One of only two equestrian Civil War monuments in the state, this statue was erected in 1913. The bronze inscription plaque was added after the general's death in 1918. The 15-foot-high monument with a 12x20-foot base occupies the center of a traffic circle at the intersection of Cherokee Road and Cherokee Parkway on the edge of Cherokee Park.

Although Castleman rose to the rank of major general in the Confederate Army, here he is depicted as a horseman in civilian dress. This honors his interests and achievements later in life, as founder of the American Saddlebred Horse Association. The champion horseman is shown riding one of his mares, Carolina.

Born in Lexington in 1841, John B. Castleman joined John Hunt Morgan's men in 1862 and led guerrilla missions of his own as well. His 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, but President Lincoln suspended the execution. After Lincoln's assassination, Castleman was banished from the United States until pardoned in 1866. Back in Kentucky, Castleman 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 many varied careers include two stints as Kentucky’s Adjutant General, as well as founder and first commissioner of Louisville’s park department.