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.