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The Red Sox are in a tough spot on the trade market

They are stuck in between on a couple different levels.

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New York Mets Vs. Boston Red Sox At Fenway Park Photo by Jim Davis/The Boston Globe via Getty Images

The Red Sox, like most every other team in baseball, are playing the long game this winter. There hasn’t been a whole lot of action, and aside from a handful of teams that has been the case for clubs other than the Red Sox as well. But whenever things happen to get moving, we all know Boston has a lot of work to do. They need multiple starting pitchers. They need multiple relievers. They need an outfielder. They should sign a second baseman. And that’s just the basic stuff and not even getting into some out-of-the-box additions they may have up their sleeve. All told, it is a not-insignificant amount of work for a single offseason.

We’ve been focusing on some potential targets for all of those open roster spots for a few weeks now, with basically all of said focus being on the free agent market. That’s obviously not the only way to add players, though, as the trade market is also a thing that exists. In fact, just this week we’ve already seen American League wildcard (or division, to be fair) hopefuls in the Angels and White Sox improve their team via trade by acquiring Raisel Iglesias and Lance Lynn, respectively. So what about the Red Sox? Can they take that path as well?

Well, Boston is in a tough spot with respect to the trade market, which is a thing you probably knew I was going to say if you read the headline. But I believe it! I mean, don’t get me wrong, they certainly aren’t in a position to be just tuning out of it altogether. That would be bad business, and for all my criticisms of the organization over the last 12 months or so I don’t think they’re dumb. We’ve heard about Chaim Bloom’s creativity since he got here, and the trade market is the place to make that happen. They say they’re serious about improving the roster and being a more respectable team in 2021, and you can’t be serious about that unless you are at least working the phones.

Red Sox Spring Training Workouts Photo by Jim Davis/The Boston Globe via Getty Images

That said, the Red Sox are a little bit of a tweener in terms of where they are on the win curve, and that’s what puts them in the aforementioned tough spot within the trade market. As I said, they ostensibly want to compete in 2021. That doesn’t mean they are going to be all-in in the way they were in, say, 2018, but it should at least mean they are going to add major-league caliber pitchers. That’s more than we could say last winter.

So what does that have to do with the trade market? Well, let’s take the Lance Lynn deal for example. Lynn is a very good pitcher who has been outstanding the last couple of seasons with the Rangers. The White Sox gave up Dane Dunning, a former first round pick and top 100 prospect who looked solid in his major-league debut this past summer, and Avery Weems, Chicago’s sixth round pick in 2019. I mentioned a package of Tanner Houck and Thad Ward as a rough estimate of a Boston equivalent, and Ian Cundall of Sox Prospects (who is much more able than me for this kind of thought experiment) threw out Bryan Mata and Chris Murphy. That seems fair!

Take whichever one of those seems like a better comp to you, or create one of your own. And consider Lynn, a very good pitcher who would jump to the top of Boston’s rotation until Chris Sale returned. Would you do it? This is where things get tricky. For as much as Lynn would very obviously improve Boston’s rotation, and even given the fact that there is arguably only one (and maybe even zero) starters available in free agency who are better than Lynn, I would not do it. While I’m all for signing one-year starting pitchers like Corey Kluber in free agency, giving up promising young players for one year of Lance Lynn, who is good but will not put them over the top, doesn’t make much sense to me.

Again, this has everything to do with where the Red Sox are as a roster. For the White Sox, I love this deal. Chicago made the postseason last year and is on the way up. They are shooting for division titles and championships as soon as 2021. Boston could feasibly luck into that, I suppose, but I would prefer trying to create that luck using only cash, not prospects. If the Red Sox are to make big trades this winter involving prospects, I would prefer that to be for players who would be here for multiple years.

And this brings us to the other layer of issues for the Red Sox on the trade market. It’s great to say you want to trade for players under control for multiple years, but assuming those are good players that’s easier said than done. And while Boston’s farm system is certainly improving, I’m not sure they have the top-end talent to go out and get those players if they even exist. So, they’re in a position where their farm system is best set up to get good, one-year players while their major-league roster is best suited for multi-year players. Not great!

And that essentially leaves them with one option, and that is to embrace the fact they are the Red Sox. That is to say: Use your money. The pandemic is causing teams to shed payroll, and any team that is willing to make a little less for their ownership in the short-term can benefit in the long run. Unfortunately teams and the league as its own entity don’t operate with that kind of long-term financial vision anymore, but call it a market inefficiency. This was what we saw with the Angels, who got Iglesias for essentially nothing because the Reds decided they couldn’t carry Iglesias’s salary. Ken Rosenthal also noted Boston could use their financial might to take advantage of the trade market this winter. He notes the possibility of essentially buying prospects, which is a good idea in its own right, but this could also be used to improve the major-league roster.

This offseason is a strange one in a number of ways, but for the Red Sox specifically I am fascinated by the idea of the trade market. And I’ve made it through this entire piece without even mentioning the Andrew Benintendi of it all, who will be difficult to get value for given all the reasons Alex Speier outlined here. The Red Sox will do things in one way or another this winter, but I’m fascinated to see what they can do on the trade market, if anything. Because from the outside where I’m sitting, I don’t really see much of a path for improvement on this route beyond the periphery of the roster.