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I have encountered the same problem of historical draft pools not populating properly. I have the amateur draft enabled and scheduled for November 15, with draft pool reveal 90 days in advance.(August 17).
However, when the draft pool is revealed on August 17 the only players listed are those who were drafted but did not sign the previous season. Then, on November 15th all the players who should be in that year's draft class are suddenly generated and appear in the draft pool.
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