Scouts and Spies: John Scobell

Meet John Scobell. 

While serving as the head of the Union Intelligence Secret Service in the Civil War, Allan Pinkerton diligently debriefed Southern refugees, deserters, and freed and runaway slaves, seeking news and reliable information regarding the location and strength of the enemy. When Pinkerton met someone knowledgeable, trustworthy, and willing, he recruited them and sent them back into the South as Secret Service Scouts and Spies. 

Scobell was an educated and well-spoken former slave from the state of Mississippi. At the beginning of the war, he and his wife journeyed with their master, a Scotsman by the same name, to Virginia where he and his wife were given their freedom. Scobell’s wife found employment in Richmond, Virginia, while Scobell made his way to the Union lines and the Secret Service office where he met Pinkerton.

As part of the debriefing, Scobell gave an account of his travels through the country, describing in detail the localities he passed as well as the roads and streams.

Pinkerton noted that Scobell was remarkably gifted and charmed everyone who met him. He often appeared lighthearted. He was as full of music as the feathered songsters that warbled in the tropical groves, carrying an endless array of melodies and an assortment of Scottish ballads, all sung with a voice both powerful and sweet. 

“Possessing the talents that he did, I felt sure that no one would suspect that he was a cool-headed and vigilant detective,” Pinkerton wrote. 

Intercepting Confederate documents

Scobell’s first scouting mission behind enemy lines was a mere two weeks after he was recruited. He was dispatched back to Virginia along with Timothy Webster, another scout, to gather intelligence and disrupt enemy communication. 

Their journey began together, with a carefully planned route through various towns in Virginia. Upon reaching Leonardstown, the two scouts parted ways, with Webster heading towards Richmond and Scobell making his way to the Confederate camp at Dumfries on his way to Centreville to meet another of Pinkerton’s Secret Service agents, a spy. 

While at a hotel in Leonardstown, Webster noticed a suspicious character and made his acquaintance. His name was Dr. Gurley, who claimed to be a deserter from the Union army and carried important dispatches for the Confederate Secretary of War, Judah P. Benjamin in Richmond. 

Immediately, Webster was intent upon finding Scobell, if possible. He knew he needed to intercept the dispatches, and he required Scobell’s help.  

As a seasoned detective, Webster knew exactly where to look, within a short distance of the locality, he saw Scobell approaching him from the opposite direction. In a few words, they devised a plan.  

The next afternoon, Scobell waited outside Gurley’s hotel for a signal from Webster. Scobell, with his wit and physical prowess, covertly followed Gurley to a wooded area a short distance from the hotel and ambushed him, taking the documents without arousing suspicion. 

By the time Dr. Gurley returned to the hotel, he realized that during the ambush the only items that were missing were the dispatches entrusted to him.  

Webster said, soothingly. "The loss of the papers won't amount to much; when we arrive in Richmond you can communicate verbally the nature of the papers you have lost." 

"That's the devil of it," blurted out the doctor. "I don't know their contents; they were entrusted to me by men who are working in the interest of the South, and as they were sealed, I have no more idea than you have what they contained." 

By the time Webster and Scobell met later that night, Scobell had already made arrangements to forward the documents to Pinkerton by a newly recruited scout — with the documents safely sewn in the lining of the scout’s coat and full instructions as to how the papers should be delivered. 

Pinkerton later noted the intercepted documents “were of a highly important nature, and conveyed information to the rebel authorities, which would have been very dangerous had they reached their legitimate destination.”  

Working with the Loyal League

The next day, Webster continued his original mission toward Richmond, now traveling with Gurley. Webster's connection to Gurley did much to advance the Union cause by way of introductions to Confederate officers, who liberally shared troop locations and movements with Webster. 

Scobell remained in Leonardstown a few days after Webster's departure to network, as it were. Scobell met with the Loyal League, an underground organization comprised almost entirely of African Americans throughout the North and South that was dedicated to the cause of freedom. Although those in the South were barred from taking up arms, they dedicated their efforts to assisting Northern troops when the opportunity offered.  

This encounter was but the beginning of Scobell’s relationship with the Loyal League. Throughout the war, Scobell ran a sort of sub-secret service agency to dispatch intelligence to Pinkerton and the Union. It was through Scobell and his operatives that the Union obtained some of the most prolific intelligence throughout the Civil War. 

A Perilous Journey and Narrow Escape

After Leonardstown, Scobell continued on his original mission to meet Hattie Lawton, another Pinkerton agent-scout-spy, to bring back intelligence. Their mission was perilous but successful. In a twist of irony, these two spies were followed by a Confederate spy, who posed as a peddler, on their way to Washington. They were ambushed by enemy horsemen. Their quick reflexes resulted in a wild chase, gunshots punctuating the silence of the forest before the Union's cavalry came to their aid and helped them reach the safety of a Union camp.  

Lauded for their invaluable intelligence and bravery, they found themselves with a brief respite before resuming their service to the Union. 

Undercover and Behind Enemy Lines

After several short-term assignments, Scobell was sent on a long-term assignment with Timothy Webster and Hattie Lawton to Richmond, who posed as a wealthy Southern couple. 

Over the course of several short-term missions, Webster had established himself in Richmond as an ardent secessionist and a Southern secret agent in the Confederate War Department under the Confederate Secretary of War Judah Benjamin and Provost Marshal General Winder.  

One of Webster’s duties was to convey underground mail between the South and the North—in the amount of 200-800 letters per month. He made many covert trips between Richmond and Baltimore via Washington, where the mail was steamed open, read, and carefully resealed for delivery to the original recipients.

Scobell assumed the cover of their illiterate servant. Ever cool-headed and vigilant, Scobell acted ignorant of the Civil War. Confederate officers dismissed Scobell simply as a light-hearted and entertaining butler, often leaving important documents in view and freely discussing war strategy in front of him. Scobell made note of everything and dispatched detailed reports back to Washington. 

The trio’s assignment was cut short in 1962 when Webster, Lawton, and Scobell were betrayed, arrested, and tried as spies. Webster was sentenced to death. Lawton was sentenced to one year in prison. Scobell was released because the Confederates could not believe a servant could be a spy for the North.  

Scobell returned to the North and continued to serve the Union cause, embodying calm resolve and subterfuge. Not much more is known about Scobell or his life after the Civil War. We do know that his bravery and quick wit undermined the Confederate war efforts and helped to lead the Union to victory. 

This blog is a part of our Scouts and Spies series. Our founder, Allan Pinkerton, and his team of Secret Service Scouts and Spies played a critical role in gathering intelligence during the U.S. Civil War, providing a tactical advantage on the battlefield. Skilled in reconnaissance and surveillance, they navigated enemy territory, monitored enemy movements, and gathered crucial information that aided military decision-making.  

Pinkerton “scouts” still play a crucial role. Organizations today rely on our research and intelligence to help shape their strategies, identify vulnerabilities, and anticipate threats, ensuring the success and safety of their operations across diverse environments. Trust in the Pinkerton legacy, and let our scouts guide your due diligence process today.