Benjamin Franklin "Frank" Stringfellow (1840 - 1913)

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Death: Died
Managed by: Doug Robinson
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About Benjamin Franklin "Frank" Stringfellow

Civil War Confederate Army Officer. He served as a Captain in the 4th Virginia Cavalry, and as a personal scout for Major General J.E.B. Stuart and confidential scout for General Robert E. Lee. He served with Stuart at Seven Pines, Stuart's ride around the Army of the Potomac, Cold Harbor, Seven Pines, and the raid at Catlett's Station. He also rode with Colonel John Singleton Mosby of the 43rd Virginia Cavalry in the raid at Loudoun Heights on January 9, 1864. By the end of the war, he was designated the "most dangerous man in the Confederacy”, with a reward of $10,000 on his head.

He went to Canada after the war, returned to Virginia in 1867, and entered the Episcopal Seminary of Virginia and was ordained as a minister in 1878. He served in many churches in Virginia and was the first Chaplain of the Woodberry Forrest School for Boys in Orange, Virginia. He became a United States Army Chaplain at the age of 57 and served in the Spanish-American War.

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Confederate Officer and Spy

When war broke out, Stringfellow returned to his native Virginia and sought a commission in the Confederate Army. Despite four denials due to his fragile health (and 94 pound weight), Stringfellow eventually secured a commission as Captain in the 4th Virginia Cavalry (his brother also served the Confederacy, although his cousins Pleasant and Robert Stringfellow served in the U.S. Army). Stringfellow rode with General J.E.B. Stuart at Seven Pines, Cold Harbor, and the raid at Catlett's Station. Stringfellow also rode with Colonel John Singleton Mosby of the 43rd Virginia Cavalry, most notably in the raid at Loudoun Heights on January 9, 1864.

However, Stringfellow's fame derived from his confidential service, sometimes directly for General Robert E. Lee, but much through J.E.B. Stuart until his death in March, 1864. By the end of the war, Stringfellow was known as the most dangerous man in the Confederacy, with a $10,000 bounty placed on his head.

Stringfellow posed as a dental assistant in Alexandria, Virginia and gathered intelligence, and later even obtained a dental license and did the same in Washington, D.C. Although Mary Surratt helped Stringfellow escape in March, 1865, he was captured and an attempt to blow up President Lincoln foiled.

Post-War Years

Stringfellow refused to take the loyalty oath after the war and moved to Canada. He returned to Alexandria, Virginia in 1867, enrolling at what became the Virginia Theological Seminary and marrying his high school sweetheart, Emma Green. Graduating, he was ordained an Episcopal priest in 1876.

At age 57, Rev. Stringfellow enlisted a chaplain in the U.S. Army, after obtaining a reference from former President Grant, who noted Stringfellow had refrained from shooting him years earlier.

Rev. Stringfellow also served in various parishes in Virginia, including in Franklin, Patrick, and Henry Counties. As rector, Rev. Stringfellow led the campaign that built Christ Episcopal Church in Martinsville in the 1890s, but moved on soon after the building was finished. He considered ministry among fellow Confederate veterans as his mission, and often regaled audiences with stories about his military escapades. He also became the first chaplain of the Woodberry Forest School, a male boarding school in Madison, Virginia which had been established by a fellow Mosby Ranger in 1889.

Stringfellow ultimately retired to Alexandria, where he died in 1913 and is buried beside his wife Emma at Ivy Hill Cemetery in Alexandria, Virginia.

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Frank Stringfellow : Lean Keen Spying Machine

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 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.

He had a close call at the end of this assignment and had to make his way through enemy lines after his escape. Following this he returned to scouting and picket duty. Stringfellow served with Stuart at Seven Pines and Cold Harbor. In July, 1862 he was put on independent scout duty by Stuart in order to reconnoiter Pope's army. In August, he located a large wagon train at Catlett's Station and led Stuart to it, almost capturing Pope in the process. Left behind at Cedar Run to watch enemy troop movements, Stringfellow was again almost captured by Yankee soldiers.

In the winter of 1863 Stringfellow returned to Alexandria to gather intelligence, having set up communication lines throughout Fairfax County. He was spotted in Alexandria, however, after he had been there only a short time. He managed to escape by hiding under the hoop skirt of a elderly Confederate sympathizer when pursued by Federal troops. Shortly after leaving Alexandria, angered by the killing of two of his men, he and a troop of about 35 Confederates attacked about fifty Yankees in house, killing and wounding many of them and taking about 25 prisoners.

In June, 1863 Stringfellow had another amazing escape. He was dining with some friends in their home near the Bull Run Mountains when they were surprised by Federal troops. Stringfellow was well known to the Yankees by now and a constant target of their search. This group had orders to kill him on sight. Aided by a black female servant, Stringfellow was able to find a tight spot in the attic to hide in. The Yankees searched high and low in the house and barely overlooked him. He then slipped out of the house, commandeered a horse from a Federal he surprised and made his escape. His luck ran out later that month, however, when he was captured and sent to Old Capitol Prison in Washington City. He was exchanged as a Captain in August. Later that month he led a raid with eleven other Confederates on a Federal Headquarters and almost succeeded in capturing another Yankee General.

In late September Stringfellow was on patrol with 2 comrades. While they were asleep 4 Yankees surprised them. Stringfellow was able to kill 1 Yankee and his comrade killed another. The other Confederate was shot but the remaining Yankees took off to alert their camp. The 2 Confederates separated, pursued hotly by the Yankees. Stringfellow escaped by hiding under a fallen cedar tree while the Yankees searched all around him. The 2 Confederates were then able to reunite and escape.

In late 1863 there was fighting around Stringfellow's boyhood home in Culpepper County. His mother was wounded in the foot and taken by the Federals in order to treat her injury. She was being held in a house that was in an area serving as a Federal regimental headquarters. Stringfellow got inside the Federal encampment and found his mother. He borrowed a woman's dress and bonnet from his mother’s female servant (who was still with his mother), slipped into the house and tended to his mother for 2 days before slipping out again and heading back to Confederate lines.

Early in 1864 Stringfellow captured a Yankee Captain who carried with him a pass for a Southern girl of Stringfellow's acquaintance. The Captain was hoping that the girl would attend a dance at his invitation and the pass would be used to get her there. Stringfellow borrowed the girl's dress and had the girl and her mother coach him on impersonating a female. The girl's father then drove him in a buggy to the end of Confederate lines where Stringfellow then went on alone. At the dance he got much useful information about Northern troop movements. One Yankee Major took a "romantic" interest in him. Another Lieutenant, became suspicious, took Stringfellow outside and accused him of being a female spy. Stringfellow, saying that he appreciated the Lieutenant's attentions, asked him if he would turn around a minute while he prepared himself to demonstrate to the Lieutenant his appreciation of his kindness. When the Yankee turned his back Stringfellow pulled his derringer and took him prisoner. He then took him out in the buggy, forcing the Lieutenant to act as if he was escorting his "date" home from the dance. Stringfellow then took his prisoner back to Confederate lines.

Stringfellow's last assignment came from Jefferson Davis himself. In March, 1865 he again impersonated a dental student in Washington. Gathering intelligence, he moved around from hotel to hotel. One hotel of his was full of detectives. One of these, a woman, had suspicions of him. In an attempt to trap him, at dinner one evening she proposed a toast to Abraham Lincoln. When everyone but Stringfellow had raised a glass she asked him why he wouldn't drink to Lincoln. In response, Stringfellow proposed a toast to "Jefferson Davis, President of the Confederate States of America." Stringfellow left that hotel soon after for new lodgings. When he was finally trying to get out of the city he was picked up by Federal troops who took him to a prison for further investigation, still not sure of his identity. Stringfellow again escaped from the prison before his identity was determined. It took him 21 days to get back to Virginia. By then the war was over.

At the war's end, Stringfellow was designated by some of his enemies as "the most dangerous man in the Confederacy", and a reward of $10,000 was offered for his capture. Stringfellow fled to Canada. During the spring of 1866 he wrote to his beloved Emma that he was undergoing a transformation,

I begin to realize that a new life is opening up to me - that "man does not live by bread alone - but by every word that proceedeth from the Father."

In 1867 Stringfellow returned to Virginia and after many months of preparation, he entered the Episcopal Seminary of Virginia, graduated and was ordained in 1876. Sometime during the post war period he married Emma Green and went on to serve many churches throughout Virginia.

Reverend Frank Stringfellow was rector of Christ Church in Martinsville, VA from 1891 to 1894 and, after leaving Christ Church, became the first Chaplain at Woodberry Forest School near Orange, VA a private boarding school for boys. The school was founded by his cousin Robert Stringfellow Walker in 1889. Walker had been a member of Mosby’s Rangers during the War.

In 1898 Stringfellow wanted to serve as a chaplain for the armed forces during the Spanish-American War. He was rejected as being too old. Stringfellow responded by writing to President William McKinley for help and asking for him to intervene. Stringfellow quoted a letter he had from President U.S. Grant. Shortly after the battle of Cold Harbor, during a mission with the purpose of capturing the Yankee Commander, Stringfellow had been close enough to Grant to shoot him in the back but had not been able to bring himself to do this. After the war Stringfellow wrote to President Grant about this incident. Grant in response wrote to Stringfellow thanking him and promising that he or any future president would be happy to grant any request of Stringfellow's. Thus, Stringfellow was allowed to become a U.S. Army chaplain at the age of 57. He returned from the war and continued his ministry until his death.

Frank Stringfellow died on June 8, 1913 from a heart attack. He is buried beside his wife Emma in Ivy Hill Cemetery, Alexandria.

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Captain Frank Stringfellow (CSA)'s Timeline

1840
1840
1913
1913
Age 73