The Red Sox Need To Pick a Lane Before the Trade Deadline

With an MLB club outperforming expectations and a farm system laden with talent, it is imperative the new Red Sox regime avoids the mistakes of the past.

BOSTON, MASSACHUSETTS - SEPTEMBER 08: A view of the baseball hat and glove of Trevor Story #10 of the Boston Red Sox during the fifth inning against the Baltimore Orioles at Fenway Park on September 08, 2023 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)

The Boston Red Sox have, thus far, outperformed expectations by quite a lot. Far from the team that many thought would be a .500 club this year, Boston entered the All-Star break as one of the hottest teams in baseball with a two-game cushion in the Wild Card standings.

The feelings around the team are as positive as they have been since 2021, as exciting young players have won back Boston’s fans.

Fans are clamoring for the team to buy, hoping to have meaningful baseball into September and beyond for the first time in several years, which in Red Sox terms is an eternity.

Manager Alex Cora has been open about his desire for the team to add at the deadline, as he has been for the past several seasons. This year’s team, though, has given the front office more reason to buy than either of the past two squads.

Ad – content continues below

As Cora put it, the team is simply too athletic to have a sustained downward streak. Even when they were playing their worst this season, they remained around .500.

Still, both Craig Breslow and Sam Kennedy have remained noncommittal about a deadline approach. Both have indicated that if the team continues to perform this well, it will force the front office’s hand, but many fans would like to see more conviction from team executives with the deadline fast approaching.

Part of the cause for concern is that the past two seasons have seen disappointing deadlines in Boston, with the team both buying and selling, making moves around the periphery that left the team more or less in the same place it was prior to the deadline. In short, the team failed to pick a lane, and it hurt the franchise. 

To all observers, it was clear that the Red Sox teams of 2022 and ’23 were not good enough as constructed to make the playoffs. Yet, the front office decided they were not bad enough to justify a complete sell-off at the deadline. The result was a noncommittal approach that left a mediocre team in baseball purgatory.

The 2022 deadline, in particular, was executed horribly. Failing to get under the luxury tax by offloading expiring contracts (like those of J.D. Martinez and Nathan Eovaldi, both of whom would leave in free agency at the end of the season) was by far Chaim Bloom’s biggest blunder – even worse than the massive free agent contracts he handed out to Trevor Story and Masataka Yoshida.

It prevented the team from being able to push more chips in entering the 2023 season. They needed to reset the luxury tax, which in turn led to another mediocre team that was too good to hold a fire sale but not good enough to invest in, at least in the eyes of the front office.

Ad – content continues below

With that as the recent precedent, it is easy to understand why Red Sox fans are approaching this trade deadline with a bit of pessimism.

If the team does nothing (or sells, although at this juncture that seems highly unlikely), fans will be irate. Statistically, teams that are on the fringe of playoff qualification are those that benefit most from deadline acquisitions, which makes a lot of sense. The ability to add a couple of wins is often the difference between landing the final Wild Card spot and facing a premature end to the season.

For Breslow, though, his first trade deadline at the helm needs to be more nuanced than simply one in which he buys up the best talent. He needs to seriously consider how much this team is worth investing in, since any realistic observer could tell you this is still not a true World Series contender.

Weighing the value of a playoff appearance for this year’s team against future success is an unenviable task.

Complicating the situation is that, for the past several seasons, a core of top prospects has been building in Boston’s minor league system. The “big three” of Marcelo Mayer, Roman Anthony (who just won the minor league skills competition during the All-Star break), and Kyle Teel are preparing to join young stars Triston Casas, Ceddanne Rafaela, and Jarren Duran on the big league club in the near future. 

With Kristian Campbell and Nick Yorke also having spent time as top-100 prospects, the Red Sox have the potential to enter a long period of sustained success, similar to that of the Braves and Orioles, thanks to their homegrown talent. It is important that they do not take a short-sighted approach and trade away that opportunity for the chance to win a Wild Card spot this season.

Ad – content continues below

In a way, the team being ahead of schedule by competing for a playoff spot this season has complicated the long-term vision for the franchise more than it has helped. Pieces that were once viewed as cornerstones of the future may now be looked at as trade assets.

Similarly, players like Tyler O’Neill and Kenley Jansen, who many at the beginning of the season thought would be traded at the deadline for significant returns, now must be kept to keep this competing team intact.

So, the question remains, what should Craig Breslow do? At this juncture, selling seems out of the question, and standing pat would cause so much resentment from the fanbase that it is all but impossible.

That leaves buying as the only lane to pick, but to do so with reckless abandon is also not the direction the team should pursue; the version of this team that will be worth going fully all-in on is still a couple of years away.

Breslow needs to buy, but he needs to buy smart. Top prizes like Garrett Crochet or Luis Robert Jr., both of whom would admittedly be great fits for the Red Sox, will likely have price tags that should keep them out of Boston.

Instead, adding an under-the-radar starting pitcher or a solid right-handed platoon bat are two much more realistic options that would improve the team this season without a prospect price tag that would jeopardize the future core.

Ad – content continues below

With All-Star Tanner Houck and breakout arm Kutter Crawford both likely to surpass their career highs in innings later this year, landing a back-end starter who can take the ball every fifth day and help relieve some of the pressure on the young starters would be a huge win for Boston.

In the end, it seems that the best choice for Breslow is to buy, but to do so carefully. While not landing a big star may disappoint fans in the short term, years of success with a homegrown core will be worth the wait.

The current Red Sox team has earned the help that should come at the deadline, but at the same time, their top-end prospects have shown that they are worth waiting for. While a sports car may be exciting, a reliable sedan will get you to work every day without breaking the bank, and that is the type of player Boston should hunt at this year’s trade deadline.