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It’s going to be a difficult trade market to navigate this winter

That’s not great news for the Red Sox.

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

The Red Sox find themselves in something of a tweener position this winter and looking ahead to 2021. They aren’t exactly an up-and-coming team, though there is some young talent that should come up and help over the next few seasons. They certainly aren’t going to be top title contenders when camp breaks next year, either. On the other hand, they also aren’t a team that is going to look to just totally bottom out in 2021. Part of that is because they have too much in-prime talent in the lineup to commit to that bit, and part of it is because that’s not really an acceptable course of action for the organization. So as a result, they find themselves in a position where they want/have to be respectable, but there’s not a real path towards true title contention.

Now, there is a whole conversation to be had about how the Red Sox got to this place and whether they should be here right now and all of that, but we’ll leave that on the backburner for the time being. Instead, I want to focus on the difficult position they’re in given this goal of theirs for the offseason. They don’t necessarily need to “win” the offseason in the sense of bringing in the most stars, but they have a ton of holes to fill. We already talked as a staff about just how many pitchers they need to bring in, and that doesn’t even get to needing another starting outfielder and a starting second baseman. Some insurance at first base certainly wouldn’t hurt either. The point is, there are a lot of players that should be added to the roster this winter.

It’s a lot easier said than done to add this much to the roster, but that’s why Chaim Bloom was hired. When he came over to take over the top spot in the front office, the number one descriptor thrown around was “creative.” And in order to do what they need to do this winter, particularly given the context of coming off a shortened, fan-less season and entering a free agency period that will likely be unlike anything we’ve ever seen, creativity is exactly what the Red Sox need. Unfortunately for them, it’s not just the free agent market that is going to be affected by *gestures at the entire world*. The trade market is going to be a difficult one to navigate as well.

If this were a normal offseason, the trade market likely would have been a hot spot for the Red Sox front office. For one thing, while there are plenty of free agents out there that doesn’t always mean there is a perfect fit. Simply having the option of trades opens up possibility to a different group of players, some of whom could theoretically be a better fit. Then when you throw in that teams can generally get players that cost less on their payroll — this is an important one for a team like the Red Sox that needs to add such a large bulk of players — along with often being able to find more players you see as potentially undervalued just by the fact that they have less experience under their belts. The best teams are built on a variety of fronts, with the trade market a big part of that.

This was supposed to be Bloom’s first real offseason with the Red Sox, and coming from the Rays it was fair to assume he was going to be active with trades. That is, until everything happened this year and made the trade market perhaps even more fraught than free agency. The biggest part of that is the farm system. Obviously most trades involve prospects going one way with major-league talent going the other way. However, it’s going to be harder than ever to agree on value for those prospects after the majority of them did not play affiliated ball all summer. Even the ones who did only played at the ominously named Alternate Site and were facing the same competition on a daily basis.

Boston Red Sox Summer Workouts Photo by Billie Weiss/Boston Red Sox/Getty Images

Take Jarren Duran, for example. Not that I believe the Red Sox would be looking to trade him this winter, but say he comes up in conversation. The Red Sox see a guy who made big adjustments to his swing and feasted in Pawtucket all summer. Other teams could very well see a guy who feasted on the same fringe pitchers that couldn’t make a historically bad pitching staff in the majors over and over, and in his last taste of non-intrasquad competition a guy who hit a wall in Double-A. Both sides of that conversation have entirely valid viewpoints, but is it really realistic that they come to even a vague agreement on value? A similar exercise could be done for a prospect like, say, Thad Ward, who wasn’t even at the Alternate Site.

So, coming to an agreement on prospect value seems nearly impossible, at least from the outside. And that’s not even the only complicating factor. This entire winter is going to be filled with financial talk, and that comes into the trade market as well. Another way trades can often go down is with one team taking on extra salary to even out value. Are there really any teams that are going to be looking to take on that kind of payroll this winter? I have a hard time seeing it, particularly after so many laid off a significant portion of their full-time staff towards the end of the year. I’m not expecting it to quite reach the NBA-type levels where, for salary cap reasons, salaries often need to basically match. But it could be closer to that than we’re used to, which just adds another layer of complexity to it.

None of this is to say there won’t be any trades this winter. That seems nearly impossible. That said, it’s also hard to see the market being anywhere near as robust as we’re used to. It’s no excuse for a poor offseason and the Red Sox can’t use it as an excuse. That said, Bloom is going to have to work overtime with the aforementioned creativity, because there are even more barriers than usual this winter.