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Dave SHey Dan, pretty puzzling..I am fairly sure the Cub uniform in the top photo is 1925 and (maybe I'm off here and you're right?) the Sox uniforms are mid-teens. Seems as if (it is the same guy) the Cub player looks older. Then the "star pitcher" throws you off with that glove? It's definitely not Killefer, left as Cub mgr. to St. Louis and never any Sox affiliation that I'm aware of.
My original instinct was of Billy Piercy who was a pitcher and retired in '26...but then again, why that mitt? And don't think any Sox connection unless he went as a coach after '26...but that throws off my Sox uniform date unless I'm off? Weird one..