What will the Yankees do with each of their own free agents?
Didi Gregorius
The question of what to do with Gregorius is going to keep Cashman up at night until the winter meetings arrive. He’s done a great job of taking over for an absolute legend in the form of Derek Jeter, but he picked a really bad time to put up one of the worst offensive seasons of his career.
Defenders of Gregorius will point out that he rushed back from Tommy John surgery to help the club. He absolutely should get some special consideration for getting back ahead of schedule. On the other hand, that surgery should have hampered his ability to throw the baseball across the diamond. It should not have robbed him of his ability to produce at the plate.
Gregorius is a good defender, but he’s not anything close to a gold glover at shortstop. That makes the fact that he slashed .238/.276/.441 in 2019 a serious problem. The Yankees really have to ask themselves whether or not his performance will bounce back as he plays his age-30 season in 2020.
Cashman does have other options at shortstop he can consider. If Gregorius leaves via free agency, it’s very likely Gleyber Torres will move back to his natural position. If the Yankees won’t want to go that route, they could give Tyler Wade a chance to take over. He’s a plus defender, but there are serious questions over whether or not he’ll ever hit enough to be a major league regular.
The Yankees will almost certainly make Gregorius an offer, but there may be more money/long-term security for him elsewhere.