Hazardous Service: Sheridan's Report on Special Operations in the Shenandoah Valley and Rebecca Wright

(above: Sheridan Preparing His Report on Third Winchester in Rebecca Wright's Classroom)

The Presidential campaign in the north was now fairly opened, and in the peculiar condition of our country at that time, I became much impressed with the idea that, under no circumstances, could we afford to risk a defeat -- to say nothing of my intense aversion as a soldier to such a result, in my case. Having ascertained through two of my most trustworthy scouts, that there was an old colored man -- near Millwood, about fifteen miles from my headquarters, who had a pass permitting him to enter and leave Winchester three times a week to sell vegetables.

I thought I might make use of him in getting inside the enemy's lines and obtaining information. My next object was to find some intelligent and reliable Unionist in Winchester who would be willing to cooperate with me. I therefore asked Gen. Geo. Crook, who was then commanding what was known as the Army of Western Virginia, if he knew of any person there that could be safely relied upon. He did not know positively, but suggested a Miss ________, whom he had met there and whom he thought to be honestly loyal to the United States government. I then sent two scouts to see the colored man and to bring him at midnight to my tent.

Arch Rowand, one of Sheridan's scouts

After satisfying myself of his truthfulness, I enquired of him if he knew Miss ______. He said yes, and I arranged with him to carry a letter to her, written on tissue paper so as to be able to compress it to an exceedingly small compass, and which I could wrap in tin-foil, so that he could keep it in his mouth, and chew and swallow it, if necessary. I instructed him to deliver it privately to Miss ______ and state to her quietly that it was of great importance, and that he would return in an hour or two for an answer. The next day I wrote a letter to Miss ______, appealing to her patriotism and loyalty and asking her for certain information, if it was in her power to give it. On the night preceding the day that the colored man was to take his marketing to Winchester, the letter was given him by one of my scouts, and the next day it was by him safely delivered to Miss _____. The lady courageously acquiesced in my request, and the result was that the first Battle of Winchester, Opequon, occurring on the 19th of September 1864, was to a certain extent fought and won on information given me by this young lady.

The following are briefly the facts: After receiving two communications from Miss _____, giving me the best information she could of the number and position of the enemy, she informed me that Kershaw's division was under orders to return to Petersburg or Richmond, and that she would notify me as soon as possible after its departure. The vegetables of the colored man, under the influence of the scouts, were promptly sent into Winchester, but it was two or three weeks before I received information from Miss ______ that the division had started. Meanwhile, the whole country seemed to be impatient at my apparently dilatory movements, and I fear that Gen. Grant became so also, as he came in person to Charlestown to see me. But on the night prior to his arrival, Miss _____ had sent me word by the faithful colored man that Kershaw's division was then marching up the Front Royal pike en route for Richmond; and when I met Gen. Grant at Charlestown and assured him that I was ready to attack, and would do so even before the date specified by him, he then gave me the since famous order, "Go in" and the order was probably given from the result of my conversation with him that convinced him that I would succeed, and I am willing to admit that my confidence arose to a great extent from the information furnished by Miss ______.

I could have defeated the enemy as he was, but, considering the great interests at stake and the loss of life that Kershaw's division would inflict, I felt that it was better to wait, and attack him diminished in numbers by the withdrawal of this division, several thousand strong, than to allow political pressure to force me to fight a battle with increased risk and greater loss to our own army.