I don't know much about Wirt Dexter other than he was a good friend of my great grandfather, James Ransom Walker (married to Louise Meeker Walker). My grandfather was Wirt Dexter Walker, my father Wirt Dexter, Jr. and my brother, Wirt Dexter III. My father died 3 years ago and my mother's memory is fading, so what I remember are from stories I was told when I was younger.
My grandfather was a Chicago businessman, one of his ventures was a grain company. He was raised in Chicago on Prairie Avenue and eventually lived on Lake Shore Dr. He was married several times (7?) with each wife younger than the other. He was one of 3 sons, I can't remember their names, I know one was "Jack", so I assume he was James Ransom Jr. I'm not aware of a James Monroe.
I hope this helps. Please keep me informed on anything else you find out about the Walkers. Thanks.
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