TC Dale,
I had the same problem and I used commish mode to move players from the Rookie League to the Winter League, but after one day of simming the AI moved them back. I had to fill the Winter League with fictional players. I believe that my 10 round draft was not enough to keep 4 levels of minors and a winter league stocked, so I changed the draft to 15 rounds and I will see if it helps.
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