New York Yankees: 5 offseason moves needed to reach 2020 World Series

HOUSTON, TEXAS - OCTOBER 13: Manager Aaron Boone of the New York Yankees reacts during the fifth inning against the Houston Astros in game two of the American League Championship Series at Minute Maid Park on October 13, 2019 in Houston, Texas. (Photo by Mike Ehrmann/Getty Images) /

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HOUSTON, TX – OCTOBER 19: Didi Gregorius #18 of the New York Yankees runs the bases to score on a single hit by Gary Sanchez #24 during the second inning of Game 6 of the ALCS between the New York Yankees and the Houston Astros at Minute Maid Park on Saturday, October 19, 2019 in Houston, Texas. (Photo by Cooper Neill/MLB Photos via Getty Images) /

4. Bring back Sir Didi

The biggest strength for the Yankees is their deep infield, where Gleyber Torres, DJ LeMahieu and Didi Gregorius are all capable of All-Star caliber play. LeMahieu and Torres are under team control beyond the 2019 season, but Gregorius is set to test free agency for the first time. The 29-year-old will be the best shortstop in what is a thin class of middle infielders.

Acquiring Gregorius in a three-team trade where he only gave up Shane Greene will go down as one of the best trades of Brian Cashman’s long tenure with the Yankees. Gregorius was an unheralded, raw infielder but has matured into a very strong replacement for Hall of Famer Derek Jeter as the captain of the Yankees infield.

Gregorius first won a full-time starting job in 2016 and began breaking out the following year. He has hit .270/.312/.467 with 96 doubles and 88 home runs since 2017, with per-162 averages pushing 30 home runs and 100 RBI. Injuries have prevented Gregorius from playing more than 140 games in the last three seasons, but he did hit 16 home runs with 61 RBI in only 82 games in 2019.

Pinning a value on Gregorius as a free agent may prove difficult for the rest of the league, as his offensive numbers are most certainly inflated by playing in Yankee Stadium. He has also had a hard time staying healthy but has not suffered a drop in production. The Yankees, however, need to keep him given their question marks at first base and third base.

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