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The Flyby: Planning for the Future

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What is your plan for the future?

Boston Red Sox v Baltimore Orioles Photo by Greg Fiume/Getty Images

Last weekend I asked you all to tell me what was on your wishlist. No, not your Christmas wishlist... your Red Sox wishlist! We had a response. Let’s dive in.


Good_Better_Betts Wishlist

What they said: While there is a part of him that wants the team to contend, and this team is actually fairly close to contention despite a slow start (60 game seasons will do that), the more realistic side of him says that the team should sell. That doesn’t mean they should sell everything, but that they should sell non-essential players like Brandon Workman, Mitch Moreland, and one or both of Jackie Bradley Jr and Kevin Pillar. The big question is J.D. Martinez, which GBB would prefer to keep around.

I’m going to choose to address the elephant in the room: J.D. Martinez. I don’t think anyone would complain if the Red Sox sold upcoming free agents. It’s not that controversial of an opinion.

The Martinez situation is much more complex. For starters, it’s not a lock that Martinez will be a free agent. But by the same coin, it’s not a lock he’ll choose not to opt out. Just a quick primer: J.D. Martinez can opt out after the 2020 season. If he does, he’ll be leaving two years and $38.75 million on the table (AAV = $19.375 million). If the National League retains the Designated Hitter rule (as it should), the number of teams that could realistically use Martinez doubles. If that happens, he should easily pass 2/38.75, even in an uncertain financial market.

Philadelphia Phillies v Boston Red Sox Photo by Billie Weiss/Boston Red Sox/Getty Images

So I’m operating under the assumption that J.D. Martinez is going to opt out of his remaining contract. And if he does, I can’t see this current Red Sox team ponying up to sign him to a new deal. This leaves two options for me. Either he is traded or we offer a qualifying offer and let him walk.

With the value of a qualifying offer being what it is, the Red Sox would need to be able to exceed that value in a trade, otherwise it makes more sense to ride out the remainder of the contract.

I’m not sure what Martinez’s trade value is, especially in this strange season, but I am reasonably sure that Martinez will not be playing for the Red Sox in 2021 at this point.


Another player I wonder about is Andrew Benintendi. At this point, there’s just no ignoring what Benintendi has brought to the team. It hasn’t been much. He has hit poorly (.103/.314/.118), he’s been a negative defensive presence, and he is inching closer to costing a relatively significant amount of money.

Benintendi will make $6.6 million in 2021 before hitting his final arbitration year leading into the 2022 season. While the Red Sox can undoubtedly afford whatever the final arbitration year ends up costing, there’s a reasonable chance the money could be better spent at that point, especially if the pitching remains in such a pitiable state.

Tampa Bay Rays v Boston Red Sox Photo by Maddie Meyer/Getty Images

Ultimately, the best deal for Benintendi may be in the offseason, as not many teams will be able to offer their best possible deal for the struggling outfielder at this time. Will he play better with a change of scenery? It’s possible, and a little sad to think about.

Whatever the case is, I feel like the short-term plan needs to be to trade anything that doesn’t have control beyond 2021 for certain, and to consider trading bigger assets with coming opt-outs. While a signing of a Trevor Bauer in the offseason would make this team much closer to competition, I’m not sure that’s actually in the cards at this point in time.

I trust in Chaim Bloom to build a competitive team long-term. But to get there, the Red Sox need to do a lot of work. And I’m not sure that much work can be done in as small a time frame as our resources may lead us to believe.