Five pressing issues Chaim Bloom will need to address on Day 1 as Red Sox boss


Now that Chaim Bloom is headed to Boston, the real fun begins.

Hiring a decision-maker was the first priority of the Red Sox offseason, but in a way, it was the easiest item on the to-do list, since even if the Red Sox remained within the organization, they were assured of making a strong hire. Outside of Bobby Valentine, John Henry and Co. have proven over the past 20 years that they don't screw up their management choices.

With a source confirming that Bloom is headed to Boston as director of baseball operations -- as first reported by the New York Post's Joel Sherman -- the ex-Rays exec must get quickly up to speed on the strengths, weaknesses, and needs of his new organization.

He'll have help, with's Mark Feinsand reporting that the Gang of Four (Brian O'Halloran, Eddie Romero, Zack Scott and Raquel Ferreira) will remain in Boston and assistant GM O'Halloran will be promoted to general manager.

That said, there's no time to waste, so let's lay out some of Bloom's most pressing issues.


There's really nowhere else to start, right? As we laid out earlier, Bloom (alongside Tampa GM Erik Neander) was aggressive about dealing veterans for youth out of necessity in Tampa. The closest they came to dealing a player the caliber of Betts is when they sent franchise cornerstone Evan Longoria to the Giants in December of 2017. The return has thus far proven underwhelming, though the deal did allow the Rays to get out from under roughly $60 million of the final $86 million on Longoria's deal, money they used to build back-to-back 90-game winners.

Betts will be a free agent next fall, so he's not locked in like Longoria was. There aren't a lot of comps to suggest what Boston might receive in return, but contenders like the Braves and Phillies should be among Bloom's first calls.

One aspect of this deal to watch will be whether Bloom seeks straight prospects in return -- as he generally did in Tampa -- or proven big leaguers. Speaking of which . . .


Be prepared to see a slew of veteran-for-prospect trades this winter, because the Red Sox desperately need to infuse one of the game's thinnest minor league systems with youth. The good news is whatever internal evaluations Bloom made of opposing organizations in Tampa can come with him to Boston.

The Rays were particularly adept at identifying talent in seemingly minor deals, whether it was landing corner infielder Yandy Diaz from the Indians to help facilitate a three-way trade involving sluggers Carlos Santana and Edwin Encarnacion, adding reliever Ryan Yarbrough (27 wins in 2 years) in a package for Drew Smyly, or snagging hard-throwing reliever Emilio Pagan in another three-way deal with the Rangers and A's. Oh, and while the Red Sox don't regret a thing about the deal that brought them Nathan Eovaldi in 2018, the Rays have been happy with left-hander Jalen Beeks.

So where might the Red Sox stop chopping . . .


The Gold Glove center fielder (he's a finalist again this year) has had a tumultuous Red Sox career, earning ALCS MVP honors in 2018, but struggling to deliver anything remotely resembling offensive consistency.

Now that he's due more than $10 million in his final year of arbitration eligibility, he's no longer cost-effective. He will almost certainly be dealt this winter, presumably for prospects.

Another name to watch is catcher Christian Vazquez. He's coming off a career year and due more than $10 million over the next two years, but the advanced analytics aren't as kind to him as numbers like his 23 homers, and catcher is a position the Rays often viewed as pretty fungible -- they've employed five different primary starters in the last six years.
Put another way: everyone is on the table.


In David Price, Chris Sale, and Eovaldi, the Red Sox feature a trio of contractual albatrosses who are due $79 million in each of the next three seasons. For the Red Sox to regain control of their payroll, at least one of them has to go -- Price seems like the best bet -- but good luck making that happen. All three are injury risks, and moving on from any one of them would represent the definition of selling low, before we even take into account how much money the Red Sox would have to eat.

Doesn't matter. Financial flexibility depends on it.


This should probably be No. 1 on the list, because long-term, it's the reason Bloom is here. Tampa was renowned as one of the most forward-thinking organizations in the game, but the Red Sox had lagged under Dombrowski, focusing their attention on maximizing the big league roster at the expense of the farm system, not to mention the next generation of data integration and evaluative tools that could not only improve the lineup, but help identify trade targets. So that's the list, but it's by no means comprehensive. The real work starts. . . now.

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