Who could be on the trade block this winter?

We’ve talked plenty about how important and potentially crazy this coming offseason is going to be for the Red Sox, and I’ve been thinking about that statement a lot. I’ve said it myself probably 20 times already, but I’m not sure I’ve ever actually thought about why I think it’s the case. Ultimately, it comes down to there being so much unknown. We don’t really know which direction the Red Sox are going to go, and how aggressive, if at all, they’ll be in a quest to build a winning roster for next year.. On Sunday, we talked a little bit about the minor-league system in the context of potential trades, both in terms of position groups from which they can deal as well as those they can try to add to.

That’s only one side of the trade conversation, though. When we talk about trades in which they deal away prospects, we know where they will be looking to upgrade this winter. Or, at least, we have an idea based on what the roster looks like right now. They need a tremendous amount of help on the pitching side, both in terms of starters and relievers, as well as second base and center field.

Today, I’m more interested in the other side of the conversation. What about trades that send major leaguers off the roster? That doesn’t necessarily mean only getting prospects back, of course. They can use some major-league talent to shore up the roster at other positions. But I would be surprised if Chaim Bloom and company aren’t engaged in some sort of trade talk all winter long. Among players already on the roster, there are six who I would look at as potential trade chips over the next handful of months.

I’ll start with someone we haven’t actually seen play since the middle of August. Andrew Benintendi has seen his stock plummet since about midway through 2018. It hasn’t been all bad since then — there was a certain catch in October of 2018 that some may remember — but he’s struggled to be better than average at the plate since then. In a small sample this season before things ended prematurely due to a rib injury, Benintendi had a wRC+ of just 43. That’s atrocious.

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All that aside, there is a good argument to hold on to Benintendi, one that mostly revolves around the idea that you shouldn’t sell low on a player. That’s a little simplistic, though, in that it assumes there is a major rebound coming. It’s certainly possible he is middling again in 2021, and then it will look like the team waited too long to pull the trigger on a deal. Personally, I wouldn’t be tripping over myself to trade him as quickly as possible as I still see the upside, but there will be teams that, like me, still believe in Benintendi long-term. The front office at least has to listen to the offers that come in.

J.D. Martinez has a chance to opt out of his contract and hit the open market this winter, but he has already said he won’t be doing that. This came as little surprise, of course, given the massive uncertainty heading into this winter’s market as well as his subpar performance in 2020 that ended with a wRC+ of 77, a shocking 59 points worse than his next-lowest mark dating back to 2014. Looking forward, there are reasons for hope for a bounce-back, including his long track record of elite performance, the small sample of 2020, and the weirdness of 2020 which included a restriction on his ability to watch video between at bats.

All that said, the Red Sox have a lot of holes to fill this winter and trading Martinez would free up some financial wiggle room to more easily fill all those holes. At the end of the day I don’t think any team will offer enough for the Red Sox to actually pull the trigger, but I certainly expect the winter to be filled with plenty of rumors.

The Red Sox are trying to build up their pool of young players, but Michael Chavis is still struggling mightily after his second season as a major leaguer. More specifically, he is still unable to catch up with high velocity up the zone, a major hole that is holding him back from being even a league-average bat. He’s versatile enough that he’ll never be totally blocked as he can fill in at first base, second base, third base and left field, but the defense doesn’t matter if he can’t get it done with the bat.

This goes back to the Benintendi discussion above with respect to selling low. Chavis alone probably wouldn’t fetch much right now, but he could be nothing more than a throw-in as soon as next July if he doesn’t fix the holes in his swing. I still believe there’s upside here, but with Bobby Dalbec up in the majors now there may not be room for both. That’s especially true if they bring in another first baseman to provide insurance for Dalbec, which I think they should. I think it’ll be part of some sort of larger deal, but to me Chavis is the most likely major leaguer to be dealt this winter.

While I think Chavis is the most likely, I would guess it is very unlikely that Christian Vázquez is dealt. I only mention him because there were rumors involving the catcher leading up to the trade deadline this past summer. There is what I think is a fair argument to be made that they could look to deal Vázquez for impact pitching and then sign J.T. Realmuto, who is the best catcher in the game and also a free agent.

It’s hard to really take a side there without knowing which caliber pitcher would come back, but just generally it feels like it’s getting too cute. Vázquez is top five at his position, signed to a team-friendly deal, plays excellent defense at the most important position on the diamond and has shown a desire to stay here for a long time. I don’t expect him to be moved, nor would I want it to happen.

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I’m going to cheat with the next one and go with two names, though it would have to be one or the other. Those two names are Nathan Eovaldi and Martín Pérez. It sounds crazy for this team of all teams to trade from their rotation, but there is a sell-high case for both of these players. Pérez is a perfect back-end arm for a contender that needs to fill out its fifth rotation spot, and won’t cost much in terms of money or years on his contract. He looked good enough for long enough this year that the Red Sox could actually get a solid return. Eovaldi was better and has a much higher upside, but as with Martinez above this could be a chance to unload some money. While I think the Red Sox should, and ultimately will, build for a winning team in 2021, the future is still the main concern and if a team is willing to overpay for one of these guys, they will think about it.

Finally, Matt Barnes seems like a pretty clear trade candidate. He’s got big talent, has performed well in the recent past including in a postseason setting, and is about to be a free agent. Even if the Red Sox do build for a winning season in 2021, they still probably aren’t real title contenders. They can still build for improvements while trading their closer.

Longtime readers know my affinity for Barnes, but even I will acknowledge that he didn’t look good this year. That, however, is actually why I think he won’t be traded. Relievers are different from other players in that their trade value increases at the deadline more than any other type of player. If I were running the Red Sox, I’d hold on to Barnes with an eye for being a second or third option in the 2021 bullpen with the idea that I can always deal him in July if things go south for the team early on again.