Targets and Chips: How the Red Sox Should Handle the Trade Deadline

The Boston Red Sox have outperformed all expectations this season, forcing the front office’s hand to supplement the current squad for the final months of a playoff push. The questions now become: Who should the Red Sox target, and, just as importantly, who should they be willing to give up?

Entering 2024, and even through the first few months of the season, many thought that the Red Sox would be sellers at the deadline. Many expected the team to ship off the expiring contracts of Kenley Jansen and Tyler O’Neill to supplement their young core that is being assembled in the upper minor leagues. 

Thanks to an absolutely phenomenal stretch of baseball starting in the second week of June, though, the Red Sox find themselves just one game back of a playoff spot with the trade deadline fast approaching.

Before this weekend’s sweep at the hands of the Dodgers, Boston had lost just one series since May 30. This has been one of the most exciting teams in baseball thanks to incredible athleticism up and down the lineup. 

Red Sox president Sam Kennedy has assured the fanbase that if the team continues to perform at its current level, there will not be any financial restraints when it comes to supplementing the roster at the trade deadline. While he has by no means promised to buy, the implication is certainly that the team will be looking to add help for the final playoff push.

This inspires a pair of questions: What type of player(s) will the Red Sox look to add, and what price tag will they be willing to pay in prospect capital to land their target(s)? 

Who Will the Red Sox Add?

The Red Sox’s needs entering the unofficial second half of the season are clear, the first of which is an additional starting pitcher. Boston’s staff has been carried this season by All-Star Tanner Houck and breakout starter Kutter Crawford.

While Houck and Crawford have been exceptional, the team needs to be concerned about their durability, as both are set to blow past their previous career-high inning marks. The Red Sox have already begun making efforts to spell their young starters, opting several times to push their starts back in favor of bullpen games to get them an extra day of rest.

Target: Starting Pitcher

While the most exciting arm for the team to target would certainly be Garrett Crochet, the young ace seems like an unrealistic target for Boston. His price tag is likely too high for a team that is one game back of the final Wild Card spot.

Another possibility that has been circulating is that the Red Sox may target some of the starters in Toronto, as the Blue Jays prepare to face some difficult decisions this coming offseason.

Yusei Kikuchi and Chris Bassitt would both add quality and depth to the Red Sox rotation. That said, there has always been a hesitancy across baseball to trade within one’s division, and Boston giving up future assets for a starter (especially a rental like Kikuchi) from a divisional rival seems unlikely. Additionally, the asking price for Bassitt in particular will presumably be pretty steep.

More Realistic Options

Crochet’s White Sox teammate Erick Fedde would be a more realistic trade target. He fits the Red Sox’s need for an innings eater but will command a much lower asking price than certain other options.

What’s more, Fedde has been excellent this season, entering the All-Star break with a sub-three ERA and a 1.13 WHIP. He would add the depth that the Red Sox need in the rotation, providing a perfect mix of quality and quantity at a much more reasonable price than a front-line starter.

Another option would be Tyler Anderson of the Angels. Anderson has been phenomenal this season, posting a 2.97 ERA and a 1.17 WHIP.

The Angels will certainly be sellers at the deadline as they look to replenish the farm system they depleted a year ago, and the 34-year-old lefty is a perfect trade piece for the Halos.

For Boston, Anderson would bring a much-needed veteran presence and would be the only left-handed starter on the staff, bringing some much-needed balance to the rotation. Like Fedde, Anderson’s asking price will likely be much more reasonable than Crochet’s given their age difference and the fact that Anderson is a true rental. 

Target: Right-Handed Bat

A second area of need for Boston is a right-handed bat. The team is incredibly left-handed heavy and struggles to hit left-handed pitching.

Once again, the most appealing option to fill this gap is a Chicago White Sox player: Luis Robert Jr. Like Crochet, though, Robert will command an absolutely massive prospect haul, and while the Red Sox have the prospect capital to pull off such a trade, they would be wise to hold on to their top prospects.

A more realistic and cost-effective option would be a reunion with Justin Turner, who has hit lefties well all season and has been hitting much better overall for the past couple of months.

Turner is familiar with Boston, as he excelled there last season, and he has playoff experience that is unmatched across the roster. He would be a phenomenal platoon bat that could spell the Red Sox’s corner infielders and DH against left-handed pitching.

While there may be some hesitancy from Boston to trade for a player from Toronto, Turner’s price tag will likely be low enough to mitigate the fear of providing a divisional opponent with a future cornerstone piece.

Who Will the Red Sox Trade?

With Boston’s needs and potential targets established, it is time to look at the prospect pool from which the Red Sox will be trading at the deadline to see who could be on the block and who should remain off limits.

To start, the “big three” of Marcelo Mayer, Roman Anthony, and Kyle Teel will likely be off the table as trade chips. All three have continued to excel, creating a core in Portland that will likely become the core in Fenway in a couple of years’ time. The trio is simply too valuable to the franchise to be traded away in pursuit of a Wild Card birth.

Trade Chips: Nick Yorke and Kristian Campbell

The next tier of prospects down is where things get interesting for Boston, as second basemen Nick Yorke and Kristian Campbell do not have the “untouchable” status of the aforementioned “big three.”

However, both are right-handed bats (unlike Mayer, Anthony, and Teel), for which the major league roster and the organization as a whole are starved. Still, between Campbell, Yorke, and Vaughn Grissom, there is a logjam at second base. If the right deal presents itself, one of those three could be on the move. 

Personally, I think Yorke should be considered amongst the “big three” (or, I suppose, the “big four”), as he was highly rated coming out of the draft and has absolutely mashed at every step of his career. He is continuing to do so at Triple-A.

At just 22 years old, Yorke could play a major role both in the future as well as this season, but it is unclear if the organization views him in this light.

Trade Chip: Wilyer Abreu

There is a logjam, too, with young major leaguers and highly touted minor leaguers in Boston’s outfield. With Ceddanne Rafaela projected to move back to center field, Jarren Duran, Wilyer Abreu, and Roman Anthony will be left competing for two spots.

Since all three bat left-handed, they are somewhat redundant, and the Red Sox may try to sell high on Abreu this season despite his years of team control. With Miguel Bleis also in the pipeline as a highly-regarded outfield prospect, there are simply too many talented outfielders and not enough room on the roster. The Red Sox would be wise to cash in on this depth and address an area of need.

Only time will tell just how aggressive or conservative Boston will be at the deadline, but with a team that is entering its window to compete earlier than expected, and a core in the minor leagues that many believe could be the key to long-term success in Boston, one thing is clear: The decisions the front office makes at this deadline will have a lasting impact on the organization.