Few legal cases in American history are as riveting as the controversy surrounding the will of Virginia Senator John Randolph (1773–1833), which—almost inexplicably—freed all 383 of his slaves in one of the largest and most publicized manumissions in American history. So famous is the case that Ta-Nehisi Coates has used it to condemn Randolph’s cousin, Thomas Jefferson, for failing to free his own slaves. With this groundbreaking investigation, historian Gregory May now reveals a more surprising story, showing how madness and scandal shaped John Randolph’s wildly shifting attitudes toward his slaves—and how endemic prejudice in the North ultimately deprived the freedmen of the land Randolph had promised them. Sweeping from the legal spectacle of the contested will through the freedmen’s dramatic flight and horrific reception in Ohio, A Madman’s Will is an extraordinary saga about the alluring promise of freedom and its tragic limitations.