Yankees: Didi Gregorius to undergo Tommy John surgery and what’s next

Yankees manager Aaron Boone and GM Brian Cashman held their first offseason press conference today where it was announced that shortstop Didi Gregorius will undergo Tommy John surgery. The shocking news comes at a terrible time for Didi who is set to become a free agent after next season.

A brutal week for the Yankees just got worse. Today’s announcement likely means Didi will miss the majority of the 2019 season. The next time we see him in the lineup could be anywhere from June all the way to August or September. The Yankees are smart not to put a time frame on when he might return but this is obviously a huge blow for the team and for Didi.

According to Boone, the injury happened during the ALDS in one of the first two games at Fenway Park. An MRI yesterday showed a tear in Didi’s right elbow which also speaks to how tough he is since he managed to gut it out for Games 3 and 4 at the Stadium.

This is a terrible way for the Yanks to start their offseason because there’s so much uncertainty surrounding a player’s return after they undergo a surgery this serious. There’s no doubt that Didi can and will eventually return to full form, but with him likely out deep into next summer the Yankees are going to have to find a replacement. Whether that’s internally or via trade/free agency.

The first name everyone will talk about is Manny Machado. The four-time All-Star was linked to the Yankees throughout this past season and is set to become one of the most sought-after free agents in big league history after this season. So it makes you wonder if this today’s news will lead to the Yankees being heavily involved in the Machado sweepstakes.

If the Yankees don’t want to spend big on Machado and commit to him long term they could always slide Gleyber Torres over to shortstop until Didi returns. That’s the move that makes the most sense considering Gleyber is a shortstop by trade and he’ll only get better defensively the more he plays there.

However, that does leave a hole at second base which is why I think the Yankees should seriously consider bringing back Neil Walker. Walker had a rough first two months this season after signing with the Yanks late into spring training but he really picked up the slack from June on and was one of the teams most clutch hitters at times. Walker is also a switch hitter with a lot of power from the left side, something the Yankees are going to need in their lineup with Didi out. With a full spring training and a chance to play everyday Walker could be a much more productive player for the Yanks in 2019.

As we move forward we’ll talk more about the Yankees plans for filling the void left by Didi, but in the meantime, let’s focus more on how this could impact Didi’s future. As we all know he’s set to be a free agent after the 2019 season and many thought there was a chance he could sign a long-term extension with the Yanks this offseason.

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Given the injury, that’s doubtful to happen anymore which is a shame. Nobody deserved a big-time extension from the Yankees more than Didi but there’s no reason to even talk about one until he’s back on the field producing at the high level he has for the past three seasons.

I’d love to see Didi with the Yankees long term and I’m sure Brian Cashman would as well, but this injury raises questions about his future in pinstripes. Especially if the Yankees do go all-in and get Machado to replace him both in the short and long term.

Personally, I hope Didi is the Yankees shortstop for years to come and is resigned next offseason for multiple reasons. He’s a gold-glove caliber shortstop and the anchor of the defense. He is by far the best left-handed hitter in what is a very right-handed heavy lineup. He’s also one of the unquestioned leaders in the clubhouse and a fan favorite. He’s clutch, he’s tough and he plays the game the right way.

He has all the attributes you want from your star shortstop just as Derek Jeter did before him and the hope is that he’ll also get the chance to help lead this franchise to multiple championships.

But more than anything I just hope this isn’t the beginning of the end for Didi as a Yankee.