Wild Rose - The Life of Confederate Spy Rose O'Neal Greenhow

Rose O'Neale Greenhow with her youngest daughter and namesake, "Little" Rose, at the Old Capitol Prison, Washington, D.C., 1862. Taken by Matthew Brady
In July 1861, a young woman named Bettie Duval, managed to deliver vital information about Union troop movements to General Pierre Beauregard of the Confederate army, stationed near a little town called Manassas in Virginia. She kept the small piece of paper hidden in a small black silk bag tucked in the heavy coil of her dark hair. Where had she gotten the information from? Rose O’Neal Greenhow, a Washington matron, Southern sympathizer, and confederate spy. When Rose heard of the Confederate victory at the first Battle of Bull Run, she always believed that it was her information that made the difference.

What led this widow to take the risk of spying for the Confederacy, and who was Rose O’Neal Greenhow?

Rose O'Neale Greenhow's family owned a small plantation in Montgomery County, in Maryland. Her father John O’Neale was a slave owner, and a drunk. She was born either in 1813 or 1814, her birth was not recorded, and no one is sure exactly when she was born. She was one of five daughters, the middle child, and the one most like her father. She was high-spirited with dark eyes, and a will of iron. Although a man of modest wealth, Rose’s father struggled to feed his wife and five daughters. Lack of money didn’t stop him from tying one on at the local tavern. His favorite hobbies were horse racing, fox hunting, cockfighting and liquor, not necessarily in that order. When Rose was four years old, her father was found dead by the side of the road, after spending the afternoon and night drinking in a tavern. His favorite slave Jacob, who he took with him on outings found him lying in a ditch. Jacob went to find help and a slave named Esther allegedly told him to ‘finish’ him off. Jacob was tried and convicted of killing his master in a drunken rage. Rose’s mother was given $400 compensation for losing her slave to the gallows.

Her mother tried to keep the family together and to save the farm, but after a few years, everything was auctioned off to pay off John O’Neale’s remaining debts. Rose and her sister Ellen were sent to live with the aunt and uncle who ran a boarding house in DC, called Hill’s Boarding House in Washington, DC in 1828 when the girls were both teenagers.

Washington, DC in the 19th Century
The nation’s capitol was nothing like the city we know today. It was squalid, for most of the 19th century it was filled with unpaved sidewalks, with cows and pigs wandering freely through the streets. Because the sidewalks weren't paved dust and mud were everywhere. Gaslight didn’t arrive until 1848. It was so hot during the summer that diplomats who were posted to Washington were given hazard pay. Europeans who came to visit were appalled at what they found. Typhoid and diphtheria ran rampant. Slavery was allowed in the district, although there were a number of freed blacks who also lived in Washington. Unless a congressman or Senator was wealthy enough to have his family with him, most of them lived in boarding houses while Congress was in session.

Rose and her sister were introduced into what passed for Washington society through the connections they made while living at the boarding house. Washington Society chiefly consisted of the families who had lived in Georgetown since the beginning as well as the wives of the members of Congress. Their days were filled with making social calls or spending their time in the visitors’ gallery watching the debates on the Senate floor, which was a popular past-time. These were the days when great orators such as Daniel Webster, Henry Clay and John C. Calhoun took the floor. Women swooned over their favorite orators (unlike today when it is hard to stay awake watching Senate debates on CSPAN).Rose’s older sister Susanna married James Peter who was related to George Washington’s Widow Martha Custis Washington, and her sister Ellen, married a nephew of Dolley Madison, James Madison Cutts. These marriages also helped to bring Rose more and more into Washington society. The next step for Rose was to make a good marriage.

Robert Greenhow, one of the most eligible bachelors in Washington, DC. Greenhow was both a lawyer and a physician, but he grew bored with the practice of medicine. At heart he was a historian and a scholar. He came from a fine Virginia family who was close to President Jefferson. Greenhow was cultured; he’d lived abroad, spoke several languages, and was working for the State Department as a translator and librarian. He was also prone to melancholy and suffered from illness. Like Rose, he had lost a parent at an early age, when his mother was killed in a fire at the theater in Richmond. It was a benefit for the infant Edgar Allan Poe whose mother, a popular actress, had recently died. Rose and Robert were married in 1835. While Rose was gregarious and social, Robert was more comfortable with his books and maps, but they shared an interest in learning and the South. While Robert was not terribly ambitious, Rose was ambitious enough for the both of them. They socialized two or three times a week, and Rose learned to throw glittering dinner parties. Rose was conscious of who the important people to know were and who weren’t. She patterned herself after her idol, former first lady Dolley Madison.

John C. Calhoun
Rose and Ellen met many members of Congress while living with their Aunt and Uncle. Rose became particularly fond of John C. Calhoun from South Carolina. He was a father figure for Rose over the years and she often sought his advice. Vice President under John Quincy Adams and Andrew Jackson, he resigned from the Vice Presidency to run for the Senate. He was part of the "Great Triumvirate", or the "Immortal Trio", along with his colleagues Daniel Webster and Henry Clay.
A strong advocate for states rights, he believed that states should be able to nullify any federal law that they disliked. He and Rose became very close, and Rose nursed him during his final illness before his death in 1850 a few days after the Senate voted to keep slavery out of California. Rose's thoughts about slavery and the South were formed by her time spent with Calhoun. She once wrote about him, "I am a Southern woman, born with revolutionary blood in my veins, and my first crude ideas on State and Federal matters received consistency and shape from the best and wisest man of this century."

Over the next two decades came triumph and tragedy. Rose gave birth to eight children, four of whom died. Robert continued his work at the State Department. He was involved with the mapping of the Oregon Territory, and was sent to Mexico on an intelligence gathering mission. But his career was almost derailed by a backstabbing colleague, who altered a translation that Robert had prepared. In 1849, their second son, Morgan died plunging both parents into a depression, and later on that year, Rose lost their next child, a daughter, soon after her birth.

They decided to make a fresh start out in San Francisco where Robert found a job, thanks to Rose, as an associate law clerk with the California Land Commission. But tragedy had followed them out west. While Rose was back east giving birth to their last child, another daughter named Rose, Robert met with what turned out to be a fatal accident. As he was walking from his office, he slipped off the planked road and fell six feet, disabling his left leg. An infection must have set in because six weeks after the accident, Robert Greenhow was dead at the age of 53.

The next few years were lonely ones for Rose. Her oldest daughter Florence married, and Gertrude and Leila were away at boarding school. Only little Rose was home with her mother. When James Buchanan was elected President of the United States, Rose once again was close to the seat of power. Her niece Adie had also just married Stephen Douglas, the US Senator who had debated Lincoln and run against him for a Senate seat from Illinois. Although the family received a settlement after her husband’s death, the money ran out and Rose had to improvise. She moved to smaller and smaller residences. The charming widow wore black clothing that just emphasized her dramatic coloring that she made herself. She even had several beaus including Senator Henry Wilson of Massachusetts who was quite smitten with her. Rose threw dinner parties, entertaining both Northerners and Southerners but the prospect of war was now very real. When Lincoln was elected as President, the world that Rose had known was now at an end.

With the Southern states seceding from the Union, Rose was eager to help any way that she could. She was recruited by Captain Thomas Jordan who was a quartermaster in the US Army before resigning his post to join the Confederacy. He taught the basic cryptography which she diligently practiced. Although she was no longer in the inner circle, Rose still had connections in Washington which she used to get information to send to the Confederate army stationed in Virginia under Beauregard.

Rose, not being a trained spy, was a little careless. She kept copies of information that she had sent, and didn’t completely destroy information that she had received. Her neighbors became suspicious of her and one of them reported her to Thomas Scott, who was the new assistant secretary of war. Thomas Scott, who had known Pinkerton when he was a vice president of the Pennsylvania railroad, had put him on the case. Allan Pinkerton was sent to spy on her and was caught after he followed a Union officer from her home. It was pouring rain and Pinkerton followed the man in his stocking feet, having removed his shoes to stand on the shoulders of his fellow spies. He was in Washington under an assumed name, Major E.J. Allen, working on counterintelligence. He had set up a network of informants in the South who were sympathetic to ending the Civil War.
Allan Pinkerton (1819-1884)
The founder of the Pinkerton Detective Agency whose emblem was an open eye and the motto 'we never sleep' was a Scottish immigrant from Glasgow, who emigrated to the US at the age of 23 in 1842. He settled in Illinois where he was appointed the first detective in Chicago in 1849. By the time of the Civil War, Pinkerton's agency had solved a series of train robberies which brought him to the attention of Abraham
Lincoln. Pinkerton developed several investigative techniques that are still used today, including "shadowing" and undercover work. Pinkerton served as head of what eventually became the Secret Service in 1861–62 and foiled an alleged assasination plot while guarding Lincoln on his way to his inauguration. He also wrote several popular detective novels based on his exploits. He died in 1884, after slipping on the sidewalk. The Pinkerton Agency continued to be involved in some of the biggest cases in history including Butch Cassidy and The Sundance Kid as well as pursuing the Napoleon of Crime, Adam Worth.

Rose was arrested in August 1861 just as she was preparing to flee to Richmond. She had been alerted by a friend that she was being watched by The Pinkertons. The detectives kept her under house arrest. They ransacked the house searching for evidence. Although they found a large number of documents, including the ones that Rose had sewn into her dress. They missed others that Rose was able to destroy. She found herself a prisoner in her own home, watched constantly, even at night; she had to sleep with her door open. Anyone who tried to visit her was arrested. Soon other prisoners were brought to her house to join her. Rose made things difficult for her guards as well as herself. She complained that her rights were being trampled on, that the food was inedible, that she had no privacy. Lincoln had suspended habeas corpus shortly after the war started. Although she was under arrest, Rose still managed to get information to her string of informants. Unfortunately some of her messages didn’t go through and were added to the pile of evidence against her.

After several months under house arrest, Rose and her daughter were moved to her former childhood home, Hill boarding house, which had been turned into a Union prison. If Rose had thought she was mistreated before, it was nothing compared to the indignities she felt she had to suffer. Although there were other women prisoners, Rose wasn’t inclined to socialize with them because she felt that they were beneath her socially. She also complained about having to share the prison with Negro prisoners. Their prison cell was filled with vermin, Rose would use candlelight to burn the vermin off the wall. She tucked clothes underneath the mattress to make it more comfortable for her little daughter. Somehow she even managed to smuggle in a pistol even though she had no ammunition. She wrote a letter to Secretary of State Seward which ended up being reprinted in both the Richmond papers and The New York Times.

After almost eight months in prison, Rose was finally brought in front of a commission to determine what to do with her. Rose was feisty and defiant to General Dix and the other members of the commission. Without counsel, she demanded to know what evidence they had against her, and complained that her rights were being trampled on. When they presented their evidence, including a letter Rose wrote that gave details of the Union Army’s movements; Rose brazened it out, giving them no satisfaction. Although her actions were treasonable, Lincoln was reluctant to have her stand trial. Treason was a hanging offense but Lincoln had no stomach for hanging a woman, nor did he want to make her a martyr for the Southern cause. Something had to be done though, Rose was considered too dangerous. Rose was given a choice, either swear allegiance to the Union or be deported to the Confederacy. Rose agreed to be deported to the South.

On May 31, 1862, after almost ten months in prison, four months on house arrest, and five months in the Capitol prison, Rose was escorted out of the city that had been her home for more than thirty years. Did she feel a pang as the wagon passed through the streets of the city where she had met her husband, given birth to her children, buried them, the avenues where she had strolled with her beaus, and her sisters? Rose would never see the city again.

Before Rose’s was allowed to set foot on Confederate soil, she had to sign a statement as a condition of her parole that she would never set foot in the North again while the war continued. At lunch, Rose cheekily raised her glass and toasted Jefferson Davis. Rose was hailed as a heroine, a true daughter of Dixie who defied the North. After her arrival, Rose was sent by Confederate President, Jefferson Davis, to Europe to drum up support for the South’s cause. Despite the fact that she suffered greatly from seasickness, Rose was eager to go. She went to France to plead with Emperor Napoleon III and to England where there was sympathy for the Southern cause. Although privately people were sympathetic to the South's cause, Rose could get no one in either Parliament or Napoleon III to publicly come out in support to the South or to recognize the Confederate States. However, she did make the acquaintance of the historian Thomas Carlyle who had written extensively on the slavery question, coming down on the Southern side. They had many long talks during Rose's stay in London.

After placing her daughter Little Rose in the Convent of the Sacred Heart in Paris, Rose decided to return to the States. She had tried her darndest to either win support or to find a way to end the way with the Confederate States remaining a seperate country to no avail. In her first two months abroad, she wrote her memoir, My Imprisonment and the First Year of Abolition Rule at Washington, which sold well in Britain. She also found time for romance, keeping company with Granville Leveson-Gower, 2nd Earl Granville.

Rose drowned off the coast of North Carolina on October 1, 1864 when the ship she was returning, The Condor, ran aground on a fallen freighter. Although the captain advised that everyone stay on board, Rose was frightened of being captured by the Yankees again. She was on her way to shore when the rowboat was overturned by a large wave. Her body was found washed up on shore a few days later. She had been weighed down by the gold sewn into her clothing. When Rose's body was found, searchers found a copy of her book "Imprisonment" hidden on her person. There was a note inside the book, which was meant for her daughter, Little Rose. The note read: 'London, Nov 1st 1863 You have shared the hardships and indignity of my prison life, my darling; And suffered all that evil which a vulgar despotism could inflict. Let the memory of that period never pass from your mind; Else you may be inclined to forget how merciful Providence has been in seizing us from such a people. Rose O'n Greenhow.'
She was given a full military burial, wrapped in the Confederate flag, buried in Oakdale Cemetary, near Wilmington, North Carolina. Her grave bears the inscription 'Mrs. Rose O'Neal Greenhow. A Bearer of Dispatches to the Confederate Government." Every year on the anniversary of her death, a ceremony is held to honor her contributions to the Confederate Cause.

A TV movie, called The Rose and the Jackal was made about Rose O’Neale Greenhow and her arrest by Allan Pinkerton starring Christopher Reeve as Pinkerton and Madelyn Osborne as Rose O’Neale Greenhow which suggests that they were romantically involved or that Pinkerton fell in love with her. Filled with bad Southern accents, the movie should be commended solely for reviving interest in Rose O’Neale Greenhow’s remarkable life. Unfortunately it is only available on VHS.

Rose O'Neale Greenhow was a strong, independent, Southern woman unafraid to speak her mind, in an era, when women were seen as nothing more than decorative. When her beloved South seceded from the Union, she didn't hesitate on taking on the dangerous task of spying for the Confederates. Using her Southern charm she was able to wheedle out information to help the Confederate cause as well as recruiting others to the cause. She was considered one of the most dangerous women in the country. Although her spying career was brief, and there is doubt amongst historians, of how much valuable information she was able to pass on, Rose did make a difference at the Battle of Bull Run.

Sources include:
Wild Rose: The True Story of a Civil War Spy – Ann Blackburn, Random House, 2006
A Treasury of Foolishly Forgotten Americans: Pirates, Skinflints, Patriots, and Other Colorful Characters Stuck in the Footnotes of History Michael Farquhar, Penguin, 2008


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