Boston's Off-Season To-Do List

Seven things the Red Sox need to accomplish this off-season

As far as the baseball calendar is concerned, 2021 is as dead as Aaron Rodgers’ endorsement career. The business of the day is all about getting ready for 2022. That’s all pretty standard stuff for this time of the year, but this isn’t a standard off-season. That’s because the Collective Bargaining Agreement, the deal between MLB and the players union, is set to expire on December 1st. If that happens, the players will get locked out by the owners and the whole baseball off-season will grind to a halt, like an Aaron Rodgers commercial shoot. For that reason, nobody really knows what the 2022 season is going to look like, kinda like Aaron Rodgers’ future with Green Bay. Will the players get locked out? Will the CBA be effectively continued in its current form? Will it change radically? What changes will there be and what effect will those changes have on already-existing contracts? Will Aaron Rodgers get a lobotomy and if so will it help?

Obviously I don’t have the answers to any of those questions, so definitely keep reading! The good thing, for me at least, is nobody has any idea about it, kinda like Aaron Rodgers’ understanding of vaccines. Not Rob Manfred, not MLB Players Union president Tony Clark. With that as a background, let’s discuss how this general atmosphere effects the Red Sox. I’ll get into it in a second, but first hello! I’m Matt Kory and this is Sox Outsider. Welcome! I’ve written at The Athletic, FanGraphs, and a bunch of other sites. Now I’m covering the Red Sox here. So please subscribe! It’s free and fun and did I mention free? Just click this red button:

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I haven’t written much about the CBA negotiations here for a few reasons. First, they’re not a Red Sox-specific issue. Second and far more importantly, I’m not a lawyer and I don’t play one on Substack, either. There is a Red Sox angle to it in that this is an important off-season for the Sox (all off-seasons are important… I know, I know), and not knowing the specifics of the CBA throws a pretty big dead fish into that blender.

The Red Sox off-season wish list looks something like this:

1. Figure out the JD Martinez/DH situation

2. Figure out the Eduardo Rodriguez situation

3. Make reasonable changes to improve the team’s defense

4. Rafael Devers extension talks

5. Xander Bogaerts extension/trade/position change talks

6. Add to the bullpen

7. potpourri

That’s a lot of stuff! How do you talk extension with Rafael Devers when you don’t know if he’ll be a free agent in two years or if something there is going to change? How do you sign free agents if you don’t know where the luxury tax threshold is? There are obviously a billionty-seven questions (I counted!) that complicate things, but let’s look a bit more closely at those topics and see if we can get some clarity.

1. JD/DH

This one is largely going to be up to Martinez himself. If he opts out of the remainder of his deal, which is one year at $19.375 million, I’d expect the Red Sox to offer him the qualifying offer (as I wrote earlier this week), which is one year at $18.4 million. At that point it doesn’t make a lot of sense for Martinez to accept the qualifying offer considering it is less money than he just turned down. There is one reason he might though: if he accepts the qualifying offer he can’t be offered it again. Accepting it would be about an $800K payout by Martinez to get that monkey off his back for future off-seasons. The thing is we don’t know if the CBA will continue into future seasons and if so what form it will take. I don’t see it as realistic that Martinez would pay that kind of money for something that could change or even disappear entirely.

So if Martinez opts out, the Red Sox likely will turn to Kyle Schwarber and see what they can work out with him. If Martinez stays in Boston, the Red Sox could still trade him, though I’m somewhat dubious of that considering they actually need a DH and a good one on a one year commitment is more or less what the Red Sox are looking for.

2. E-Rod

Eduardo Rodriguez will be a free agent. The Red Sox could offer him the qualifying offer, though that’s roughly a $10 million jump in pay. That’s a lot, but perhaps that’s what the Red Sox think the market will bear. We’ll see. If they do offer him the qualifying offer, it will be pretty hard for them to propose a contract to him with an average annual value (AAV) of less than $18.4 million. In other words, forget offering four years, $50 million.

The other and probably even more important item is, do the Red Sox really want to keep Rodriguez around? I happen to think he’s a pretty good pitcher, and the Red Sox need starters, but there are a bunch on the market. Perhaps it’s better to let E-Rod go and put that $18.4 million towards a better pitcher. The right answer depends on the market and what E-Rod’s contract demands are.

3. Fixing The Team Defense

This one is complex. An outfield of (left to right) Alex Verdugo, Enrique Hernandez, and Hunter Renfroe is probably somewhere just short of league average. Not great, but it’s not killing you either. The problem is the infield, primarily the left side, though the publicly available metrics kinda hate Bobby Dalbec’s defense at first, too. The easy thing to do is move Xander Bogaerts to second base and sign Carlos Correa.

But seriously, folks. Is this mic on?

Now that we’ve all had a good laugh, the difficulty of fixing this in one off-season has probably dawned on you. How do you move Bogaerts off shortstop a year before his opt-out (i.e. a year before free agency) without damaging your relationship with him? I don’t imagine even requesting such a move would go over so well with either Bogaerts or his agent, Scott Boras.

As for Devers, the Red Sox could move him to first base, but there are two huge problems with that. The first is presumably they’re trying to get Devers to sign a contract extension. Moving him to first isn’t a great statement of trust. The other problem is more logistical. The Red Sox already have two acceptable and promising first basemen in Bobby Dalbec and their best prospect, Tristan Casas, who should be ready in a year or less.

How do you fix that mess? Well, you don’t move Devers and create it in the first place. Or, try this on for size: you move Devers to first base, Dalbec to DH, you let JD and Schwarber walk (or trade JD if he stays), and you sign a third baseman on the free agent market or trade for one. Creative, right? But here’s the thing: does it make the team better? I’m not sure it does.

The best outcome is for Devers to mature a bit and stop making stupid errors, something I do think he can do. The Bogaerts thing is a whole different kettle of rotting fish and I’m glad I don’t have to wake up at 3am with that problem digging a hole in my cerebral cortex. Fortunately Bloom gets paid the big bucks to figure that out so you and I don’t have to.

4. Devers Contract?

Devers will be a free agent following the 2023 season. He’s a premium bat and a total goofball and the Red Sox would be nuts to let him get away. They’ve done pretty well at letting guys who should never get away get away recently (and historically!) so don’t count them out there, but hopefully this one is different.

The question, as always, is money. How much and over how many years? I’d also throw in this one: do the Red Sox see Devers as a third baseman long term or would they seriously consider moving him off the position? If he’s not a third baseman to the Red Sox, I’d shop him. There is bound to be another organization that thinks he can play third, and the difference between those two is a lot of value.

Hopefully the Red Sox don’t feel that way, and in that case, what should they offer Devers? There are three All Star third basemen who have signed long term, big money contracts in the recent past. Manny Machado got 10 years, $300 million ($30 million AAV) from San Diego. Nolan Arenado got seven years, $260 million ($37 million AAV) from Colorado. Anthony Rendon got seven years, $245 million ($35 million AAV) from the Angels. If the Red Sox bought out Devers’ two arbitration seasons (2022 and 2023) for $25 million, maybe they could get away with something like seven years at $30 million per, or if they want to do 10 years, maybe that drops the AAV a bit to $27 million or $28 million. So something like nine years, $235 million? Or maybe 12 years, $305 million? I could be undershooting it. Devers is young and a supremely talented hitter, but he’s also not great defensively generally, and not in the same ballpark as Machado, Arenado, or Rendon.

Regardless, the Red Sox should be discussing this with his representatives soon.

5. X

I won’t rehash it again, but I thought the guys at the Sox Prospects Podcast did a great job talking about this on their most recent episode. They said they’re not sure the Red Sox can get away with trading Mookie Betts and trading Xander Bogaerts and I wholeheartedly agree. The combined Red Sox fan anger might be enough to mess with the gravitational forces around Fenway Park, and I’m not doing a bullet point about that.

6. The bullpen

I’ve heard a lot of people discuss how the team is going to sign some relievers this off-season. Maybe they will. I really haven’t seen enough of Chaim Bloom to know what he’ll do now that he has the full resources of the Boston Red Sox behind him. That said, I think spending big money on the bullpen isn’t very likely. I expect him to root around the edges of the free agent market and make waiver claims and generally try to make under-the-radar additions to the pen. It won’t be sexy, but then neither was last off-season and that worked out pretty well. That said, heck, go sign Kenley Jansen. Sure. Why not?

7. Potpourri

There are obviously a whole bunch of things that the team will do that don’t fall into any one of the above buckets. I’m sure there will be a surprise trade or a free agent signing we didn’t see coming. Maybe the Yankees will leave Aaron Judge unprotected in the Rule 5 draft.

On the whole this off-season is going to be either exciting and fascinating or incredibly annoying if the players and owners can’t get together on an agreement that moves the game forward. Here’s hoping I don’t have to go to law school to keep this newsletter running.

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