On January 16, 1862, Henry Floyd Gamble was born in the North Garden community of Albemarle County, Virginia to Henry Harmon and Willie Ann (née Howard) Gamble. Henry Harmon Gamble, who was of Scottish-Irish and Indigenous American descent, was the foreman on the estate of his master. Willie Ann, who was of primarily African-American descent, had been enslaved on Howard’s Neck Plantation in Goochland County, Virginia. The master of that land tract was her father and Eliza Howard, who was also enslaved, was her mother.
Upon attaining emancipation after the ending of the Civil War, the Gambles settled near Charlottesville, Virginia, where he worked in order to support their family, which included ten children. Willie Ann had astute insight and, in her ambition to improve the future of her son, Henry Floyd, was able to secure a position for him to work as a houseboy in the home of Dr. John Staige Davis.
Around 1875 the Flanagan Bank went bankrupt and with it, the approximately $500 savings of Henry Harmon Gamble and the opportunity for Henry Floyd to attend school. According to the archives collection of the West Virginia Department of Arts, Culture and History website, Henry Floyd Gamble recalled, “… having all his savings in the bank, he lost it all in the failure. The payment on his property and the support of a wife and ten children took all that Father and children could make. For that reason, I could not attend school, but hired a night teacher while I worked at the University of Virginia in the home of Dr. John Staige Davis, professor of medicine in the University. The present Prof. J.S. Davis, Jr., the son of my employer used to teach me and really showed great interest in my progress, till his father prohibited him from giving me further lessons. Nevertheless from ’79 to ’82, I made progress under my night teacher. By 1882, I had saved about $50.00 and entered the preparatory department of Lincoln University.”