What Should the Red Sox Do at the Trade Deadline?
It's difficult to wrap one's mind around the possibilities, but let's try
Baseball’s trade deadline is on Tuesday, August 2, at 6pm Eastern Time. Or tomorrow evening. I could’ve just said that. So yeah, tomorrow evening. Tomorrow evening is the big moment, the line of demarcation, the Rubicon. By that moment we will know far more about the Red Sox and their direction as an organization, what they’re planning for the future, both short term and longer term, than we do right now.
Much has been speculated in the media, both here and elsewhere, and that’s because there are so many different ways the team could choose to go that it’s honestly difficult to figure out where to start a piece like this. The Red Sox could buy, they could sell, they could buy and sell, they could sell and buy, they could bell, they could suy, they could just piss off to a mountain top somewhere and refocus on what matters. The options are dizzying.
I was listening to Blue Jays Happy Hour with Nick Ashbourne and Andrew Stoeten (a fun show I enjoy a lot; I can listen to smart, funny people talk about just about anything, even if it is the Toronto Blue Jays) and they were listing players who were known to be available on the trade market and discussing their fits with the Blue Jays roster. It made sense. The Jays are very likely in the playoffs, they have some roster spots to upgrade, and so looking at who might be available and assessing their fits with Toronto’s roster is a reasonable way to analyze what might happen at the deadline for the Blue Jays.
The Red Sox aren’t in nearly such a neat box. In fact, the Red Sox box is more like a regular box that was ripped apart and partially swallowed by your dog. As of this writing, Boston is 3.5 games behind Tampa for the last Wild Card, but there are three teams between the Rays and the Sox as well: Baltimore, the White Sox, and Cleveland. That’s not an insurmountable deficit, but the number of teams between them and a playoff spot makes it far more difficult than it might initially appear. Before Sunday’s games, FanGraphs gave the Red Sox a 23.8 percent chance to make the playoffs. That’s not awful, but it’s not good either. If you had a 25 percent chance to win something, you probably shouldn’t put any money on it.
And yet that’s where the Red Sox find themselves. We’ll see how much money they put on it.
I’m going to try to set the scene a bit with what we know before delving into what we don’t know. But first, please subscribe to Sox Outsider. It’s free and fun and you can always change your mind if you decide free and fun just isn’t good enough. Thanks.
The Red Sox list of potential free agents is impressive. I’ve written it out before, but here it is again, just for fun:
Nathan Eovaldi
Enrique Hernandez
Christian Vazquez
Michael Wacha
Rich Hill
Jackie Bradley, Jr
JD Martinez
Kevin Plawecki
Xander Bogaerts (opt-out)
Matt Strahm
James Paxton (team option)
That’s three fifths of the rotation (four fifths if you count Paxton), two thirds of a starting outfield, the DH, both the starting and backup catchers, a semi-reliable reliever, and the star shortstop.
That’s a lot.
That’s the kind of roster turnover the Red Sox are facing this coming off-season. And now here they are, coming off an 8-19 month of July, facing the above stated playoff odds. Take off your Red Sox hat and ask yourself: what would you do?
Some reports say the Red Sox may try and do both buying and selling. They might try to deal some of their guys whose contracts are ending and bring in some players with longer term. That’s a fine idea, and I’m open to seeing how they pull it off, but the first thing that comes to mind is the deals then-GM Ben Cherington made at the 2014 deadline when they traded Jon Lester to Oakland and John Lackey to St. Louis. The idea was to target major leaguers with term in those deals. In other words, they dealt free-agents-to-be for players with term, just what reports say these Red Sox may try to do. And back in 2014 it didn’t go great.
They got Yoenis Cespedes and Allan Craig. Cespedes had a year and a half on his deal and Craig had just signed a five year deal with St Louis. Sounds great except Cespedes didn’t want to be in Boston and Craig was so bad he couldn’t crack the major league roster, so he spent most of the last four seasons of his contract getting paid a major league salary to play for Pawtucket.
Perhaps Bloom can pull it off better than Cherington did but that’s a tough needle to thread.
Specific to this season’s Red Sox, the wild card (so to speak) in all of this is the injuries the team has suffered. The Red Sox, lest we forget, went 20-6 in June and while it was against a weaker schedule, it also came with a healthy roster. The Red Sox are still missing important pieces, but with roughly 60 games remaining, if those important pieces return soon, it’s not unreasonable to think this team could play well enough to grab one of those Wild Card spots. Provided they don’t detonate the roster by 6pm tomorrow.
So what is the team’s health status? Apparently Devers will be back tomorrow (Tuesday, August 2) against Houston. The rest of them? Harder to say. Devers makes a big impact by himself as we’ve seen this year, but Trevor Story, Enrique Hernandez, Wacha, Hill, Paxton, Josh Taylor, and of course Chris Sale could all help this team as well. If those guys are coming back soon enough to have an impact, maybe it’s worth holding on to the most tradable guys, even if there is a market for them.
That’s the other thing though: what is the market? Can the Red Sox get something truly impactful in return for JD Martinez? Can they get a long term piece for Nathan Eovaldi? In that case, maybe it is worth it to deal guys in their 30s for longer term players. If Bloom can improve the playoff chances of the 2023 and ‘24 and ‘25 Red Sox, perhaps it’s worth it to lower those of the ‘22 team.
A deal I think back to that fits this mould is another one Cherington made at the 2014 deadline. The Sox traded one of the best relievers in baseball at the time, Andrew Miller, to Baltimore for starting pitching prospect Eduardo Rodriguez. That deal was a masterstroke as Rodriguez threw 856 above average innings for the Red Sox over the next six seasons. Sign me up for that again, please.
But there was a major difference between then and now. In 2014 the Red Sox were out of it. Now, they’re not out of it. It feels like they are because they’ve played so badly for the past month, but a one out of four shot to make the playoffs isn’t nothing. It’s not necessarily something you bet the farm on, but adding players who can be around long term, or at least longer term, isn’t a bad idea. In theory.
The Red Sox haven’t made any attempts to re-sign any of their projected free agents since the season started. But they have effectively publicly stated that they’re not going to trade their two best players in Xander Bogaerts and Rafael Devers, even though it’s quite possible if not quite likely that Bogaerts departs after the season. That’s not exactly “Going For It!” but it’s something along that road. It also means that unless it harms their playoff chances this season, all those guys should be available for the right price.
The Red Sox do have starting pitching depth, at least in names and numbers if not actual availability. But as we saw last season when the Red Sox acquired Kyle Schwarber at the deadline, injured players can be traded, and what’s more, they can make a major impact on their new teams as well.
So with that as a 1,000 word background, if I had to guess, and I don’t but I will, I’d say a few of these items happen:
The Red Sox trade JD Martinez to a National League team for a couple prospects, or perhaps a prospect and a decent reliever with a few seasons left of team control.
The Red Sox trade one of their free-agent-to-be starting pitchers, either Wacha, Hill, or Eovaldi for minor leaguers.
The Red Sox actively explore some go-for-it type of moves, but ultimately pass on them for various reasons.
After all that, they’ll hope the team can get it together on the field enough, that the injured players can come back healthy and contribute enough, that they can make a push for a playoff spot. And as the excellent Chris Hatfield points out, if they wait until the 19th of August, they can call up top prospect Triston Casas to take over at first base. So that’s at least one reinforcement potentially on the way.
That all said, the Red Sox could do way more than that. It wouldn’t be unreasonable for the GM of a team coming off the month the Red Sox just had to blow their roster sky high. Or they could do nothing. Because that same team just put together a great month of June when they were healthy and because that was the roster the front office put together for the season in the first place with the idea of competing for a playoff spot.
The only things we know are these: 1) it could be a crazy day and a half, and 2) regardless of what happens by tomorrow at 6pm, there’s going to be a ton of work to be done during the off-season to fix this roster.
Thanks for reading.