So far, it’s been a reasonably tumultuous tenure for Boston Red Sox Chief Baseball Officer Chaim Bloom in Boston.
The latest edition of the Red Sox off-season saw the Fenway faithful bid adieu to another organizational cornerstone in Xander Bogaerts, and for that, Sox fans have rewarded Chaim Bloom with the hottest seat in professional baseball.
John Henry certainly deserves a large portion of the blame, but Chaim Bloom has carried Henry’s directives of getting money off the books in a horrific fashion.
In 2019, Chaim Bloom inherited a somewhat gutted Red Sox organization, left depleted by the championship efforts of Dave Dombrowski. One thing he did acquire was a very solid major league roster, a year removed from a World Series title, propped up by some of the best collection of homegrown talent the Sox have seen on the 25-man roster in quite some time. But recent moves have many questioning the overall plan for the organization.
Boston Red Sox and the Mookie Betts Disaster

And this is where the frustration begins.
The conversations seemed endless at each of these crossroads when extending a Red Sox homegrown star was the talk of the town.
At first, it felt crazy to not extend Mookie Betts, one of the most exciting players in recent memory to come through the Sox system that all of New England watched blossom into one of the best Red Sox outfielders of all time and quite possibly the greatest defensive right fielder in the nearly 150-year history of professional baseball. Letting him take his perennial MVP talents to another city felt impossible until it didn’t.
When it seemed inevitable that Mookie would not extend in Boston long-term, but that never happened. And not only did it not happen, it almost seemed like Chaim went out of his way to make it not happen.
Yes, the Sox got Alex Verdugo, and he’s extremely easy to root for. Alex is an absolute gamer, a dirt dog by every definition, and an excellent fit for Boston. Should he be the cornerstone for a trade involving Mookie Betts?
Only if there is a fishnet of top-tier system prospects coming behind him. Jeter Downs never once looked like an MLB-caliber bat, never. Connor Wong could work his way into being a serviceable major league catcher with above-average defensive skills and the ability to consistently put the bat on the ball.
But what the Red Sox desperately needed in that deal for Mookie was the return of electric, major-league arms. While Tony Gonsolin was out of reach, both the Twins and the Dodgers had elite arms that could have made their way to Boston had Bloom forced the issue.
What Bloom did regarding Brusdar Graterol was insanely frustrating. As a part of this three-team deal, the Twins were sending Graterol to Boston. At the time, this was a 21-year-old relief pitcher with an absolutely electric power sinker that topped out at over 100-MPH.
The videos on him at the time were silly. He handcuffed hitter after hitter with a menacing combo of movement and velocity. But Chaim and the Sox didn’t like what they saw in Graterol’s medical history when it was discovered he had undergone Tommy John surgery in 2016. Chaim shut it down, and Andrew Friedman, being the shark he is, reworked the deal and brought Graterol to LA.
Last year Graterol logged 49.2 innings out of the Dodgers pen posting a 3.26 ERA and a sub-1.00 WHIP while tallying 43 strikeouts to just 10 walks. He also finished the season with four saves and 10 holds in 46 games for the Dodgers, while Sox fans watched a mismatched disaster of a bullpen blow middle and late game leads all year long.
How do those medicals look now, Bloom?

What was the Red Sox plan with Andrew Benintendi and Hunter Renfroe?
It’s easy to see the motivation to move on from Hunter Renfroe in the off-season heading into 2022.
The soon-to-be 31-year-old outfielder was coming off one of his best offensive seasons as a pro. And despite leading all of MLB in outfield assists, Renroe’s defense in right field was always a cause for concern, especially with the wild right-field dimensions of Fenway Park.
So flipping him for a solid MLB outfielder and some prospects really did make a ton of sense. But moving Renfroe to bring back Jackie Bradley Jr. and his absolutely horrid contract is still a serious head-scratcher and a glaring miss in a string of high-profile deals for Bloom. It’s bad enough that Bradley Jr. was coming off one of the worst statistical seasons in MLB history for a former All-Star, but the $ 9 million he was owed in ’22 and the $ 12 million he was owed in ’23 made the deal all the more disgusting.
While some people felt that Andrew Benintendi needed to be moved, it’s a much less obvious move than the Renfroe departure was, but the return was just as bad.
The angle that Beni needed a change of scenery was certainly acceptable, but giving him away for nothing was not. Bloom sent Benintendi to KC in exchange for Franchy Cordero, an outfielder who was the exact same age as Benintendi at the time and never really showed that he was going to be able to limit his strikeout numbers or reach the power numbers that would make his problems with making contact acceptable.
The man took impressive batting practice, but that was about as impressive as the offensive game ever got. The Red Sox also received Josh Winckowski, a young RHP with a big frame and fastball that runs up to the high 90s. After a somewhat promising start in 2022, he limped to the finish with a 5.89 ERA and a 1.5 WHIP. At just 24 years old, there is hope that he can contribute to the Sox pen in 2023. The rest of the deal included Freddy Valdez and Grant Gambrell, two longshot MLB hopefuls.

The Red Sox and the Xander Bogaerts debacle
This is a difficult topic, as the wounds are still fresh. Looking at Xander Bogaerts in San Diego Padres brown and yellow is horrific.
There were many signs on and off the field that screamed to keep X in Boston. There are no reasons to recite his numbers or accolades; they’re there. He handled himself as well as anyone could have hoped. He was incredible in the community, loved by fans, and respected and adored by teammates. He showed up when the lights were brightest and was the first to speak up and take the blame when the Sox didn’t get the job done. And most beautifully of all, he was only ever a Red Sox.
This was fumbled and flubbed in so many ways by Bloom and the Red Sox; it’s hard to even know where to begin.

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If Marcelo Mayer is one of the major factors for not bringing Bogaerts back, it’d be helpful if someone within the organization could be honest about it because that is a mildly acceptable reason why Xander lives in California now. But the way that Bloom and his team handled this situation was not.
The worst part of all this is that with every passing day, the Red Sox contingency plan at shortstop appears to be no plan at all. They were never in the Carlos Correa sweepstakes and never should have been. They pump faked like they were interested in Dansby Swanson as they have a hand full of other high-profile free agents this Winter.
It seemed like maybe Story would move over despite the shoulder injury, but now there are rumblings that they could be in the trade market for Xander’s replacement in the middle of the diamond as opposed to an internal solution. It just feels like the plan was to not pay Bogaerts and live with whatever happens next, and Red Sox nation simply deserves better.

Red Sox: So What happens with Rafael Devers?
We’ve watched Mookie leave for next to nothing. We’ve watched Bogaerts go for precisely nothing. We’ve watched Beni leave and make an All-Star team and win a Gold Glove and saw Hunter leave and have another solid year in Milwaukee.
So how does this all play out with Rafael Devers, one of the best all-around hitters in professional baseball?
Well, answer this. If you were Raffy Devers and had a front-row seat to the Mookie and X situations, would you be in a hurry to sign an 8-12 year deal in Boston?
With this front office? With this ownership group?
Why would you?
Make no mistake, he will get paid, and he will get paid a lot of money in a lengthy deal. And it feels like the organization on the name of that check will be anyone but Boston. A few short years ago, it seemed unthinkable that the Red Sox would not have Betts, Bogaerts, or Devers on their roster in 2024, and now that seems probable.
What’s The Plan?
So what is the plan? Are the Boston Red Sox fans no longer supposed to expect championships? Should they plan on being in the basement of the East?
Is the Red Sox organization no longer a viable destination for baseball’s brightest stars simply because the ownership group has directed the front office to cut down on spending? And for what? Why now? Has John Henry decided we have enough titles? That we no longer do what it takes to play deep into October? And if all or even any of this is true, is it this way now so that he can invest in hockey teams in Pittsburgh?
Soccer teams in Liverpool, basketball teams in Vegas? Are Red Sox fans being told we no longer play for championships because he doesn’t feel like it? It’s getting hard to see how someone can come to any other conclusion but that, and Boston Red Sox fans absolutely deserve better.

