When the North and South were locked in the death struggle of the Civil War, spies made a major contribution to the war effort on both sides.  One of them was Rose O’Neal. While one might expect that she’d be working for the Union side since she spent much of her adult life in Washington, DC, she actually became a fierce secessionist who spied for the Confederacy. The plot twist of her life story? She died because of the gold sewn into her dress that she was trying to smuggle.

A Life of Privilege

Rose O’Neal was the third out of the five daughters of John O’Neal and Eliza Henrietta Hamilton. Their family owned a plantation in Montgomery County, northwest of Washington, DC. Rose was just four years old when her family’s valet murdered her father, and so her mother raised them before she moved in with her aunt Maria Ann Hill in Washington DC in 1830. Maria had a popular boarding house that allowed Rose to meet prominent Washington DC figures, one of whom was a Virginian lawyer, doctor, and linguist named Robert Greenhow Jr. and would soon become her husband.

Mrs. Rose Greenhow. (Mathew Benjamin Brady, Public domain, via Wikimedia Commons)

Their marriage took Rose all over the country, from Washington DC, where Robert worked for the US Department of State, up to Mexico City when they moved there in 1850. They again moved to San Francisco, California, just two years later, and then back to the East Coast in 1853. A year later, Robert was killed in an accident and left Rose to care for their four daughters.

Rebel Rose

Raised in a slaveholding family, Rose decided to become an advocate for secession after her husband’s death. Her stand was solidified when she met Senator John Calhoun of South Carolina, who became his friend. Soon, Army Captain Thomas Jordan, a sympathizer from the South, approached and asked her if she wanted to be a part of the network of spies in Washington DC, to which she agreed.