John Breckinridge Castleman (June 30, 1841 – May 23, 1918) was a Confederate officer and later a United States Army brigadier general as well as a prominent landowner and businessman in Louisville, Kentucky.

By birth, he was closely related to a future 14th U.S. vice president, John Cabell Breckinridge; their respective maternal grandmothers were sisters.

He led guerrillas in the attempted burning of supply boats in St. Louis, Missouri and was arrested in October 1864 at Sullivan, Indiana.

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.

"[3] According to a newspaper eulogy published following his death, John B Castleman could also be described as an early advocate for social justice in the city of Louisville.

A May 26, 1918, tribute to him published in the Courier Journal entitled "A Negro's tribute to General Castleman", written by African American educator and community member J. Raymond Harris, heralded Castleman for his commitment and kindness to the African American community of Louisville.

Harris starts his eulogy with "Will you give me space in which to speak of the great sorrow that has come to the colored people in General Castleman's Death" [4] Harris makes sure to note Castleman's Civil War service alongside the Confederacy, but speaks of his road to redemption saying "yet no hero on the other side ever held so high a niche in the hearts and minds of colored Kentuckians.

"[4] Elsewhere in the eulogy, Harris speaks truth to the selfless nature of Castleman by saying "His Kindness to us, his willingness to help with counsel and advice, were unstudied and uncalculated the result of neither the politician's bid of popularity nor of the selfish man's desire to advance his own self interests.

injustice or proscription raised its hand against African Americans, Gen. Castleman's voice was heard pleading for toleration and amicable adjustment.” Another example of Castleman's standing up for racial justice in his time can be found in a 1924 Courier Journal article written by 19 African American faith leaders published six years after his death.

Castleman supported his wife both financially and emotionally in her battle to secure voting rights for all women at a time when it was unpopular, even dangerous, to do so.

[5] 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.

He intended to build a country estate there, but as Louisville expanded around it quickly, the land became much more valuable as a subdivision.

An Op-ed in the Courier-Journal claimed that "It was Cowan who successfully lobbied for the state legislation to create a Louisville Park Commission.

It was Cowan who first invited Olmsted, the renowned landscape architect, to Louisville and who secretly coached the firm on how to price their work in order to win the bid....

His statue at a traffic circle in the Cherokee Triangle neighborhood, the John B. Castleman Monument, became a well-known local landmark.