3. Didi Gregorius Never Develops As A Yankee
The Yankees traded for Didi Gregorius after the 2014 season with him set to fill the hole left at shortstop by Derek Jeter’s retirement. As we now know in 2019, Didi eventually developed into a productive offensive player for the Yankees, but at the time he was seen as a defensive wizard without much of a bat. In his first season with the team in 2015, Didi slashed just .265/.318/.370 and recorded just 9 home runs, 56 RBIs and 139 hits in 155 games.
The team still seemed committed to having him be the shortstop at least for the foreseeable future, but the acquisition of Simmons may have changed that. Simmons was heralded as the best defensive player in the game, and while his numbers were similar to Didi’s for the time being, he was seen as a young talent who had potential to develop into a superstar. Whether the New York Yankees would have moved on entirely from Didi if they acquired Simmons is obviously a mystery, but regardless he would have likely played a lesser role on the team. This would have not only taken away so many clutch Didi moments, like his 2017 AL Wild Card Game and ALDS heroics, but also would have stripped the team of a player that became a key voice in that clubhouse and one of the hearts of the team.
Simmons certainly could’ve become a very nice player for the Yankees, but Didi’s charisma and clutch playoff moments became a staple of the late 2010s Yankees, and the team would have had a very different identity if Simmons was the one playing shortstop every day instead of Gregorius.