If it was not clear by this point, Thomas Nelson Conrad had a bit of an ego. The theatrical flair and rhetorical ability that he demonstrated during his time at Dickinson College and the Georgetown Institute also translated to a knack for self-publicity, much to the benefit of historians.
In May 1887, Conrad published a series of pieces in The Times, a newspaper based in Philadelphia, Pennsylvania, detailing his adventures during the Civil War. The pieces did so well (or at least stoked his ego sufficiently) that Conrad decided to turn them into a ghost-written book in 1892 titled “A Confederate Spy: A Story of the Civil War.” Conrad was not happy with just that book either; he also revised and expanded the memoir and re-published it as “The Rebel Scout: A Thrilling History of Scouting Life in the Southern Army” in 1904.
Much of what we know about what Conrad did during the Civil War comes from these books and articles. They are an excellent primary source of information about the Confederate Secret Service, which like most spy agencies did not keep a lot of detailed records.
However, Conrad’s ego is blatantly obvious in the books. He frequently stretches the truth to make the mundane parts of the war seem exciting and sexy. There are a number of retold stories about Conrad that sound completely unbelievable, such as hiding in a woman’s hoop skirt to avoid federal soldiers. Furthermore, “The Rebel Scout” is full of dialogue and stories that Conrad suddenly “remembered” in the 12 years since he wrote his first book.
This is all a disclaimer to say that maybe parts of this narrative may not be perfectly accurate, considering how prone Conrad was to self-mythologizing. However, we do not have many other sources to go by.
We can be reasonably sure that after his release from the Old Capitol Prison in 1861, he went straight to the Confederate Army of Northern Virginia to enlist.
According to Conrad’s memoirs, one of the first people he met upon his release was Dabney Ball. Ball was a member of the inner circle of Confederate cavalryman James Ewell Brown Stuart (better known as Jeb Stuart).
He held the rank of major, in charge of all the chaplains in Stuart’s cavalry, but he was better known as “The Fighting Parson.” He joined Stuart’s First Virginia Cavalry in July 1861, earning his nickname for his non-ecclesiastical involvement at the First Battle of Bull Run, the first major land battle of the war. According to accounts from other soldiers, Ball rode his horse to the front lines of the battle and fired every shot in his revolver at federal troops from only a few feet away.
Ball took Conrad under his wing, recognizing his intelligence and talent, and personally recommended him for service to Stuart. Jeb Stuart’s cavalry is infamous in Confederate war history for his stunning victories against federal forces. Conrad had great admiration for the cavalryman; he named the horse he rode in the later years of the war after the reliable commander who had treated him so well.
Despite the contradictory nature of the assignment, Stuart gave Conrad two jobs. He would serve as both a chaplain in the Third Virginia Cavalry and as a scout. Conrad had the theological training and experience to pass off as a convincing chaplain. Additionally, he had an intimate knowledge of and a large social circle in northern Virginia, allowing him to slip easily across enemy lines.
According to his memoirs, Conrad was running reconnaissance missions within a few days of enlisting. In the relative calm after the First Battle of Bull Run, he easily snuck into the headquarters of Union generals while disguised as a chaplain with the federal army. Neither side had gotten used to the idea of spies reconnoitering their generals.
His extensive knowledge of Washington, D.C., and the surrounding area would prove very useful in his first major assignment. At that point in the war, the Confederate government was desperate for cash because of the extensive federal blockades of their ports. The rebel government realized that the war would not last very long if they could not obtain a foreign loan.
Conrad was called from the first to the War Department in Richmond, where he was told his first assignment. He was to meet British and French agents in Washington and convey them to Richmond without detection.
As identification, he was given a note from the War Department that described a gash on his tongue and a scar on his left index finger. He shaved his full beard down to long sideburns, bought norther-made shoes and replaced his plug chewing tobacco with the short-cut tobacco popular in the north. Wearing a gray civilian suit, he set out on his trusty scouting steed — named Jim Crow, I kid you not — for enemy territory.
Getting into the city was the easy part. Conrad stealthily crossed the Potomac River into Maryland at an unmonitored ford and then simply walked into the city, appearing as another farmer from Maryland.
After searching the registers of local hotels, he managed to find the agents as well. They were easily convinced by the gash on his tongue that they had the right man. With the help of a sympathetic cobbler, he stowed the agent’s documents in their shoes and rented a carriage from another friendly Confederate.
The hard part of the mission was getting back into Virginia. The borders of the city were crawling with guards who would have questioned the presence of the agents.
Conrad was forced to go underground (quite literally). Along the old Chesapeake and Ohio Canal, which paralleled the river into Maryland, there was a large culvert that allowed a small stream to flow by.
There was one problem: the roof of the carriage was too high. Thinking quickly, Conrad drove to the house of another Confederate sympathizer, who ordered his slave to get Conrad a handsaw. In “A Confederate Spy,” Conrad recalls spending nearly an hour sawing off the roof. He describes it as “the hardest job I ever had.”
The effort paid off for Conrad. The mission was ultimately successful and the agents made it to Richmond, negotiating a $3 million loan that would help finance the war. Conrad also earned a reputation as a scout who could cross back and forth from Washington easily, transferring valuable information for the Confederacy.
After that mission, Conrad began making regular trips to Washington, D.C., developing a spy network that would serve the Confederacy later in the war. Initially, he frequently spent nights outside the city at the hotel of John Surratt Sr., who was an interesting character himself.
The entire Surratt family was heavily involved in the Confederate cause. One of his sons, Isaac, enlisted in the 33rd Confederate Cavalry, and his other son, John Jr., was a courier for the Confederate Secret Service. Throughout the war, the Surratts were suspected of operating a secret courier network from the hotel. John Surratt’s wife, Mary Surratt, was executed after the war for aiding John Wilkes Booth’s escape after the assassination of Abraham Lincoln.
However, Conrad later decided to move his operations closer into town. One of his old Washington friends, Thomas Green, owned a house in the heart of the capitol at the corner of Constitution Avenue and 17th Street. Green had bought the old Van Ness house, located where the Organization of American States is today, in 1846, and during the Civil War, it was one of the most prominent private residences. Green, a Confederate sympathizer, had aided Conrad in his adventures since his release from the Old Capitol Prison and was likely more than happy to help.
By the spring of 1862, Conrad writes that he had set up a relatively strong intelligence-gathering operation based around the house. Conrad used multiple double agents in the federal government to gain critical military information, which he then covertly relayed to Richmond.
One critical component was a friend in the federal War Department who worked as a clerk and occasionally passed him information. Early in the war, the clerk copied the contents of a file describing a major campaign planned by George McClellan, who was leading the Union army at the time. The clerk left the copy of the documents sitting on his desk during his lunch break. Conrad, living close by, simply walked into the office and picked them off of the desk.
The documents described troop and equipment movements in McClellan’s planned Peninsula Campaign which was supposed to capture the Confederate capitol in Richmond. However, Robert E. Lee and the Confederate army were able to beat back the federal forces, possibly using the information obtained by Conrad. The campaign also made Jeb Stuart famous after he rode his cavalry around the entire Union army.
However, Conrad may have needed to put more thought into his choice of headquarters. If you are running a covert spy ring in enemy territory, it may not be the best idea to locate it in one of the most famous houses in the area. Furthermore, Green was fairly well known as a Confederate sympathizer and already on the federal government’s radar.
Another one of Conrad’s old friends from the Confederate Army, Edward Norton, had wormed his way into the ranks of the U.S. Federal Detective Police. According to Conrad, he was one of the right-hand men of Lafayette Baker, the chief of the agency in charge of intelligence and counterintelligence.
Conrad and Norton would regularly meet to exchange information, which worked fairly well until about the middle of the war, when Norton found out that Baker was planning to raid the old Van Ness house. To top that, Norton could only meet Conrad to tell him a few hours before the raid was planned to occur.
As soon as Norton told him, Conrad fled the city as fast as he could. According to his memoirs, he had a serendipitous meeting with the mother of one of his former Georgetown Institute pupils as he was trying to leave town. She loaned him the money that he needed to pay off a boat captain to let him pose as a crew member. He avoided detection by federal inspectors and made it successfully to a hideout in King George County, a little way outside of Fredericksburg and 50 miles from the detectives on his trial.
However, this did not happen until much later in the war (Conrad never lists a date in his memoirs beyond that it happened after the summer of 1863). In the meantime, Conrad was working his way up in the ranks of the Confederate secret service.
Two days after the Battle of Fredericksburg ended in December 1862, Conrad made his way to Richmond to visit Confederate President Jefferson Davis. Conrad suggested to Davis that he might better serve the Confederate cause as not just a scout but as a spy in command of a handful of men. Davis agreed to write an order to the commander of fortifications in Richmond asking him to promote Conrad, but with a warning.
“'I cannot bear to think of our young men being shot down or hanged as spies, but go back to your camp and think well of the results,'” said Davis, quoted by Conrad in his memoir. “'Then if you can reach no other conclusion, the detail shall be granted.'”
Conrad says that he had no change of heart that night. The next day, he went to the commander and was promoted to the rank of captain. No longer just a scout, he was now a real Confederate spy.