The Old Jail building served as the Charleston County Jail from its construction in 1802 until 1939. In 1680, as the city of Charleston was being laid out, a four-acre square of land was set aside at this location for public use. In time, a hospital, poor house, workhouse for enslaved people fleeing bondage, and this jail were built on the square. When the Jail was constructed in 1802 it consisted of four stories, topped with a two-story octagonal tower. Charleston architects Barbot & Seyle were responsible for 1855 alterations to the building, including a rear octagonal wing, expansions to the main building and the Romanesque Revival details. This octagonal wing replaced a fireproof wing with individual cells, designed by Robert Mills in 1822, five years earlier than his notable Fireproof Building. The 1886 earthquake badly damaged the tower and top story of the main building, and these were subsequently removed.
The Old Jail housed a great variety of inmates. John and Lavinia Fisher, and other members of their gang, were convicted of robbery and murder and were imprisoned here in 1819 to 1820. Some of the last 19th-century high-sea pirates were jailed here in 1822 while they awaited hanging.
The jail was also active after the discovery of Denmark Vesey's planned uprising. In 1821, he formulated a plan to win freedom for the enslaved people of the city, but the authorities were informed of the plot before it could take place. In addition to several hundreds of enslaved and free African Americans jailed for their involvement, four white men were also convicted of supporting the plot. Vesey spent his last days in the tower before being hanged.
Increased restrictions were placed on free and enslaved African Americans in Charleston as a result of the Vesey plot, and law required that all black sailors be kept here while they were in port. During the Civil War, Confederate and Federal prisoners of war were incarcerated here. It is one of more than 1400 historically significant buildings within the Charleston Old and Historic District.