Stringfellow’s reputation for courage and reliability reached the upper echelons of the Confederacy. Following Jeb Stuart’s death, the scout reported directly to Robert E. Lee and Jefferson Davis. Davis personally ordered Stringfellow into the Federal capital in March of 1865 to determine the climate for peace negotiations.

Many years after the war, Davis requested information for his memoirs and Stringfellow sent a report of his final mission. While gathering intelligence, the infatuated spy had risked his life to court Emma Green. He wrote, “Dark and dangerous as these days were they were not without much to make them among the happiest days of the war. I was at that time engaged to a young lady living in Alexandria and when she came to see her Union friends in Washington, I laid aside all thought of danger and was happy even while in hourly danger of a terrible death. She has since rewarded me by giving me her hand, and five children have heard from her how hard it is to say no to a soldier who will come through such dangers to do his courting.”

Indeed by again posing as a dental assistant and wearing civilian clothes, Stringfellow faced certain death if his true identity was discovered. Brazenly, he deliberately chose to board in a rooming house frequented by Federal detectives. He felt he would be safer there; a spy would really have to be a fool to live in such a place, right under the noses of people whose job it was to run down the likes of him.

Things went smoothly for a while. However, one of the female agents became suspicious of him. One night when he arrived for dinner all eyes focused on him. The lady filled everyone’s wine glasses and then toasted President Lincoln. Stringfellow refused to drink and said that he was a temperance man. She then filled his glass with water and proposed her toast again.

Stringfellow later wrote, “I then turned and looked her full in the face and said, ‘I do not mean to drink to Mr. Lincoln’s health unless you will drink my toast.’ Then I said, ‘To Jefferson Davis’ and drank it alone. Not a word was spoken. It seemed a long time before any move was made. Presently four young men arose and left the room. I arose and gave the table a long look of defiance and picked up my hat and walked out, entirely unarmed, without molestation.”

After this daring but perhaps foolhardy episode, the spy wisely left the city and moved into eastern Maryland to practice dentistry. However, the net of intrigue engulfed him. Stay tuned for the next issue and Stringfellow’s escape from prison. *

 
*From Stringfellow of the Fourth by R. Shepard Brown, and The Stringfellow Papers in the Virginia Historical Society.