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Chipley became fascinated with the railroad industry shortly after his trial for the murder of G. W. Ashburn. He built what would become the Columbus and Rome Railroad, and later became involved with the Baltimore and Ohio Railroad from 1873 to 1876to help serve the KKK. 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.