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He was a rule 5 draft pick, not a regular pick. He also couldn't have been in the White Sox organization for 8 years as you claim, because the Sox didn't even get him until 2017.And one other thing that holds guys back is attitude. Especially at that level. He was with the Chicago organization for what 8 years, 4 at the AAA level, had his opportunity whatever the reason so moving from team to team is a bit oversold. He’s 29, not some 21-22 year old with upside.
As for where he played, you might want to take a better look at his minor league stats, and you'll find he was moved from location to location on a regular basis, but still ended up a .291 minor league hitting. The wrap on him was that he was a defensive liability behind the plate. That said, his play behind the plate, and hitting, was consistently better than others.
In the Major League portion of the Rule 5 Draft, players not on a 40-man roster, plus who were signed at age 19 or older and have been in professional baseball for four years were eligible to be selected.
Then there's the fact that Yermin's early years of pro ball were pretty much confined to leagues in the Caribbean, not in the states. Big difference there. Go ahead and put any spin on this that you'd like, but read what the Rule 5 Draft actually was, where he was picked by the Sox.