She is beautiful, beguiling, smart, haughty, politically adept, and willful — a slave owner and a socialite, a Catholic and a fierce anti-abolitionist, a mother of four daughters (one dead in her teens), a widow in middle age, and a confidante of the great men of her time, some of whom are now the enemy.

She was born Maria Rosetta O’Neal and orphaned in childhood when a slave murdered her father. Now she calls herself Rose O’Neal Greenhow. By birth, she is a Marylander, but her dramatic journey will take her at last to the Old North State.

Greenhow is living in Washington, D.C., when secession brings on the war. She is 47, refined and charming, the six-year widow of the soft-spoken Dr. Robert Greenhow, a physician and historian who held a post with the U.S. State Department. As an orphan taken in by her aunt, proprietress of the Congressional Boarding House, she became familiar with many of the leading men of government. Through her husband’s contacts, she has deepened these bonds and come to be on intimate terms with many key players on both sides of the conflict.

Two of these men become crucial correspondents once her social circle is cleaved by war: Jefferson Davis and Gen. Pierre Gustave Toutant Beauregard.

An invitation to a Rose Greenhow dinner party is coveted. She resides on 16th Street, between I and K streets, in a tony section of the city, just a short distance from the dilapidated white mansion occupied by the President of the United States. The company is elite, the wine and spirits the best, the conversation witty and weighty. And the star attraction is always Greenhow herself, her auburn hair fashionably gathered in a shimmering mass behind her head. When let down, it reaches below her knees.

Although Greenhow speaks her mind freely, her greatest gift is listening.

She listens to the chatter at the dinner table as the courses are served and the wine is poured from crystal decanters. She listens as the men smoke their cigars and sip their after-dinner brandies. Later, with some special man, she listens to pillow talk. The man is likely married, with a high position to uphold, but he can trust Greenhow to keep their secret. She is a social climber and no more interested in scandal than he is.

Becoming a spy

A young lieutenant from Virginia, Thomas Jordan, recognizes her unique abilities, how perfectly placed she is to aid the Confederate cause. He recruits her as a spy. The role appeals to her patriotism as well as her vanity, and before long she has a chance to try it on.

“On the morning of the 16th of July, the Government papers at Washington announced that the ‘grand army’ was in motion, and I learned from a reliable source (having received a copy of the order to M’Dowell) that the order for a forward movement had gone forth,” she records in her memoir, My Imprisonment and the First Year of Abolition Rule at Washington. “The heroes girded on their armour with the enthusiasm of the Crusaders of old, and vowed to flesh their maiden swords in the blood of Beauregard or Lee. And many a knight, inspired by beauty’s smiles, swore to lay at the feet of her he loved best the head of Jeff. Davis at least.”

But Greenhow has other plans. “At twelve o’clock on the morning of the 16th of July, I despatched a messenger to Manassas, who arrived there at eight o’clock that night,” she writes. “The answer received by me at mid-day on the 17th will tell the purport of my communication — ‘Yours was received at eight o’clock at night. Let them come: we are ready for them. We rely upon you for precise information. Be particular as to description and destination of forces, quantity of artillery, &c. (Signed) THOS. JORDON, Adjt.-Gen.’”

By return messenger, Greenhow outlines the Union Army’s plan to cut the Winchester railroad and thus intercept Gen. Joseph Johnston, rushing in from the west to reinforce General Beauregard at Manassas Junction, Virginia. The Army acts on her intelligence, and the result is a rout of Union troops under Gen. Irvin McDowell at the First Battle of Bull Run.

Just before the battle, Greenhow entrains for New York and does not return until July 23 at six o’clock in the morning. At that hour, she is thronged by friends anxious to congratulate her for the Confederacy. Among them is a secret courier: “A despatch was also received from Manassas by me — ‘Our President and our General direct me to thank you. We rely upon you for further information. The Confederacy owes you a debt. (Signed) JORDON, Adjutant-General.’”

On August 11, 1861, Greenhow sends another — much longer — dispatch to Lieutenant Jordan. In precise detail, she reports the location and status of every fortification around Washington, including their armaments and garrison strength. She comments on the political views of key officers. She describes the defensive forces ringing the city: their dispositions, weapons, even the number of mules and wagons.

But she has been a little too flamboyant in her role and has caught the attention of Thomas A. Scott, the Assistant Secretary of War. He enlists a detective named Allan Pinkerton, head of the Union Intelligence Service. Pinkerton writes, “She had now become an avowed hater of the Union, and it was feared, from her previous association with officers in the army, that she was using her talents in procuring information from them which would immediately be communicated to the rebel government in Richmond.”

Accompanied by several detectives, he steals up on her house at night, in a driving rainstorm. Two men hoist him high enough to peer through the parlor windows. He witnesses this scene: an infantry captain, about 40 years old, huddles in intimate conversation with Greenhow. After a few minutes, the man draws a folded paper from his pocket and offers a map to her. Pinkerton recognizes the captain and is convinced he is sharing information with the treasonous Greenhow.

Pinkerton arrests Greenhow on August 23, 1861. Detectives rifle through her correspondence but find nothing incriminating — she has used only pen names and writes in cipher.

Under arrest

For five months, Greenhow languishes under house arrest with her youngest daughter, Little Rose. She is watched constantly, yet she manages to carry on a lively correspondence with her Confederate contacts right under the noses of her guards.

Her house is officially commissioned a federal prison, and other political captives arrive — not all of them to her liking. “A woman of bad repute, known and recognised by several of the guard as such, having been seen in the streets of Chicago in the exercise of her vocation … was brought to my house, and placed in the chamber of my deceased child adjoining mine,” she complains in her memoir. “For what object I know not, but this woman was allowed unrestricted intercourse with me, the order being given that our meals should be served together.”

Her long, impassioned epistles to her old friend William Seward, now Lincoln’s Secretary of State, are answered by matter-of-fact letters denying her freedom.

In January, things get worse: she and her young daughter are removed to the second floor of the Old Capitol Prison.

Strangely, in all the months of her imprisonment, Greenhow has not been charged with any crime, let alone tried in a court of law. Despite Pinkerton’s certainty that she is a spy, he can produce no direct evidence, no eyewitness testimony to corroborate what he is sure he witnessed.

So Greenhow and her daughter remain under guard — too dangerous to release, too embarrassing to put on trial. At long last, she wears them down. The government will banish her south, never to return on pain of arrest.

Thus on June 6, 1862, she and her daughter enter Richmond like royalty, cheered on by crowds of admirers. Now that she is known, her usefulness as a spy is over. She remains in Richmond, writing her memoir. In the summer of 1863, Jefferson Davis sends her abroad as a diplomatic emissary for the Confederate government.

On August 5, 1863, she sails out of Wilmington aboard the Phantom. The vessel is spotted by the watch of the Niphon off New Inlet, and a larger blockading ship, the Mount Vernon, gives chase — but it is no match for the speed of the Phantom.

Safely arrived in England, championed by the essayist Thomas Carlyle, Greenhow finds a publisher for her memoir. She presses Lord Palmerston to recognize the Confederate States of America. In Paris, she argues military strategy with Napoleon III. She successfully negotiates with Charles Francis Adams, U.S. Minister to France, to secure the release of a young third lieutenant, Joseph D. Wilson, who is suffering severe mental distress. Wilson was captured when the Kearsarge sank the commerce raider C.S.S. Alabama off Brest.

After many months abroad, Greenhow says a heartrending farewell to Little Rose at the Convent du Sacré Coeur in Paris, a safer place for her than aboard an inbound blockade runner.

Her final days

The vessel that carries Greenhow home across the Atlantic is the Condor, one of four Glasgow-built sister ships, probably the largest and fastest blockade runners on the seas. When it slips harbor, heading south, the Condor’s departure is noted. Three U.S. Navy ships are ordered to intercept it: Niphon, Alabama, and Kansas.

In the dead of night on October 1, 1864, the Condor crosses the bar of Cape Fear. At 3:40 a.m., lookouts aboard the Niphon spy the ship and open fire. The Condor is now only 800 yards off Fort Fisher, which opens fire against the U.S. ships with long-range rifled artillery. Rockets flare overhead, lighting up the chase. It’s a dirty night, with a freshening wind and a cold drizzle to spoil visibility.

All at once, dead ahead, Capt. William Nathan Wrighte Hewett spots what appears to be a U.S. warship. He swerves the Condor hard to starboard to avoid a collision — and runs the ship right onto the shoals.

There was no warship: just the hulk of another blockade runner, the Night Hawk, which ran aground two nights ago and is being worked by a salvage crew. The Condor lies close under the guns of Fort Fisher, and the federal ships dare not venture any closer.

But Greenhow demands to be put ashore at once. She is determined that she will never go back to prison, and she will not take the chance of being captured. A lifeboat is lowered into the frothing sea. Aboard it are Wilson, Holcombe, two seamen, and Greenhow. She is dressed in black silk and carries a leather valise heavy with dispatches for the government in Richmond — and 400 gold sovereigns, about $2,000, royalties from her book sales that she intends to donate to the relief of veterans.

Almost the moment the lifeboat hits the water, it broaches on a swell and capsizes. The occupants are tumbled into the sea. The men manage to cling to the overturned boat and are hoisted back aboard the Condor. But Greenhow, a 50-year-old woman heavily dressed and chained to six-and-a-quarter pounds of gold, additional pounds of paper, satchel, and chain, is carried under.

After a Catholic Mass at St. Thomas the Apostle, the funeral cortege of eight carriages and scores of mourners on foot accompanies Greenhow’s coffin to Oakdale Cemetery in Wilmington in a torrent of rain. Mrs. De Rosset comments sadly, “Not a tear of affection was shed at the grave, for no one in the midst of all the trappings of sacred honor and cherished tradition really knew Rose Greenhow.”

As Greenhow’s coffin is lowered into the grave, the rain quits and the sun bursts out of the gray sky. But the weight of her treasure, the legacy of her imprisonment, has carried her too deep to rise.

Philip Gerard is an author and chairman of the department of creative writing at the University of North Carolina Wilmington.

Selected Sources

The author is indebted to Mac Whatley, adjunct curator of the American Textile History Museum’s machinery collection, for a tutorial on the workings of blockade runners; also the Documenting the American South project and the William Madison Randall Library at UNC Wilmington for electronic access to My Imprisonment and the First Year of Abolition Rule at Washington by Rose O’Neale Greenhow, first published in London by Spottswood and Co. Other published sources include the following: Wild Rose by Ann Blackman (Random House, 2005); Confederate Spy: Rose O’Neale Greenhow by Nash K. Burger (Giniger/Franklin Watts, 1967); Gray Phantoms of the Cape Fear by Dawson Carr (John F. Blair, 1998); Spies for the Blue and Gray by Harnett T. Kane (Hanover House,1954); Masters of the Shoals by Jim McNeil (Perseus/ DeCapo, 2003); The Spy of the Rebellion: A True History of the Spy System of the United States Army Vol. I by Allan Pinkerton (M.A. Winter and Hatch,1883; ebook abvailble at googlebooks), who arrested and oversaw the detention of Rose O’Neale Greenhow; additionally useful was the online Dictionary of American Fighting Ships curated by the U.S. Navy History and Heritage Command, The Washington Navy Yard.