Confederate Spy Rose Greenhow Influences Characters in Avenue of Betrayal

by Sandra Merville Hart

Avenue of Betrayal, Book 1 of my new “Spies of the Civil War” series, releases on February 8, 2022. Here’s a bit of historical background for the story.

Though the series is about a fictional family, there are actual historical spies who touch the stories.

Avenue of Betrayal is set in Washington City (Washington DC) in 1861, where a surprising number of Confederate sympathizers and spies live.

Perhaps the most famous female Confederate spy who lived in Washington DC when the Civil War began was Rose O’Neal Greenhow. When many other Southerner sympathizers left, the widow remained with her eight-year-old daughter, Rose. Colonel Thomas Jordan asked Rose to be an agent shortly before leaving the city to fight for the South. Spying to uncover troop movements and government communications appealed to her. She agreed to send messages based on a cipher he provided.

Coded messages were sent on a “Secret Line,” which involved several couriers in a chain that passed on messages in common places such as docks, taverns, and farmhouses.

Rose’s spy network from Boston to New Orleans was the largest in the war—48 women and 2 men. She learned battle plans for Bull Run and passed this vital information to Confederate General Beauregard. The First Battle of Bull Run was a Confederate victory.

Several other messages about Washington’s defenses and troop information were sent from Rose to Beauregard. Thomas A. Scott, Assistant Secretary of War, asked Allan Pinkerton, head of Lincoln’s Intelligence Service, to find Confederate spies and put Greenhow under surveillance.

About a month after the First Battle of Bull Run, Pinkerton discovered incriminating evidence. The home was searched. Rose and her daughter were placed under arrest at her home. Because she managed to get other secret messages out, they were moved to Washington’s Old Capitol prison. The Federals decided to send her South.

On June 4, 1862, she arrived in Richmond, where she was taken to the best hotel. Confederate President Jefferson Davis called on her the next day, saying, “But for you there would have been no battle of Bull Run.” Rose wrote that his words made up for all she’d endured.

Rose’s real-life story influences the fictional characters in Avenue of Betrayal.


Monson, Marianne. Women of the Blue & Gray, Thorndike Press, 2018.

Winkler, H. Donald. Stealing Secrets, Cumberland House, 2010.

Zeinert, Karen. Those Courageous Women of the Civil War, The Millbrook Press, 1998.