very first time.

The Boston beat reporters (or the sources that feed them anyway) seemed to think Minnesota Twins Vice President and General Manager Thad Levine had the inside track of taking the job until this morning, when it was reported that Levine is no longer a candidate. I have to believe that a large portion of Levine’s interview entailed his justification for signing a 32-year-old Christian Vazquez to a 3-year, $30 million contract after 2022. That one move alone should be enough to dismiss a candidate from consideration. 

Former Red Sox pitcher Craig Breslow, a Theo Epstein disciple who is now Assistant General Manager/Vice President and Director of Pitching for the Chicago Cubs, appears to be the leading candidate at the moment. The Red Sox have had serious problems developing pitchers for the past ten years and are currently two starting pitchers short of competing for a championship. Thus, his pedigree as a connoisseur of young pitchers makes Breslow a very attractive candidate. Chicago’s farm system is ranked in the top six in MLB according to every reputable publication, and Breslow can count 2023 Cy Young candidate Justin Steele and Top-100 prospects Cade Horton (#30) and Ben Brown (#91) among his pitching developmental achievements. 

Longtime Red Sox employee Eddie Romero is also reportedly getting serious consideration for the role. Romero’s roots with the team date all the way back to 1986 when his father, utility infielder Ed Romero, was a member of the BoSox club that had their hearts ripped out by the New York Mets in the ’86 World Series. Eddie began his own Red Sox career as an assistant scout in 2006 before rising through the ranks to become Director of International Scouting in 2012. Franchise slugger Rafael Devers and young studs Brayan Bello and Cedanne Rafaela were discovered under the watch of Romero, who has been a rising star in the organization for 17 years. 

There’s also the possibility that the Red Sox add multiple officers to the top rung of the front office. When Bloom was relieved of his Chief Baseball Officer post, General Manager Brian O’Halloran was promoted to Executive Vice President of Baseball Operations. This theoretically leaves the positions immediately above O’Halloran (Chief Baseball Officer) and below him (General Manager) currently vacant. Unless one of the open positions is eliminated and absorbed within O’Halloran’s new role, Red Sox fans can expect to see multiple executives brought in from outside or elevated from inside the organization. 

I have no clue how these three roles differ regarding the day-to-day operational aspect of things. However many people the Red Sox hire, they must be people that Henry and Werner trust to succeed in their roles regardless of the state of the team.

The head of baseball operations is not a temp position. You don’t hire somebody for that role because they specialize in the one aspect of team-building that your team needs at that moment in time. You hire somebody that you feel can orchestrate a plan and then pivot accordingly, regardless of the current landscape of the team and the league. If you could blend Dave Dombrowski’s talent for writing checks with Chaim Bloom’s talent for research and analysis, you’d have the perfect baseball executive. Fenway Sports Group needs to hire the candidate that best exemplifies that hybrid of styles.

The mission here should be for Henry, Werner, and Kennedy to hire a couple sharp baseball minds and slot them into a functional hierarchy where they can all work together in a positive environment to give Alex Cora the tools he needs to bring home another championship.

When I say “positive environment,” I mean an environment that is mostly devoid of John Henry and Tom Werner. These guys have a lot of money, and that money has brought a lot of joy to baseball fans across New England for the past two decades. But they clearly gum up the works whenever they show their faces in the office.

Here is my plea to you, John and Tom:

Hire the right person and then stay away from Fenway Park. Spend your days managing hedge funds, yachting, reading Variety, cutting ribbons with giant scissors, galivanting with trophy wives, painting Campbell’s soup cans, and whatever else multi-millionaires do until 7:05pm.

Learn from Jerry Jones’ mistakes. You may love baseball, but you are not baseball guys. 

Stay in your lane.

By Luke

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