That does appear to be a Cubs uniform. Cy played for them at the beginning of his career from 1912 to 1917, and then with the Phillies until 1930.
Here is that V100 card again, and then 3 photos, the first showing him with the Cubs, and the other 2 with the Phillies.
To me these images all appear to be the same player, with the deep set eyes that became even more so as an older player, the shape of his nose and shape and positioning of his nostrils, the pronounced ridges and distance between nose and lips, the same lips and jawline. It seems like his face really aged from the time of the V100/Conlin cards, losing its fullness and looking like an old man before his time (cursed day games!).
It seems he may have just been having a bit of fun posing as a right handed batter with an unknowing photographer.
Brian
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