Madison Gregory was born in Huron County, Ohio, in 1848. He married Ester Randall on December 26, 1870, in Kankakee County, Illinois. Their three daughters, Lillie Gregory Martin, Jennie Gregory, and Ethel Gregory Wagenbach, were born in Kankakee County. In the early 1880s, the family moved to Brown County, where they acquired 320 acres of land by Federal Land Patent in 1884-1885. In May 1885, he broke a leg in a fall from a horse, and the injury required amputation. He died two weeks later from complications of the surgery. His grave is unmarked somewhere in the open space behind this monument. A newspaper article announcing his death said that he was a gentle man who made many friends in his short time in Brown County.