Yankees: How Brian Cashman’s brilliance framed the franchise’s resurgence

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NEW YORK, NY – APRIL 24: Didi Gregorius #18 and Aaron Judge #99 of the New York Yankees smile in the dugout in the fifth inning after Didi Gregorius drove them both home with a home run in the fifth inning against the Minnesota Twins at Yankee Stadium on April 24, 2018 in the Bronx borough of New York City. (Photo by Elsa/Getty Images) /

When Yankee Captain Derek Jeter retired following the 2014 season, the Yanks needed a replacement at shortstop—something they hadn’t thought much about for almost twenty years. On December 5th, 2014, Brian Cashman surprised the baseball world by dealing twenty-five-year-old Shane Greene, who struck out 81 batters in 78 2/3 IP, in a three-team trade that sent shortstop Didi Gregorius from the Diamondbacks to the Yankees.

Gregorius, who had started the 2014 season in Triple-A, struggled early in the 2015 campaign, succumbing to the tremendous pressure of replacing Derek Jeter. By midseason, Gregorius was beginning to blossom offensively while displaying Gold Glove-caliber defense at short. Needless to say, the rest has been history for Didi.

In an American League loaded with talent at shortstop, namely Xander Bogaerts, Francisco Lindor, Carlos Correa, and Andrelton Simmons, Gregorius has flourished, averaging 24 HR’s, 81 RBI’s, and 141 Games over the past three seasons. Besides his play on the field, Didi has become a fan-favorite, known for his victory tweets, charismatic personality, and infectious smile. Didi’s game-tying three-run home run in the 2017 AL Wild Card game followed by his two home runs off Corey Kluber in game 5 of the ALDS effectively cemented his presence as the long-term Yankee shortstop.

After the Yankees were eliminated from the 2018 Playoffs by the Boston Red Sox in the ALDS, it was announced that Gregorius would undergo Tommy John surgery for an injury suffered in Game 2 of the series. According to Manager Aaron Boone, Didi played through the injury without complaint, which gained even more respect from his teammates and the Yankee fan base.

Even while sidelined while recovering from Tommy John surgery, it has been rumored that the Yankees and the soon-to-be free agent Gregorius have discussed a contract extension.