Capt. John B. Castleman - Company "D" 2nd Kentucky Cavalry

Capt. John B. Castleman
- Company "D" 2nd Kentucky Cavalry
Patricia A. Kaufmann

The illustrated cover bears a pair of 5¢ London prints tied by a Tullahoma, Tenn., circular date stamp, but the franking is not the point of interest on this cover—the addressee is. The cover is addressed to “Capt. John B. Castleman, Col. Duke’s Regiment, Melvinville, Tennessee”.

Born in Lexington in 1841, John B. Castleman dropped out of college to enlist and command Company “D” of the 2nd Kentucky Cavalry, a regiment of “Kentucky Orphans”—so-called because their service to the Confederacy estranged them from their home State, which did not secede from the Union. Under the command of the famous raider, Brigadier General John Hunt Morgan, and his brother-in-law, Colonel (later General) Basil Duke, the 2nd Kentucky Cavalry fought in the western theater of operations against the United States Armies of Ohio, Tennessee, and the Cumberland.

Castleman’s escapades included attempting to free POWs from Camp Douglas near Chicago and burning U. S. supply boats at St. Louis. In October 1864 he was captured and sentenced to death for spying.

Partial charges and specifi cations preferred against John Breckenridge Castleman, (then) Major of the Second Regiment, Kentucky Cavalry of the Rebel Army included “Lurking and Acting as a Spy”, i.e., “Castleman, did, on or about the 26th day of August, 1864, secretly, in disguise and under false pretenses, enter and come with the lines of the regularly authorized and organized military forces of the United States, and did secretly and covertly lurk and travel about as a spy in the dress of a citizen, and under and assumed name, and did seek information with the intention of communicating it to the enemy, and remained within said military lines until arrested as a spy at Sullivan, Indiana, on or about the 30th day of September, 1864 within the  military lines and the theater of military operations of the Army of the United States, at a period of war and armed rebellion against the authority of the United States.”

Conspiring to Destroy Government Property in Violation of the Laws of War. Charged that “Castleman did, on or about the 26th of August, 1864, enter the states of Illinois, Missouri, and Indiana, in pursuance of an agreement with Jacob Thompson,  Clement C. Clay, Jr. [Confederate commissioners in Canada], James A. Barrett [Missouri Order of American Knights leader], Captain Hines, and others unknown, to burn and destroy government arsenals, depots, and storehouses, and steamboats in government employ, and incite others thereto, with the purpose and intent of hindering and impeding the efforts of the lawfully constituted authorities of the United States in suppressing an armed rebellion against its authority.”

The levee at St. Louis was a favorite target of the Confederate Secret Service and their copperhead allies, “OAK”. Not counting Castleman’s action, there are at least four documented instances of multiple-boat burnings at St. Louis during the course of the war. These accounted for the destruction of 18 boats.

Although sentenced to death for spying, President Lincoln suspended the execution. After Lincoln’s assassination, Castleman was banished from the United States until pardoned in 1866. Back in Kentucky, he settled in Louisville, obtained a law degree, established an insurance company, and revived Louisville’s militia unit. The unit volunteered for service during the Spanish-American War and invaded Puerto Rico. Castleman was promoted to brigadier general and served as military governor of that island. His was the kind of dashing military career that captures our imagination and brings life to the postal history we collect.

Although Castleman rose to the rank of general after the War, he is represented in civilian dress in one of only two Civil War statues in the state of Kentucky that depict equestrians. The other is John Hunt Morgan. The 15-foot high bronze statue of Castleman honors his interests and achievements later in life, as a founder of the American Saddlebred Horse Association. His Kentucky troops were, for the most part, mounted on Saddlebreds.