top of page
  • Writer's pictureSSTN Admin

The Possible Future of Didi Gregorius (Guest Post from Derek McAdam)

Two years ago, no one thought that Didi Gregorius would ever be leaving The Bronx. Now, it seems the Yankees are in a bind to determine whether or not to keep their star shortstop.

In 2015, Gregorius was acquired in a three-way trade from the Arizona Diamondbacks that sent Shane Greene from the Bronx to the Detroit Tigers, and Robbie Ray and Domingo Leyba to Arizona. Gregorius was seen as the long-term replacement at shortstop for Derek Jeter, who had retired the previous year. From 2015-2018, Gregorius hit .274 with 81 home runs and drove in 299 runs. His average slugging was .447 and average OPS was .766, putting him above average in both categories during this span (.

The main question that looms around Yankee nation this off-season is whether or not the Yankees will re-sign Gregorius. The answer may not be that simple…


The players love him: After every Yankees victory, Gregorius takes the win onto Twitter and shouts out every player who contributed to that win. On many of the dugout shots, he is interacting with other teammates with the largest grin on his face. There are not many players that bring the energy to the bench and clubhouse like Gregorius does every day.

The city loves him: This is one of those Derek Jeter stories where if Didi was let go, the Yankee fans would not take it lightly. His presence on social media after every Yankees does not just show his appreciation for his teammates, but also shows the humbleness of himself. Gregorius never includes himself or his accomplishments in any of his posts, and fans absolutely love it.

A breakout season in the making?: When the Boston Red Sox extended Xander Bogaerts to a six year, $132 million contract, the first notion by many fans, including myself, was that he was very much overpaid. However he has had a career season, hitting over .300 and setting career highs in doubles, home runs, RBIs, OPS, and walks. He also made his second career All-Star team and has been one of the highs of a disappointing Red Sox season.

If Gregorius can lock into a long-term contract, could he have a season like Xander Bogaerts? It is a question that cannot be answered until next season.


The Tommy John long-term effect: As of September 23rd, 2019, Gregorius has not had the greatest campaign in the final year of arbitration. His batting average is the second lowest of his career at .243 and his on-base percentage is the lowest he’s ever produced at .283. Much of this can more than likely be attributed to Tommy John Surgery he underwent in October 2018. The biggest risk the Yankees will take is if they lock him into a large deal and his struggles continue.

The cost: There is no doubt that Gregorius’ market will be absolutely demanding, as he one of the top free agents this off-season. Bogaerts’ extension will begin during the 2020 season, making his AAV around $21 million. Gregorius may not be able to top that, but he can definitely demand between $16-20 million per season, making him the second highest paid shortstop in the league. Turning 30 this February, he can probably get a five-year contract for around $80-100 million and still be able to hit free agency again once he’s 35. There’s no doubt the demand will be there for his services, so this number may even increase.

A loaded infield: Brian Cashman has loaded the farm system with solid players, many of which the fans have seen this season. Gio Urshela, Mike Ford, Tyler Wade, and Thairo Estrada are just a few of the many young infielders who have all had to step in and do their part for the team this season. The “Next Man Up” philosophy has taken over the team. All of these players have contributed to the success of the 2019 club in one way or another and will be back for several years to come. Miguel Andujar will also be returning from shoulder surgery, which leaves the Yanks with even more options. Gleyber Torres would more than likely return to shortstop – his natural position, leaving D.J. LeMahieu to play second base most of the time.


My Prediction: The Yankees let Didi Gregorius test the free-agent market, where he then signs with another team.


dr sem.png

Start Spreading the News is the place for some of the very best analysis and insight focusing primarily on the New York Yankees.

(Please note that we are not affiliated with the Yankees and that the news, perspectives, and ideas are entirely our own.)


Have a question for the Weekly Mailbag?

Click below or e-mail:

SSTN is proudly affiliated with Wilson Sporting Goods! Check out our press release here, and support us by using the affiliate links below:

Scattering the Ashes.jpeg

"Scattering The Ashes has all the feels. Paul Russell Semendinger's debut novel taps into every emotion. You'll laugh. You'll cry. You'll reexamine those relationships that give your life meaning." — Don Burke, writer at The New York Post

The Least Among Them.png

"This charming and meticulously researched book will remind you of baseball’s power to change and enrich lives far beyond the diamond."

—Jonathan Eig, New York Times best-selling author of Luckiest Man, Opening Day, and Ali: A Life

From Compton to the Bronx.jpg

"A young man from Compton rises to the highest levels of baseball greatness.

Considered one of the classiest baseball players ever, this is Roy White's story, but it's also the story of a unique period in baseball history when the Yankees fell from grace and regained glory and the country dealt with societal changes in many ways."


We are excited to announce our new sponsorship with FOCO for all officially licensed goods!

FOCO Featured:
carlos rodon bobblehead foco.jpg
bottom of page