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.

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.

Rebel Rose worked by providing the Union military movements to the Confederates before the Battle of Bull Run, and they relied on her for further information. As written in an article by Smithsonian Institution,

…she used her ample charms and guile to pass along to Confederate officials information on the defenses of Washington and Union troop movements. She is credited with alerting the rebels of enemy military operations just prior to the Battle of Manassas.

Meanwhile, in the Union, soon-to-be-famous detective Allan Pinkerton was assigned to the Secret Service, and one of his first tasks was to monitor O’Neal Greenhow. Pinkerton kept a close eye on her visitors and eventually confirmed that she was, in fact, working for the Confederates and was placed under arrest. Several documents in her house further confirmed the suspicion, and in January 1862, she was transferred to the Old Capitol Prison, with her youngest daughter allowed to stay with her.

She was released from prison four months later, and she went straight ahead on a diplomatic mission to Europe still for the Confederacy. There, she met with Queen Victoria and some other aristocrats. She also wrote her memoirs while in London, titled “My Imprisonment and the First Year of Abolition Rule at Washington.”

Death by Gold

Before Rose traveled back to the United States, she was able to sell her memoirs. When she boarded a British blockade runner that would take her home, she had both military dispatches and $2,000 worth of gold sewn into her dress.  USS Niphon, a Union gunboat, rammed the ship, and O’Neal Greenhow somehow managed to escape aboard a rowboat. Soon, her escape boat capsized, too, and Rose drowned after being pulled down by the weight of more than 6 pounds of gold sewn into her already heavy dress.  While 6 pounds doesn’t seem like a lot, it’s dead weight in water, unlike the body which floats pretty well.  If you don’t believe us, take a 5-pound weight in the pool and see how hard it is to swim with that extra weight. Just stay in the shallow end, okay?

Her remains were buried in Wilmington, North Carolina, with a tombstone that says, “Mrs. Rose O’Neal Greenhow. A Bearer of Dispatches to the Confederate Government.”