Secret Agents in Hoop Skirts

This post originally appeared in September, 2017, and has been updated. 

As March is Women’s History Month, it’s a perfect time to revisit the role so many women played in the Civil War. Since women weren’t allowed to fight on the battlefield, many of them worked behind the scenes passing on intelligence on battles and strategy. Since ladies didn’t normally engage in affairs outside the home, they weren’t considered a threat, which perfectly hid their activities. One of the best of these was Elizabeth Van Lew.

The Civil War was a trying time in America’s history, and brought out the best and worst in people. The nation divided itself into North and South, with the livelihood and culture of the South hanging in the balance. A person’s sensibilities on the issue of slavery did not always necessarily align with their state’s position on the matter.

Female spies on both sides of the conflict were known as secret agents in hoop skirts. Historian Elizabeth Leonard, author of All The Daring of the Soldier: Women of the Civil War Armies, claims “One of the things that made women so effective as spies during this time period was that few people expected them either to engage in such ‘unladylike’ activity, or to have the mental capacity and physical endurance to make them successful.”41jOmt0slzL._AC_US436_QL65_

Out of the hundreds of female spies on both sides of the conflict, some played a prominent role in the war. One of these was a spy for the Union named Elizabeth Van Lew, or Crazy Bet, as she was better known. Elizabeth was born in 1818 in a huge mansion on a hill in Richmond, VA where her father owned a successful hardware store.Elizabeth_van_Lew_Mansion Elizabeth quickly became the most stubborn of the three offspring in the family. Her parents were from the north, and sent Elizabeth to Philadelphia for her schooling. There she also developed strong abolitionist feelings. She returned to her Richmond home after school, and her father died shortly thereafter. She convinced her mother and brother to free their slaves, some of whom she also paid to educate, all in direct opposition to the way Richmond leaned in the war effort.

When war broke out, Elizabeth and her mother began their humanitarian services, visiting Union soldiers being held captive in Richmond’s Libby Prison and plying the guards with gingerbread and buttermilk. The commanding officer of the prison was David Todd, a half-brother to Mary Todd Lincoln. One of her former slaves whom Elizabeth gave an education to also enlisted in the underground spy ring, coming back to Richmond to become a maid in Jefferson Davis’s home, where she passed on to Elizabeth tidbits she overheard.


Elizabeth Van Lew

As part of her disguise, Elizabeth pretended to be slightly off in the head, hence the name “Crazy Bet.” She played the part, dressing in unflattering clothes, not washing her hair, and mumbling to herself. The Confederate soldiers who were in charge of the prison took no notice of the woman and talked openly in front of her. She was able to gather valuable information for the Union, while also smuggling out letters and helping some men escape.ElizabethVanLewSecretRoom

Her cleverness was noted by Union General Benjamin Butler, who enlisted her aid as a spy in 1863. She then put together a network of more than a dozen helpers, many of whom were her former slaves. Elizabeth used a lot of the standard tricks of the day–invisible ink, hollowed-out eggs, hiding coded messages in plain sight. She became one of the most successful Union spies of the war. So skilled was she at spying General Grant wrote to her, “You have sent me the most valuable information received from Richmond during the war.”

When the war ended, and Elizabeth’s part in the Union victory was revealed, she was unwelcome in her hometown of Richmond. She asked for all her missives during the war be returned to her, and she promptly destroyed most of the evidence of her involvement. One message survived, showing her attention to detail and how important her work had been:

DEAR SIR, — It is intended to remove to Georgia all the Federal prisoners; butchers and bakers to go at once. They are already notified and selected. Quaker [a Union man whom I know] knows this to be true. Are building batteries on the Danville road  … Do not underrate their strength and desperation. Forces could probably be called into action in from five to ten days; 25,000, mostly artillery. Hoke’s and Kemper’s brigades gone to North Carolina: Pickett’s in or about Petersburg. Three regiments of cavalry disbanded by General Lee for want of horses. Morgan is applying for 1,000 choice men for a raid.”


She was awarded the post of postmaster of Richmond by Ulysses S. Grant, but that post was later rescinded. She had used all her family’s wealth in pursuit of her spy efforts and depended on others to provide for her until her death in 1900. She was posthumously inducted into the Military Intelligence Hall of Fame in 1993.


Becky Lower writes mostly American historical romances, but occasionally crosses the pond to England to import her characters to the States. In addition to History Imagined, she has a weekly blog at

While doing research for a new American historical series, she was surprised to find many female spies during both the Revolutionary War and the Civil War. Becky would probably have become one of these secret agents in hoop skirts had she lived a couple centuries ago.

Click here to find out more about Becky’s books: