William Dudley Chipley William Dudley Chipley ( June 6 , 1840 – December 1 , 1897 ) was an American railroad tycoon and statesman . He created two railroads in the Florida Panhandle and served one term as mayor of Pensacola , Florida and in the Florida State Senate . Early life . Chipley was born in Columbus , Georgia , the son of Doctor William Stout Chipley and Elizabeth Fannin Chipley . Chipley ' s grandfather , the Reverend Stephen Chipley , was one of the founding citizens of Lexington , Kentucky . William Stout Chipley was renowned for his work relating to brain diseases and held two jobs : a professor of medicine at Transylvania University and the warden of the Eastern Asylum for the Insane in Lexington . Chipley moved with his parents back to Lexington when he was four years old , and was raised for all of his formative years in Kentucky . He graduated from the Kentucky Military Institute and Transylvania University . Military service . After graduation from Transylvania , he enlisted in the 9th Kentucky Infantry , fighting for the Confederacy . He was elevated to the position of lieutenant colonel and was wounded at the battles of Shiloh and Chickamauga before being taken prisoner at the Battle of Peachtree Creek near Atlanta . As a prisoner of war , Chipley was transported to Johnson ' s Island on Lake Erie in Ohio , and served time there until the war was over . In mid - 1865 , he settled in Columbus , Georgia and married Ann Elizabeth Billups , the daughter of a prominent Phenix City , Alabama planter . Chipley would later be implicated in the Ashburn affair . He was brought to trial , in which the federal government attempted to jail Chipley for his role in the murders of the soldiers he fought during the Civil War . With Alexander Stephens representing the defense , Chipley was found not guilty by a jury of his peers . It was only revealed later that Mrs . Chipley had in her possession a letter Stephens wrote to Chipley , in which the government apologized to Chipley and offered him freedom because the prosecution had no evidence . Chipley turned down the offer , and instead waited for vindication at the trial . Railroad executive . Chipley became fascinated with the railroad industry shortly after the Ashburn affair trial . He built what would become the Columbus and Rome Railroad , and later became involved with the Baltimore and Ohio Railroad from 1873 to 1876 . It was at this time that he moved to Pensacola , Florida , where he built the town ' s first railroad ( this line would eventually become a part of the Louisville and Nashville Railroad ) . He also built the Pensacola and Atlantic Railroad , linking the Atlantic coast of Florida with the Gulf Coast states for the first time . His achievements in the railroad industry inspired the residents of Orange to name their town Chipley in 1882 . Statesman . Chipley created the Democratic Executive Committee in Muscogee County , Georgia in the late 1860s , and was its first director . He later served as director of the Florida Democratic Executive Committee . After opening the two rail lines in Pensacola , he parlayed his industrial success into one term as the mayor of the town ( 1887 – 1888 ) . He also served in the Florida State Senate from 1895 to 1897 , and lost his bid for United States Senator in 1896 by one vote . While on a trip to Washington , D . C . , Chipley died on December 1 , 1897 . He was in the middle of a trip to lobby lawmakers to base more industrial endeavors in Florida . He was buried in Columbus , while the townspeople of Pensacola erected an obelisk in the Plaza Ferdinand VII in his honor .