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On this day in 1861, Allan Pinkerton, head of the new secret service agency, arrested Washington, D.C. socialite and Confederate spy Rose O’Neal Greenhow under house arrest. She was a wealthy and well-connected widow from Maryland who openly sympathized with the Southern cause and was close with Massachusetts Sen. Henry Wilson. She formed a substantial spy network which she managed to run even while under police supervision, and her intel led to the Confederate victory over Union forces at the First Battle of Bull Run in Virginia. Eventually she and her daughter were transferred to the Old Capitol Prison, later to be released and exiled to the South. Greenhow traveled to England and France to drum up support for the Confederate army and on her return voyage a Yankee war vessel ran her ship aground in North Carolina. Weighted down by a substantial amount of gold, Greenhow’s lifeboat overturned and she drowned.
(History.com)
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