OTD in History… August 23 & 24, 1861, Confederate Spies Rose Greenhow and Eugenia Phillips were arrested

By Bonnie K. Goodman, BA, MLIS

Confederate spy Rose O’Neal Greenhow and her daughter “Little Rose.” Source: Wikipedia

On this day in history August 23 and 24, 1861, two notorious Confederate female spies Rose O’Neal Greenhow and Eugenia Levy Phillips were arrested by Union officers and placed under house arrest in Greenhow’s attic during the American Civil War. Rose Greenhow, a Catholic “wealthy widow” and socialite mingled in Washington’s elite circles that included “presidents, generals, senators, and high-ranking military officers.” Once the seven Southern states seceded from the Union and formed the Confederate States of America, Greenhow, who was friends with Confederate President Jefferson Davis, was put in charge “pro-Southern spy network” in Washington, D.C., which included Eugenia Phillips, the wife of Union supporting former Alabama Congressman Phillip Phillips.

Confederate Spy Eugenia Levy Phillips. Source: Jewish Women’s Archive

Eugenia Phillips was probably the fiercest supporter of secession and the war than the other Jewish women. Historian Jonathan Sarna called Phillips, “a fiery patriot and provocateur in the cause of the South,” while doyen Bertram Wallace Korn called her “a fire-eating secessionist in skirts.” (Sarna, 265, 31) Phillips was also a staunch supporter of slavery. In July 1861, Greenhow relayed information to her handler Confederate Army Captain Thomas Jordan, for the Confederate Secret Service. The intelligence helped the South win the First Battle of Bull Run on July 21, and even Jefferson Davis gave Greenhow credit for the Confederate victory. Both Greenhow and Phillips used their charms to garner information from “gullible Union officers and politicians.” (Sarna, 31) Greenhow in particular obtained information from her friend, Massachusetts Senator Henry Wilson.

Greenhow was born Maria Rosetta O’Neale in 1813, on a plantation in Montgomery County, Maryland outside of Washington, DC. Born into a Catholic family, Rose was the third of five children. Her father’s Black valet violently murdered him in 1817, leaving the family in poverty. Rose and her older sister Ellen moved to their aunt, Mrs. Maria Ann Hill’s boarding house in 1830 located at the Old Capitol Building, the building would later become later the Old Capitol Prison where Greenhow and her daughter would be imprisoned for five months in 1862.

In the middle of Washington, both O’Neale girls were introduced to Washington society. Rose went on to marry Robert Greenhow Jr., who was both a doctor and lawyer and worked in the State Department. Her sister Ellen married President James Madison and First Lady Dolly’s nephew James Madison Cutts. Ellen and James Madison Cutts daughter would go on to marry Illinois Democratic Senator Stephen A. Douglas. Rose and Robert Greenhow had four daughters, including the young Rose O’Neal Greenhow, “Little Rose,” who would be imprisoned with her mother. The family lived in Mexico City and San Francisco, where Robert Greenhow died in 1854. Upon moving back to Washington, Rose became committed to “preserving the Southern way of life.”

Eugenia Levy Phillips was born in Charleston in 1819. She married U.S. Congressman Philip Phillips of Mobile, Alabama when she was 16 and went on to have nine children. Phillips was a leading figure in Alabama politics from the 1830s to the 1850s when he was elected to the United States Congress in 1852. After one term, he established a law practice in DC where the Phillips remained in DC throughout the Southern states secession from the Union. Eugenia and her husband differed significantly in their political beliefs Phillips was a Unionist and a moderate while Eugenia was probably one of the most fierce secessionists in DC. Eugenia also socialized with other secessionists and women suspected in DC particularly Rose Greenhow a well-known Confederate spy.

Eugenia Phillips’ associations and excessive antagonism toward the Union made her a target for government surveillance. Eugenia was hardly innocent in Washington she mingled with Northern social circles she was able to obtain information from Union soldiers and officials, which she conveniently passed to the Confederate government. As Eli Evans recounts, “She even enlisted in a form of female espionage, using her charms on gullible Union officers and politicians to get information that she managed to deliver clandestinely to the young Confederate government.” (Sarna, 31)

In Washington, Rose Greenhow kept company with some of the most influential political figures. According to Ann Blackman in her book Wild Rose, Rose O’Neale Greenhow, Civil War Spy, they included, “John C. Calhoun; Senators Daniel Webster, Stephen A. Douglas, and Thomas Hart Benton; Dolley Madison; Chief Justice Roger Brooke Taney; John and Jessie Benton Frémont; diarist Mary Boykin Chesnut; Presidents Martin Van Buren, John Tyler, James Polk, and James Buchanan; and her Confederate correspondents Jefferson Davis and General Pierre Gustave Toutant Beauregard.” (Blackman, 11) Republican US Senator Henry Wilson from Massachusetts was Greenhow’s source for most of the information she passed to the Confederacy. Rose had many illicit love affairs to obtain information particularly with Wilson, who wrote her love letters.

On July 9 through 16, 1861, Rose relayed encoded messages to Confederate General P. G. T. Beauregard, which included Union General Irvin McDowell’s plans. Rose sent the messages with “courier Betty Duvall, and her dentist, Aaron Van Camp, as well as his son who was also a Confederate soldier, Eugene B. Van Camp.” The movements helped the Confederate Army secure victories at the First Battle of Bull Run on the plains of Manassas. Had the Union won the battle they could have easily moved on to the Confederate capital of Richmond, and squash the entire rebellion in mere months. The victory at the first Battle of Bull Run ensured the conflict would be a full-blown Civil War. Jordan relayed Davis’ gratitude to Rose writing her, “Our President and our General direct me to thank you. We rely upon you for further information. The Confederacy owes you a debt”. (Signed) JORDAN, Adjutant-General.”

Rose’s high ranking associations within the Union and Confederacy put her on the new Secret Service agency’s head Allan Pinkerton’s radar. On August 23, 1861, Pinkerton arrested Rose and placed her under house arrest at her 16th Street home. Greenhow sent away one of her daughters and only Little Rose was with her during her detainment. Soon Pinkerton rounded up other women he suspected of spying for Confederacy including her courier Lily Mackell and then Eugenia Phillips. Although Greenhow tried to burn everything, the Union officers found intelligence, including coded messages, reports to Jordan and “maps of Washington fortifications and notes on military movements.”

On August 24, 1861, Pinkerton’s Union officers came into Eugenia and Phillip Phillips home arresting the both of them. Phillip remained under house arrest for a week, but Eugenia and two of their daughters, Fanny and Caroline (Lina) as well as Eugenia’s sister Martha Levy where taken to Greenhow’s house to be imprisoned. The Union arrested Greenhow the previous day for relaying to Confederate General McDowell plans for the first Manassas Campaign. There all five women remained imprisoned in two rooms in Greenhow’s attic with hardly any amenities. Eugenia Phillips described it in her journal, “The stove (broken) served us for table and washstand, while a punch bowl grew into a washbasin. Two filthy straw mattresses kept us warm, and Yankee soldiers were placed at our bedroom door to prevent our escape.” (Journal of Mrs. Eugenia Levy Phillips, 1861–1862)

Despite the fact that Union officers had no evidence to charge Eugenia and her family for a crime, they still kept them imprisoned occasionally allowing Phillip Phillips who had since been released to visit and bring food baskets, albeit under strict Union supervision. Eugenia believed her loyalty to her country should not be considered a crime to imprison her for, writing in her memoir she claimed; “Again I ask what is my crime? If an ardent attachment to the land of my birth and expression of deepest sympathy with relatives and friends in the South constitute treason -than I am indeed a traitor. If hostility towards black Republicanism, its sentiment and policy-it is a crime-and I am self-condemned…!” (Rosen, 288)

Southern women were outraged at the North’s treatment of women with no reason, especially the imprisonment of Eugenia’s two daughters. Phillips had to use his influence with Edward Stanton, Senator Reverdy Johnson from Maryland, and Supreme Court Justice James M. Wayne who was the former mayor of Savannah to secure his family’s release. However, the Union exiled the Phillips family from the nation’s capital and forced them to relocate to the Southern states. The whole family was also required to take an oath as a condition of their parole to “not to take illegal actions against the Union”

Upon being released from the Greenhow prison Eugenia and Phillip Phillips were sitting in the parlor where Rose Greenhow was still a prisoner passed by with two Union guards watching her, threw a ball of yarn at Eugenia and stated: “You dropped your worsted when you left my house.” (Rosen, The Jewish Confederates, 288.) Rose then went along with her guards who were not suspicious of the encounter. Phillips was an acquaintance of Jefferson Davis’ wife, Varina Davis. After her release from house arrest, Eugenia met with the then Confederate President Davis in his home, bringing him a “coded message” from Rose that was hidden in a ball of yarn. Eugenia’s devotion to the Confederacy brought her admiration from Southern Christian society. Evans recalls, “Mary Chesnut referred to [Eugenia] and fellow spy Rose Greenhow as ‘saints and martyrs and patriots.’” (Sarna, 30)

After Eugenia Phillips was released from Fort Greenhow as Pinkerton and the Union officers called it, Rose Greenhow remained on house arrest until January 18, 1862, when Rose was transferred to the Old Capitol Prison. She stayed there with her daughter Little Rose, who was eight, for five months, during that time she continued sending coded messages through her prison window. Pinkerton finally released Greenhow and her daughter on May 31, 1862, on the condition she stays within the boundaries of the Confederacy. Upon Rose’s arrival in Richmond, Virginia, she received a hero’s welcome from Jefferson Davis. Davis recruited Rose as courier running the blockade to Europe, where she also was on a diplomatic mission to England and France meeting with Napolean III and Queen Victoria advocating they should recognize the Confederacy. During the time, Rose became engaged to, “Granville Leveson-Gower, 2nd Earl Granville” and published her memoirs in 1864, My Imprisonment and the First Year of Abolition Rule at Washington.

On August 19, 1864, Rose began her trip back aboard British blockade-runner ship the Condor. On October 1, the Union gunboat USS Niphon attacked the Condor off the coast of Wilmington, North Carolina at Cape Fear River, Rose fearing the Union officers would arrest, took a rowboat to escape, a wave capsized the boat, and Rose drowned because of the $2,000 in gold sewn into her clothes for safe keeping. Along with her body, they found a small notebook in code and her memoirs with a letter for Little Rose. Rose also left a journal of her last year in Europe written in code, recently discovered and deciphered.

It would not be very long for Eugenia Phillips to again to make a breach her agreement with the Union after her first imprisonment. After leaving Washington, they first traveled to Norfolk, Virginia and then on to Richmond through Savannah and eventually settled in New Orleans in the closing weeks of 1861. Although conditions were unfavorable for Phillip to create a law practice, the family settled there because the Phillips believed they were safe from the Union army invasion in the Deep South, and therefore Eugenia would be safe from suspicion. By April however, the Union army was closing in on the Mississippi River, and New Orleans was surrendered on April 29, 1862. By May 1, 1862, Major General Benjamin F. Butler of Massachusetts took over command of the city. On May 15, because of New Orleans women’s disrespectful behavior Butler issued his infamous General Order №28, known as the “Women order,” which was designed to force the women of New Orleans to restrain themselves from having hostile outbursts towards Yankee soldiers or face dire consequences.

Eugenia, however, still managed to fall into Butler’s fury. The Phillips’ house was situated next to the city hall, and the day of Union Officer Lieutenant DeKay’s funeral procession passed by the street, Eugenia along with her children were laughing, mocking and cheering on the terrace of her home. Although Eugenia denied that, the laughter was caused by the funeral procession there have been two stories as to her reason for laughing, including laughing at her children at a party and hearing of a Confederate military victory. Butler called Eugenia to the Customs House

Butler screamed at Eugenia, “You are seen laughing and mocking at the remains of a Federal officer. I do not call you a common woman of the town, but an uncommonly vulgar one, and I sentence you to Ship Island for the War.” (Journal of Mrs. Eugenia Levy Phillips, 1861–1862)

On June 30, 1862, she began her imprisonment on Ship Island living at first in a former railroad boxcar and then in an abandoned post office building. Butler allowed Mr. Phillips to send Eugenia some food mostly beans and spoiled beef, and she would not have survived with Phoebe’s assistance. The harsh conditions took a heavy toll on Eugenia Phillips, her health was nearly destroyed by the rotten conditions, the deprivation of food, and as well Eugenia suffered from brain fever which was considered nervous exhaustion. Her pride and loyalty to the Confederacy were the main reason Eugenia was not released. After nearly three months on September 11, 1862, Eugenia was finally released. When she arrived home her husband when opening the door to her believed in Eugenia’s word’s “thought it was my ghost” he was not sure she was still alive. Publicly her whereabouts while she was imprisoned where vague, as Eugenia explains, “Butler gave out the idea that I had been “released after a few days’ confinement,” so that everyone, including my family in Georgia, believed that I was safe.” (Journal of Mrs. Eugenia Levy Phillips, 1861–1862)

Butler regretted that Eugenia’s imprisonment had the opposite effect that he wanted to project, he wanted to make treasonous behavior towards the Union an example of what happens to women who display such behavior just because they are women, and would not be punished. Instead, as historian George Rable writes in his opinion Butler turned “an irksome rebel into a martyr,” which was the main reason he chose to release her from Ship Island. Eugenia Phillips according to George Rable “had shown considerable public relations acumen, and her prison journal reveals an ironic sense of humor, especially in her wry proposal to use a steam device to pump moisture into the rock-hard bread. Though not exactly besting Butler, she had played the wily Massachusetts politician to a draw.” (Clinton 142) Despite the cruel punishment that awaited her, Eugenia remained loyal to the Confederacy. As William Garett noted, “her proud Southern spirit never quailed and she remained firm to the last in the opinions she had expressed.” (Rosen, 293.)

These two southern women were unwavering in their support for the Confederacy and showed their devotion in extreme ways, through illegal means, as spies and rebels they endured the price with imprisonment. Eugenia Levy Phillips’ devotion to the Confederacy appeared “unquestionable,” as Lauren Winner has described her; Eugenia’s actions were beyond what was required of any Southern women supporting the war. Eugenia Phillips, as Winner notes, “was so unswerving in her devotion to the Confederate cause that the Union suspected her of being a spy.” (Clinton, 195) Although Eugenia was Jewish and a practicing Jew, she saw herself especially during the war as first a Southerner who would support her country at all costs which she did.

Rose Greenhow also was unflinching in her support of the Confederacy, she was a spy, blockade runner, and the first women to diplomatically represent any nation, rebel or otherwise, and she was lauded by the Confederate government for her sacrifices. Rose’s sacrifices were deep; she died for the Confederate cause and would not have had it any other way. Blackman expresses, “Rose was on the wrong side of that struggle. She was, as she said herself, “a Southern woman, born with revolutionary blood in my veins.” Yet even those of us who could never accept her politics cannot help but be amazed at her resilience and zeal. Rose Greenhow was a woman of courage, imagination, and conviction, who took risks, enormous risks, for the Confederate cause, in a war for which she was willing to give her life — and did.” (Blackman, 17) Despite the overt racism in the South, women and religious minorities such as Rose Greenhow and Eugenia Phillips were rewarded with an equality unseen in the Union, and would not be seen in over a half a century.


Blackman, Ann. Wild Rose: The True Story of a Civil War Spy. New York: Random House Trade Paperbacks, 2006.

Clinton, Catherine, and Nina Silber. Divided Houses: Gender and the Civil War. Oxford: Oxford University Press, 1992.

Phillips, Eugenia L. “Journal of Mrs. Eugenia Levy Phillips, 1861–1862.” Marcus, Jacob R. Memoirs of American Jews, 1775–1865: 3. Philadelphia: Jewish Publication Society of America, 1956.

Rosen, Robert N. The Jewish Confederates. Columbia (S.C.: University of South Carolina Press, 2000.

Sarna, Jonathan D. Jews and the Civil War: A Reader. New York: New York University Press, 2010.

Winner, Lauren F. “Taking up the cross: conversion among black and white Jews in the Civil War South,” Catherine Clinton, ed. Southern Families at War: Loyalty and Conflict in the Civil War South. Oxford [England]; New York : Oxford University Press, 2000.

Bonnie K. Goodman has a BA and MLIS from McGill University and has done graduate work in Judaic Studies at Concordia University, where her thesis was about the unconditional loyalty of Confederate Jewish women during the Civil War. She is a journalist, librarian, historian & editor, and a former Features Editor at the History News Network & reporter at Examiner.com where she covered politics, universities, religion and news. She has a dozen years experience in education & political journalism.

Bonnie K. Goodman BA, MLIS (McGill University) is a Professional Librarian (CBPQ) & historian. Former editor @ History News Network & reporter @ Examiner.com.

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