Benjamin Anderson ( soldier ) Benjamin M . Anderson ( 1836 – February 21 , 1865 ) was a partisan soldier for the Confederate States of America during the American Civil War . He had gained military experience while serving under William Walker ' s filibuster ing campaign in Nicaragua . During the Civil War he served under Thomas Hines during Hines ' espionage efforts behind Northern lines . While jailed for his war activities in a Cincinnati , Ohio jail , he committed suicide by a self - inflicted gunshot to the head on February 19 , 1865 . Biography . Anderson is believed to have been born in 1836 , to James and Mary Anderson of Louisville , Kentucky . In early 1856 he became a captain for Colonel Jack Allen ' s Kentucky Rifles , a group under William Walker . At the Siege of Granada , Nicaragua ( November 24 – December 11 , 1856 ) , he was seriously wounded . After the initial seven states seceded from the United States to form the Confederate States of America , Anderson journeyed in March 1861 to the then - capital of the Confederacy at Montgomery , Alabama , to volunteer the services of several Kentuckians for the Confederate Army . On April 17 , 1861 , Anderson took his " Davis Guards " to New Orleans , where they were originally assigned to the First Louisiana Infantry . He was quickly promoted from Captain to Major of the First Kentucky Infantry ( July 19 , 1861 ) in Virginia to Lieutenant Colonel of the Third Kentucky Infantry in the Western Theatre of the War on October 25 , 1861 . He assisted in the evacuation of the Confederate government of Kentucky from Bowling Green , Kentucky in February 1862 . Once again , he would be seriously wounded at the Battle of Shiloh , and would resign his commission on May 24 , 1862 . He briefly returned to the Confederate Army as a staff officer , but eventually tired of it . He took an Oath of Allegiance to the Union cause to Union Brigadier General Jeremiah T . Boyle . However , he was now a social outcast to those with Southern sympathies , and he was followed continuously by Union detective s . There is some belief that he joined the Copperheads or Confederate " Sons of Liberty " afterward . He was involved in Thomas Hines ' plans to free Confederate prisoners in Chicago ' s Camp Douglas , but he may have been a double agent . By October 1864 , he came back to Louisville , where he and General Boyle became partners in an oil venture . On December 18 , 1864 , he was arrested for his part in Hines ' activities . During January 1865 he and seven others were tried on conspiracy charges for the actions involving the attempt to free prisoners at Camp Douglas . Feeling he had betrayed the Union people whom he befriended , and renouncing the Confederate cause , he said he " would prefer being dead than disgraced " . He shot himself in the head while in jail in Cincinnati on February 19 , 1865 , and remained in pain until February 21 , when he died . Of the others , two were acquitted , one was hanged , one escaped before being hanged , and the other two served 3 – 5 years at the Ohio Penitentiary , the judgment being made on April 19 , 1865 . He is buried in Cave Hill Cemetery in the Anderson family plots .