MLB Notebook: Looking for some answers from new Red Sox executive Chaim Bloom

On Monday afternoon, the Red Sox will introduce Chaim Bloom, their new chief baseball officer, to the media and, by extension, Red Sox fans across the region.

There will be the usual pictures taken and hands shook -- all the pageantry that usually accompanies these sorts of coronations.

But there will also be questions -- lots of them -- to be asked. Some will be rather straight forward and easily answerable; others will be tougher and Bloom may not want to -- or be able to -- address them.



Looking ahead, here are 20 of them:

1. You've interviewed for a handful of other recent GM openings (Mets, Giants and others). What did you learn from those experiences and what -- other than being offered the job -- was different about this one?


2. With the Rays, you presided over the smallest payroll in the game; in Boston, you're inheriting a team which had the largest this past season. How different will it be operating with a budget that, even with expected cutbacks, will be almost three times bigger than you're accustomed?


3. How do you intend to balance remaining competitive with rebuilding the farm system with an eye toward long-term contention?


4. The last two people to hold the job you accepted were fired less than two years after winning a championship. Did that give you pause at all?


5. To what extent do you expect Red Sox ownership to be involved in the decision-making process when it comes to personnel decisions?


6. The Rays have been seen as one of the most innovative organizations in the game, while the Red Sox, despite winning a title just last year, are thought to have fallen behind when it comes to analytics and creative thinking. Is that accurate and if so, what do you intend to do about it?


7. Having spent most of your career in the American League East, you've seen plenty of the Red Sox over the last 15 seasons. Is that an advantage as you step into this position? And how to do you maximize that advantage?


8. Before you were hired, the Red Sox made a number of internal promotions with their scouting staff. Are you comfortable inheriting staff members and not having more say in the makeup of such an important area of your staff?


9. How do you view the relationship between the top baseball executive and his manager? Some organizations now "suggest'' lineups and batting orders -- will you do that here?


10. Mookie Betts, a franchise player, is a year away from free agency. What will your approach be toward him this winter?


11. You helped introduce the notion of the "opener'' in Tampa Bay; in your new job, your roster includes four starting pitchers who are owed almost $90 million in 2020 alone. Can veteran starters -- especially when they take up approximately 40 percent of your projected payroll -- still be counted on in the modern game?


12. Speaking of starting pitching, the Rays were strong in developing young arms while the Red Sox haven't done so in better than a decade. What's the secret sauce the Red Sox have been missing?


13. How will you view the role of your new GM Brian O'Halloran? What will his responsibilities be? For that matter, how do you envision working with Eddie Romero and Zack Scott?


14. Will you be bringing anyone from the Tampa Bay front office here? Are there limitations about how many former colleagues you can hire from the Rays?


15. Fan support in Tampa Bay is almost negligible; the Red Sox, by contrast, drew just shy of three million fans last season. Have you thought about how different your day-to-day experience will be here?


16. J.D. Martinez has the ability to opt-out of his contract later this week. Would you prefer him to stay, or would you rather have additional payroll flexibility? And would you be willing to sweeten his present deal to entice him to remain?


17. As someone coming in from the outside, what is the state of the Red Sox minor league system and their international operations? How can they be improved?


18. Is it getting harder to find market inefficiencies and be innovative when most teams have access to the same data? And if so, how can you take advantage of the resources here to establish a competitive advantage over other organizations?


19. The current roster features a number of talented players (Rafael Devers, Andrew Benintendi among them) with 0-3 years of major league service time. Will you be prioritizing contract extensions for any of them this winter?


20. Given the authority to do so, will you ban the playing of "Sweet Caroline'' at Fenway?

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