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The most dangerous spy


    Occasionally, looks can be deceiving. For Frank Stringfellow, a blue-eyed, blond-haired, beardless, 94-pound teacher of Latin and Greek in a Mississippi schoolhouse, the old saying holds true. He is neither as famous as Belle Boyd nor as controversial as Rose Greenhow. Yet, at least one historian (Bakeless) rates him the most dangerous spy in the Confederate army.


    Since spying has been described as "the most dangerous and thankless form of Civil War military service," (Foster) this is hardly an appellation assigned to a weakling. Though nineteenth-century espionage no doubt had its moments of tedium, it was nevertheless full of hair-raising escapades, narrow escapes, and the knowledge that immediate execution awaited the spy luckless enough to be caught. Stringfellow himself admitted that he always expected his current mission to be his last.


    Benjamin Franklin Stringfellow was rejected for service four times (probably because of his frail appearance) before he managed to join the 4th Virginia Cavalry. He began "secret service" operations almost at once, becoming one of J.E.B. Stuart’s prime agents.

Going undercover


    As described in Bakeless’s book, one of Stringellow’s early assignments had him posing as a dental assistant, actually living in the home of the dentist. A cover story was devised in the most minute detail, including an assumed identity, and fake baptismal and medical certificates. The agent memorized all there was to know about the man he was impersonating—a real dental assistant who was with the army and hundreds of miles away.


    His job was to read all the daily newspapers (which were full of military intelligence; the press considered it a sacred duty to keep the public informed, in spite of outcries by the generals.) After reading the papers, he wrote out a report and left it in a certain place outside the dentist’s office. Each night another agent picked it up and, presumably, delivered it to the Confederate government in Richmond.


    One day a man with his face wrapped in a towel disappeared 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. 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





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