The Yankees are playing hardball with Didi Gregorius in free agency

Didi Gregorius might return to the Yankees in 2020 but Brian Cashman is determined not to overpay to bring the shortstop back to the Bronx. 

The free agency of Didi Gregorius has caused some consternation for Yankees fans. The 29-year-old is a cult hero in the Bronx due to the way he managed to inherit the shortstop position from Derek Jeter with such poise and grace. That doesn’t mean he’s a lock to return to the team in 2020 though.

GM Brian Cashman isn’t a man who is inclined to give into romantic narratives. It would have been easy for the Yankees’ front office to extend a qualifying offer to Gregorius that would have reduced his ability to garner a big offer from another team in free agency. Instead, New York elected to make the fiscally conservative decision to allow him to enter free agency unfettered. Cashman and his front office were not interested in Gregorius accepting the qualifying offer and earning $17.8 million next year.

As a result, Cashman now freely admits that there will be a “competition” for the player’s services this winter. The Yankees are interested in bringing Gregorius back into the fold, but they are only willing to do so on a team-friendly deal.

In fairness to the Yankees, they have plenty of leverage. If Gregorius does sign elsewhere, the organization will simply move Gleyber Torres from second base to his more natural position of shortstop. DJ LeMahieu would then take over at second base where he’s already proven he can provide Gold Glove caliber defense.

That scenario would reduce manager Aaron Boone’s flexibility in 2020 though. That’s why bringing Gregorius back could still make sense for the Yankees. LeMahieu’s versatility allows him to play a number of positions for the Yankees. Gregorius is also a better defensive option at short than Torres. There’s a strong, logical argument to be made that the Yankees must re-sign Gregorius to maximize their infield talent next season.

Of course, Cashman has other issues on his mind. He knows that his offseason will largely be judged by his ability to acquire an ace to anchor his pitching staff. Signing either Gerrit Cole or Stephen Strasburg in free agency would adequately address the team’s biggest weakness. Signing either superstar would also require New York to pay a small fortune. That’s arguably the biggest reason why Cashman is adamant that he won’t overpay to bring Gregorius back next season.

The good news for Gregorius is that he is almost certainly the top shortstop available on the free agent market. Other organizations, however, will have to trust that he can fully recover from the Tommy John surgery that cost him serious time in 2019. A close look at his offensive numbers shows a sharp decline over where he was before the injury. It’s unclear whether his struggles are due to age or the rust associated to his long injury layoff.

Yankees fans can expect Gregorius’ free agency to take plenty of twists and turns as the Winter Meetings grow near. The one certainty regarding his status is that Cashman isn’t going to overpay to keep him in pinstripes. That could easily cause Gregorius to ply his trade elsewhere in 2020.