The Great Libby Prison Tunnel Escape During the American Civil War, Libby Prison in Richmond, Virginia, became one of the most notorious Confederate prisons for Union soldiers. The conditions were horrific — overcrowded rooms, starvation, and disease were common. But in February 1864, a group of determined Union officers decided to risk everything for freedom. Led by Colonel Thomas E. Rose and Major A.G. Hamilton, they spent weeks secretly digging a tunnel using crude tools — knives, spoons, and