General James Longstreet was a West Point graduate who quickly rose through the ranks of the US Army after graduation. He resigned from the Army at the rank of Captain and took a position with the Confederate Army in 1861. During the Civil War, Longstreet was deemed Lee's "war horse" and served closely with Lee. After the war, Longstreet moved to New Orleans to try his hand at business. He eventually switched to a political career and was appointed to several positions with the US government including Surveyor of Customs, IRS agent, Marshal, and Ambassador to Turkey. Longstreet's willingness to work with the US government during Reconstruction and his political ties with Ulyses Grant and the Republican party made him an outcast in the South which may have soured his early business career.

Longstreet settled in Gainesville, Georgia where he spent the remainder of his life at his farm and vineyard.