Elizabeth Van Lew (1818–1900)

Van Lew was born on October 15, 1818, in Richmond, to John Van Lew of Long Island, New York, and Eliza Baker of Philadelphia, Pennsylvania. Despite their Northern roots, the Van Lews owned slaves, lived in a mansion on Church Hill, and belonged to Richmond society. After attending a Quaker school in Philadelphia, however, Elizabeth Van Lew began to develop antislavery views, and following the death of her father, her mother freed some of the family's slaves. When Virginia seceded in the spring of 1861, Van Lew did not succumb to Confederate patriotism as so many other Southern Unionists did. Instead, she immediately committed herself to finding ways to undermine Confederate war aims.

Early in the war, Van Lew and other Richmond Unionists—including John Minor Botts, F. W. E. Lohmann, and William S. Rowley—banded together to form an underground network, which eventually targeted the Confederate prison system in particular. During the summer of 1861, Van Lew and her mother visited captured Union soldiers being held in Richmond prisons. If their motivation was at first compassionate—they brought the men food and tended to their wounds—it soon turned tactical. Prisoners were an important source of information, and Libby Prison, which housed hundreds of Union officers, often in desperate conditions, was located just six blocks from the Van Lew mansion. Van Lew never was able to gain entrance there, however, and instead bribed guards for various purposes, such as having prisoners transferred to hospitals where she might visit them. In several cases, she passed information to inmates using a custard dish with a secret compartment. In 1864, as the head of a Richmond spy network managed by Union general Benjamin F. Butler, she may have helped some of the 109 prisoners who tunneled out of Libby.

Van Lew, codenamed "Babcock," was always meticulous. Before developing her own cipher, she tore important messages into pieces and transported them by multiple couriers and through various relay stations, including a small family farm south of the city. Messages also were hidden in the soles of shoes and the shells of eggs. Still, Van Lew's politics always made her suspect in the Confederate capital. According to many histories, she turned this to her advantage by exploiting people's belief that her Unionism was merely a symptom of mental instability. Supposedly nicknamed "Crazy Bet," she is said to have wandered Richmond in shabby clothes, muttering to herself or singing nonsense songs. Historian Elizabeth R. Varon, however, has argued that no evidence exists for this account of Van Lew's methods. "To remember Van Lew as Crazy Bet is misleading, counterproductive, and indeed unjust," she wrote in her 2003 biography of Van Lew. She argues that Van Lew did her best to maintain a facade as a loyal Confederate, instead exploiting people's belief that a Southern "lady" would never spy for the North. In the end, Varon writes, the Crazy Bet stories fail to credit Van Lew's intelligence and meticulousness. Indeed, that may have been their point.

Mary Richards Bowser, a former Van Lew family slave, also may or may not have used the "crazy" technique in her spying. Van Lew arranged for Bowser to be educated in the north and sent as a missionary to Liberia. During the war, Bowser worked as a servant for Jefferson Davis's family in the Confederate White House, where she collected information and passed it on to Van Lew or other spies.

In March 1864, a month after the Libby escape, Union raiders failed in an attempt to enter Richmond and free additional prisoners. Colonel Ulric Dahlgren, the dashing twenty-one-year-old son of a Union rear admiral, who had lost his right leg at the Battle of Gettysburg (1863), was killed, and Confederates claimed to find on his person evidence that he and his men planned to murder Davis and burn Richmond. Contemporary historians have uncovered support for the charges, but at the time Northern public opinion was inflamed, especially after reports that Dahlgren's corpse was handled disrespectfully. Van Lew herself was so outraged that she risked her entire operation to see that Dahlgren's body was surreptitiously exhumed and properly reburied.

Van Lew remained active in intelligence gathering until end of the war, and when Richmond fell, after the long siege of nearby Petersburg, she came to the aid of wounded civilians, regardless of their politics.

Following the war, Van Lew became involved in Republican politics. In 1869, Grant appointed her postmaster of Richmond, a position she held during his two terms, helping to modernize the city's postal system and employing a number of African Americans. She sponsored a library for African Americans that opened in Richmond in 1876. Van Lew was dismissed as postmaster in 1877, a victim of gender and partisan politics. Partly as a result, in her later years she supported African American rights and woman suffrage.

The elderly Van Lew was treated as a pariah by Richmonders, who, according to her family doctor, "shunned her like the plague." Children, including the future novelist and social critic Ellen Glasgow, were encouraged to see her as a witch, and her Church Hill mansion was said to have been haunted after her death. According to Varon, it was in response to the elderly Van Lew that the Crazy Bet stories may have originated. Van Lew's inheritance, meanwhile, was long gone, spent in the aid of her family's former slaves and her own espionage. When she died on September 25, 1900, a circle of her friends in Boston, Massachusetts, including the family of Paul Joseph Revere, a soldier she had assisted at Henrico County Jail in 1862, paid for her funeral. She was buried in Shockoe Cemetery in Richmond. The City of Richmond acquired and demolished her mansion soon after her death, allegedly out of spite, and built a school on the site.