Red Sox Mailbag: After chaotic search, do Sox regret moving on from Chaim Bloom?

The Red Sox have a new chief baseball officer, and once the World Series wraps up Craig Breslow will have a chance to hit the ground running. Now with the offseason set to officially kick off within the next week or so, it’s as good a time as any to empty the mailbag and answer your questions.

Today we cover the chaotic head of baseball operations search that led to Breslow’s hiring, Boston’s top offseason priorities, potential trade targets and more.

Would the Red Sox have just stuck with Chaim Bloom if they knew in advance that they’d have such a hard time interviewing top, experienced candidates? — Adam V.

My intuition is no, but on some level Red Sox ownership must realize now how badly they’ve damaged their own standing within the wider baseball landscape.

Once upon a time being the Red Sox’ head baseball executive would have been considered a top three job in the sport, one anybody would leap at the opportunity to have. Red Sox ownership clearly felt this way, with CEO Sam Kennedy dismissing concerns about how candidates might view the franchise’s recent instability by saying “this is the Boston Red Sox” and that if anyone wasn’t on board with the challenge of working in Boston, “thanks but no thanks.”

The fact so many ideal candidates, including several with close ties to Boston, said “thanks but no thanks” themselves is an indictment of Red Sox ownership and their treatment of top executives this past decade.

Fenway Sports Group is going to have to own that and take a cold, hard look in the mirror, but as it pertains to Bloom, if they no longer believed he was the right man for the job, then they were right to move on and likely still feel that way. Breslow could turn out fantastic and in a couple of years hiring him could look like a stroke of genius, but on some level things obviously didn’t play out like the Red Sox envisioned.

The Sox have many holes to fill, in what order should they address the needs? Where do they start? — Tom H.

Pitching. Specifically the starting rotation. Over the past two seasons the lack of reliable starting pitching has sunk the club, and that needs to change going forward. The Red Sox can’t keep counting on unreliable or unproven arms to carry the load, so before they do anything else they need to go out and get some big-time arms.

Fortunately, this is a great year to be in the market for a starting pitcher. There are at least a dozen quality starters available on the free agent market, and that doesn’t include the possible trade candidates the Red Sox could try and acquire.

The biggest get would be 25-year-old Japanese superstar Yoshinobu Yamamoto, who is expected to win his third straight Sawamura Award (Japan’s equivalent to the Cy Young) and boasts both excellent stuff and terrific control. Other free agent targets include Philadelphia’s Aaron Nola, San Diego’s Blake Snell, Texas’ Jordan Montgomery or Minnesota’s Sonny Gray, and Milwaukee’s Corbin Burnes, a former Cy Young winner, is believed to be a likely trade candidate due to his looming free agency next offseason and deteriorating relationship with the club.

MLB notes: The Red Sox need starting pitching, and there will be plenty available this offseason

The Red Sox likely need to add at least two starters to really shore up next year's rotation, and once they do that then they'll be in a much better spot to address their other holes. Shaking up the outfield, adding bullpen depth and squaring away the designated hitter position should all be priorities, but if the Red Sox can't pitch deep into games then none of that will matter.

What's the best case scenario with our outfield on Opening Day? — Mike S.

The Red Sox outfield is in a fascinating place, to such a degree that it's hard to even define what a best case scenario might look like. So instead, let's examine three approaches the club could take: status quo, youth movement or dramatic shakeup.

In a status quo scenario, the Red Sox outfield might look similar to how it did last year, only likely somewhat more streamlined. In this case the Red Sox might go with Masataka Yoshida in left, Jarren Duran in center and either Alex Verdugo or Adam Duvall in right, with Verdugo either being traded and Duvall re-signed or Verdugo sticking around and Duvall allowed to leave in free agency. This is a pretty good outfield, but maybe not the most interesting to consider, so how else could things go?

In a youth movement scenario, the Red Sox could hand the keys to their prospects and move on from some of the veterans. In this case, we'd see Jarren Duran joined in the outfield by Wilyer Abreu and possibly also Ceddanne Rafaela, with Verdugo likely traded, Duvall allowed to leave and Yoshida possibly moved to full-time DH. This group could have an incredibly high ceiling, but it would be very risky as well. With Rafaela likely needing a bit more seasoning in the minors, this scenario feels like the most unlikely of the bunch.

How about if new chief baseball officer Craig Breslow is feeling ambitious and wants to make serious waves? Well, a great way to do that would be by trading for Juan Soto, one of baseball's brightest young stars. That would transform the lineup overnight and immediately elevate the Red Sox outfield into one of the game's best. Breslow could also target another exciting, less obvious name instead, but in either case it's conceivable next year's outfield could look radically different.

All three approaches have merit, so it will be interesting to see which way Breslow goes.

MLB Notes: Trading for Juan Soto would be risky, but Red Sox should still do it

I want the Red Sox to be better next year, but I don't want them to trade A-level prospects to do so (Mayer, Anthony, Teel). I would even be reluctant to part with Abreu, Rafaela or Duran. Do you foresee them parting with farm depth because of the relatively weak free agent market? — Eliot B.

The nice thing about the Red Sox farm system is there's enough depth to deal from without necessarily parting with any of the players you just mentioned. Boston is particularly loaded with infield talent, so if the Red Sox wanted to make a trade that would be the logical pool to draw from.

Some prospects who'd make sense to deal include former first-round pick Nick Yorke, Chase Meidroth and Blaze Jordan, all of whom are highly regarded and would have value on the market but whose paths to the big leagues could be blocked. Whether it's one of those three or someone else in a similar boat, the Red Sox could maximize their value and bolster the MLB roster without gutting the farm system as a whole.

Of course, if the Red Sox want to land a front-of-the-rotation starter with years of team control or an All-Star bat, they'll likely need to include one or two top prospects as well. This isn't something we ever saw during Bloom's tenure, but perhaps Breslow will take a different approach and start dealing from the surplus of talent Bloom acquired.

Why isn’t the firing of Sam Kennedy ever discussed? Hiring a new CEO who could then hire his own baseball ops executive who could then decide on Cora or a new field manager. Just seems so logically orderly and crisp this way. — @GOPinBoston

The simple answer is because the Red Sox front office is happy with Kennedy's job performance and has never given any reason for us to believe otherwise. Beyond that, the Red Sox also made Kennedy a partner in Fenway Sports Group back in March 2021, so Kennedy doesn't just report to the club's ownership group, he's part of it himself.

The other thing to remember when it comes to Kennedy is his job is to oversee all aspects of the Red Sox, and the on-field product is only a part of that. Kennedy also oversees the club's sponsorships, broadcast rights, marketing, real estate and everything else that comes with running an MLB organization, so if things are more or less going smoothly in those other areas then ownership wouldn't have an incentive to shake things up at the CEO level.

Now, given that the Red Sox have fired their last three baseball bosses in relatively quick succession, you could reasonably argue whoever made those hires ought to be held accountable. The trouble is those decisions aren't being made by one person alone, but by John Henry, Tom Werner, Kennedy and other influential powerbrokers within the Fenway Sports Group inner circle. Those people also want Alex Cora to stick around, which is why the Red Sox are only swapping out one link in the chain of command rather than the whole thing.

How quickly do you think the Red Sox could be a contender again? — Daniel L.

If they're willing to invest in the club and make bold moves, I don't think it's crazy to imagine the Red Sox being championship contenders as soon as next season. Just look at the Texas Rangers. Last year they went 68-94, now they're in the World Series.

The Red Sox are capable of a quick turnaround as well, and they've proven it numerous times over the past decade. They went from utter darkness in 2012 to a World Series title in 2013, back-to-back last-place finishes in 2014-15 to three straight AL East titles and the 2018 World Series, and then from the COVID-19 nightmare in 2020 to the 2021 ALCS run.

The problem, obviously, has been sustaining success so the turnarounds aren't needed in the first place, but right now the club is uniquely positioned for the future. The farm system is loaded with both quality and depth and several key pieces are already in place at the big league level for the next four years or longer. The Red Sox have financial flexibility, intriguing trade pieces and fewer holes than you might expect, so if the organization is ready to make its move, the transformation could be swift and dramatic.

It's obviously premature to say next year should be World Series or bust, but there's no reason fans shouldn't expect significant improvement from the Red Sox in 2024.