The first Union flag to wave over Richmond in four years was raised in 1865 by this famous and effective Union spy. Born into a prominent Richmond family, Elizabeth Van Lew returned from her schooling in Philadelphia as an adamant abolitionist determined to fight slavery in the bastion of the South. “Slave power,” she wrote in her diary, “is arrogant, is jealous and intrusive, is cruel, is despotic.” Outspoken and rebellious, she appeared to her neighbors to be more than a little eccentric and soon became known as “Crazy Bet.”
After Virginia seceded and Fort Sumter fell, she used her reputation for innocuous idiosyncracy as a shield behind which her shrewd and resourceful mind devised schemes to abet the Union cause from within Richmond. Her first target was the Confederate Libby Prison, which imprisoned Union captives. Pretending to make a merely humanitarian gesture, Van Lew brought baskets of food, medicine, and books to the prisoners. What she brought out would have shocked the guards she learned to charm and deceive.
Not only did Van Lew help some prisoners escape, she also gleaned valuable information from various sources inside the prison. Newly arrived Union prisoners secretly recounted the strength and dispositions of Confederate troops they had seen on their way from the front to Richmond. Of even more use was information carelessly conveyed to the “harmless Crazy Bet” by Confederate guards and by the prison’s Confederate commandant, Lieutenant David H.Todd (Mary Todd Lincoln’s half-brother).
She even managed to penetrate the home of President Jefferson Davis by convincing one of her former servants to secure a position in the Davis household staff. At first, Van Lew simply mailed the information she retrieved in letters posted to Federal authorities. As her work continued, her methods grew more sophisticated. She devised a code involving words and letters that prisoners would underline in the books she lent them.
Van Lew also sent her household servants–though she had freed the family’s slaves, many of them chose to stay with her–northward carrying baskets of farm produce. Each basket held some eggs, one of which contained encoded messages in place of its natural contents. She sent her information directly to Benjamin Butler as well as to Grant through an elaborate courier system. It was so fast and effective that General Grant often received flowers still fresh from his spy’s large garden. Grant would later say of her efforts, “You have sent me the most valuable information received from Richmond during the war.”
After the war, President Grant rewarded Van Lew with a job as postmistress of Richmond, which she held from 1869 to 1877. Although revered in the North, she was, needless to say, ostracized by her Richmond neighbors. “No one will walk with us on the street,” she wrote, “no one will go with us anywhere; and it grows worse and worse as the years roll on.” Failing to be reappointed postmistress under Rutherford B. Hayes, she lived on a annuity from the family of a Union soldier she bad helped in Libby Prison. She died in Richmond, probably in 1900.