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Chaim Bloom’s offseason to-do list

What does he have to get done?

Boston Red Sox Summer Camp Photo by Jim Davis/The Boston Globe via Getty Images

The Red Sox have a lot of work to do this winter, and having not made the postseason they have plenty of time to prepare. Chaim Bloom doesn’t need my help, but I’m going to give it to him anyway. That’s just the kind of guy I am. There are a lot of specific decisions that will be made throughout the winter, but there are some broad strokes to be focused on as the offseason moves along. Here’s a brief to-do list of general tasks for the Red Sox front office to take care of this winter, in a rough order of how they’ll have to go about things.

The Alex Cora decision

The first order of business is for sure who will be leading the team on the field. With Ron Roenicke out, this month they will be focusing mostly on the managerial opening. Before they can make a hire, though, they first need to decide on what to do about former manager Alex Cora. From the outside, it seems that if they want him back, they can have him back. He is a candidate for the Tigers job, too, but presumably he will take the Red Sox job if that is available. But Bloom and company need to make this decision quickly, because if they want to move in a different direction, they need to start lining up interviews with other candidates.

Hire a manager

Whether it’s Cora or someone else, the sooner they can fill the manager position the better. They obviously don’t want to rush this decision and it’s important to get it right, but at the same time there are benefits to having someone in place as soon as possible. We still don’t really know what next season is going to look like, and one of the issues for Roenicke this summer (besides his roster being very bad) was that he couldn’t really communicate with his players like a manager usually does. That could be the case for part or all of next season as well, and given that it would behoove whoever the new manager is to be in place early and have as much of the winter as possible to start building relationships with players in the organization.

New York Yankees v Boston Red Sox Photo by Maddie Meyer/Getty Images

Outline a Rule 5 plan

One of the somewhat underrated storylines to keep an eye on heading into this winter is the roster crunch that is coming with the Rule 5 Draft. This is not an imminent decision, but in roughly midway mid-November teams will need to add prospects to the 40-man roster for the Rule 5 Draft. Among Red Sox players who are likely to at least be considered are: Jay Groome, Bryan Mata, Hudson Potts, Jeisson Rosario, Connor Seabold, Connor Wong as well as fringier possibilities like Eduard Bazardo, Joan Martinez and Pedro Castellanos. That’s at least six definite names along with some other fringe decisions as well. They need to figure out if they have room for all of them early and look to make trades if they don’t, whether that be trading names on this list or potentially players already on the 40-man.

Non-tender decisions

One of the ways to alleviate this potential 40-man crunch is to not tender contracts to some arbitration-eligible players. There are some players for whom that is clearly not an option. Eduardo Rodriguez and Rafael Devers, for example, are going to be tendered contracts. However, there are some fairly easy decisions to be made to clear roster spots. Players like José Peraza, Zack Godley and Dylan Covey are easy non-tender candidates.

How many starting pitchers?

We all know the focus is going to be on the pitching this winter, but they need to decide how many starters they are comfortable with to start next season. Nathan Eovaldi and Martín Pérez — who has a team option for 2021 that will certainly be picked up — are presumably shoo-ins, but beyond that there are questions. Can they really plan on Eduardo Rodriguez being part of the Opening Day group? Are they comfortable with Tanner Houck starting off in the majors after just three starts? What about Nick Pivetta after two? What about depth beyond the top five? I am of the opinion that they need to add at least two starters that will be part of the Opening Day group if everyone is healthy, but whether or not the front office agrees that decision needs to be made before hectic player movement begins.

What’s the plan, long- and short-term, at second and in center?

On the position player side of things, the two positions to watch for are at second base and in center field. In the short-term, they have to decide if they saw enough from Christian Arroyo and Yairo Muñoz to give them a chance to hold down the position at second base. In center field, they need to decide if they need to target a center fielder or if they are comfortable with either Alex Verdugo or Andrew Benintendi in that position and target a corner outfielder instead. Both of these decisions are more complicated by the presence of Jeter Downs at second base and Jarren Duran in center. Both of these prospects would have spent most of 2020 at Double-A, presumably, but there was obviously no minor-league season. They did get their time at the Alternate Site, but it’s hard to know how much to read into those performances since the games were makeshift and they faced the same pitchers all summer. However you judge them, Bloom and company need to figure out if they expect one, both, or neither to be ready by midseason, and if not whether or not they should keep a spot open for 2022.

Talk Extensions

The 2021 roster will be the early focus of the offseason, but the front office should and presumably will be looking to make headway on longer-term conversations with the core of the roster. Xander Bogaerts can opt out after the 2022 season. Rafael Devers is a free agent after 2023. Alex Verdugo is a free agent after 2024. None of these players need to be locked up in a long-term deal this winter, but the organization would be foolish to not at least start conversations and get a feel for how the players are feeling about their future with the team.