Yankees shortstop Didi Gregorius was once viewed as the heir to Derek Jeter’s throne and a permanent fixture in the team’s infield. Not so much anymore…
When the Yankees obtained Didi Gregorius from the Arizona Diamondbacks in December of 2014, it was not overlooked that he was the team’s heir replacement for retiring Derek Jeter.

Only 25 at the time, Gregorius ingeniously stepped up to the task of replacing a legend by batting a respectable .265 with 56 RBI in 155 games in 2015. There was even talk Gregorius was a cinch to later be appointed Captain of the Yankees, mimicking Jeter.
From there, Gregorius took off, smacking 20, 25, and then 27 home runs over his next three seasons with the Yankees. A run producer, Gregorius averaged in the mid-eighties in RBI during that stretch.
The Yankees breathed a sigh of relief as scouts and fans could not predict the heights that Gregorius would reach as the years moved on.
The talk was whether or not the Yankees would be able to afford Gregorius as he worked his way up the ladder from the major league minimum in his first year.
Drawing salaries of $2 million, then $5 million, then $8 million, Gregorius reach a height of almost $12 million to play for the Yankees this season. What was it going to cost the Yankees to wrap him up for the next four or five seasons?
For the Yankees, It Gets Complicated
That was then this is now. The question is no longer about dollars – it’s about whether the Yankees have any interest at all in Gregorius as he enters his free agency in November.
And it goes beyond the shoulder injury Gregorius suffered that kept him out of all but 75 or so games this season. Instead, it’s about the descending production when Gregorius is in the lineup.

Never a high-average hitter, Gregorius has fallen to .248 with an alarming .288 on-base percentage. Flashes of power are still there with 16 home runs and 58 RBI this season, but his OPS at .757 is only slightly higher than the major league average of around .745.
Moreover, a guy is playing next to him who’s only 23 and having a career year. A natural shortstop, Gleyber Torres was shifted to second base only to accommodate Gregorius.
And here’s the kicker. Without Gregorius and with Torres playing short, DJ LeMahieu has a home at his natural position, second base. The Yankees can marvel at LeMahieu’s ability to report to the ballpark, having to check the lineup to see where he is going to play.
But they also might have cause to wonder what the cost was to LeMahieu. Might his numbers have been even higher than they are?
As a lefty, Gregorius has value to the Yankees predominantly right-handed regular lineup. And his penchant for reaching the short porch at Yankee Stadium is noticeable as well. But the ultimate question is – how much power do the Yankees need? Already this year, they are about to break their own record for most home runs in a season by a team.
Facing Reality – Sir Didi And The Yankees
In February, Didi Gregorius will reach 30 years of age. Not old, but old enough when you considerGregorius has only one year remaining on what is generally considered to be a position player’s prime (27-31). Again, the Yankees have reason to pause before offering Gregorius a contract that is likely to extend him to the age of 35 on the open market.
In this light, it almost reaches the point of being a no-brainer for the Yankees to not pursue Gregorius this offseason, especially given the remarkable career that lies ahead for Gleyber Torres.
There is, though, the element of the player’s character, as well as his stature as a fan favorite at Yankee Stadium, and generally, throughout New York City. Sir Didi (the title is real), speaks five languages fluently and gives of his time to raising money for Gastroparesis Patient Association for Cures and Treatments. To prove it, in 2017 he took a pie to his face to raise money, posting the self-deprecating video on Twitter:
I got Challenge by @jingle_BELLS_25 #GPPieFaceChallenge #SmashGP🎗🎗 i here by challenge @Yankees @ElGarySanchez @AaronHicks31 @TheJudge44 pic.twitter.com/v3z6Hmtt0W
— Sir Didi Gregorius (@DidiG18) November 7, 2017
But as we know, baseball is big business, and we can be assured the Yankees are looking at Gregorius mainly in that vein. For Gregorius himself, baseball is populated with plenty of good to great shortstops, and it remains to be seen what the marketplace will bear for a player of his caliber.
No doubt, Yankees fans will be split on this one. My feeling, with regret, is the Yankees will pass on Didi Gregorius, with good reason. And indeed, we are seeing the final days of Sir Didi in Pinstripes.
One writer for the New York Post perhaps put it best when he described the future of Didi Gregorius with the Yankees as “foggy”. We’ll see. Your thoughts…
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