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Chuck Conners did.  I had his Cubs baseball card as a kid.
Robin Roberts did.  I remember him as a Cub.
Walker Cooper did,  I remember he hit a home run to beat the Sox in an intracity game.
Monte Irven played on the Cubs at the end of his career.
Frankie Frisch was the first Cub manager I remember.  But I don't think he was ever a player on their team.

My guess is Frankie Frisch.