The Boston Red Sox's search for a new top baseball operations executive remains ongoing, more than a month after dismissing Chaim Bloom following nearly four seasons at the helm. Former Red Sox relief pitcher and current Chicago Cubs assistant general manager Craig Breslow appears to be the frontrunner for the position, according to Alex Speier of the Boston Globe.
Breslow has become a well-regarded figure around the league since transitioning to front-office work. He's been credited with helping turn around the Cubs' pitching development processes, which had previously been a longstanding organizational weakness. Two things can be true simultaneously: Breslow may prove to be a great hire if he lands the job, but he's not who other executives imagined the Red Sox would hire when the position first opened up.
The expectation was that the job looked good enough -- on account of Boston's young talent and financial might -- to attract an established executive from another post. Instead, the Red Sox have been rebuffed by both blossoming general managers like Sam Fuld (Phillies) and Brandon Gomes (Dodgers) and former general managers James Click and Jon Daniels. (Popular target Mike Hazen signed an extension with the Arizona Diamondbacks.)
Why, precisely, have the Red Sox had trouble attracting blue-chip execs? MassLive's Sean McAdam recently explained part of the problem by noting that the incoming executive will inherit a manager and a slew of assistant general managers, all of whom have outlasted other top executives:
And increasingly, sources add, there's concern about the surrounding infrastructure. The new hire will not only be inheriting manager Alex Cora, whose job has been guaranteed by ownership for at least 2024, but also, a front office that includes several executives who've been part of the organization for more than two decades, along with various other department heads who come with the job.
It's worth noting that a source expressed similar concerns to CBS Sports about Boston ... back when Bloom took the job in 2019.
These Red Sox are a great example of the inscrutable and, at times, illogical nature of front offices. Clearly owner John Henry isn't happy about missing the playoffs three times in four years, but it's unclear if he knows what the actual problem is with his team. He's at once signaling that Bloom was the issue by keeping everyone except him in place, yet he's also signaling that the Red Sox front office is missing something by pursuing external candidates.
Without getting too inside-baseball-y, the situation calls to mind a scene in Moneyball where author Michael Lewis reveals how weird power dynamics can become in front offices. To set the scene: Lewis is detailing then-Oakland Athletics general manager Billy Beane's attempt to obtain then-infield prospect Kevin Youkilis from the Red Sox as part of a larger trade:
What [Beane] doesn't know is that Theo Epstein has new powers -- new Red Sox owner John Henry listens to everything he says -- and has used them to establish Kevin Youkilis as the poster child for the Boston Red Sox farm system.
Epstein was, at the time, an assistant general manager. If Lewis' account was accurate -- and it's accompanied by an Epstein quote that suggests so -- Epstein had more say in the organization's strategy than the average assistant GM. (Henry would later elevate Epstein to general manager.)
Other executives passing on the job makes sense if they believe Henry places too much weight in the opinions of his assistant general managers and field manager. How is one supposed to go about reshaping a disappointing organization if they're unsure the owner is willing to step away from the status quo?
Another source said this week, when discussing a different possible job opening, that the new generation of executives has become wiser and choosier about which gigs they pursue. They used to reason that there are only 30 top jobs, and that you have to take one when it's offered to you. Now, they view it as they would a trade or a free-agent signing: with greater scrutiny.
Breslow, or whomever the Red Sox end up hiring, may prove to be the perfect person for the job. Either way, Henry may want to examine why others have decided that an otherwise attractive situation isn't worth their time.
