A crucial piece of intelligence can turn the tide of an entire battle or even a war. During the Civil War before the Third Battle of Winchester, that intelligence was obtained from two of the most unlikely of sources—a school teacher and a slave.
By 1864, the war was not going well for the North. Lincoln had staked the Republican Party’s political future on military victory over the Confederacy. Yet Confederate General Jubal Early’s army had nearly marched on Washington. Another military disaster on the battlefield would be disastrous.
As General Philip Sheridan recalled, “I deemed it necessary to be very cautious, and the fact that the Presidential election was impending made me doubly so, the authorities at Washington having impressed upon me that the defeat of my army might be followed by the overthrow of the party in power, which event, it was believed, would at least retard, if, indeed, it did not lead to the complete abandonment of all coercive measures.”
Sheridan’s solution: better intelligence.
“I could not risk disaster. . . . I determined to take all the time necessary to equip myself with the fullest information, and then seize an opportunity under such conditions that I could not well fail of success.”
So the Jessie Scouts, some of Lincoln’s special forces, were charged with gathering that intelligence, including by forging connections and building relationships like those with Thomas Laws and Rebecca Wright.
“They learned that just outside of my lines, near Millwood, there was living an old colored man [Thomas Laws], who had a permit from the Confederate commander to go into Winchester and return three times a week for the purpose of selling vegetables to the inhabitants.”
One Sunday evening, Private James Campbell and another Scout approached the enslaved African American Laws and his wife as they were sitting on the steps of their cabin. “Two unknown men came through the yard and struck up a conversation with me about Winchester. I told them I could go to Winchester any time I choose as my master lived there, that was, in Berryville.” The two Scouts returned to Sheridan’s headquarters with the information about their potentially valuable informant. The general wanted to determine whether Laws was reliable. Campbell returned to the cabin with an invitation for Laws: “The general wants to see you tonight.”
“They carried me to the general,” Laws recalled. “When I got there, the general and I took our seats on an old log that was laying by the camp.” Among other inquiries, Sheridan asked Laws if he knew Rebecca Wright. The twenty-six-year-old Winchester native was a Quaker schoolteacher, Union supporter, and ardent abolitionist recommended by General Crook as a possible informant.
Wright lived in a divided house. Her sister Hannah was a “dyed-in-the-wool Rebel,” and her brother David was conscripted into the Confederate Army. At the same time, the Confederates imprisoned her father for his fervent Unionist beliefs. “After a little persuasion,” Laws agreed to carry a message to Wright for the general. Campbell carried Sheridan’s letter behind enemy lines to Laws and stayed at Laws’ cabin until he returned from his mission. “[Laws’] message was prepared by writing it on tissue paper, which was then compressed into a small pellet, and protected by wrapping it in tin-foil so that it could be safely carried in the man’s mouth,” or swallowed if the Confederates searched him.
Rebecca Wright remembered the middle-aged Laws as a “quiet, dignified” man, “very” well dressed in a white shirt, coat, and tie, who approached her in her yard asking if he could see her privately. She took him into the school room where she taught, and he asked if she was “a Union lady” and if she knew General Sheridan.
“When she said she did not, I thought I was between Heaven and Earth,” remembered Laws. Risking his life, Laws “ventured anyhow and gave her the letter.”
Understanding the gravity of the situation and her actions, Wright took the letter. “I turned to my mother for guidance, not taking my sister into my secret for, that I knew would be fatal.” Wright remembered saying to herself, “I will pay no attention to the letter.” She showed the missive to her mother, stating, “The Rebels would kill us if they should find out.”
“That is true,” Wright’s mother responded. “But men are dying for their country, and thy life and my life may be needed, too. I would not persuade thee. Settle it with thy conscience. Go to thy room and give thyself to prayer.” Rebecca Wright thought deeply about what she was about to embark on and prayed.
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Finally, according to Sheridan, “the brave girl resolved to comply with my request, notwithstanding it might jeopardize her life.” Wright not only took on the task at great peril, but after the war, she would be spit on, ostracized, and hated by her neighbors, and her life would be threatened.
In a reply sent via Laws, Wright informed Sheridan of a convalescing Confederate officer who had visited her mother’s boarding house the night before and casually revealed that a division of infantry and a battalion of artillery commanded by Major General Joseph B. Kershaw had started back toward Richmond to join General Lee.
The crucial intelligence gave the general confidence to attack Early’s weakened army in and around Winchester. Although it would be the bloodiest battle of the war to date in the Shenandoah Valley with thousands of casualties on both sides, the Union victory in the Third Battle of Winchester and subsequent action “electrified the country,” Grant later wrote in his memoir. The engagement gave the Union a decisive victory exactly when it needed it most.
“Her answer proved of more value to me than she anticipated,” recounted Sheridan in his memoirs. Combined with the Battle of Atlanta, the victory changed the morale of the North and the polls shifted toward Lincoln who all summer had been projected to lose badly to the Democratic nominee for president who had been soaring in the polls. After the war, Sheridan wrote to Wright, “It was on this information the battle was fought, and probably won.”
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