Five questions ahead of this Red Sox offseason

We don’t know exactly how long this World Series between the Houston Astros and Atlanta Braves will last, but we know it will end at some point next week at the latest, which means that the offseason for the Boston Red Sox and every other team begins at that same point. The front office is surely already 100% focused on what will happen, and with some big option decisions things should be interesting right away for the Red Sox.

I have also just recently started shifting my thinking from the 2021 team to 2022 and beyond and what should be happening this winter to maximize any window that has open up or will open up soon enough. I haven’t yet developed many strong feelings about what should be done, but do see a handful of really interesting decisions to be made. Below are five questions I am most interested in at this moment in time. To be clear, these are not necessarily the five most important questions for the winter or anything so grandiose. It’s just five things interesting me today.

And we should also mention this is all in a scenario where the offseason moves along as normal, which as we all know is no sure thing with the CBA set to expire in early December, which is something we’ll touch on plenty throughout this winter. For now, though, that factor overcomplicates things from a big picture perspective about this Red Sox roster. These are in no particular order.

1. Can Kyle Schwarber and J.D. Martinez coexist? And what happens if not?

I’m cheating right off the bat with two questions in one, because what are you gonna do? Sue me? Good luck! Anyway, Schwarber very much enamored himself with Red Sox fans in his short time in Boston in this second half, and for good reason. His approach at the plate was a needed change from what we saw in the first half (even if the overall production from the lineup was more than fine during that time) and his general presence in the lineup seemed to steady a sinking ship. But defensively, they never quite found a great fit. A big factor in that specific problem was the presence of Martinez, and both have options for 2022.

It is basically certain that Schwarber will be a free agent as his mutual option has virtually no chance of being picked up on both ends. Martinez, meanwhile, seems likely to stick around rather than triggering his opt-out, though nothing is set in stone. But in the likely scenario Martines does indeed stick in Boston, I’m fascinated to see where they go from there? Can they go a full season trying to squeeze both Martinez and Schwarber into the lineup? I think there is genuine interest from the Red Sox in keeping Schwarber, but that’s more theoretical. In practice, I just don’t see how you can have both on the roster, and I don’t see a scenario where they get enough back to make it worth trading Martinez. But Chaim Bloom thinks differently sometimes, so I’m not ruling anything out.

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2. Will they trade an outfielder?

This is something that I haven’t really heard a whole lot of yet but it potentially makes a lot of sense and is something I think we’ll see speculated upon more once the real wheeling and dealing begins. I should make clear off the bat that it wouldn’t make sense to trade any of their outfielders just for the sake of doing it, and they’d need legitimate help back to consider it. That said, they could get just that for the outfielders they could put out there. I don’t think Enrique Hernández is going to be put up in any serious talks, but three other names could.

Alex Verdugo might be the most interesting name to dangle out there, but again not just for the sake of doing so. He’s a good player who can play both corner spots fairly well, he has a propensity for big moments, and he’s under control through 2024. That said, he’s not a star and the Red Sox have corner outfield help. Hunter Renfore is coming off a career year and would be the classic sell high candidate. Front offices are too smart now to take advantage of the sell high mantra to the extent some fans make it out to be, but surely there are some teams out there believing in enough of his performance to give up value. And then Jarren Duran could theoretically be squeezed out of this group if the team thinks highly enough of the other three. I don’t know that I’d bet on it, but if they want to get a big fish in the trade market he’d be a hell of a starting point in those talks.

Whether they target pitching or second base help, or potentially something else, there are three very different roads they could take to a similar place. I think I’d probably look to trade Renfroe for pitching (but again, not with the idea that I have to) and then sign a cheap outfielder to split time with Duran. Dealing an outfielder, for what it’s worth, would also theoretically make it easier to keep both Martinez and Schwarber as discussed above.

3. Where’s the big splash?

While I’ve been a bit disappointed in the lack of aggression from the front office in recent winters, I’ve never been a believer that the aggression is never going to come back. This offseason, CBA snags aside, would seem like the perfect time to do so. That said, I also don’t expect them to do anything too crazy and make multiple big splashes. I think we’re only going to see one, though I’m not sure where. The rotation would seem like the most obvious choice, but I’ll get into that one in the next question. Bullpen big splashes doesn’t seem like a Bloom kind of move, for better or for worse. So instead, I think they’ll go big at middle infield and push Christian Arroyo to the bench. Arroyo is a better player than I thought he’d turn into, but he’s probably not better than a fringe-average starter, and that’s without getting into his injury history. But as a top player off the bench he’s a great fit on a contending roster.

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4. Is the top of the rotation good enough?

The rotation is going to be a fascinating piece of the puzzle this winter, as is the case every year. But while that usually revolves around a search for top-of-the-rotation solutions, it may not be the case this offseason. Nathan Eovaldi is coming off a season in which he’ll get Cy Young votes, and Chris Sale is still Chris Sale, and coming off a full winter. And then after those two they have more back-end options with Nick Pivetta, Garrett Whitlock (who could certainly be more than that, but I wouldn’t go into the season thinking of him as more than a number four), and Tanner Houck.

It seems clear to me they should add one more in the middle of that group, but I actually don’t think it needs to be a top-tier pitcher. Don’t get me wrong, I wouldn’t complain if they made a push for Max Scherzer or someone of that stature, but I think what they really need is someone to slot in as a clear number three. Whether that’s bringing back Eduardo Rodriguez and hoping for better defense and luck, or going in another direction is a different discussion, but in terms of tier for the first time in forever I don’t feel like they need help for that portion of the roster. Someone to slot between Eovaldi/Sale and Pivetta/Whitlock/Houck should be the baseline.

5. What’s the plan behind the plate?

This actually might be the question I’m most interested in, though I also think I know the answer. That answer, I believe, is that they’ll stick with the same duo they rolled with in 2021 with Christian Vázquez and Kevin Plawecki. I don’t believe that’s set in stone, however. The former is coming off something of a disappointing year and has a team option for 2022. That being declined wouldn’t be super shocking to me. Plawecki, meanwhile, is arbitration-eligible, and while his estimated salary is not at all unreasonable, the Red Sox have two other catchers in Connor Wong and Ronaldo Hernández on their 40-man who could feasibly be seen as backup candidates. I don’t think he’ll be non-tendered, but I also don’t think it’s a slam dunk, and even if he isn’t he could still be traded.