Benjamin Franklin String-fellow: The Spy Who Spared a General

At five feet, eight inches tall and weighing barely 100 pounds, the diminutive Frank Stringfellow proved to be one of the Civil War’s most effective spies, acquiring and passing a bevy of secrets to the Confederacy about Union troop movements and plans throughout the conflict.

A scout in the 4th Virginia Cavalry, Stringfellow repeatedly donned civilian clothes, disguising himself as a dental apprentice, a store assistant, and even a woman, enabling him to operate freely and extensively in Washington, D.C., as well as in Union-occupied Alexandria, Virginia. In one instance, in August 1862, Stringfellow guided Confederate cavalry on a raid at Catlett’s Station, Virginia, where the Union Army of Virginia, under the command of Major General John Pope, was headquartered. After overrunning Federal troops guarding Pope’s tent, the Confederates seized documents, including Pope’s dispatch book filled with valuable intelligence. The information was used to aid General Robert E. Lee in his decisive defeat of Pope’s army at the Second Battle of Bull Run.

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From left: Benjamin Franklin Stringfellow; Second Battle of Bull Run; John Pope; J.E.B. Stewart; Catlett's Station, Virginia

At five feet, eight inches tall and weighing barely 100 pounds, the diminutive Frank Stringfellow proved to be one of the Civil War’s most effective spies, acquiring and passing a bevy of secrets to the Confederacy about Union troop movements and plans throughout the conflict.

A scout in the 4th Virginia Cavalry, Stringfellow repeatedly donned civilian clothes, disguising himself as a dental apprentice, a store assistant, and even a woman, enabling him to operate freely and extensively in Washington, D.C., as well as in Union-occupied Alexandria, Virginia. In one instance, in August 1862, Stringfellow guided Confederate cavalry on a raid at Catlett’s Station, Virginia, where the Union Army of Virginia, under the command of Major General John Pope, was headquartered. After overrunning Federal troops guarding Pope’s tent, the Confederates seized documents, including Pope’s dispatch book filled with valuable intelligence. The information was used to aid General Robert E. Lee in his decisive defeat of Pope’s army at the Second Battle of Bull Run.

In April 1864, General Lee wrote to Confederate President Jefferson Davis, informing him of a report that Union General Ambrose Burnside was marching with 23,000 troops through Alexandria and toward Confederate positions outside Richmond, Virginia. Lee believed the report came from Stringfellow and was trusting enough of it to ask Davis that troops previously diverted to North Carolina be summoned back to Virginia to strengthen Confederate defenses there.

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From left: Convalescent camp; Ambrose Burnside; Marshal House, Alexandria, Virginia; Erecting a stockade, Alexandria, Virginia

Stringfellow’s daring led to capture on multiple occasions. After his first arrest, the Union failed to identify him as a spy and released him within days as part of a prisoner exchange. After his second arrest, he was jailed at the Old Capitol Prison in Washington, D.C., and interrogated by operatives of Union spymaster Allan Pinkerton, who threatened him with execution. Stringfellow was in his Confederate military uniform when captured, though, and was thus treated as an ordinary prisoner of war, rather than a spy, and subsequently exchanged once again.

Union soldiers captured Stringfellow for a third time in April 1865, but he escaped during his transfer to a prison in Maryland. At the same time, a manhunt was underway following the assassination of President Lincoln, and Union authorities briefly suspected Stringfellow might be an accomplice of John Wilkes Booth, since the pair had once shared the same boarding house. Stringfellow fled to Canada, where he remained until 1867, when he returned to the United States to marry.

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From left: William McKinley; Ulysses S. Grant; Stringfellow grave

Later ordained an Episcopal priest, Stringfellow wrote a letter to President Ulysses S. Grant, revealing that in 1864, he had once been close enough to shoot Grant, then commanding the entire Union Army, but could not bring himself to pull the trigger. Grant responded to the letter, thanking Stringfellow for sparing his life and promising that he or any future president would accommodate any request made by the former spy. In a letter to President William McKinley in 1898, Stringfellow referenced Grant’s offer, and asked that he be allowed to serve as an army chaplain in the Spanish-American War. McKinley agreed.

Stringfellow died of a heart attack in 1913 at the age of 73 and is buried at the Ivy Hill Cemetery in Alexandria, Virginia.