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Posted By: davidcycleback

From the uniform the player is wearing, the photo could be 1907. It was in vogue for the Major League players to wear their collars up like that around the time. One rule of thumb for baseball uniforms is that players had almost entirely quit wearing high top cletes by the 1910s-20s-- so a player wearing high top black shoes will date 1880s-early 1900s. White high top cletes usually indicates 1870s (though sometimes wore 1860s and early 1880s as well).

All I know about military schools is that I had a childhook friend who's parents threatened to send him to St. Joseph's Military Academy whenever he did something bad.