One of the many, many, many changes that have been made by the Rob Manfred-led MLB is the institution of a lottery draft to determine the top six picks. This was a decision made to force teams have second thoughts about tanking.
It also came with a rule about how often you can actually qualify for the lottery.
If you are a team in a big market, or one that paid into MLB revenue sharing, you cannot pick higher than 10th in consecutive years.
The Chicago White Sox obviously play in a pretty big market, despite always being thought of as the second team — and acting like a small-market team.