Didi Gregorius
Didi Gregorius plays a position that the White Sox has covered but that doesn’t mean they should completely ignore his free-agent presence. He is a shortstop and the White Sox current guy, Tim Anderson, is coming off a season in which he won the Major League Baseball batting title. That doesn’t mean either he or Gregorius would be terrible designated hitters.
When good hitters hit the open market you have to at least consider them. Anderson and Gregorius are both two of the best hitting shortstops in the world. Gregorius had three great seasons in a row from 2016-2018 but an injury-plagued 2019 season made him come back down to earth. He only had a .238 batting average and a total of 16 home runs and 61 RBIs. The power numbers aren’t terrible when you consider that he only played in 82 games but everyone including Didi knows that he is capable of more.
As much of a long shot as it might be, a player of his caliber in the prime of his career needs to be evaluated by every team when he hits the open market. He also has some playoff experience which the White Sox seriously lacks. If they plan on being in the 2020 postseason, they might want to think about bringing in some of that type of experience and Didi surely has it.