OTM Roundtable: What to do about the trade deadline?

We are now roughly a third of the way through the season, which means teams are starting to make real evaluations as to where they stand as a roster and what they could potentially do through the rest of the season and into October. The trade deadline is still a little less than two months away, but the general trade talks between front offices are starting to pick up right around now. And so that was the topic for this week’s staff roundtable. I asked everyone to just speak generally about this year’s deadline, both regarding where the team stands in terms of how big of an acquisition they should be willing to make and also in terms of timing and whether or not there’s a value to being first to the table.

Keaton DeRocher

Three Days Grace once said “It’s never too late.” I’m going to go the opposite way and say it’s never too early, especially if it keeps Max Scherzer off of the Yankees. Jake and I talked early deadline on the Red Seat Podcast and much of our focus was on Scherzer. The pitching has been better than expected this year, and even though we’re now over 50 games into the season, the sample size it still feels like they’re playing with house money and fortifying it with a player like Scherzer is exactly what the Red Sox should do. I also don’t think it’s a bad idea to get in early on the relief pitcher market because every trade deadline they get more and more expensive, so if you can be the team to start the market this year I’d jump on it.

Michael Walsh

I don’t think I’m confident enough in this year’s Red Sox team yet to justify a major acquisition. As I’m writing this, the Sox just lost their third in a row to the Astros, and have the Yankees, Astros, Blue Jays, and Braves lined up for their next four series. That’s definitely a worrisome stretch, but if they can come out of it unscathed and are still 10 games over .500 by the end of June, I’d be fine with buying at the deadline.

However, I’m not in favor of being a set buyer or seller. It’s possible to buy in the right areas that will help you this year and in the future (i.e. the Marlins acquiring Starling Marte in 2020) as well as sell your guys that have short-term value. This kind of buyer-seller combo approach is the position I’d like to see the Sox take no matter where they are in the standings.

Shelly Verougstraete

Even with this recent skid, I think the team is good enough to justify trades to plug in some holes. While I’d love to get Max Scherzer, I’m not sure if the Nationals are ready and/or willing to listen right now. I’d love to see the team make a small deal for a first baseman or reliever, and then pull the trigger on a starter towards the end of July.

Photo by Jeff Zelevansky/Getty Images

Mike Carlucci

The Red Sox should be aggressive in the trade market this year. The team is good, if flawed, and jumping in early could be the difference between a second half well over .500 and one at .500 if there’s a slump. When the Brewers traded for C.C. Sabathia in July of 2008 they got a head start on the competition and rode their acquisition straight into October. Since we are only in year two of the Bloom Administration, giving up a haul of prospects for a pending free agent isn’t the way to go for a team looking to have sustainable success, but the idea isn’t bad to follow. Depending on how the Sox view their prospects they could use depth in the rotation, bullpen, bench...basically everywhere.

Enrique Hernández is a great start. Another multi-position guy could help a team with strong core and a few good position players close to the majors but not ready just yet. A “failed” prospect like Nick Pivetta who was had for a bargain price last summer would be another great strategy. Sometimes a guy just needs a new team to look at his skills and a fresh start. It might fail but at least there’s talent on that type of lottery ticket. Pick up a broken reliever who was good a few years ago, a starter who hasn’t broken out but from a team that needs a bat, and be aggressive. The team will live or die on the success of the core, rounding out depth and scooping up those back-of-the-roster players teams will be scrambling for towards August can’t hurt. This is what Chaim Bloom was hired for.

Phil Neuffer

I’m trying to avoid too much recency bias, but the Houston series and the Rays’ recent surge have derailed the Red Sox and shown that some of the team’s issues entering the year weren’t magically solved. I am still far more optimistic about this team than I was over the winter and think they’ll contend for the playoffs all season, but trying to solve those underlying issues at the trade deadline is a risky play, especially since Chaim Bloom is clearly building a foundation for long-term contention. I’d like to see the Red Sox be very patient with the trade market and look to maybe make smaller upgrades with the future in mind rather than just going all-in because of a decent start to the year. However, if they bounce back from this past week and are doing more than just hanging around Wild Card contention near the end of July, then pulling the trigger on a huge deal, especially one that could fortify the rotation, would look a lot better.

Full BreakingT Red Sox Collection

Take a look at the entire shirt collection from our friends over at BreakingT, including the one pictured above.

Jake Kostik

I’m torn regarding a trade deadline acquisition. On the one hand, I do believe that the Red Sox will be within playoff contention still at the end of the month (despite the fact I think they finish below .500 in June), but I’m not sure buying is the right play this year.

By all accounts, the Red Sox are doing significantly better than many of us expected. They look like a team that will be in the race until the end of the season. But my feeling is that they are doing it a year earlier than expected. Making a move will cost something, most likely, especially if it’s a move of merit. If the Red Sox can make a move with guys who will be Rule 5 eligible, like Danny Diaz, Brett Netzer, or Alex Scherff, then they should 100 percent be willing to make that move. As it stands, the Red Sox have a lot of players they will need to add by December in Jarren Duran, Jeter Downs, Brayan Bello, Gilberto Jimenez, Thad Ward, and Josh Winckowski.

TL;DR - Not sure I make a move right now, not sure I even make one in June. I wait until July, see how things are looking, and if we do any moves at all, it’ll feature upcoming Rule 5 guys that we won’t be rostering anyway. No major acquisitions. Save it for the offseason. There’s a value to being first to the market, but I’m not sure that it makes sense for us.

Brady Childs

With the second wild card and the Sox still being in the middle of their window despite them seemingly not caring all that much that the window is still open, they should be doing all they can to make the playoffs this year. As a certain former assistant GM noted, this is the time feelers start getting sent out, so now is the time to start thinking trade. One of my takes was that the lineup was too right-handed with players that should be platooned being played full time. There are certainly moves they can make to address those concerns, but they may have in-house solutions to some of those problems with Jarren Duran and Tristan Casas.

I don’t think there’s value in overpaying for like, Eduardo Escobar right now just so you can do it. The teams holding the chips aren’t in any hurry to deal these guys. They have almost another two months to field offers and evaluate the best ones.

Bryan Joiner

I agree with what we’ve said on the Over the Monster Podcast — shock — that this stretch is going to go a long way toward determining what the Sox will do in the trade market. I think the “when” part is after this stretch no matter what, but whether or not they can escape this madness with a winning record will determine how they want to play their hand, so to speak. The better they are, the better the chance we see some small early deals, and the better they are after that, maybe one big one (for Max Scherzer, please).

Jake Devereaux

The Red Sox have absolutely shown enough to warrant Chaim Bloom going out and spending some assets to beef up this team’s chances to win the division. The offense has been one of the best in all of baseball, as has their record, and surprisingly their starting pitching in many ways. Bloom needs to go out and add two things, a bat upgrade at first base or second base, a rental is fine. He doesn’t need to spend significant capital to get them, but adding someone who is a little better with the stick should help.

The big thing that Bloom should do is go out and trade for Max Scherzer. Scherzer is going to be a free agent after this year and would allow one of the Red Sox starters to transition to the bullpen. Bring him here, sign him to a 4-5 year extension if he wants it and lean back as a finally healthy Chris Sale and Scherzer propel the Red Sox to the World Series. There are plenty of free agents in the rotation after this year including Eduardo Rodriguez and Martín Pérez, the latter of whom has a team option. Nathan Eovaldi is only under contract for one more season. I’d much rather spend a little prospect capital to get a half year of Scherzer this year and then pay him rather than Eduardo Rodriguez. Plus if you get him, the Yankees won’t!

Matt Collins

I do think there is value in getting in on the market early in the right situations, but for the Red Sox I’m not sure the time is now for rentals. I think they should be in the process of starting to push in, particularly in a year in which it looks like there is no team that is going to run away with things. That said, I’d rather wait until the end of June and see where this team goes before making a move for a big rental. On the other hand, if there’s a player who fills a hole while being under control beyond just this year — Joey Gallo, hello — that’s something I’d at least start some dialogue on as soon as possible.