History Behind the Story #10: Rose O’Neal Greenhow
Spoiler alert! In Southern Rain, my historical heroine, Shannon, is recruited by a respectable society matron-turned spy for the Confederacy. I had always known Rose O’Neal Greenhow was a spy, but it had never really struck me how huge it was that she was at the top rung of society in Washington, D.C. and yet still doing quite a bit more than dabbling in espionage. She also always struck me as a bit shady, but is that accurate, or just a reflection of history-telling that has dubbed her as “unladylike?” Let’s delve into her story, shall we?
Maria Rosetta O’Neal was born in Maryland in either 1813 or 1814 (there is some dispute about this). Reports differ as to which of her parents died first, but we do know that it was upon her mother’s death when she was about 13 that Rose, as she was called, was sent along with her sister to Washington, D.C., to live with relatives.
When Rose was about 21, she married Dr. Robert Greenhow, “a federal librarian and translator with medical and law degrees.” I have also seen him labelled as a historian. Rose hobnobbed with the elite in Washington, including Dolley Madison. Rose was, apparently, involved in political intrigues, one involving Cuba, before the Civil War, and she made it a point to befriend politically powerful men, like John C. Calhoun and James Buchanan.
Robert was transferred to the West Coast in 1850, where Rose lived for a few years before returning to Washington, D.C. to give birth to her fourth child, understandable since she was by that time around 40, and she would want to be near friends and family. But tragedy struck when her husband fell from an elevated sidewalk in California and died from his injuries in 1854, leaving Rose to raise their 4 daughters alone.
Rose did get a pension, since her husband had been a Federal employee, so she bought a house not far from the White House and resumed her role as society hostess. She was a friend to politicians on both sides of the aisle, and she was always politically active. She campaigned for James Buchanan and helped him get elected.
Keep in mind that, at the outbreak of the Civil War, she was in the stage of life (her late 40’s) when most women in her era would be contemplating being grandmothers and slowing things down a bit. Not Rose. She instantly sided in her heart with the Confederacy and became a spy. Some sources say that she was recruited by U.S. Army Captain Thomas Jordan, who set her up as a spy before leaving the U.S. military and going to join the Confederate military. Rose stayed in Washington when most Southerners had evacuated, so she was obviously presumed to be on the side of the North. With her many political connections, she was in a position to hear anything a gentleman in power might accidentally let slip.
It was through Henry Wilson, a Senator on the Military Affairs Committee, that Rose heard that the Union Army was concentrating its forces in a plan to converge on Manassas, Virginia. It wasn’t Shannon Ravenel whom Rose ended up drafting, though. 😊 It was a young woman named Bettie Duvall, who allowed Rose to hide a ciphered note in her hair. Bettie then snuck out of Washington dressed as a lower-class farm woman and made her way to Fairfax Court House, Virginia, which was occupied by Confederate troops. She startled Confederate officers by unravelling her hair and pulling a note from its confines. They decided to trust her and, thus armed with knowledge of Union General McDowell’s plans, were able to consolidate their own forces and meet the attack at Manassas, and to win.
I think one thing that I never really realized was how extensive Rose’s spy network was. I always imagined her passing along notes when she could, doing a dab here and there. But her network consisted of 48 women and 2 men and spanned several states. That’s 50 employees – that we know of. It was not at all unlikely that she would try to recruit someone like Shannon, a young woman with Confederate sympathies who was married to a Union officer.
In addition, Rose’s network wasn’t just extensive, it was sophisticated. She used an intricate cipher to code and decode messages. It survived and was able to operate through both of her imprisonments.
But Rose did have a weakness: she wasn’t the greatest at storing her information. She kept extremely incriminating documents in her home, such as reports, maps, burned papers, and copies of messages to Beauregard.
So, this was all evidence against her, but how did she initially get busted? Thomas A. Scott, an assistant to the Secretary of War, received an anonymous tip that Rose was a spy. The North had just formed the Union Intelligence Service, with Allan Pinkerton as its director. He was assigned to personally monitor Rose, an indication of how much damage the Union felt she was capable of inflicting, since Pinkerton was also the go-to man for McClellan’s Army of the Potomac in collecting very important information like how big the Confederate armies they were going to face would be.
I am going to quote one of my sources, since it gives such a vivid account, on what happened next. “On August 22, 1861, Pinkerton cased Greenhow’s house and noticed a young Union officer entering. Standing on the shoulders of a fellow officer, he spied into the front parlor and noticed the officer and Greenhow speaking in hushed tones and looking over a map of Union fortifications. Pinkerton waited until the officer left the residence and tried to flag him down. When the officer ran, Pinkerton followed. Unfortunately, the officer ran to the provost-marshal station and had Union soldiers arrest Pinkerton. He was thrown into a holding cell in a nearby guardhouse. By bribing a guard, Pinkerton was able to send a message to Scott about what he just witnessed. Scott summoned Pinkerton to the War Department and, after confirming his story, arrested the officer immediately.
“The War Department then went after Rose. As she was returning from a walk the next day, Rose was approached by Union soldiers and arrested. The soldiers then searched her house. The map of Union fortifications that the officer showed her yesterday was found with other incriminating materials and Rose was placed under house arrest with her youngest daughter ‘Little’ Rose. Other raids of Confederate-sympathizers and spies were conducted in DC in the following weeks and suspected spies, like Rose’s friend Eugenia Phillips, were imprisoned in Rose’s home. The house became known as ‘Fort Greenhow.’” John Thomas’s fears for Shannon in that scene at the end of Southern Rain were very real, then: if she had been involved, it was quite likely she would have been arrested and imprisoned along with Rose.
Now, keep in mind, this imprisonment of Rose was in her own home, with her youngest daughter allowed to remain with her. That seems pretty gracious of the Union to me, given the swift and rough justice usually applied to spies. I think the trouble was that they didn’t quite know what to do with Rose. You have this society lady in beautiful clothes, who knows all the “best people,” and she has connections everywhere. This probably put the authorities in a very difficult position. They would look like monsters if they imprisoned her in a real prison, and no one would ever believe how much damage she had done. If found guilty, hanging her was out of the question. It wouldn’t be until after the assassination of Lincoln that a woman would be sentenced by the federal government to die by hanging. And, if I’m not mistaken, the federal government would have had jurisdiction here, for two reasons: 1. Rose was living in D.C., which falls under the federal government’s wing; and 2. She could easily have been tried by the federal government anyway because she would have been accused of treason, espionage, and conspiring against the Union Army. Frankly, Rose could have been sentenced without a trial, since President Lincoln had suspended habeus corpus in certain areas or with certain people in cases involving far less evidence of treason than Rose had given them. “But she’s wearing a hoop skirt!” Someone had to have said that, right?
My big question is: why would Rose have risked so much, especially after getting caught the first time? She was born in Maryland, a state that hadn’t even seceded. There was significant Confederate sentiment in certain parts of Maryland, but Rose hadn’t lived there in a long time. Her home was Washington, D.C. Washington was, to some extent, thought of as a “Southern city,” but no one disputed that it by rights belonged to the Union, and if you were going to be on the Confederate side, you simply needed to leave, as most did (not that I don’t get the brilliance of Rose staying if she intended to become a spy). But I’m struggling to come up with why Rose identified with the South so much that she was willing to put her neck on the line. Her husband had worked for the federal government. One of her older daughters had married a Union officer and urged her mother to stay away from secessionists.
I think it had to be either that she was passionately attached to the South or she was bored. The latter is not impossible. She was a very intelligent woman confined by society to a very limited role. She couldn’t go out and use her skills in a job. She couldn’t openly offer her talents to either military. Could it be that she liked feeling useful, as though her contributions accomplished something? Or at the very least, it seems possible that she liked the suspense and danger involved.
But there was no end to the trouble Rose caused the authorites, even after she was arrested. She continued spying, even after the military and government authorities made concession after concession to her.
Her friend, Mrs. Phillips, was able to convince the authorities to release her to the South, and she continued to communicate with Rose and send information via smuggled letters. She also continued to get information to Confederate authorities for Rose. Sometimes Rose’s Union friends (like Senator Henry Wilson) would drop by and still let information slip! I have to imagine that Rose was just that good at dragging stuff out of people.
Collecting information was her true strength as a spy. Rose continued to communicate with her network by using handkerchiefs of various colors that she would wave out her windows. Some say she used her window blinds and flickers from candles as signals later on. She also smuggled a letter to Secretary of War Seward asking that she be released, a letter she proceeded to copy and send to the South, where it was printed in a Richmond newspaper, much to Seward’s annoyance. So a question arises here: Were the authorities being kind to her and Rose took advantage, or did the authorities never imagine Rose could, as a woman, do any damage while under house arrest and she took the initiative to prove them wrong? What a conundrum!
Anyway, the War Department got annoyed and transferred Rose and Little Rose to Old Capital Prison in January of 1862. Even there, Rose was able to smuggle in a Confederate flag, and she waved it from the prison window. Can’t you just picture her saying, in a honey-accent, “Officer, I’m just a widow in reduced circumstances, imprisoned, away from my home – wouldn’t you just let my friend in to see me, please?” And then, of course, he melts, and then next thing we have is Rose waving the Confederate flag singing, “La la la la la!” from the window. That kind of makes me laugh. And kind of not. She was really pushing it. Maybe she was really secure in the fact that they would never hang a woman? I mean, come on, she had a nine-year-old daughter to think of – she had to have been pretty confident they would never truly press charges.
And it seemed she had good reason. Two of the reasons given for not putting her on trial were that she was so dangerous that she could expose government secrets and that she might make a mockery of government officials. My guess is that the “mockery of government officials” part means that a lot of high-up gentlemen were squirming, knowing that they had let sensitive information fall in Rose’s presence. She had some dirt on people.
She was ultimately released in May, told to go to the South, and informed that she had better not leave the Confederacy. If that sounds crazy to you (the government releasing her and just expecting her to follow their orders), it wasn’t really crazy for the time. Soldiers captured as prisoners by both armies were often “paroled,” meaning that they were told to go home and stay put. Most resources I’ve read says most men followed the terms of their parole.
She was met with great enthusiasm in Richmond, the socialites taking her in, and she even had an audience with Jefferson Davis. But Rose did not stay put. She was sent by the Confederacy on a diplomatic mission to Britain and France. Again, I am torn. It was really bad to violate the terms of her release. On the other hand, she was a woman becoming a diplomat in 1862. Whatever the circumstances, that was a huge accomplishment. And Rose did not twiddle her thumbs on her diplomatic mission! In fact, she became engaged to the Earl of Granville, which is pretty major if you think about how rare marriageable nobility was, and how many ladies would’ve killed to have married into said nobility. While she was there, she penned her memoirs, entitled, My Imprisonment and the First Year of Abolition Rule at Washington.
I had been thinking that, while she might have had slaves, she didn’t have deep economic ties to slavery, like a planter would have. She had been born to a wealthy slaveholding family, but she simply had a house in the City of Washington. And yet, seeing the title of her book, and its snarky reference to abolitionists, her feelings began to be a little clearer to me. Rose was a huge advocate for the Southern way of life, and she was very pro-slavery in sentiment. If the Southern way of life was her abiding passion, that would probably be reason enough for her instantly to side with the Confederacy. Why she repeatedly put her neck on the line is still less clear, unless she just felt that passionately.
In any event, Rose didn’t let even her journey home go to waste. She brought back $2,000 worth of gold for the Confederate cause. She was travelling on a British blockade runner (if you remember from our last History Behind the Story post, the Union Navy formed a very effective blockade of Southern ports). When the ship approached Wilmington, North Carolina, the captain thought he saw Union ships. While he was attempting to escape, the ship became grounded. Rose had two other Confederate agents with her, and all three were worried about being captured, so they requested a rowboat to paddle to shore in. (I’m definitely seeing Rose’s love for adventure coming through.)
But this is where Rose’s story ends. The boat capsized, and Rose drowned. She was given full military honors by the Confederacy (another thing that was highly unusual for a woman), and she was thereafter a “revered symbol for the Confederate Cause.”
I always hesitate to make moral judgments of people who lived in a different time period. But I’m curious: what do you think of Rose? Power woman or dastardly spy? Tell me what you think!
P.S. You can see all of Rose’s captured correspondence at archives.gov here:
Duke University also has a collection here: https://library.duke.edu/rubenstein/scriptorium/greenhow/. At that link is a list of four books if you are interested in pursuing your interest of Rose Greenhow.
P.S. Also, the featured photograph is Rose and Little Rose, captured while Rose was imprisoned at Old Captured Prison. It was captured by the Mathew Brady’s famous studio.
That’s a wrap on our History Behind the Story Series for Southern Rain. But never fear, I’m thinking of doing a similar series covering the history of Northern Fire! Thanks for hanging in there with the series! It’s been fun!
Rose O’Neal Greenhow, https://www.battlefields.org/learn/biographies/rose-oneal-greenhow.
Rose O’Neal Greenhow: American Confederate Spy, https://www.britannica.com/biography/Rose-ONeal-Greenhow.
Confederate Spy Rose O’Neal Greenhow Dies, https://www.history.com/this-day-in-history/rose-greenhow-dies.
Seized Correspondence of Rose O’Neal Greenhow, https://www.archives.gov/research/military/civil-war/greenhow.
 There is some dispute among sources as to how vital this information was to the Confederate victory at Manassas. Some sources say everyone knew the Federals were converging on Manassas. I could see that. But I am also hesitant to believe those sources because there is a certain dismissive tone to them that I have found quite common when a woman’s role in history is the topic, especially if the woman stepped outside of a woman’s then-proper roles. It seems unlikely that Jefferson Davis and the entire South would have regarded her as a heroine if the information she passed along was common knowledge. Confederate General Beauregard later testified that he requested more troops because of the information the ladies passed along to him. If he hadn’t had enough troops, he might have lost the battle – who can say?
 Some sources refer to Rose’s capacity as unofficial, but it seems pretty clear that Confederate President Davis sent her.
 Sources say that the gold was sewn into her dress or carried by her in a satchel and dragged her down into the water. I don’t know why, but that seems a little fanciful to me. I do not doubt the gold was on her person. I do doubt that she would have been able to walk in said dress if she had had enough gold to plunge her to and keep her at the bottom of the ocean. I feel like it’s more likely that she got caught in a current, either caused by the ship or the tides. Or perhaps she couldn’t swim. Or perhaps she got tangled in her hoop skirt. There seem to be so many possibilities.