The Red Sox Want To Buy Pitching At The Trade Deadline. . . But How Would They Pay For It?

On Monday, as the Boston Red Sox sat with a 33-33 record and a run differential of exactly zero, GM Brian O’Halloran was asked if the team would be sellers at the trade deadline. It’s a reasonable assumption to make, given that FanGraphs gives the Red Sox just an 11.5% chance of making the postseason. And yet, O’Halloran unequivocally told The Athletic’s Chad Jennings that, no, the Red Sox would not be sellers this year, that they would be looking to improve the team. Furthermore, he said they’d already begun looking for pitching help.

So the Red Sox, apparently, want to be buyers. But to be a buyer in baseball you need to be willing to sell something, and that something is almost always the same thing: prospects. And this is where O’Halloran’s messaging just gets confusing, because, up to this point, trading prospects is not something Chaim Bloom has been willing to do. In fact, other than perhaps the deal that sent Jay Groome to the Padres for Eric Hosmer, it’s something he flat out hasn’t done (and even in the case of that deal, Groome was more of a post-prospect at that point, and was essentially dealt because the team would have otherwise needed to put him on the 40-man roster in the offseason.) So why would Bloom start trading prospects now, with a Red Sox team that currently looks like it needs a minor miracle to make the postseason?

Putting aside the blockbuster Juan Soto-type deals, let’s take a look at what it cost to buy Major League pitching last year:

• The Phillies acquired Noah Syndergaard in exchange for Mickey Moniak and Jadiel Sanchez. Moniak was the first overall pick in the 2016 draft, but had struggled to transition to big league baseball and Sanchez was a single-A lottery ticket. That was a pretty cheap price to pay — neither prospect was among the Phillies top 20 at the time — but then again, Noah Syndergaard really wasn’t good last year. A Syndergaard-type would do little to help the 2023 Red Sox.
• The Twins acquired starter Tyler Mahle from the Reds for Spencer Steer, Steven Hajjar, and Christian Encarnacion-Strand. Unlike Syndergaard, Mahle performed like a solid mid-rotation starter last year, and it cost the Twins dearly to get him. Steer was one of the team’s top-10 prospects, a guy who had been having an outstanding year in the upper minors and had started to crack top-100 lists. He’s currently having a very strong rookie year, with an OPS+ of 119. Hajjar and Encarnacion-Strand were ranked 18 and 23rd in the Twins system, respectively. It’s hard to say what the 2023 Red Sox equivalent of this deal would be, as, unlike Steer, almost all of the top prospects in the Sox system are still in the lower minors, but think something like Nick Yorke, Blaze Jordan, and Chase Meidroth.
• The Cardinals acquired starter Jose Quintana and reliever Chris Stratton from the Pirates for Major League reliever Johan Oviedo and prospect Malcom Nunez. Nunez was a top-10 prospect in the Cardinals system, while Quintana, like Mahle, was a solid mid-rotation guy. The Red Sox equivalent of Nunez may be someone like Meidroth or Eddinson Paulino.
• The Yankees acquired Frankie Montas for prospects Ken Waldichuk, Luis Medina, JP Sears, and Cooper Bowman. Now this was a haul for the Oakland A’s. Waldichuck was the Yankees’ #5 prospect and #70 in all of baseball, while the other three guys floated around New York’s top 20. The equivalent Sox package might be headlined by Ceddanne Rafaela and filled out by guys like Wikelman Gonzalez, Mikey Romero, and David Hamilton.

The pattern is pretty clear: if you want to trade for a Major League starter, you need to dip into your pool of top prospects. Given Chaim Bloom’s history in charge of the Red Sox, it’s damn near impossible to see him doing that, especially in light of the fact that the 2023 Red Sox appear to be going nowhere.

So, then, was O’Halloran lying when he said the Sox will look to be buyers, or was he using the term in a somewhat untraditional sense? Likely, it’s a combination of both. As we have repeatedly observed, the Red Sox simply are not being forthcoming with their fans about their current strategy; Bloom and Sam Kennedy insist that they are trying to compete for World Series championships, when in reality what they are doing is trying to compete for the last postseason spot while building toward a yet-to-be-determined date in the future. They are determined to avoid publicly admitting that they are doing anything other than going all out for a championship, and selling at the trade deadline would undercut this message.

So when O’Halloran says they’ll be looking to improve the team, he’s probably talking about pursuing a similar trade deadline strategy as they did last year: don’t sell key pieces and try to improve on the margins. But is the the right strategy?

That’s what Dan and Bryan discussed to open the latest Monsters of Sox Podcast as they tried to figure out just what this Red Sox team is. Then, as usual, they tried to figure out what Bryan’s angry about this week, including Triston Casas’s defense, Rafael Devers dominance over Gerritt Cole, and (hopefully for the last time) Matt Dermody.

As always, thanks for listening!