Didi Gregorius is having a great postseason, which could cost the Yankees

Didi Gregorius is a cult hero for Yankees fans, but Brian Cashman has a business decision to make about the shortstop’s future this offseason.

When Derek Jeter’s historic tenure with the Yankees finally ended, Didi Gregorius took up the mantle as the team’s starting shortstop with a remarkable combination of flair, grace and production. The fact that Gregorius will be a free agent this offseason presents the team’s front office with a very difficult choice to make this offseason.

Gregorius’ mammoth grand slam in Game 2 of the ALDS against the Twins may be the Yankees’ defining moment of the postseason to date, but the veteran infielder’s regular season made home one of the weakest bats in Aaron Boone’s lineup. His final slash line of .238/.276/.441 were actually the lowest numbers in each category for Yankees starters when the regular season ended. From Gregorius’ perspective, 2019 was a terrible time to put up the weakest offensive season of his career.

In fairness, it must be noted that he came back from a severe injury earlier than anyone could have reasonably expected. His Tommy John surgery could easily have kept him out until the tail end of the regular season. Instead, he managed to come back and play 82 regular season games. It’s fair to wonder whether or not rushing back from injury might have had a significant, negative effect on his offensive output on the season.

Despite his weak offensive stats, he was still an above-average player overall for the Yankees. His steady defense at shortstop contributed to his WAR of 0.6 on the season. That certainly doesn’t qualify him to be a star, but it proves he’s still a valuable contributor for a team that won the AL East rather comfortably. Add all of these statistics up and there’s a logical case to be made for Cashman re-signing Gregorius or letting him walk via free agency.

Expect the Yankees to make a strong effort to keep Gregorius in the fold for several more seasons. They won’t rush to offer him any sort of raise over the $11.75 million he made this season, but Cashman and company aren’t going to look for him to take a significant pay cut either. If the Yankees can sign the 29-year-old to a deal that doesn’t take him into his mid to late-30s they should pounce on the opportunity.

The reason why the Yankees should work hard to re-sign Gregorius is alarmingly simple. The simple truth is that there aren’t any good alternatives available to the organization. Tyler Wade may have a role on the big league roster next season, but he doesn’t project as an everyday starter for a team with legitimate World Series aspirations. Gleyber Torres has the ability to move over and play shortstop, but the organization has been steadfast in their determination to keep them at second base for the long haul. That leaves the Yankees with zero internal options to fill in for Gregorius.

Finding a top-flight shortstop via trade or in free agency would also prove to be nearly impossible for the Yankees. Elvis Andrus is the only prospective free agent who could be a better shortstop than Gregorius in 2020 and beyond. However, he’s even older than Gregorius. The Yankees aren’t going to hand a lengthy, lucrative contract in free agency to a 30-year-old middle infielder who may or may not be able to handle the bright lights of New York City.

All of this equals good news for Yankee fans who want to see Gregorius back in pinstripes next season and beyond. The difficulty in replacing him at shortstop makes an agreement between the two parties a very likely outcome this offseason. Gregorius returning to the Bronx in 2020 isn’t a lock, but it’s much more likely than any other alternative at this point.