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Yankees: Five moves they should attempt to make during the Winter Meetings

By Mac Josephson

NEW YORK, NY - OCTOBER 03: Didi Gregorius #18 of the New York Yankees celebrates with Brett Gardner #11 after hitting a three run home run against Ervin Santana #54 of the Minnesota Twins during the first inning in the American League Wild Card Game at Yankee Stadium on October 3, 2017 in the Bronx borough of New York City. (Photo by Al Bello/Getty Images)
NEW YORK, NY - OCTOBER 03: Didi Gregorius #18 of the New York Yankees celebrates with Brett Gardner #11 after hitting a three run home run against Ervin Santana #54 of the Minnesota Twins during the first inning in the American League Wild Card Game at Yankee Stadium on October 3, 2017 in the Bronx borough of New York City. (Photo by Al Bello/Getty Images) /
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NEW YORK, NEW YORK – SEPTEMBER 17: Didi Gregorius #18 of the New York Yankees follows through on his fourth inning two run double against the Los Angeles Angels of Anaheim at Yankee Stadium on September 17, 2019 in the Bronx borough of New York City. (Photo by Jim McIsaac/Getty Images) /

Re-sign Didi Gregorius or trade for a left-handed hitter

The Yankees haven’t closed the book on re-signing Didi just yet but it’s not looking very likely that he’ll be back in 2020. Even after an injury-plagued down year in 2019, the 29-year-old shortstop should still be able to cash in on a multi-year deal with a club looking for middle infield help.

Didi struggled offensively last season, but a lot of that can be attributed to him coming back to soon from TJ surgery. As long as he stays healthy he’s going to have a more productive season on both sides of the ball in 2020 and the Yankees and every other team interested in signing him knows that.

There will probably be teams that offer Didi a deal for three or four years, but if he wants to return to New York it would probably only be on a one-year deal. The Yanks declined to give him the qualifying offer of $17.8M earlier this offseason because they were afraid he would accept it but I think they’d still love to have him back for another year just for less money. They’re not going to outbid another club to bring him back but there’s still a need for Didi on this roster.

Gleyber Torres could easily shift over to shortstop next season and DJ LeMahieu could move back to second but Gleyber isn’t the defender Didi is at short which is a concern. Didi is also the Yankees best left-handed hitter when he’s at his best and their lineup is still going to be very right-handed heavy next season even if they bring back Brett Gardner. In addition to that Didi is one of the top leaders in the Yankee clubhouse and a true fan favorite which can’t be understated.

I hope the Yanks find a way to bring Didi back, but if they can’t they could look to add another left-handed bat via trade. A deal for switch-hitting superstar Francisco Lindor seems like a pipe dream for now, but a trade for Pirates All-Star first baseman Josh Bell is something the Yanks could potentially pull off according to Jim Bowden of The Athletic.

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