John Breckinridge Castleman John Breckinridge Castleman ( June 30 , 1841 – May 23 , 1918 ) was a brigadier general and prominent landowner and businessman in Louisville , Kentucky . He studied law at Transylvania University before the Civil War . Military career . During the Civil War , Castleman recruited 41 men in his hometown of Lexington , Kentucky , who went to Knoxville , Tennessee , to form the Second Kentucky Cavalry company under John Hunt Morgan . Castleman was promoted to major in 1864 . He led guerrilla s in the attempted burning of supply boats in St . Louis , Missouri and was arrested in October 1864 at Sullivan , Indiana . He was convicted of spying and sentenced to death , but his execution was stayed by Abraham Lincoln . Following the war , Castleman was exiled from the United States , and studied medicine in France . He was pardoned by Andrew Johnson and returned to Kentucky in 1866 . He revived the Louisville Legion , a militia unit , in 1878 and became adjutant general of Kentucky in 1883 . The unit became the 1st Kentucky Volunteers in the Spanish - American War , and Castleman was commissioned a colonel in the U . S . Army . His unit participated in the invasion of Puerto Rico , and after the war he was promoted to brigadier general and served as military governor of the island . Business career . He graduated from the University of Louisville School of Law in 1868 , married , and founded an insurance company , Barbee and Castleman , with his father - in - law . The company represented Royal Insurance Company of Liverpool in the Southern United States . In 1870 , Castleman bought a tract of land called Schwartz ' s Wood in what was then the outskirts of Louisville . He intended to build a country estate there , but as Louisville expanded around it quickly , the land became much more valuable as a subdivision . It became the western half of Louisville ' s Tyler Park neighborhood . Political career . Castleman never ran for office , but his military and business reputation gave him considerable influence . As a Delegate to the 1892 Democratic National Convention , he successfully lobbied for the nomination of Grover Cleveland . After Governor William Goebel was shot in 1900 , Castleman was again appointed adjutant general of Kentucky and helped avoid conflicts in the fallout of the assassination . In Louisville , he had great influence as Commissioner of the Board of Parks for over 25 years , during which time he helped establish Louisville ' s Olmsted Park system , which spurred development in various parts of Louisville and became one of the city ' s prized possessions over the next century . In 1905 , he was a key figure supporting Louisville ' s Fusionist Party , an anti - corruption party . Although the Fusionists never won many elections , they eventually caused reform in Louisville ' s election system to come about . Death and legacy . Castleman died in 1918 and was survived by his five daughters . His statue in the Cherokee Triangle neighborhood , the John B . Castleman Monument , became a well known local landmark . The horse he rides in this great equestrian statue is his beloved Caroline . He was buried in Cave Hill Cemetery . His autobiography " Active Service " was published by Courier - Journal Job Printing Co . , 1917 .