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#1
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Boss Schmidt would make sense. He played in the second game that day and was an absolute beast. I think that is the trainer and not an umpire (medical bag). I don't think it is Siever unless he was a coach after his playing career. His last major league game was in 1908 and this happened in 1911.
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#2
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Harry Tuthill the Detroit Tiger trainer with the bag.
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