September 15, 1864 (Thursday)
“I have nothing new to report for yesterday or today,” wrote Phil Sheridan to General Grant. “There is as yet no indication of Early’s detaching.” Jubal Early’s Army of the Valley had been, in Sheridan’s mind, too strong to attack, but rumors held that an entire division would soon be leaving the Shenandoah Valley to return to General Lee’s main body in Petersburg. A Union soldier who had escaped capture in Winchester told of Confederate pontoon boats that had passed through the town, but Sheridan questioned his reliability.
And yet, he tried to uncover Early’s movements. “Have you any information from your scouts from Culpeper or other points south?” he asked his cavalry commanders. “[General Richard] Anderson, who is temporarily in command of Longstreet’s corps, is still here. It seems strange that he should remain, with only one division of the corps here.”
That was indeed strange. Anderson had left one division with Lee and another along the route to the Shenandoah Valley. With him was Kershaw’s Division, but neither he nor the division were in Winchester as Sheridan supposed. At sunrise of this date, the men of the division marched south along the Valley Pike. By dusk, they were just north of Front Royal, fifteen miles away from Winchester. They would, over the next few days, continue south through the Luray Valley toward Thornton’s Gap.
But this was hidden well from Sheridan, who continued to be perplexed by the Confederate army before him. To gain for himself some knowledge of the enemy’s position, he vigorously organized a legion of scouts. This, he hoped, “would give better results than had the method hitherto pursued in the department, which was to employ on this service doubtful citizens and Confederate deserters.”
And so Sheridan called for volunteers. It was hazardous duty, but the rewards, if successful, would be great. “These men were disguised in Confederate uniforms whenever necessary, were paid from the Secret Service Fund in proportion to the value of the intelligence they furnished, which often stood us in good stead in checking the forays of Gilmore, Mosby, and other irregulars.” He had unleashed his patrols in the direction of Winchester the night previous, but by dawn, they had found no changes to the Rebel pickets.
Sheridan concluded that Anderson still remained in Winchester, but could do nothing to prove it. His own cavalry could not best their Rebel counterparts because Early kept them too close to his infantry and there was no chance to get around them for a peek behind the scenes.
Sheridan was understandably frustrated. There had been no victories for his army since he took command. There had been setbacks and a few cavalry skirmishes, but Early’s Confederates remained not only in the Valley, but north of Winchester.
And so Sheridan turned to General George Crook, who had spent quite a bit of time in and around Winchester. Might there “be found in Winchester some reliable person who would be willing to co-operate and correspond with me?” This was, of course, going against his better judgment. He had wanted to use scouts rather than civilians, but he had few choices.
General Crook knew of such a person, and suggested Rebecca Wright, “a young lady whom he had met there before the battle of Kernstown, who, he said, was a member of the Society of Friends and the teacher of a small private school. He knew she was faithful and loyal to the Government, and thought she might be willing to render us assistance, but he could not be certain of this, for on account of her well-known loyalty she was under constant surveillance.”
Sheridan hesitated, but finally decided to make an attempt. There had been an older black man named Tom Laws, whom he had employed for information and sent two messengers to his house. Once in contact with him, Sheridan asked if he knew of Rebecca Wright. The man did, and Sheridan immediately composed a letter.
I learn from Major Gen. Crook that you are a loyal lady and still love the old flag. Can you inform me of the position of Early and his forces, the number of division in his army, and his probable or reported intentions? Have any more troops arrived form Richmond, or are any more coming or reported to be coming?
I am very respectfully, your most obedient servant.
P.H. Sheridan, Maj. Gen. Commanding
You can trust the bearer.
Sheridan wrote his message on thin 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. The probability of his being searched when he came to the Confederate picket-line was not remote, and in such even he was to swallow the pellet.”
Tom Laws would slipped through Confederate lines and into Winchester. The next day, around noon, he appeared at the school where Miss Wright taught. As it turned out, two nights previous, the teacher had entertained a Confederate officer. Everything was about to fall into place.1
- Sources: Official Records, Series 1, Vol. 43, Part 2, p89, 90, 92; Make Me a Map of the Valley by Jed Hotchkiss; Personal Memoirs by Philip Sheridan; From Winchester to Cedar Creek by Jeffry D. Wert; The Last Battle of Winchester by Scott C. Patchan. [↩]