The Red Sox missed the boat on Edwin Encarnacion

CLEVELAND, OH - SEPTEMBER 26: Edwin Encarnacion
CLEVELAND, OH - SEPTEMBER 26: Edwin Encarnacion /

The Red Sox are prepared to throw cash at J.D. Martinez to DH through his declining years. Last year a comparable hitter was available for half the price.

Imagine the following scenario: The Red Sox have a huge hole in their lineup and the easiest place to upgrade is in the DH spot. There’s one obvious slugger who fits the bill perfectly. Over the last three years, he’s hit an average of 38 home runs per season with an OPS north of .900. He’s old enough that he won’t require an inordinately long commitment, but possesses the type of profile that tends to age very well. It seems like a match made in heaven right?

No, the above situation is not a description of the current J.D. Martinez sage. It is actually the exact situation the Red Sox found themselves in last winter.

Let’s flashback to the 2016-2017 offseason. David Ortiz had just departed and the Red Sox looked poised to add a big bat in his place. Edwin Encarnacion was the clear favorite as he was a DH by trade and was the best hitter on the market by a wide margin. The Red Sox decided, however, that their path to success was run prevention. Following in this direction, President of Baseball Operations Dave Dombrowski acquired Chris Sale to lead the rotation and Mitch Moreland to man first base. Confident that the improvements to the team’s rotation and infield defense would suffice, Dombrowski bowed out of the Encarnacion sweepstakes. Later Encarnacion would ink a three-year $60 million pact with the Cleveland Indians.

Dombrowski’s plan worked for the most part. The Red Sox went on to win 93 games and an AL East crown. However, the Red Sox suffered a season-long power outage throughout the lineup. They finished last in the American League in home runs and the lack of a middle of the order presence was always clear.

This offseason, the Red Sox appear to have their sites set on 30-year-old slugger J.D. Martinez. According to reports, the Red Sox have offered him a five-year deal worth $125 million. This seems like an awful lot of money for a bat-only player on the wrong side of 30, but the Red Sox don’t have a great alternative. The best alternative was the man available last year.

From the standpoint of a team building philosophy, long free-agent deals are a bad idea. It is almost impossible to accurately predict a player’s performance five years into the future. The last few years of these contracts are almost always albatrosses and most analysts admit that the Martinez’s contract won’t look good in 2021. Yes, hindsight is 20-20, but it wasn’t hard at the time to see that the contract Encarnacion signed with the Indians was a steal.

To better illustrate why the Red Sox missed the boat on Encarnacion, compare his numbers with the marks put up by J.D. Martinez in the three campaigns leading up to their respective free agencies.


So Martinez was marginally better. He’s also three years younger than Encarnacion was at the time, which helps to alleviate the pain of a five or six-year commitment. However, the difference between these two players does not nearly equate to a contract that represents more than double the earnings Encarnacion will receive.

Over the next two seasons, Encarnacion will probably generate 90% of the offense Martinez offers; he’s getting up there in age, but he hasn’t yet given serious reasons to suggest a steep decline is coming. Had the Red Sox had Encarnacion last year, perhaps a stymied offense could have led them over the Astros. There’s no guarantee that this was the case, but a three-year deal was a better fit for the Boston’s window.

The Red Sox’s window opened this past season and with the impending free agency of their core, it looks like it is probably going to last another three years long. If Red Sox had signed Encarnacion they would not have lost flexibility when the rebuild came. Now they will likely have a $25 million roadblock for at least two seasons.

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The Red Sox’s offer to Martinez is an admission by the front office that they made a huge mistake last offseason. How individuals age may vary and maybe Martinez will be a productive 35-year-old. What we can say for sure, however, is that the Red Sox would much rather be on the hook for two years and $40 million with Encarnacion than whatever J.D. Martinez signs for. The Red Sox should have jumped on a weak market for Edwin Encarnacion last year; this year J.D Martinez will make sure they will pay the price.