City Cast DC logo

Meet Confederate Spy Rose O’Neal

Posted on February 25, 2025   |   Updated on September 30, 2025
Kaela Cote-Stemmermann

Kaela Cote-Stemmermann

Rose O'Neal Greenhow and her daughter Rose, photographed at Old Capitol Prison in Washington, D.C. in 1862.

Rose O'Neal Greenhow and her daughter Rose, photographed at Old Capitol Prison in Washington, D.C. in 1862.  [Mathew Brady Studio/Library of Congress]

D.C. has long been a bastion of spy activity for both international and domestic parties. But long before opposition research and party spies became commonplace, D.C.’s right-leaning spies needed a little more finesse.

Rose O’Neal was born on a rural farm in Montgomery County and became one of Washington’s most powerful women and notorious spies.

As a young girl, she joined the ranks of D.C.’s socialite scene, with many famous Washingtonians like First Lady Dolley Madison and high-ranking military officers. When the Civil War broke out, she quickly aligned herself with the Confederacy and used her connections to pass key information to Southern generals. She even ran a pro-Southern spy network in D.C.

When she heard of the Union Army’s plan to advance on Manassas, she hid a coded message in the hair of a conspirator, who then warned Confederate troops. This information secured the Confederate victory at the First Battle of Bull Run.

City Cast

The Dark and Twisted Pasts of D.C's Famous Sites

00:00:00

“She was known to be very beguiling, and she was seductive and attractive,” local author JoAnn Hill told us. “She used her looks as an asset and would do whatever she needed to do to get information.”

The Old Capitol prison on Capitol Hill.

The Old Capitol prison on Capitol Hill. (Photograph by William Redish/Library of Congress).

Despite her ability to solicit information, O’Neal wasn’t very good at hiding it. Incriminating documents were found in her home, and O’Neal and her daughter were thrown into the Old Capitol Prison (where the Supreme Court now stands).

But she kept spying. O’Neal sent messages out by waving handkerchiefs and burning candles in her window. After she was released, she went on international missions for the Confederacy, until she died trying to escape a Union gunboat with $2,000 in gold sewn into her dress.

More Dark DC History Stories

Share article

Hey DC

Stay connected to City Cast DC and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

DC History

See All
DC HistoryMarch 30

The Rise & Fall of DC’s Iconic Wrestling Institution

At the height of the Great Depression in 1935, a small-time D.C. wrestler named Joe Turner opened what would become the city’s most succe...

 Joe Turner's arena
DC HistoryFebruary 17

Washington DC’s First Chinese Restaurants

D.C.’s Chinatown is a bit lackluster in terms of authentic cuisine, but that wasn’t always the case. Restaurants were some of the first C...

Port Arthur restaurant, Washington D.C. The largest Chinese restaurant in the city in 1909, owned by early restaurateurs Ung Wah. (Streets of Washington/Flickr)
DC HistoryJanuary 27

How This Storm Compares To DC’s Largest

Sunday’s snowstorm in D.C. was remarkable, not only because of how much snow we got but because the combo of cold temps and sleet means i...

Horse-driven sleigh on a snowy path near the Lincoln Memorial (Bettmann/ Getty Images)
DC HistoryNovember 18, 2025

6 Spy Sites In Washington, DC That Changed History

This nondescript park in Foggy Bottom, close to the State Department, has seen its fair share of spy activity.

Peirce Barn 1972. (HABS Survey/NPS)
DC HistoryOctober 23, 2025

DC’s Secret Séance History

In Gilded Age Washington, D.C., séances and Ouija boards weren’t just parlor tricks — they were part of a craze that swept through societ...

An illustration from the 19th century of a spiritual séance. (clu/Getty Images)
DC HistorySeptember 23, 2025

From The Archive: How DC Became a Showcase of Brutalism

Love them or hate them, Brutalism has become a central part of D.C.’s iconography over the years. Here's why.

DC Metro ceiling. (Ralph Grunewald/Getty Images)
DC HistoryAugust 26, 2025

The Glen Echo Carousel that Became a Civil Rights Movement

Tucked away in Glen Echo Park is one of the world's most elaborate and historic carousels that played a surprising roll in the Civil Righ...

The Glen Echo Dentzel carousel gets a last minute touch up before the season's inaugural ride. (The Washington Post/Getty Images)
DC HistoryAugust 11, 2025

The Wildest DC Political Scandals (That Didn’t Happen on Capitol Hill)

Case in point: the ongoing drama surrounding Ward 8 Councilmember Trayon White, who said on Friday (during his swearing-in ceremony after...

Portrait of Washington DC Mayor Marion Barry

The latest in DC

DC, Explained

How Adams Morgan Got Its Name

How community members gave Adams Morgan and a uniting cause.

A rooftop view of homes covered in snow.
Food & DrinkApril 15

DC's Best New Restaurants and Bars

Welcome to our rolling list of all the best new restaurants opening in Washington, DC!

Steak at Bazaar Meat by José Andrés. (Photo by Liz Clayman)
DC's BestApril 14

DC Blooms Better Than the Cherry Blossoms

The city is filled with flowering trees and bushes that get overlooked thanks to the spotlight-stealing cherries.

Gardens at Hillwood Estate. (Photographed by Erik Kvalsvik/ Courtesy Hillwood Estate, Museum & Gardens)
Local CivicsApril 13

Why the Holocaust Museum Self-Censored Before Trump Even Asked

The Holocaust Museum has been quietly changing its content since President Trump returned to office to avoid drawing the administration’s...

The United States Holocaust Memorial Museum. (ajay_suresh/Wikimedia Commons)
Food & DrinkApril 9

DC's Top Food Critic’s Favorite Spots

The food critic at the Washington Post has long been seen as an all-powerful — and totally anonymous — figure in the local restaurant ind...

Washington Post food critic Elazar Sontag. (Photo courtesy of Elazar Sontag)
Neighborhood GuidesApril 8

Get to Know 11th Street NW in Columbia Heights

11th Street in Columbia Heights is one of my favorite hangout spot in the District. You can garden, snack on crispy pig ears, and grab fr...

11th Street NW, Columbia Heights. (Google Maps)
DC, ExplainedApril 6

Inside the Story of Elon Musk’s Failed DC Hyperloop

Before Elon Musk's DOGE there was his fantastical hyperloop. But, it went down as one of the biggest transport flops in D.C. history. We...

President Donald Trump speaks during a news conference with Elon Musk. (The Washington Post/Getty Images)
DC, ExplainedApril 2

Mosh Madness: DC’s Next Big Music Festival Is Also a Basketball Tournament

Mosh Madness, D.C.’s premier music festival slash basketball tournament is back for its second iteration this spring. On April 11 the DMV...

Pretty Bitter rock as ballers try to block. (Photo by Bailey Payne)