Confederates have boasted of their spies Belle Boyd and Rose Greenhow, but one of the most valuable spies of the war was Elizabeth Van Lew. A proud Virginian and staunch Unionist, Van Lew used her leverage among Richmond’s social elite and Confederate officials to gain entrée to Libby Prison over the objections of warden David Todd (a stepbrother of Mary Todd Lincoln’s). As a volunteer nurse, she delivered medicine and food to sick and starving inmates—who gave her information to pass northward. She helped plan jailbreaks and hid escapees in her home. She even got a black servant, Mary Bowser, hired as a servant in the Confederate White House, where Bowser could overhear what President Jefferson Davis said and read what was on his desk. Eventually Van Lew developed an entire network of informants and established a direct connection with Union officers.
Van Lew’s evident kindness toward Yankee prisoners made her a social pariah—“We had threats of being driven away, threats of fire, and threats of death,” she later wrote—but she persisted, deflecting suspicion by behaving oddly enough to earn the nickname “Crazy Bet.” Yet on April 3, 1865, the day Union troops marched into Richmond, she flew the Stars and Stripes in front of her house, on the 2300 block of Grace Street (where an elementary school now stands). “You have sent me the most valuable information received from Richmond during the war, ” Ulysses Grant wrote to her after the war. As president, Grant gave Van Lew a much-needed job in the Richmond post office. Still, she was “held in contempt & scorn by the narrow minded men and women of my city for my loyalty,”’ she wrote. “Socially living as utterly alone in the city of my birth, as if I spoke a different language.”