Born 1799 in North Carolina. Purchased land 1818 in Gibson County. Cockrum and Jacob Warrick Hargrove laid out the town of Oakland (now Oakland City) on January 15, 1856. Cockrum and his son William Monroe Cockrum, along with sympathizers in Warrick, Gibson, and Pike counties, aided enslaved blacks seeking freedom. Cockrum died November 19, 1875.
James W. Cockrum's barn, originally located on this property, was used to hide freedom seekers. The Underground Railroad refers to a widespread network of diverse people in the nineteenth century who aided slaves escaping to freedom from the southern U.S.