Civil War’s Great Locomotive Chase West Virginian James J. Andrews Was a Trained Secret Agent For the Union

James J. Andrews was very probably far more than just a quinine smuggler intending to make a lot of money through the destruction of a key railroad system in 1862 that would have placed the Union army in a critical location from which the key transportation center for the Confederacy, Chattanooga, could be isolated and captured. The “smuggler,” Andrews, developed two separate plans to sabotage key railroad connections and actually executed the second plan that was the basis for Walt Disney’s “The Great Locomotive Chase.”

STRATEGY

Major General Ormsby M. Mitchel, commanding Federal troops in middle Tennessee, sought a way to contract or shrink the extent of the northern and western borders of the Confederacy by pushing them permanently away from and out of contact with the Ohio and Mississippi valleys. This could be done by first a southward and then an eastward penetration from the Union base at Nashville, which would seize and sever the Memphis & Charleston Railroad between Memphis and Chattanooga (at the time there were no other railway links between the Mississippi river and the east) and then capture the water and railway junction of Chattanooga, Tennessee, thereby severing the Western Confederacy’s contact with both the Ohio and Mississippi river valleys.

At the time, the standard means of capturing a city was by encirclement to cut it off from supplies and reinforcements, then would follow artillery bombardment and direct assault by massed infantry. However, Chattanooga’s natural water and mountain barriers to its east and south made this nearly impossible with the forces that Mitchel had available. But if he could somehow block railroad reinforcement of the city from Atlanta to the southeast, he could take Chattanooga. The Union Army would then have rail reinforcement and supply lines to its rear, leading west to the Union-held stronghold and supply depot of Nashville, Tennessee.

James J. Andrews, a civilian scout and part-time spy, proposed a daring raid to Mitchel that would destroy the Western and Atlantic Railroad as a useful reinforcement and supply link to Chattanooga from Atlanta and the rest of Georgia. He recruited the men known later as “Andrews’ Raiders”. These were the civilian William Hunter Campbell and 22 volunteer Union soldiers from three Ohio regiments: the 2nd, 21st, and 33rd Ohio Infantry. Andrews instructed the men to arrive in Marietta, Georgia, by midnight of April 10, but heavy rain caused a one-day delay. They traveled in small parties in civilian attire to avoid arousing suspicion. All but two (Samuel Llewellyn and James Smith) reached the designated rendezvous point at the appointed time. Llewellyn and Smith joined a Confederate artillery unit, as they had been instructed to do in such circumstances. Andrews’ proposal was a combined operation; General Mitchel and his forces would first move on Chattanooga; then, the Andrews’ Raid would promptly destroy the rail line between Chattanooga and Atlanta. These essentially simultaneous actions would bring about the capture of Chattanooga. Andrews’ Raid was intended to deprive the Confederates of the integrated use of the railways to respond to a Union advance, using their interior lines of communication.

When the Union Army threatened Chattanooga, the Confederate States Army would (from its naturally protected rear) first reinforce Chattanooga’s garrison from Atlanta. When sufficient forces had been deployed to Chattanooga to stabilize the situation and hold the line, the Confederates would then launch a counterattack from Chattanooga with the advantage of a local superiority of men and materiel. It was this process that the Andrews raid sought to disrupt. Source: Wikipedia

Historians unfamiliar with special operations and espionage have managed to relegate Andrews to the status of a smuggler and opportunist by misunderstanding the efforts Andrews made to develop smuggling routes and “safe houses” occupied by fellow smugglers — as a cover story for his espionage. No amateur military strategist could have developed two separate plans to destroy the key railroad connection between southern industrial areas and their armies operating in Tennessee where they threatened Kentucky. Andrews seemed to know the military value of what he was proposing better than some less imaginative Union commanders.

It appears that the Union army developed an espionage capability that remains essentially unknown to researchers even today. As mentioned above, few historians have experience in espionage and special operations and they fail to understand the tactics utilized and the desired end state of operations. As a result, historians normally carefully record only the cover story developed to shield the operation from discovery. In the case of James J. Andrews, his preparations to operate deep within the Confederacy carry hallmarks of a carefully designed, deployed, and well functioning espionage operation.

Like an actor getting into “character,” a spy must avoid doing something unnatural in the “role” being played and a very common mistake made by amateurs is the failure to get into proper “character” for the operation being conducted or, when in character, appearing in places or carrying out activities that are incongruent with the character’s “costume.” The terms used to describe these role-playing aspects of espionage are “cover for status” and “cover for action.” Cover for Status is a person’s presumed identity — his costume. A person can pretend to be a student, a businessman, a repairman, or even a smuggler, etc. Cover for Action explains why the person is doing what is being done. The purpose of using good cover for action and cover for status is to make the presence of the person conducting the operation look routine and normal to observers who might sound an alarm

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First, Andrews — and possibly his Union army “handler” who was normally the Inspector General of the military unit being supported — developed a carefully designed “cover for status.” Andrews became a smuggler operating between the two warring sections who clandestinely delivered scarce medical items, particularly quinine, from the North where it was relatively inexpensive into the South where it was in high demand. The bitter powder was effective in treating the “chills and fever” associated with malaria that was widespread in the southern United States. Due to scarcity, its value increased exponentially in the south. In his smuggler “cover for status” role, Andrews maintained a careful “cover for action” by actually smuggling goods into the South that allowed him to be able to bribe his way to freedom if apprehended as a “smuggler” when he would have been hanged as a spy if either his “cover for status” or “cover for action” failed him. In order to afford bribes in case the “contraband,” the quinine, was confiscated, Andrews, the spy, probably carried a gold piece beneath the heel of each boot.

Second, his capability misunderstood, historians also thought his reputation as a “scout,” actually a spy, was too well known in the Union army to have been a part of any covert capability. Union army commanders were provided with an ample “Secret Service Fund” and in many cases, the secret agent was paid according to the value of the intelligence brought from within enemy territory. For example, General Phil Sheridan provided a cash award of $1500 to a telegraph operator named Keefer who tapped the telegraph line into the French Consulate in New Orleans and broke the French diplomatic code. The rumor that Andrews was to receive either $20,000 or $50,000 if his locomotive raid was successful is certainly possible. Counterintelligence was not appreciated by either side during the Civil War and military “scouts” were often relating their exploits in newspapers and having photographs made while wearing the enemy uniform. To them the enemy was far away and was unlikely to learn of a spy’s true name since many probably operated in alias. War stories told between operations were a common occurrence.

James Andrews had the foundation of a perfect cover story, too. He was from Holiday’s Cove, today’s Wierton, in western Virginia’s Hancock country. While he actually resided in Kentucky at the outset of the Civil War, it was unlikely that he would claim residency there while deployed but would claim to be a Virginian in order to maintain an excellent cover. His accent probably was more southern than northern and this helped with his cover for status.

Andrews was in his early thirty’s 30’s and would have been subject to conscription while in Confederate territory since the draft was imposed in early spring 1862 and all white males between the ages of eighteen and thirty-five were subject to this law. He would have to have developed an additional level of his “cover for status” in order to avoid the draft and he and his “handler” ensured he would remain independent of suspicion — and conscription — by also appearing to spy for the Confederacy while he was in the North. Passing useless “throw-away” information to Confederate officers ensured that Andrews remained capable of moving back and forth through the opposing sections. Russell Bonds explains historian confusion about espionage in his book, Stealing the General, by explaining the view from William Fuller, the train conductor who pursued Andrews and the hijacked train:

“His adversary William Fuller would later write that Andrews was a ‘convenient, useful and good friend (?) of both the north and south, according to the latitude of his place at any given time, but his last service was intended for the Federals… Andrews was in the business of a spy and contraband agent for the money.”

A key question emerges: How was Fuller was able to draw these conclusions from a single day of chasing Andrews? It is highly unlikely that the conductor on a train would be able to develop this degree of insight from a day spent chasing the stolen train. William Fuller became a key source for the story subsequently told about James J. Andrews who was doing exactly what a trained, skillful secret agent should have been doing as he lived his “cover for status” while conducting his “cover for action.”

First, in the spring of 1862, he met with General Don Carlos Buell in Nashville and persuaded him to support the plan for eight men to infiltrate southward near Atlanta to steal a train and burn a key covered bridge over the Tennessee River. This operation failed when the volunteering southern train engineer failed to arrive at the selected rendezvous illustrating the recruitment of a key support asset that reveals Andrew’s previous efforts in developing a support auxiliary team that is vital to conducting operations in enemy territory. As a second attempt was being considered, Buell no longer supported the failed plan and Andrews subsequently was able to gain access to a second general officer, General Ormsby Mitchel, who was persuaded to support the plan. Being able to meet a second general officer suggests that Andrew’s handler was the Inspector General at the Army headquarters, a level higher than that of either Buell or Mitchel. Secret agents posing as smugglers never have access to general officers on their own.

A rumored story about Andrews previously spying inside the Confederate’s Fort Donelson is also quite plausible Another Union scout/spy named Charles Carpenter managed to enter both Fort Henry and Fort Donelson during Grant’s campaign against these strong Confederate fortifications. 

Andrews also believed in what he was doing as he planned the high risk deep penetration raid that may have shortened the Civil War, if successful. His motivational speech to his volunteer soldiers is not what would be expected of an opportunistic smuggler motivated by money. Again, from Russell Bonds:

“’Now, my braves,’ Andrews had told his gathered volunteers in their initial meeting outside Shelbyville, ‘there is little doubt that we will burn the bridges, and that General Mitchel will occupy Chattanooga, the most strategic point in the Confederacy … Our work is the entering wedge to more important movements which will result in a speedy suppression of the rebellion, the restoration of the peace, and our return to our homes and peaceful pursuits.’” 

Some smuggler …. His stoicism as he awaited execution by hanging also tends to expose an experienced covert operator who knew the risks he was talking and accepted them.