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Elizabeth Bentley. Courtesy of the Library of Congress (LC-USZ62-109688).

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Bentley, Elizabeth Terrill (01 January 1908–03 December 1963), Communist party activist and government witness, was born in New Milford, Connecticut, the daughter of Charles Prentiss Bentley, a newspaper editor and department store manager, and Mary Burrill, a schoolteacher. After growing up in small towns in Connecticut, New York, and Pennsylvania, Bentley enrolled in Vassar College and in 1930 received an undergraduate degree in English. While at Vassar, she became involved in a variety of Socialist causes but did not demonstrate any interest in more radical left-wing ideas. For two years following graduation, she taught languages at the Foxcroft School in Middleburg, Virginia, but left in 1932 for Columbia University, where she earned her M.A. in Italian in 1935. While working on her graduate degree, she accepted a fellowship that took her to the University of Florence for the 1933–1934 academic year....

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Belle Boyd. Albumen silver print, c. 1864, by Unidentified Artist. National Portrait Gallery, Smithsonian Institution.

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Boyd, Belle (09 May 1844–11 June 1900), Confederate spy, was born in Martinsburg, Virginia (now West Virginia), the daughter of Reed Boyd, a store owner and manager of a farm, and Mary Rebecca Glenn. Both parents were from prominent Virginia families, and young Belle (christened Isabelle) was educated at Mount Washington Female College in Baltimore. When the Civil War broke out, she returned to her home and began raising funds for the Confederate army....

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Coplon, Judith (17 May 1921–26 February 2011), Soviet spy during the Cold War, was born in Brooklyn, New York. Her father Samuel Coplon was a respected toy merchant; her mother Rebecca Moroh Coplon was a milliner. She and her older brother Bertram were raised in modest but comfortable circumstances. The petite Judith (just over five feet tall as an adult) was vivacious, pretty, and smart. At Brooklyn’s James Madison High School, she won awards, and her brilliant academic record earned her a scholarship to Barnard College. She threw herself into extracurricular activities, joined a communist youth group, and became an editor of the school newspaper. A history major fascinated by the development of the Soviet state, she compiled a superior academic record and graduated cum laude in 1943....

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Greenhow, Rose O’Neal (1815?–01 October 1864), Confederate spy, was born in Montgomery County, Maryland. Many O’Neals, their surnames variously spelled, inhabited the area. Speculation centers on a planter, John O’Neale, slain by a slave in 1817, and his wife, Eliza Henrietta (maiden name unknown), as her parents. In early adolescence she and a sister went to Washington, D.C., to live with an aunt, Mrs. H. V. Hill, who managed a popular boardinghouse on Capitol Hill. There she was tutored in the social graces as well as academic subjects and met many of the nation’s powerful. Darkly beautiful, vivacious, and quick-witted, she was very popular and dubbed “Wild Rose.” The boarder she admired most was ...

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Harrison, Marguerite (23 October 1878–16 July 1967), journalist, spy, world traveler, and writer, was born Marguerite Elton Baker in Baltimore, Maryland, to Elizabeth Elton Livezey and Bernard Baker. Her wealthy family made its fortune in transatlantic shipping, and she spent many summers in Europe, where she enhanced her language skills. Her education was a combination of private tutors and attendance at St. Timothy’s School in Catonsville, Maryland, where she experienced some social awkwardness, but she also learned much about the wider world that would influence the rest of her life. After high school, she attended Radcliffe College for one semester and then in 1901 quickly married Thomas Harrison against her parents’ wishes. In contrast to her family’s high standing and social connections, Thomas came from a family of lesser means and status....

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Massing, Hede Tune (1899–08 March 1981), Communist spy and later Federal Bureau of Investigation informant, was born to a Polish-Austrian couple. Hede’s mother was the daughter of a prominent Polish rabbi, while her father was a circus acrobatic rider. When Hede was a young girl, the family moved to the United States and lived in Massachusetts and New York City. Massing’s father tried to start a catering business but failed....

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Rosenberg, Ethel (28 September 1915–19 June 1953), and Julius Rosenberg (12 May 1918–19 June 1953), accused spies, were both born in New York City. Julius was the son of Harry Rosenberg, a garment worker, and Sophie Cohen. Ethel was the daughter of Barnet Greenglass, a sewing machine repairman, and Tessie Felt. Julius and Ethel Rosenberg were both raised in poor, orthodox Jewish families in the slum-ghetto that was New York’s Lower East Side during World War I. Both graduated from the Lower East Side’s Seward Park High School. Julius also received religious instruction at Downtown Talmud Torah and Hebrew High School in New York. Ethel, who had musical interests, studied piano and sang as the youngest member of Hugh Ross’s Schola Cantorum before her high school graduation at the age of fifteen....

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Van Lew, Elizabeth L. (17 October 1818–25 September 1900), Unionist and Federal spy, was born in Richmond, Virginia, the daughter of John Van Lew, a New York–born hardware merchant, and Elizabeth Baker, the daughter of a former mayor of Philadelphia. Van Lew’s father had made a fortune in his successful hardware business, and the family moved in the highest circles of Richmond society. The Van Lews retained northern connections and sent Elizabeth to Philadelphia to be educated. When she returned to the South, she was a fervent abolitionist and convinced her mother to free the family slaves in the 1850s after her father’s death....

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Velazquez, Loreta Janeta (26 June 1842–?), purported soldier and spy, was born in Havana, Cuba, to an unknown Spanish father and an unknown French-American mother. Given the degree of hyperbole in The Woman in Battle (1876), the primary source of information on her life, there is even some question as to whether Velazquez herself actually existed, or whether the identity was a nom de plume adopted to describe her at least partially fictional exploits. Recent research into the details of her narrative, however, suggests that although there is some contradiction and inconsistency in her text—which she claimed to have written without notes—enough remains that can be corroborated to suggest that some version of the truth is retold there....