During the time of Prohibition, Estill Springs was home to prominent local mobster and bootlegger Parker Jones. Parker and his gang took advantage of the heavily wooded terrain to distill their bootleg booze. Parker and his men also used Estill as their primary logistics hub to traffic the booze through Middle Tennessee, Alabama and Georgia. Jones remained in Estill for several years, "owning" mayors, city councilmen, and police officers. The government dispatched dozens of revenue agents to arrest him and his men. However, when they finally arrived at his hideout, they found nothing and Parker was never seen in Estill again.