Didi Gregorius Free Agency Preview

Didi Gregorius
CLEVELAND, OH - OCTOBER 11: Didi Gregorius #18 of the New York Yankees celebrates his two-run homerun as he runs the bases in the third inning against the Cleveland Indians in game five of the American League Divisional Series at Progressive Field on October 11, 2017 in Cleveland, Ohio. (Photo by Gregory Shamus/Getty Images)

Didi Gregorius Free Agency Preview

Didi Gregorius has entered the free agent market. Also, it was announced that Sir Didi will not have the qualifying offer attached to him. The Yankees declined to give him that and he will be free of any draft pick compensation. It’s important to take stock of what Didi brings to the table. Any team that decides to sign them would find themselves getting a bit of an upgrade at an important position.

The Case for Didi

Didi Gregorius has done well to establish himself as a very good offensive shortstop since he got to New York before the 2015 season. He made the transition away from Derek Jeter a little easier to stomach for New York Yankees fans. Over the past five seasons with the Bronx Bombers, Gregorius has amassed a 15.7 WAR, which puts him 8th in the entire MLB for qualified shortstops. He has hit 97 home runs which ties him for seventh in MLB in that category. Didi has amassed a slash line of .269/.313/.446 and that is decent enough for a shortstop. He also keeps the strikeouts down by only striking out 13.5% of the time. He would be an upgrade for most teams seeking a shortstop.

The Case Against

Didi Gregorius does not walk nearly as much as one would like him to. He only takes ball four an astounding 5.3% of the time, good for 12th worst in the entire league for the past five years. Gregorius is also a very average fielder. Over the past five seasons, he has amassed a -1q defensive runs saved. It is not terrible by any means, and he usually makes up for it with the bat, but it is a concern for any team looking to sign him.

His health is another question as well. Didi had to have Tommy John surgery in 2018 that limited his playing time in 2019. While it doesn’t seem like he has lingering effects from it, a shoulder injury caused him to struggle mightily down the stretch in 2019. He only hit .190/.247/.380 in September with three home runs. It is a cause for concern, given that he is heading into his thirties. A lingering shoulder injury could really hamper his power production.

The Situation with the Yankees

Didi Gregorius was not given a qualifying offer, as mentioned before. It makes sense, as the Yankees have a number of infield options and really don’t need to pay a premium for Didi. He was earning $11.7 million this past season. The qualifying offer would have guaranteed him $17.8 million. It’s likely that the Yankees didn’t feel comfortable with this, and Didi would have actually had good reason to accept. After a down season, it would have been a great contract to reestablish his value and head into free agency again next offseason.

Teams That Have a Need

Like with any free agents, there is always a surprise team or two that come out and make bids for players. However, as always, there are teams that have a better fit to sign a player to a long term deal, as is the case here. Unfortunately for Sir Didi, there are not many contending teams that could use a shortstop. 

The Cincinnati Reds could look to upgrade their infield offense. The team could shift Freddy Galvis to second base and plug Gregorius right into short. The Reds have not had a steady presence at shortstop, as even Jose Peraza had taken a step back this season. The Reds would probably be the closest to contending that Gregorius might find a job with.

The Philadelphia Phillies are another team that could move some pieces around and is able to plug Didi in at shortstop for an upgrade. The Phillies are known to spend big when the time is right and they may view Didi as enough of an upgrade over their current option of playing Cesar Hernandez at second base. Jean Segura would move to second base to accommodate Gregorius.

The Milwaukee Brewers are another team that could use an upgrade at shortstop. Orlando Arcia has not morphed into the player that the team wanted. It would likely be a step back defensively, but a step forward offensively. Even still, this team needs pitching more than it does an offense behind the pitching so this is likely out.

The Washington Nationals would also be a team that could use a middle infielder. The team might not feel that Carter Kieboom is ready for the big time. With Brian Dozier, Howie Kendrick, and Asdrubal Cabrera becoming free agents, they could bring in Didi as a way to build a stronger infield depth.


There is no clear path for Didi Gregorius to sign, but it is clear it likely won’t be with the New York Yankees. It is doubtful that he will return to his career year of 2018, but that doesn’t mean he can’t help a team up the middle for a few more years. He won’t be getting a mega-deal like Gerrit Cole, but he could be an underrated signing like DJ LeMahieu last offseason.


Please enter your comment!
Please enter your name here

This site uses Akismet to reduce spam. Learn how your comment data is processed.