Historian Russell Kirk described him as "a radical man yet a political conservative" with "alternating ferocity and compassion, his duels, his beautiful letters...his fits of madness...his brandy and opium, his passionate Christianity, his lonely plantation life, and his quixotic opposition to the great political and economic powers of the day." Kirk was describing the man who would unknowingly contribute to the cultural richness Sidney enjoys today.

John Randolph of Roanoke was one of the leaders of perhaps the most powerful family in the South from the late 1700's until at least the Civil War. He had served as the legislative leader in the Virginia Assembly for his cousin, Thomas Jefferson. History records that he ruled the Assembly with an iron hand - and a whip. He was the unquestioned master of a string of plantations in the Tidewater area of Virginia. Jonathan Daniel's, in his book The Randolphs of Virginia described the family as "America's foremost family," and Randolph as an orator and businessman "with few peers."