O'Donnell: Mosby’s Greenback Raid & the South’s Information War

Modern conflicts are increasingly fought less on traditional battlefields and more through irregular warfare like disrupting supply chains, conducting psych ops, and other strategic maneuvers—including timing attacks with an eye toward media coverage and upcoming elections.

Perhaps no one in American history perfected the art of irregular warfare like Confederate partisan leader John Singleton Mosby and his Rangers, who although they never numbered more than a few hundred men, terrorized and disrupted thousands of Union troops in the Shenandoah Valley.

Despite being pursued by Lincoln’s special forces, Mosby’s Rangers constantly threatened Union positions and attacked the rails. One operation in particular in mid-October 1864, known as the Greenback Raid, captured national headlines.

Led by Mosby himself, this mission targeted an undefended stretch of the railroad near Duffields Depot in Northern Virginia and a western-bound passenger train scheduled to pass at 2 a.m. The presidential election loomed in November, and every attack on railroads and wagon trains that made headlines in the Northern newspapers damaged public opinion of the Lincoln administration’s handling of the war.

Along the way Mosby’s men encountered a small party of Jessie Scouts, Union soldiers dressed in Confederate butternut. The scouts fled when attacked, but one unfortunate soldier was captured. Ranger Ewell Atwell was given the unenviable duty of executing him for the capital offense of wearing a Confederate uniform as a spy. “Ewell had a record for killing men in a fight, but he told me that he just did not have the nerve to take that fellow out under the stars and all alone by themselves stand him up and shoot the life out of him. So he told him to turn his back and run for it and he would give him five steps start. How much that was worth to him in front of Attwell’s [sic] revolver, God knows. Attwell [sic] swore to the men that he did not know.”

The full story of Mosby, his Rangers and the Union soldiers who hunted them is told in my new bestselling book, The Unvanquished: The Untold Story of Lincoln’s Special Forces, the Manhunt for Mosby’s Rangers, and the Shadow War That Forged America’s Special Operations. The book reveals the drama of irregular guerrilla warfare that altered the course of the Civil War, including the story of Lincoln’s special forces who donned Confederate gray to hunt Mosby and his Confederate Rangers from 1863 to the war’s end at Appomattox—a previously untold story that inspired the creation of U.S. modern special operations in World War II.

The book also tells the story of the Confederate Secret Service, the unofficial hidden hand of the Confederate government which operated out of the opulent St Lawrence Hotel in Montreal, Canada. One of its most important objectives was to erode Northern morale through manipulation of news coverage of the war. Covert operative George Nicholas Sanders bragged to President Jefferson Davis that his goal was “the Democracy [the Democratic Party] having possession of the press.” Among other efforts, he sent tens of thousands of dollars to various Democrat news organizations, plying them with cash in order to shape a narrative of how hopeless and fruitless the war had become.

Although independent, Mosby, as a savvy guerilla leader, fully understood his role in providing fodder for that narrative in selecting this particular train, knowing “it would create a greater sensation to burn it than any other.”

After their encounter with the Jessie Scouts, the Rangers picked their way in the night through a gap in enemy lines without being detected by patrols or reported to any of the nearby enemy camps. A bright, clear moon shone down on Mosby and approximately eighty of his Rangers as they lay exhausted, sleeping on a steep frost-covered bank next to the railway track they had sabotaged. The Rangers were jarred from their slumber by the screech of steel brakes, a deafening explosion, and showers of red-hot cinders, steam, and ash. “A good description of the scene can be found in Dante’s Inferno,” quipped the erudite Mosby in his memoirs.

“Above all could be heard the screams of the passengers—especially women.” They had timed their arrival to the minute to minimize the danger of the “extremely hazardous enterprise.” Mosby justified the risk: “I knew it would injure Sheridan to destroy a train and compel him to place stronger guards on the road.” Mosby also carefully selected the location of the attack to minimize injury to the passengers: “I preferred derailing the train in a cut to running it off an embankment, because there would be less danger of passengers being hurt.”

As the massive black locomotive veered off the displaced track and into the deep cut in the earth, the boiler exploded, creating mayhem and confusion. Mosby jumped up from his sleep, literally pushed his men down the steep bank, and ordered them to pull the frantic travelers from the train before setting fire to the ten passenger cars.

When a car full of German immigrants traveling west to get homesteads refused to leave their seats, Mosby suggested they set fire to the coach to encourage them. “They don’t understand English, perhaps they understand fire,” said one Ranger as he threw a parcel of lighted New York Heralds into the train.

“The Germans now took in the situation and came tumbling, all in a pile, out of the flames. I hope they all lived to be naturalized and get homes. They ought not to blame me, but Sheridan; it was his business, not mine, to protect them.”

Mosby remained atop the bank, as he had been injured a few weeks earlier in a skirmish when his horse was shot and his foot trampled by a Yankee cavalryman’s horse. Leaning on a cane and able to wear only one boot, he directed the Rangers as they helped the passengers out of the train and up the steep bank. One participant described the scene as “a romantic situation.” He expressed jealousy of his fellow Ranger, Jim Wiltshire, “the luckiest dog on earth with the ladies,” when a young woman of “remarkable beauty” begged him, “Oh, captain, protect me, for I am a Mason’s daughter!” Reportedly the gallant Wiltshire replied, “And I, miss, am a Mason’s son. Be not alarmed,” then swooped her up as she fainted in his arms and took her to safety.

Another woman attempted the same tactic, insisting a Ranger inform Colonel Mosby, “My father is a Mason!” Mosby only wryly responded, “Well, tell her I can’t help it.”

“As soon as the passengers had gathered on the railroad bank, and the ladies were assured of their personal safety, their spirits revived, and they appeared to enjoy the adventure,” one contemporary chronicler recalled. The ever-silver-tongued Mosby mingled with the passengers, assuring them, “[The Federals] will not guard the railroad, and I am determined to make [them] perform [their] duty.”

The attack resulted in only one casualty—a Federal officer who was shot as he attempted to escape. Mosby and his men left the civilians “to keep warm by the burning cars” while they took fifteen horses and twenty soldiers as prisoners, including the two US paymasters carrying satchels of greenbacks totaling over $168,000. At Ebenezer Church near Bloomfield, Virginia, Mosby would later divide the enormous bounty equally among his men while eschewing any portion for himself. He immediately sent the satchels ahead with a small party of three men to more easily evade the enemy.

On the return march, Mosby rode next to one prisoner, a well-dressed German lieutenant in a beaver overcoat and high boots on his way to join Sheridan’s army. The Confederate colonel inquired, “We have done you no harm. Why did you come over here to fight us?” The German replied, “Oh, I only come to learn de art of war.” A bit later, the same man came riding up to Mosby dressed in old clothes to complain of having been relieved of all his finery by one of the Rangers. “I asked him if he had not told me that he came to Virginia to learn the art of war. . . . Very well, this is your first lesson.”

The Gray Ghost’s irregular warfare tactics had the Yankees playing constant catch-up. Not content with their enormously successful Greenback Raid, the Rangers also crossed the Potomac and struck the canal and B&O Railroad in Maryland. Once again, the Union Army would be forced to divert troops from many other areas to more closely guard the railroad and the canal to ensure lines of communication and supplies between Shenandoah, Baltimore, and Washington were not disrupted. “My object had then been accomplished,” concluded Mosby. Military communications from the field revealed the extent of Yankee anxiety: “At least 1,000 good calvary should be attached to this command to protect us against the sudden dashes of the guerilla forces infesting this part of the country.”

The Democracy had an oversized role in shaping the narrative. Mosby’s irregular warfare tactics combined with the information war conducted by the Confederate Secret Service and aided by the complicity of the Northern newspaper editors produced news headline after headline swaying public opinion and eroding Northern morale on the eve of the 1864 presidential election—the most important election in American history up to that point.

Patrick K. O’Donnell is a bestselling, critically-acclaimed military historian and an expert on elite units. He is the author of thirteen books, including his new bestselling book on the Civil War The Unvanquished: The Untold Story of Lincoln’s Special Forces, the Manhunt for Mosby’s Rangers, and the Shadow War That Forged America’s Special Operations, currently in the front display of Barnes and Noble stores nationwide. His other bestsellers include: The Indispensables,  The Unknowns, and Washington’s Immortals.  O’Donnell served as a combat historian in a Marine rifle platoon during the Battle of Fallujah and often speaks on espionage, special operations, and counterinsurgency. He has provided historical consulting for DreamWorks’ award-winning miniseries Band of Brothers and documentaries produced by the BBC, the History Channel, and Discovery. PatrickKODonnell.com @combathistorian