Theodora, originally named Carolina, then Gordon, Theodora, and finally Nassau, intermixed privateering with a blockade running and charter service to the Confederate States as a transport and picket ship. She was built as Carolina at Greenpoint, N.Y., in 1852 for service as a coastal packet out of Charleston, S.C., occasionally crossing to Havana, Cuba. Upon outbreak of Civil War she was strengthened and refitted as the Gordon, under Capt. T. J. Lockwood, and placed in commission as a privateer at Charleston on 15 July 1861.
Gordon captured the American brig William McGilvery off Charleston on 25 July 1861 and the American schooner Protector fell into her hands off Hatteras Inlet on the 28th. She was reported to have run the blockade out of Charleston 27 times by October 1861. At that time she was under charter to the Confederate States for the daily reconnoiter of the Union warships off that port. Of so light draft that she could slip over the bar without being confined to the channels, she kept barely out of reach of the guns of the Federal warships, which finally ignored her, being aware of her speed and the futility of chase. On 4 and 5 October 1861, with officers of Nashville, Mr. John Slidell and two young ladies of his family on board, she boldly approached to within 3 miles of the Federal fleet in broad daylight and found herself ignored. This set the stage for her charter by authority of Secretary of State Hunter, to run the Federal Blockade with Confederate diplomats, John Slidell and James M. Mason, to the West Indies.
Gordon, with her name changed to Theodora, slipped over the bar at Charleston at 1 a.m., 12 October 1861, having embarked Mason and Slidell and their parties to run the blockade to the West Indies. Too fast to be overtaken at sea, her light draft enabled her to hug the coast to escape the Federal blockading fleet. On 14 October she chased the American armed schooner H. W. Johnson into the mouth of the Harbor at Nassau, New Providence, Bahamas. Two days later she came off Cardenas, Cuba, dipped the Confederate flag in salute to an approaching Spanish steamer, and was escorted into port where she landed her distinguished passengers on the 18th. This mission proved to be one in a chain of events that led to the famous "Trent Affair" and brought on bitter relations between the United States and England.
Theodora continued to run the blockade out of Charleston and Wilmington, primarily to Nassau, where she caused consternation to observant commanders of Federal warships. By making herself a target of chase, she unsuccessfully attempted to lure USS Flambeau away from Nassau during 17-18 December 1861, hoping to allow opportunity for British steamer Gladiator to escape from that port with her cargo of munitions said to be sufficient to arm 25,000 Confederates. She got safely into Mobile, changed her name to Nassau under British colors, and continued to slip in and out of Wilmington until 28 May 1862. On that day she was discovered running for Fort Caswell, N.C., and was cut off by Federal warships State of Georgia and Victoria. She continued running close to land until stopped by direct shots by Victoria, then hauled down her British colors as her crew put off in boats for shore. A well directed shot from Victoria landed in the midst of the crew as they reached shore, killing one and injuring another. The remainder of the crew escaped into the woods.
Theodora was under command of the famous blockade runner, Captain Walker, when captured. On 28 May 1862, a prize crew of 24 officers and men from Victoria found her loaded with Enfield rifles, ammunition, clothing and medicines intended for the Confederate Army. She was sent to New York for adjudication as a prize of war.
