25 Smartest Moves of the Past 25 Years: Yankees trade for Didi Gregorius

Even if the particular legend hadn’t been a force on the field at time of retirement, it’s still never easy to replace a legend. Derek Jeter’s retirement at the conclusion of the 2014 season left the Yankees with a hole at shortstop.

There was no real MLB-ready option in the minor leagues, and while there were free agent shortstops available, the Yankees didn’t make much of any splash that winter in that market. From the beginning, one of the possibilities they were connected to was a trade with the Diamondbacks, who had a pair of shortstops who had split time at the position in 2014: Chris Owings and Didi Gregorius.

That ended up being the direction the Yankees went in, and it couldn’t have worked out much better.

Trade Details: Didi Gregorius to NYY; Domingo Leyba, Robbie Ray to ARI; Shane Greene to DET

Transaction Date: December 5, 2014

NYY Stats (2015-19): 660 games; 2,658 PA; .269/.313/.446, 97 HR, 102 OPS+, 15.5 fWAR

Going into the 2014 season, Owings and Gregorius competed for Arizona’s shortstop position, with Owings coming out on top. Gregroius ended up appearing in 80 games for the Diamondbacks that season, but he was also their clear second choice, and even spent 57 games in Triple-A that year.

Between that, him being older than Owings, and the Yankees’ obvious hole at shortstop, Gregorius ended up being a fit for a trade to New York. In early December, it was made official and he went to the Yankees as part of a three-way trade that also included the Tigers. For their part, the Yankees gave up Shane Greene, who had a solid debut season in 15 starts that year.

Gregorius’ tenure as the new Yankee shortstop didn’t start amazingly, as he was OPSing just .580 through the end of May. He was better over the course of the rest of the season, getting his numbers up and finishing with an OPS+ of 89, and a WAR of 3.1 thanks to his solid defense. He was also one of the only Yankees to somewhat show up in the AL Wild Card Game loss, recording one of the mere three hits they put up that day.

Over the next couple years, his hitting production steadily increased. From 2015 to 2018, his wRC+ went from 89 to 97 to 109 to 122. Gregorius transformed from a guy hitting in the bottom of the lineup to the middle, and deservedly at that. While he never ended up making one due to the position being a bit loaded in the AL, by the end of that stretch, he was a genuine All-Star candidate.

Besides just a general improvement, he also became a bat the Yankees relied on for big moments. In the 2017 AL Wild Card Game, his first inning home run tied the game after the Yankees had fallen behind early.

In the ensuing ALDS, Gregorius hit two home runs off Corey Kluber in Game 5 against Cleveland, helping the Yankees complete the rally from falling behind 2-0 in the series. In 2019 against the Twins again, his Game 2 grand slam gave the Yankees a commanding lead as they went up 2-0 in the series in an eventual sweep.

Didi also became a fan favorite for his affable character as well. There were his victory tweets that always followed shortly after a Yankee win.

Those and stuff like the “Toe-Night Show” made him a beloved member of the roster.

Near the end of the 2018 season, he suffered a UCL tear that required Tommy John surgery that offseason. The injury kept Gregrorius out through June in the 2019 season. When he did come back, he had a bit of down year considering what he had done the previous couple seasons (though he did hit a thrilling ALDS grand slam against Minnesota). Between that and the emergence of Gleyber Torres, who came up through the minors playing short, the Yankees decided to let him walk in free agency after 2019.

Torres’ move to shortstop hasn’t exactly worked, and the Yankees are seemingly on the lookout for someone else to play the position. Despite some people clamoring that the Yankees should’ve kept Didi, doing that likely wouldn’t have been the best decision either. While he was pretty good in the shortened 2020 season, he was very bad in 2021. His 71 OPS+ was the worst of his career, excluding his 62 in 2012, in which he only played eight games.

As for what the Yankees traded away, they’re didn’t miss out on that much. As Gregorius struggled to start 2015, Greene got off to an excellent start, leading some to wonder if the Yankees had given away a possible rotation-topping arm. They didn’t.

After putting up a 3.00 ERA through four April 2015 starts, Greene quickly fell off a cliff and finished the year with an ERA nearing 7.00. By 2016, he was reliever. While he had some solid seasons out of the bullpen over the years, making an All-Star team in 2019, on the whole, his career ERA is 4.52 makes for a below-average 95 ERA+.

Didi Gregorius walked into an unenviable situation in 2015 when he had to replace Derek Jeter. While he didn’t have a ton of production from late-stage Jeter to replace, there was far more to do to replace him in the hearts and minds of fans. While pretty much no one could do that fully, Gregorius did about as well as anyone could asked for.