Pinckney Benton Stewart Pinchback was born on May 10, 1837 to parents William Pinchback, a successful Virginia planter, and Eliza Stewart, his former slave. The younger Pinchback was born in Macon, Georgia during the family’s move from Virginia to their new home in Holmes County, Mississippi.  In Mississippi, young Pinchback grew up in comfortable surroundings on a large plantation.  At the age of nine, he and his older brother, Napoleon, were sent by his parents to Ohio to receive a formal education at Cincinnati’s Gilmore School. Pinchback’s education was cut short, however, when he returned to Mississippi in 1848 because his father had become seriously ill.  When his father died shortly after his return, his mother fled to Cincinnati with her children for fear of being re-enslaved in Mississippi.  Shortly thereafter, Napoleon became mentally ill, leaving 12 year old Pinckney as sole-provider for his mother and four siblings.  

Pinchback found work as a cabin boy on a canal boat and worked his way up to become a steward on the riverboats which ran the Ohio, Mississippi, and Red Rivers.  He was taken under the wing of professional gamblers who worked the riverboats, and soon became a skilled swindler himself.  During these years, he sent as much money as possible to Cincinnati to help support his mother and his siblings.  In 1860 when he was 23, Pinchback married Nina Hawthorne, a 16 year-old from Memphis, Tennessee with whom he would have four children.  When the Civil War began the following year, Pinchback ran the Confederate blockade on the Mississippi River to reach Union-occupied New Orleans, Louisiana where he raised a company of black volunteers to fight for the North.  In 1863, after being passed over for promotion a number of times, Pinchback resigned from service.  At the close of the war, he moved his family to Alabama to test out their new freedom.  After encountering dreadful levels of prejudice in Alabama, Pinchback moved his family to New Orleans.

Upon settling in New Orleans, Pinchback