The Anatomy of the Mookie Betts Trade Part I

Intro

2018 was supposed to be the start of a dynasty. The beginning of years of success, built around a solid, young core. At the end of the 2018 World Series, it looked as though the Red Sox had their foundation.

Mookie Betts, Andrew Benintendi, and Jackie Bradley Jr. patrolled the Fenway Park outfield. They were supplemented by an infield of Xander Bogaerts and Rafael Devers. Mookie had even won the 2018 American League Most Valuable Player Award!

Mookie Betts was a bonified star in Boston. Photo by Maddie Meyer/Getty Images

It was not a matter of whether or not this core would win another World Series. The only question was how many. The Boston Globe’s Alex Speier even wrote a book about this and the work that went into building it. The sky was the limit! 

Yet five years later – only Rafael Devers remains. How did this happen? And why? 

Examining What Happened

You can’t explain the dismantling of the 2018 core without examining the series of decisions that put the Red Sox into a difficult position. It all started at the end of the 2019 season. Weak pitching development and suspect contract choices had left them with a solid core of position players but not much else.

You don’t win a World Series without good pitching, and there are many pre-2004 Red Sox teams that prove this point. The 2019 Red Sox, with worse pitching than 2018, did not even make the playoffs. By the end of 2019, it was clear that the team was at an inflection point. 

Going into 2020, the Red Sox had two pitchers who had issues remaining healthy. They had another that was deeply unpopular with the fanbase and showed signs of underperforming.

By 2020, the contracts of Chris Sale, Nathan Eovaldi, and David Price were albatrosses that hindered the team’s ability to make moves elsewhere. There was also the problem of trying to unload a portion of Price’s salary in order to get under the luxury tax threshold.  

David Price’s overpriced deal had a lot of negative impacts on the Red Sox. Photo by Michael Ciaglo-USA TODAY Sports

The need to sign arms with miles already on them was present because of poor pitching development. Aside from Eduardo Rodriguez, who was acquired as an essentially major league ready arm from the Orioles, the Sox had to rely on pitchers who already had years of experience on their arms. That limits your window significantly. 

The Red Sox could have used the dismantling of the core to rebuild their farm system. Maybe acquire some good pitching arms so they could avoid this situation in the future.

The releases of Jeter Downs and Franchy Cordero, who were acquired in trades for Betts and Benintendi, respectively, are an early indicator that the Red Sox failed. Boston was unable to leverage the dismantling of the core in the most effective manner possible.

Jeter Downs was supposed to be one of the big prizes of the Mookie Betts deal. Instead, just three years later, he is no longer with the team. Photo by Katie Morrison / MassLive

The jury is still out on the ultimate success of the Benintendi trade, which the Sox used acquire Josh Winckowski. He has shown some indicators of talent. There are also two other pitching prospects that are still toiling in the lower tiers of the farm system. 

It is clear that the decision to package Price’s contract with Betts blunted the return that they could have received from the Dodgers. We’ll explore that as well. 

A Look Ahead

The bulk of this series will focus on the Mookie Betts deal. This is a history series so I try to avoid the “hot take” nature of contemporary sports commentary. We have a generally good idea about the three players received in that trade. This, along with Mookie continuing to produce at a high level in Los Angeles. I feel confident doing a deep dive on the Betts trade. 

In this series, I am going to dive into this series of events, explain the historical context, and give my analysis. I’ll avoid making heavy handed judgments and leave the final judgment to you, the reader.  

Featured Image by Christian Petersen/Getty Images

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