Benjamin Franklin Stringfellow was born on June 18, 1840 at The Retreat near Raccoon Ford on the Rapidan River. The Retreat was his family home. He graduated from Episcopal High School in Alexandria in 1860 and went to Mississippi to teach Latin and Greek. When the War erupted he returned to Virginia to serve the Confederate States of America.

Stringfellow wanted to serve but he had some difficulty persuading the Army that he was physically capable. After all he was only 5 feet 8 inches and weighed around 100 pounds. He was rejected by The Little Fork Rangers, the Madison County troop, the Goochland County Dragoons, and the Prince William County troop. But what Stringfellow lacked in physical brawn he made up for in brains. He targeted the Powhatan Troop, Company E of the Fourth Virginia Cavalry, then captured 3 of their soldiers at gunpoint and marched them to the Company Cammander’s tent. The Commander was persuaded that the young man had some skills to offer and they swore him in on May 28, 1861.

He began right away with spying and his first assignment was to report on Yankee troop movements in and around occupied Alexandria, VA. He knew Alexandria well as his fiancée, Emma Green, lived there. Stringfellow soon caught the eye of J.E.B. Stuart at the Battle of First Manassas. Stuart had heard of Stringfellow and asked him to serve as his personal scout. Stringfellow became acquainted with other well-known scounts such as Redmond Burke, Will Farley, and John S. Mosby. In fact Farley and Burke had a hand in training Stringfellow.

Stringfellow moved in an out of battle and in and out of undercover. He fought at the Battle of Dranesville in November, 1861 and then from January to April, 1862 he was back in Alexandria, posing as a dental apprentice, collecting intelligence for the Confederacy. His job included reading the paper and passing on information to a courier each night. In those days troop movements were actually published in the newspaper. One day a man with his face wrapped in a towel raced into the dentist’s office with Stringfellow and horrified those in the waiting room with howls of excruciating pain. He left still holding the towel to his face. But the man was a fellow agent with so urgent a message it couldn’t wait to go through the usual nocturnal channels of communication. One of the people in the waiting room was a federal officer who never guessed he had just witnessed a classic scene of espionage. But this dental position ran aground when the dentist’s wife began to show more than friendly interest in Stringfellow. The dentist, already aware of his assistant’s true identity, noticed his wife’s seeming infatuation and promptly reported Stringfellow to Union authorities. Frank the spy fled for his life.

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