The Final Chapter: The Anatomy of a Trade Part IV

We’re going to conclude this series by taking a cursory look at the other elements of dismantling the 2018 core. If you missed any of the previous parts and would like to check them out, no worries! You can click on the links below to catch up.

A lot of the elements of these deals are too new to have a true historical perspective on. As a baseball historian, I try to avoid indulging too heavily in “hot take” culture. 

The Benintendi Misfire

Photo by Winslow Townson/AP Photo

There’s the issue of trading Andrew Benintendi. This one is a bit harder to analyze because we have yet to get a good look at the prospects that were acquired in that trade. Josh Winckowski could be good, but we’ll need more of a sample size at the major league level to really decide.

The bigger issue with that trade is that he was traded when his value was at its lowest. The only major league ready player acquired in the draft, Franchy Cordero, will be suiting up for the Orioles next year.

Benintendi is not nearly the player that Mookie Betts is. However, trading him at a low point in his value was the opposite of what you do when you want to maximize your return. 

Benintendi was traded after a lackluster and injury shortened 2020 season. As a general rule, I have a hard time assigning too much value to statistics from the 2020 season.

It was only 60 games, had an abbreviated spring training, and the regular season was effectively played in a regional bubble. Assessing Benintendi is even more challenging because he only played 14 games before going down with a season ending injury. 

Benintendi had received criticism from the team for his decision to bulk up before the 2019 season. Manager Alex Cora said this was against the team’s wishes. Benintendi’s speed and athleticism were big parts of his game.

During that off-season, Benintendi opted to change up his game and try to increase his power. The result was decreased performance at the plate in 2019. 

To make matters worse, his power didn’t actually increase. He hit three fewer home runs in 2019 than he had in 2018. He also struck out more and walked less. This was reflected in his On Base Percentage (OBP) going from .366 to .343. Essentially, he was worse by every metric, but he wasn’t terrible

After 2020, the decision was made to move on from Benintendi. He was traded to the Kansas City Royals in a three-team trade with the New York Mets. In return, the Red Sox received Franchy Cordero, Josh Winckowski, and three players to be named later.

As I said earlier, it is difficult to assess whether that trade will pan out. I do, however, think we can assess whether or not moving on from Benintendi was the right move. 

I would argue not. Benintendi was not due to hit free agency until the end of 2022. He was under team control, so he was fairly affordable. The Sox had signed him to a two year, $10 million deal before 2020. So he wasn’t even due to hit free agency until 2022. It made no sense to move a player who had performed well in the past when their value as at its lowest. 

Benintendi went on to redeem himself in Kansas City. He won a Gold Glove in 2021. Then, was an All-Star in 2022. He was ultimately traded to the New York Yankees in July, but suffered a season ending injury shortly thereafter.  

It is difficult to say whether or not this rebound would have happened in Boston. However, it definitely shows that Benintendi could still perform at a high level. Trading Benintendi left a hole in the outfield that the Red Sox have been desperately trying to fill ever since.

He just signed a five-year, $75 million deal with the Chicago White Sox. It is impossible to know what kind of deal he may have signed to remain in Boston if he had remained. 

The Mishandling of Bogaerts

Photo by Paul Rutherford/USA Today

The other major failing was the decision to not lock up Xander Bogaerts before the 2019 season, or at the very least not committing to a direction with him. The six-year deal that was signed before 2019 had an option after 2022 that allowed Xander to maximize his value if his performance continued trending upwards.

It was a perfectly safe deal for Xander to take because he could simply opt out of the deal, and he would still have $120 million guaranteed. The risk was disproportionately borne by the Red Sox. If the Red Sox had locked up Bogaerts before 2019, they would have had a key piece for the future.

If the Red Sox had no desire to actually lock him up long-term, then they erred by not trading him. They could have maximized the return on prospects to build to the next window. The Xander situation was one that left fans frustrated and confused as to what management is even attempting to do with the team.

It’s too early to tell whether or not the Sox dodged a bullet by not committing to Xander for over a decade. However, I would have felt safer if that decision were made before 2019.

The JBJ Conundrum

Photo by Charles Krupa/AP Photo

I want to talk a bit about Jackie Bradley Jr. – mostly because his situation is difficult to categorize. JBJ was always a streaky (leaning towards lackluster) hitter with electric fielding abilities. Jackie could make plays that very few other fielders could make. If something looked impossible, you could bet that JBJ would have a fighting shot at it.

He won a Gold Glove in 2018, and he was incredible to watch on the field. However, for as incredible as Jackie was in the field, he was difficult to watch at the plate. JBJ always had a tendency to have a super-hot streak that was bookended by extremely cold periods.

When JBJ was on, he was on. But when he was off, he could end a rally quicker than anyone you have ever seen. JBJ was decent in 2018 and 2019. In 2018, he had a .234 batting average with a .314 OBP. In 2019, he had a .225 batting average and a .317 OBP.

He found some degree of power in 2019, hitting 21 home runs. After 2020, the Red Sox decided to move on, having made the calculation that his glove wasn’t worth his bat. He did improve at the plate in 2020. However, the small sample size made it difficult to understand whether or not it was sustainable. 

As it turns out, the Red Sox were actually right to let him go. He signed a two-year deal with the Milwaukee Brewers and only posted a .163 batting average with a .236 OBP. His bat was about as effective as a National League pitcher. No amount of defensive productivity can make up for that degree of being an offensive blackhole. 

Unfortunately that’s not the end of the story. The Red Sox actually traded to bring him back in 2022, where he proceeded to a .210 batting average and .257 OBP in 91 games. He was eventually released on August 4th of that year. 


So – there you have it. A thorough dissection of the dismantling of the Red Sox core with an in-depth focus on the Mookie Betts trade. There is a lot that could still be written about this. I acknowledge that I did not mention Christian Vazquez or even the complete bungling of Blake Swihart’s development. 

The 2018 Boston Red Sox were in equal parts a fascinating and captivating team. It was a young core that was begging to be the foundation of a dynasty but their potential was halted by poor decision making. It’s also a team whose story is not yet finished and with side characters whose stories are begging to be told.  I look forward to tracking this team in the coming years and diving back into this story in future posts. 

Featured Photo by Darren McCollester/Getty Images

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