Chipley was raised in Kentucky, and as a young man attended the Kentucky Military Institute and Transylvania University. After graduation, he joined the Confederate Army, enlisting in the 9th Kentucky Infantry. He was promoted to the position of lieutienant colonel, and saw action, and was wounded, at the battles of Shiloh and Chickamauga. On July 20, 1864 at the Battle of Peachetree Creek, Copley was taken prisoner by Union troops and was taken to Johnson's Island on Lake Erie in Ohio where he remained until the war was over. Upon his release he moved to Columbus, Georigia and married.
In 1868, Copley was implicated in the assasination of George W. Ashburn. The Ashburn Affair occured while Georgia was still under military rule, and happened after Ashburn, a newly appointed Georgia judge who had remained loyal to the Union during the Civil War, was murdered by five "well-dressed men wearing masks." The accused murderers were among some of the most prominant white citizens of Columbus, Ga. Chipley and the rest of the accused were represeted by the former vice -president of the Confederacy, Alexander Stephens, and was found not guily. The federal goverment admitted that the prosecution lacked evidence and apologized to Chipley.
After the Ashburn Affair, Chipley became involved with the railroad industry and built the Columbus and Rome Railroad and also played a role in the Baltimore and Ohio Railroad. In 1876 he moved to Pensacola, Florida and not only built the town's first railroad, a line that would eventually connect with the Louisville and Nashville Railroad, but also built the Pensacola and Atlantic Railroad, linking the eastern coast of Florida with the Gulf Coast states.
He served as the mayor of Pensacola from 1887 to 1888, and in the Florida State Senate from 1895 to 1897. He ran for an unsuccesful bid for the United States Senate in 1896, losing by only one vote.
During a trip to Washington, D.C. to lobby lawmakers to bring more industry to Florida, Chipley died.