Gotcha!

Wherein the Rebel Rose is nabbed

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On August 23, the somewhat sour-faced Scot took pleasure in a good night's work. He had found the Rebels' leak in Washington and plugged it. Rose O'Neal Greenhow was now his prisoner.

Rose Greenhow

The man was Allan Pinkerton, and he was on temporary absence from his detective firm (the famed Pinkerton National Detective Agency) by special request of Major General George McClellan to found the Union Intelligence Service in Washington to root out spies, especially those that had delivered news to Confederate Brigadier General G.T. Beauregard about the build up and movement of Union forces. In reality, Beauregard probably didn't need their reports since the army had moved so slowly and destructively. But in the paranoia following Bull Run, spies were given undue importance. Besides, there was no area of the defense of Washington McClellan wasn't sure he could improve.

As far as spies went, Greenhow wasn't a particularly a good one. She had been born in Port Tobacco, Maryland around the time of the British raid that burned Washington, but when her father was killed by rebellious slaves in 1817, young Rose went to live with an aunt in the rebuilt Washington City. At her boarding house, Rose grew-up around Washington's social elites and Members of Congress and important national figures came to enjoy being around the high-spirited young woman. She fell in with Dolley Madison's social circle and met the man she would marry (with Dolley's blessing, of course), Dr. Robert Greenhow.


Robert and Rose stayed deeply entrenched in the society - such as it was - of Washington. They became particularly attached to John C. Calhoun of South Carolina (holding the positions of Congressman, Vice President, Secretaries of State and War, but most often Senator) and the young circle of Southerners (including Jefferson Davis) who associated with him, drinking in his philosophy of the union of sovereign states. The two had eight children, and finally departed Rose's beloved Washington hoping to capitalize on the movement of Americans to California looking for gold. But Robert died shortly after arriving in San Francisco, and the family returned to Washington in mourning.

Like the rest of the nation, Rose became more polarized through the 1850s. She also emerged from mourning as one of the most eligible single ladies in town. The uncharitable said she was shamefully involved with several men, her defenders say she was naturally flirtatious. Either way, when South Carolina seceded, rather than leave town like many Washington secessionists, she schemed to subvert the "Abolition Government" from within.

Her first target was Senator Henry Wilson (R-MA), an abolitionist who had succeeded her friend Davis as head of the Military Committee in the Senate. Wilson was utterly smitten by the razor sharp socialite, even if she loved the "slave interests" he regularly decried on the Floor. Wilson spilled his guts to her about the war preparations, and wrote her passionate letters signed "H". We don't know whether their romance progressed beyond verbal passions - Greenhow was calculatingly coy in her tell-all book about this and all her other dalliances - but Wilson was at her house constantly.

But the suspicious romance of an abolitionist and a secessionist did not go unnoticed and one of the first to act on the knowledge was a staffer for Bvt. Lt. General Winfield Scott, Captain Thomas Jordan. Officially an assistant quartermaster, Jordan was from the Shenandoah Valley and was helping the Quartermaster Bureau prepare for the war by recruiting a ring of spies in the national capital. One of these was Greenhow, who he judged to be capable of running his ring. By May 16, Jordan was already a captain in the Confederate Army, and when Virginia announced its intention to secede on May 21, formally resigned from the U.S. Army, leaving Washington.

Greenhow sent Senator Wilson's stories and others she collected to Jordan when he reappeared at Manassas Junction as Brigadier General G.T. Beauregard's adjutant and chief of staff. It was to now Colonel Jordan that Greenhow sent a warning that the Union army had left the vicinity of Washington on July 16. A week later she welcomed the straggling troops back from their loss at Manassas with glee.

Allan Pinkerton

Allan Pinkerton returned to Washington shortly afterwards and brought the revolutions he had brought to detective work to counter-espionage, especially shadowing and undercover work. Using his favorite pseudonym, E.J. Allen (and adding the title "major" to keep in the spirit of the times), he quickly identified the outspoken secessionist Greenhow as a possible Confederate agent. Not that Rose made it too difficult a task, with her frequent tirades against "the Abolition Government" and her romantic interests in every high-ranking officer and government official. She also liked to brag that even though McClellan had shut-down mail service to the South, she could forward letters for anyone who wanted her to.

He and his men began to shadow Greenhow's house at 800 16th Street, NW (today the site of the Hay-Adams  Hotel, famous in the 1980s again for espionage as the spot Ollie North solicited donors for the Iran-Contra scheme) and one rainy night in mid-August, Pinkerton himself confirmed the hunch. A cloaked man entered the house and Pinkerton sneaked up to the window, removing his boots so he could stand on one of his men's shoulders and see in.

The man was a captain assigned to the provost-marshal, the forerunner to Military Police responsible for security in Washington. He greeted Greenhow warmly, pulled out a map and appeared to describe positions to her. Pinkerton watched them disappear into a backroom and, by his account, they returned an hour later arm-in-arm (Pinkerton doesn't mention the effect on his men's shoulders). The captain left and Pinkerton rushed to follow him, alone and still shoeless, but the man realized he was being followed, and dashed into a building on 15th and Pennsylvania. Pinkerton burst in after him, but found himself surrounded by soldiers from the provost-marshal. He refused to break cover and undo his breakthrough, so the bedraggled man was thrown in jail as a drunk to sleep it off.

The captain was arrested the next morning and Pinkerton had everything he needed to nab Greenhow at the next opportunity. August 23, he and several of his men stationed themselves just out of sight on her front porch. Both Pinkerton and Greenhow wrote colorful and self-serving accounts of the day. "As I have said, on Friday, August 23, 1861, as I was entering my own door, on returning from a promenade, I was arrested by two men, one in citizen's dress, and the other in the fatigue dress of an officer of the United States Army," Greenhow wrote later. The latter was Pinkerton (whose proper name Greenhow never learned properly, though Major Allen was what he gave her that day).

I had stopped to enquire after the sick children of one of my neighbours, on the opposite side of the street. From several persons on the side-walk at the time, en passant, I derived some valuable information; amongst other things, it was told me that a guard had been stationed around my house throughout the night, and that I had been followed during my promenade, and had probably been allowed to pursue it unmolested, from the fact that a distinguished member of the diplomatic corps had joined me, and accompanied me to that point. This caused me to observe more closely the two men who had followed, and who walked with an air of conscious authority past my house to the end of the pavement, where they stood surveying me.

As she does throughout her account of the event Greenhow makes time to describe all the valuable information she destroyed and agents she saved:

I continued my conversation apparently without noticing them, remarking rapidly to one of our humble agents who passed, 'Those men will probably arrest me. Wait at Corcoran's Corner, and see. If I raise my handkerchief to my face, give information of it.' The person to whom this order was given went whistling along. I then put a very important note into my mouth, which I destroyed; and turned, and walked leisurely across the street, and ascended my own steps.

Pinkerton told her they were there to arrest her for spying for the Confederacy. She demanded to see their warrant. He quietly told her they had none, but the Assistant Secretary of War had verbally told them to arrest her under a special suspension of habeus corpus. Greenhow loudly informed the men that it was good they had caught her outside, because if the same violation of her Constitutional rights had occurred indoors she would have shot them dead. "That would have been wrong," one of the detectives said, "as we only obey orders and all have families."

Pinkerton brought Greenhow inside and subdued her, in his account (in hers, she decided to cooperate "for I knew that the fate of some of the best and bravest belonging to our cause hung upon my own coolness and courage"), and had his men turn her house inside-out, but so that nothing could be seen from the street in case another spy wandered into the trap. Pinkerton probably would not have objected to Greenhow's account: 

Men rushed with frantic haste into my chamber, into every sanctuary. My beds, drawers, and wardrobes were all upturned; soiled clothes were pounced upon with avidity, and mercilessly exposed; papers that had not seen the light for years were dragged forth.

Greenhow continues with the story of boorish, loutish Pinkerton men searching everywhere (including a full-body search by a female detective she reserves particular vitriol for), just minutes behind the clever heroine who destroys evidence to save her friends and co-conspirators. At the end of the day, they discover nothing, but keep her locked up anyway. Pinkerton, on the other hand, wrote as if he had discovered a secret portal into Jeff Davis' parlor and Greenhow had been running the war for him all along.

[She] possessed almost superhuman power, all of which she has most wickedly used to destroy the Government... She has used her almost irresistible seductive powers to win to her aid persons who were holding responsible places of honor and of profit under the Government... She had her secret and insidious agents in all parts of this city and scattered over a large extent of country... She had alphabets, numbers, ciphers and various other not mentioned ways of holding intercourse with traitors.

Pinkerton claimed the evidence had helped him snare Lily Mackall by the end of the day, too. Lilly had been a courier for Greenhow, but she also was her best friend and the two were hardly ever apart. She had come over that afternoon to visit and been surprised at the door, like Greenhow. The next day was even more successful for Pinkerton, who nabbed Greenhow's other courier, Bettie Hasler, the same way, as well as dragged in Eugenia Phillips, her sister, and her two daughters. 

None were particularly inspired arrests, since the week before they had been to the Old Brick Capitol (today, site of the Supreme Court, but then converted into a prison for suspected traitors) bringing treats for the secessionists imprisoned there and hurling invectives at the guards. Phillips, however, was the wife of a former Congressman from Alabama, Philip Phillips, who as a staunch Unionist had chosen to remain in Washington and practice law, and was already raising hell at the War Department. Sensing that things might be getting away from him, Pinkerton decided to hold all the women at Greenhow's residence for the time being.

But the arrests continued, including the mayor of Washington City, James Berret. Berret had actually served on Lincoln's inaugural committee, but when Congress had passed an act establishing the Metropolitan Police Department, it made him an ex officio member of the board of a Federal institution. As a member of the Federal government, he was now required to swear an oath of loyalty to the Union, per another law passed by the Congress recently. Berret refused to, saying that his oath as mayor of Washington City was more than sufficient an expression of loyalty (Henry Addison, mayor of Georgetown, made it worse by tripping over himself to swear the oath). So Pinkerton rounded him up and tossed him in the Old Brick Capitol for good measure.

Print Sources:

• Furgurson, 124-130.