On September 14, 2023, Greg May discussed his eye-opening new book, A Madman's Will: John Randolph, Four Hundred Slaves, and the Mirage of Freedom, about a sensational antebellum Virginia will that freed almost 400 people from slavery. John Randolph of Roanoke—one of Virginia’s best-known statesmen—was a relentless defender of the slave states’ rights, so his deathbed declaration that he wanted to free the people he enslaved took nearly everyone by surprise. But it soon emerged that Randolph had left inconsistently written wills. His lifetime of eccentric behavior gave his heirs ample room to claim that none of Randolph’s wills was valid because he had been mad. The resulting litigation took twelve years. It gives us vivid insights into the intimate lives of antebellum Virginians and a wholly unexpected look at how Virginia’s courts dealt with questions concerning slavery. Although the courts ultimately upheld the will that freed Randolph’s slaves, the story does not have a happy ending. Virginia law required the new freedmen to leave the state, and before they could settle 3000 acres purchased for them in western Ohio, a mob of angry white farmers drove them away. Gregory May is a historian who writes about the early American republic. He graduated from William and Mary and Harvard Law School, clerked for Justice Powell on the United States Supreme Court, and then practiced law for thirty years. He is the author of Jefferson’s Treasure, a political biography of Treasury Secretary Albert Gallatin. The content and opinions expressed in these presentations are solely those of the speaker and not necessarily of the Virginia Museum of History & Culture.