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Confederate spy Frank Stringfellow’s March 1865 arrest

28 July 2009 One Comment

Following his brave but foolhardy toast to Jefferson Davis in a Washington boarding house, Frank Stringfellow headed into Eastern Maryland. He posed as a dentist but sensed that the net of intrigue was about to snare him. Thus he rented a carriage and headed southward towards the Potomac River to return to Virginia.

The carriage came to a sudden stop and Stringfellow looked out the windows to see a Union soldier holding the reins of the horse and two others poked carbines through the windows into the scout’s face. He indignantly protested that he was a dentist plying his trade and showed them his papers. They read the papers, winked at each other, and said they would escort him to the picket post.

The Federals rode on each side of the carriage, but occasionally they had to drop back because of the narrowness of the road. During these precious moments the scout began eating the incriminating letters he carried. He had a piece of cake which made the letters more “palatable.” But his mouth soon became so dry he couldn’t swallow. He reached out the window and broke off a pine branch then sucked on the needles to renew the saliva for his unpleasant task.

But when they arrived at the picket post, his heart sank as the Union soldiers discovered a letter sewn into the lining of his coat. He had forgotten the incriminating evidence which contained an outline of the defenses of Washington. Despite his denial of any knowledge of how the letter got into his coat, a sergeant was assigned to escort Stringfellow to prison. From there he would be taken to Washington and a certain noose. The doomed scout looked for an avenue of escape.

He offered to treat his guard to dinner at a tavern. While dining, the scout noticed a high open window behind his guard. After eating he stood and stretched, and his heart leaped when he noticed an ax in the corner. Stringfellow’s hand closed around the ax handle. Freedom was within easy reach. His mind swirled. To kill in battle was one thing. To send a person to his death like an assassin was another. He trembled and broke out in sweat. He couldn’t do it. He slowly released the handle. They reached the makeshift prison after dark and Stringfellow knew his only chance for survival was to escape that night. Watch for the next episode and Stringfellow’s escape!*

*From Stringfellow of the Fourth by R. Shepard Brown

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