Rose O’Neale Greenhow

Rose O’Neale Greenhow, Confederate Spy

1817–October 1, 1864


Confederate Spy




Wild Rose, Rebel Rose


“The fate of the slave rests with his Southern Master—as the Masters with God! But will you free him? Never, either extermination or eternal slavery is his lot according to the lights before me.”

Just before dawn on October 1, 1864, a dark shape with three funnels churned through the waters off the North Carolina coast. It was the side-wheel steamer Condor, using the last hours of night to conceal her approach to Wilmington. Defended by Fort Fisher, the port city offered the only surviving sanctuary for Condor and her ilk: Confederate blockade-runners slipping through the garrote of Union warships that was slowly strangling the South to death. Suddenly the steamer’s pilot, fooled by a beached wreck that looked like an enemy vessel, veered rashly and slid up on the shoals, helpless as a fish out of water. Union ships were already circling for the kill, but the skipper assured his passengers that Fort Fisher’s rifled guns would offer protection until the high tide lifted their steamer off the bar.

Several passengers weren’t so sure. One of them, Rose Greenhow, had been a prisoner before and had no wish to reacquaint herself with Yankee hospitality. With a formidable persuasiveness that had duped senators, snared lovers, and charmed royalty, Mrs. Greenhow convinced the captain to let her make a run for shore in one of his lifeboats—to brave the windswept waters in twilight rather than the humiliation of capture. He reluctantly complied, allowing the determined woman to be lowered, along with several other passengers, into a dinghy that was to whisk them to safety. The sea, however, had other plans for the hapless party, sending a breaker over the shoal to strike the boat broadside. In the chaos that ensued, all the passengers swam to safety save one: Rose Greenhow disappeared with the foam, never to be seen alive again.

Being placed under house arrest didn’t stop Rose O’Neale Greenhow from being one of the Confederacy’s most effective spies. She simply sneaked notes and coded messages to her daughter, who would slip them past the Union guards.

It was a storybook end to a storybook life. Though born in Montgomery County, Maryland, to a rather ordinary drunk who would leave his Catholic family little money, Rose O’Neale ended up securing a privileged place in the country’s most powerful circles. Alluring, brilliant, and spirited, she became one of the great provocateurs of the age and a celebrated heroine of her country, driven by a defiant patriotism that was matched only by her scorching race hatred. She has to be one of the most fascinating women in American history.

She certainly was fascinating to her contemporaries. Indeed, the detectives who tracked her movements in 1861 referred to her in their messages as the “fascinating widow.” Rose had become such an engaging character by growing up in one of the most colorful cities in the country. Her mother, stuck with a dead husband and too many mouths to feed, had sent Rose and her sister to live in Washington when they were still teenagers. There they lived with Aunt Maria and her husband, Henry Hill, at Hill’s Boarding House, a popular location for Southern politicians to call home while Congress was in session. After her older sister married into a prominent Georgetown family, Rose found herself attending the same social events as Andrew Jackson and Daniel Webster. She was getting an intimate education in the many-layered world of capital power broking and glad-handing. Moreover, she was doing so from the vantage point of a very attractive young lady of breeding whose long, dark hair and stimulating conversation could make the mostseasoned debaters stumble over their words. Through her sister Ellen, she met and befriended the great Dolley Madison, ageless arbiter of capital society, and developed an unabashed preoccupation with John C. Calhoun, presidential pretender, states’ rights sanctifier, and slavery defender. In time, she would grow close to this ferociously eloquent Southern icon—close enough to tend to him while he lay on his deathbed in 1850.

By that time another man had captured much more than her admiration. Dr. Robert Greenhow, a physician by training and a State Department official by trade (he spoke several foreign languages fluently), met Rose at the altar in 1835 in a Catholic ceremony officiated by the Reverend William Matthews, the first American to be ordained a Catholic priest in the United States. Theirs was a typically worldly Washington match, complete with a diplomatic posting to Mexico City. But in 1854, Robert died after a fall in San Francisco. It was more than just a devastating blow emotionally: For the second time in her life, Rose found herself facing an uncertain future—and this time she had a family to raise.

If she didn’t have lots of money, she at least had lots of friends. Important friends. One of them was James Buchanan, the perpetually womanless Washington operator from Pennsylvania who assumed the presidency in 1857. Few in the city were as close to the Keystone State’s most famous bachelor, and Rose assumed an importance in capital schmoozing that Dolley Madison herself would’ve envied. Stunning in her forties, with an air of seductive mystery and a whiplike retort for every politically volatile observation offered within earshot, the incomparable Widow Greenhow had become as venerated a capital fixture as Lafayette Square. It was under such circumstances that Rose, an earnest student of the Calhoun school of pro-slavery, anti-centralization politics, became a prisoner in her own city.

The Republicans had come to town. Like a rabble of nouveaux riches, they lorded over their secessionist and Democratic opponents, opening the capital gates to all manner of abolitionist filth and their opportunistic lackeys. Such was Rose Greenhow’s view of the 1860 revolution. That shameless “Black Republican” beanpole Lincoln had ruined what had been a most civilized place to live. The good ol’ days of the Buchanan regime were quite over. Warned by her Southern circle to get out of town while the getting was good, Rose stayed. Her daughter Gertrude, racked by typhoid fever, could not be moved. But another reason seemed to compel this most Southern of belles to stay put.

This was her city. Her home. There may have been a changing of the guard, but she wasn’t going to let that intimidate her. When Gertrude died, it marked the fifth child that Rose had to bury. Anchored by long experience and deep emotion, the Widow Greenhow wasn’t going anywhere.

Which is why Thomas Jordan paid her a visit early in 1861. A captain in the regular army, Jordan planned on defecting to the Confederacy and revealed to Rose his plans for building a spy network in Washington itself. She was an ideal addition to his grandiose plans: poised, connected, established. Presented with an opportunity to play a vital role in the struggle against “Black Republicanism,” she responded with enthusiasm. Jordan gave her a cipher code to be used in her messages to him and to other agents in the network, and she committed it to memory. Before long she had recruited a small cabal of fellow spies who reported back to her on military developments in and around the capital, of which there were many indeed. And she herself excelled at seducing information out of contacts in the government, not least of whom was a man who signed his love letters with the letter “H”—probably Massachusetts senator Henry Wilson, though H’s identity continues to inspire debate.

But as important as all this information was, it was nothing compared to the bold stroke that Rose contributed to the Rebel cause in July 1861. Upon learning that Union general Irvin McDowell was heading out to advance on P. G. T. Beauregard’s Rebels at Manassas Junction, Rose sent an accomplice, Betty Duvall, out across the Chain Bridge that linked the capital with Virginia. Duvall, dressed as a simple farm girl, carried a ciphered message in her hair that had been composed by Rose, detailing McDowell’s plan. Beauregard acted on the intelligence by alerting Joseph Johnston, his colleague in the Shenandoah Valley, who proceeded to quickly transfer his troops to Manassas by rail. By the time McDowell arrived at Bull Run, he was facing a much larger force than anticipated. The ensuing Union rout was made possible by the Confederates’ ability to concentrate their forces.

Whether or not Rose Greenhow is responsible for thwarting an early Federal advance on Richmond and ensuring that the rebellion would extend into a four-year bloodfest of catastrophic proportions is debated to this day. General Beauregard, however, was certainly thankful. And Rose’s neighbors, most of whom were pro-Union, did not doubt that she was up to something nefarious. After all, the woman had plenty of male callers, many of whom were in uniform—a very suspicious thing indeed for a house that was openly pro-South. The capital was a lousy place to keep secrets, as Rose herself used to her advantage. And so, alerted by suspicious citizens, the assistant secretary of war called on an old colleague to keep an eye on “Rebel Rose”: Allan Pinkerton.

Pinkerton, the Scottish-born head of the secret service, went about the assignment with his usual aplomb. Despite his formidable reputation, he wasn’t the greatest detective around—indeed, his later intelligence gathering for the Army of the Potomac would prove outrageously inaccurate. Nor were his tactics very original. (In an attempt to gather evidence that Laurel and Hardy would’ve considered ideal material, he once stood bootless and precariously perched on the shoulders of two fellow agents in a Washington downpour while clumsily attempting to peer into the parlor window of the Greenhow residence.) Nevertheless, he was tenacious and resourceful. And Rebel Rose wasn’t exactly the most tactful spy in Washington. In about a month, the intrepid sleuth had enough evidence to move on his quarry. On August 23, 1861, Pinkerton, accompanied by several colleagues, made his move, arresting Greenhow on the street before her residence. “I have no power to resist you,” she sniped upon hearing of her fate, “but had I been inside of my house, I would have killed one of you before I submitted to this illegal process.”

The authorities searched her house, confiscated any and all papers they came across, and put the grande dame under house arrest—which, it soon turned out, proved about as effective as containing a bad stench by enclosing it in chicken wire. Rose continued her clandestine activities right under the noses of her captors. She encoded the needlework she gave to friends, encrypted her conversations with visitors, wrote letters with cleverly worded messages in the clear that not even her censors could detect, and—most effectively—used her eight-year-old daughter, Little Rose, as a go-between. For their part, the authorities added insult to injury by using “Fort Greenhow,” as the house came to be called, as a prison for other female felons, most of whom weren’t the sort of people Rose would’ve associated with willingly. The spy mistress seethed.

Catching on to her activities, the government moved her to Old Capitol Prison, which—in a cruel bit of irony—used to be the boardinghouse in which she grew up with her sister. In fact, Rose was held for a time within the very room in which she nursed Calhoun during his final days over a decade before. Little Rose was incarcerated along with her mother, and the two became heroines throughout the South. Though a trial was arranged, it proved more trouble than it was worth—an opportunity for this spirited beauty to vent her secessionist views and become a martyr. As Lincoln did with many folks who became irritating to his administration, he banished her to the South to let her fellow traitors deal with her.

And deal with her they did. Welcomed as a celebrity, the Widow Greenhow met with President Jeff Davis, whose government gave her $2,500 as a reward for services rendered. In time they would call on her services once again, this time in a much more significant capacity. A year later, in August 1863, Rose Greenhow boarded a famously swift Confederate vessel appropriately named Phantom that was to deliver her safely to Europe. Once there she was charged with pulling off what the Rebel government had hitherto failed to do: convince Great Britain and France that it was in their best interests to actively support the struggling Confederacy. After a three-week stopover in Bermuda (where she noted that “the Negroes are lazy, vicious and insubordinate”), Rose and her daughter were delivered to England, where her most significant accomplishments were the publication of her memoir (My Imprisonment and the First Year of Abolition Rule at Washington), a journey across the channel to meet with French emperor Napoleon III and to enroll Little Rose in Catholic school, and a romantic affair with an unknown Englishman. Her diplomatic efforts, however, were a failure. In short, Rose was too late: By the middle of 1863, the European powers had all but ruled out the possibility of joining the fracas in America. Though feted as a daring and intelligent emissary of Southern culture, her hosts across the Atlantic were loath to do more than enjoy her engaging company. And her unfortunate habit of hotly defending the institution of slavery did nothing for her cause.

And so it was back to her beloved South aboard the Condor, having left her daughter behind to be educated in Europe. When the waters claimed Rose in 1864 off the coast of North Carolina, they were aided by the weight of gold—four hundred British sovereigns, to be exact, worth more than $2,000. The treasure, profits from her memoir, was kept in a bag she had attached to a chain around her neck. It might just as well have been a noose.


House arrest was genuinely humiliating for Rose Greenhow, and not just because she was held prisoner in her own home. The soldiers assigned to guard her weren’t exactly the flower of Union manhood. In fact, some of them were slobs. She wasn’t allowed to lie down for a nap without one of them sitting nearby. And when dressing, she was required to keep the doors open, offering a perfect opportunity for the guard to sate his prurient curiosity. Such conditions would have been hard on anyone, but for a woman as proud as Rose Greenhow, they were almost debilitating. Inherently defiant, she was hardly a demure inmate. Later, while incarcerated in Old Capitol Prison, she lighted a candle one night while rummaging through her belongings. Ordered to put it out, Rose fired up another just to piss off the guards. One of them shouted from the yard that he would fire into her room, but it only inspired her to gather up more candles, light them, and place them all defiantly on her windowsill. When another guard, yelling at her for sending signals from her window, pounded on the door to get her to stop, she simply threatened to shoot the fellow with a pistol. It wasn’t loaded, but nobody knew that. (The prison staff deprived her of the weapon the next morning.)

Enemy Mine

Few people hated Abraham Lincoln more than Rose Greenhow. And yet Stephen Douglas, the “Little Giant” who debated Lincoln so famously in 1858, was her nephew—a nephew who, much to her chagrin, became closer to Lincoln in the months leading up to the latter’s inauguration. In fact, Douglas literally stood at the president-elect’s side and held his hat while Lincoln was sworn in.

As galling as this was to Rebel Rose, it couldn’t have hurt as much as the relationship she had with her own son-in-law. Tredwell Moore, Florence Greenhow’s husband, was a soldier stationed out west when the war began. Though he and Florence expressed sympathy for the South, they were strict Unionists, a fact Florence never failed to mention in her letters to her fire-eating mother back in Washington. Moore hated being stuck in Nevada as the country blew apart and wanted more than anything to become an officer in the Ohio volunteers to fight secessionists. Like everyone else who wanted to secure a commission, he turned to someone with influence—in this case, his mother-in-law. Rose soon found herself in the unlikely situation of writing a letter to Secretary of the Treasury Salmon Chase—a radical Republican—to ask that Tredwell be given the posting and promotion he needed to come east and kill those on whose behalf she was risking her life in acts of espionage. Civil wars are hell.

Moore did end up getting into the war. But his mother-in-law’s precarious financial situation compelled him to send her money on a regular basis—a total of $10,000, according to him, which he and Florence attempted (unsuccessfully) to reclaim from the settlement of Rose’s estate after her death.

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