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Anthony S.It suddenly dawned on me that perhaps the overprint was of a player who'd been traded during the printing run. In that case as we see on Demmitt card, for example, they use the same picture, but change the team logo on the uniform. And it never quite looks right. That would also explain why none of the T206 Cincy cards quite match up.
So I checked the transactions for 1908 and 1909. The Reds made quite a few during those two years. None of the pictures of the traded players quite matched up with that ghost overprint until I got to Jake Weimer, who was traded by the Cincinati Reds on July 10th 1908 to the New York Giants. I just checked the T206 Weimer and the NY insignia on his jersey has that funky look like the T206 Demmitt. Then I checked the face...
So my guess is that they had the T206 Weimer card as a Cincinnati Red all ready to go, but didn't release it due to trade to the Giants. They changed the team logo on his chest and then released the card with him as a New York Giant.
EDIT TO ADD: I've been holding my T206 Weimer (not the exact card in the photo I used which I grabbed from Ebay, mine is not slabbed) next to the ghost image on the Casey and to me it looks like an exact match.