The Awesome Life and Strange Death of Leroy Key: The Andersonville Regulator Who Mounted Up

This episode, we delve into the Civil Weird tale of QMSgt. Leroy L. Key. Born in Mississippi to a slave-owning family, he broke away before the war and settled in Illinois—a decision that would shape his future in surprising ways. During the Civil War, Key fought in two regiments, one infantry, and one cavalry. He then was captured in what was called the “Frozen Fight” in Jonesville, VA. After his capture Key became the organizer and de facto leader of a group of Union prisoners known as the “Regulators.” They took it upon themselves to put an end to the brutal reign of the “Raiders,” a gang that preyed upon the most vulnerable among their fellow inmates. Key and his fellow Regulator captains not only dismantled the Raiders’ power structure but also established a rudimentary system of prisoner-led justice—and execution. After surviving Andersonville and the war, he returned to Mississippi, he worked as a lawyer and served in the Freedmen’s Bureau, helping formerly enslaved people secure basic rights and protections during the tumultuous Reconstruction era. Tragically, Key’s life was cut short; he died at age 39, from a possible suicide in Springfield, IL where he left behind a wife and 8 children. Let’s make it Civil Weird!