While a student at the Episcopal School in Alexandria, Frank Stringfellow fell in love with Emma Green, daughter of a prominent furniture maker. His love for Emma would motivate him to undertake audacious missions which provided invaluable information to the Confederacy.

His first official covert mission in January of 1862, sent him into Alexandria to pose as a dental apprentice. Thus he wore civilian clothes which meant that if caught, he would be hung as a spy. He arrived at the office of a local dentist and Southern sympathizer, Richard Sykes, with appropriate papers to assume his new identity, Edward Delcher of Maryland. The real Delcher was a southern sympathizer who had passed through Alexandria and later joined the Confederate Amy in Vicksburg. Stringfellow learned everything about the man he was impersonating, as well as the skills of a dental assistant.

Each evening Stringfellow condensed newspaper information and left an envelope under the roof eaves for a courier to collect. Although he desperately wanted to see Emma, he made no contact for fear of endangering her. Things went smoothly for several months, but in early April Emma entered the dentist’s office. The waiting room was filled with four or five patients including a Pinkerton detective, as well as Mr. and Mrs. Sykes. Her eyes froze on her beau and she cried “Frank!” joyfully, and rushed towards him. With coolness of mind, he replied she must have mistaken him for another. Emma realized the gravity of the situation and apologized for her mistake.

That evening the dentist’s wife warned Stringfellow that her greedy husband had betrayed him. They heard the sound of approaching hooves and the spy bolted out the bedroom window. The Union soldiers spotted him and he led them on a merry chase through the streets and alleys of the old town. He grew winded and exhausted, but cleverly eluded them by submerging in a stream and breathing through a straw.

He later retrieved his hidden horse, and returned to the Confederate cavalry in time to scout for Jeb Stuart during Stuart’s famous “ride around McClellan.”

Source:  Stringfellow of the Fourth by R. Sheppard Brown