Jessie Scout Tom Cassidy Captured; “Looking in a Noose” For Thirty Days; Eventually Exchanged For a Confederate Major

Where they rode and what they did no man now remembers — few men but themselves ever knew — and they left no written record of their service; the vague memories of those many nights are held in dusty, inner chambers of the mind, to which, long since, the tongue has lost the key. 

William Gilmore Beymer 

was usually a civilian.] We scouts were men who dressed in the enemy’s uniform in order to deceive their pickets and capture them so that the main body could be surprised. Or, we would ride up to a Southern citizen, man or woman, for information, and since we were dressed in the Confederate uniform they would tell us everything they knew. Of course, under strict military law, we were subject to the penalty of spies if taken within the enemy’s lines.’”

Scouts caught in the enemy’s uniform faced execution in the field, frequently without the military formality of a drum-hear court martial, and several of Rowand’s colleagues were found hanging by their own horse’s reins previously attached to bridles. These volunteers were taking their lives in their own hands when they stepped out of ranks and went to their headquarters to be issued a Confederate uniform. Later and when operational, they would have to not only appear to be a Confederate soldier but they must be able to sound like southerners and also be able to discuss the military unit they claimed to be from as if they really were assigned there. One mistake in the presence of actual Confederates could result in death at the end of a rope or leather reins.

For example, a Confederate physician captured by remaining on the field to treat wounded at Gettysburg and was sent to New York City to await parole and exchange. On his own recognisance, he wandered around the city and related a curious experience:

“One day I was strolling aimlessly along Broadway, cautious not to get off very far for fear I would get lost, when a man stepped in front of me, bowed gracefully and said ‘Good morning.’ He was at least six feet tall and would have weighed 180 pounds. He was very erect with square shoulders and the carriage of a trained soldier. He was elegantly dressed, his hair black and eyes large, dark and penetrating, while a heavy black moustache drooped gracefully around the corners of his mouth. His lower jaw was rather broad and firmly set as he showed his white teeth and smiled at me, he seemed to say ‘now I have you.’ I was uncomfortable, he saw it and was evidently amused. He said ‘I think I know you.’ I replied ‘No sir, you do not, and I certainly do not know you.’ He said ‘Yes. I met you once.’ I asked where? He said ‘In the Valley of Virginia.’ I asked at what place? He said ‘Two years ago I took dinner with you in Strasburg at the house of a widow lady, Mrs. Eberle, you had three friends with you. While you were at dinner two cavalrymen came in and took seats at the table. I sat directly in front of you on the opposite side of the table and my companion sat next to you on your right. You asked me what cavalry we belonged to and I told you Ashby’s command. You then asked me a number of questions about Ashby, where he was, the size of his command, etc.’ Then looking me straight in the eyes, he said, in a low, measured somewhat incisive tone, ‘My friend who sat on your right was hung by your people.’ The announcement went through me like a dagger of ice. I not only remember the two cavalrymen, in their bright new unsoiled uniforms, and the conversation, but vividly recalled the features of the man who stood before me and I distinctly recalled, with a shiver, that the handsome young fellow who sat by my side at dinner, was none other than the dashing and fearless Jack Sterry, whom I had seen hanged at White Plains….”

The Confederate physician had encountered Jessie Scout team that normally operated in pairs and the chance encounter on New York City’s Broadway reveals the degree of knowledge that had to be known by a scout in order to survive in even casual conversation, much less a hostile interrogation that resulted in the carefully prepared Jack Steery to be hanged.

A reporter for Leslie’s Illustrated Newspaper encountered two of these scouts as they prepared to move into Confederate territory during the night of December 8, 1864. He wrote:

“…Denny’s guests were congregated in his parlor …when the flow of conversation was interrupted by the entrance of two men in Confederate uniforms and overcoats who without even passing the compliments of the evening took seats by the fire and removed their hats to better enjoy the warmth, a proceeding that somewhat surprised the press while exciting their curiosity.

“We were not long however in becoming acquainted with the status of the mysterious visitors equipped for the warpath as revealed by the pistol butts from their holsters convenient for instant use.

“Their identity was revealed to us covertly by our host, as members of the secret organization known as the ‘Jessie Scouts’ upon whom General Sheridan relied to be kept informed as to the enemy’s plans and movements and that these two men, who were as dumb as oysters, would abide with him till the midnight hour and steal away on their perilous mission.

“This was my first contact with this mysterious band, who could well say they carried their lives in their hands, and as they sat there in the play of the firelight, with lips sealed, for instinctively none questioned them, they riveted my gaze and started my fancy and they rose in my mind as heroes of the highest magnitude for the spy must of necessity be a noble and courageous character. He must be patriotic, quick-witted, intelligent and terribly in earnest or he will never undertake the Secret Service of the Army.

“How unjust, I thought, that with all these qualifications and more, that if captured, that he cannot share even the lot of his fellow captives of the rank and file, the lot of the prisoner of war. His position is disgrace, insult and speedy death. On the altar of his country, he has laid his all, and yet his country is united with all other countries in maintaining an understood international law that dooms him to a dishonorable grave. Shame on such a law. The spy is a soldier that daily bears the heaviest burdens and risks. Let him, say I, have a soldier’s honor.

“Possibly others in the room were occupied with similar thoughts about the strangers and speculated as to whether this would be their last mission in their country’s cause; whether a rope or a volley from a file of men, would reward their venture. It is not pleasant to one with a prospective doom hanging over him to have it anticipated in the unconcealed glance of the solicitous friend, hence fearful that they with whom my mind was filled would read my thoughts intense, I sought another part of the room.

“The ‘Jessie Scouts,’ named in compliment for the accomplished Jessie Benton Fremont, were under the command of Major Young…”

whether found at Fishers’ Hill or Woodstock. He sent us out with 15 of the scouts, and gave orders for 50 picked men out of the 5th N.Y. Cav. to accompany us. It turned out afterward that out of the 50 picked men were about 9 that had seen service, and the other men were new recruits. We rode all that night and the boys got sleepy and tired. I was asleep in the saddle and about 3 o’clock I awoke with a start and felt instinctively that something was wrong. It was very dark. We could not even see a star. I carried a little pocket compass with me at all times. I struck a match, looked at it and saw that our boys being asleep the horses had concluded to go back towards Winchester.

“I rode to the head of the column where Major Young and Campbell were, and said: ‘Major Young, are you going back to Winchester?’ He said: ‘No.’ I said: ‘That is where you are heading for.’ He said: ‘No.’ Campbell said no. I struck a match and showed them my little compass and Young was very angry about it and said: ‘Take the lead.’ And I did. And knowing we had to strike the picket about daylight, I traveled pretty fast through those dark woods. Some of the boys were unhorsed. There was a good deal of strong language used at the speed I was going, but just about daylight we struck the pike, came in sight of a vidette [a mounted sentry], and the Major sent me forward and I took him in.

“We captured the reserves and were in good shape to get back. But Young was somewhat elated at the capture and a Union man there by the name of Kuhn walked by me and said: ‘200 in the back road.’ He didn’t have to hit us with a club those days to drive anything into us. I knew that what that man meant was, there were 200 Confederate cavalry in the back road about a mile and a half back of the main pike. I rode up to Young and said: ‘Kuhn says there is 200 in the back road. Get out of here.’ Young said: ‘No. We will stay a little while.’ I said: ‘If you do, you’ll get the devil knocked out of you.’ Campbell came up and asked Young to get out, but Young wouldn’t.”

Kuhn was a one-armed butcher in Woodstock who was a source for the Jessie Scouts and was well known to Rowand. Alerting the scout as he walked by him is known as a “brush pass” in espionage activities and this normally occurs in plain sight. Kuhn remained faithful to the scouts and in 1912 when Harpers reporter Beymer completed his book that included chapters on both Rowand and Henry Young, Rowand and Beymer discussed the need to send a copy to their one-armed friend.

Rowand continued to explain the raid and its unanticipated consequences in a letter to his father that probably left the elder Rowand, a Quaker, horrified:

“I quote now from a letter dated January 23, 1865, written to my father:

“We had a very nice affair of it had we got away with them. But we didn’t. We were overtaken at Woodstock by 200 of them. As they came in sight of us they charged us at Chew’s Run, 1 mile this side of Woodstock. We repulsed them. The Major here sent orders for the main column to push ahead with the prisoners, leaving the scouts as a rear guard. As we were moving along between the Run and Maurytown, 4 miles distant from Woodstock, there was 20 Confederates dashed up a hill to our right and not 20 yards distant, gave the Confederate yell and they came right into us. We had about 10 yards distance for a few minutes. They being reinforced, we were forced to fall back.

“On coming in sight of the main column they were in full gallop. The Major sent me to stop and even threatened to shoot the sergeant. But the enemy were too many for the new recruits. The enemy kept us on the jump for 10 miles. They got all our prisoners. Eight scouts were gone; one was known to be killed, 3 wounded — 2 mortally, and 4 captured, only one of the captured being dressed in full gray. The enemy followed us to Fishers’ Hill where their pursuit ended. My horse was wounded. They killed Young’s horse, but we got Young away from them.

Rowand provided another account of the fight in a letter later sent to Beymer:

“The Confederates came on the scouts at Woodstock. The cavalrymen — new recruits — would not stand. The scouts did the best they could to keep the prisoners, but they soon saw they had enough to do to get away themselves. The loss was all their prisoners, 42 of the cavalry, and Riley and Cassidy were captured. Riley escaped by jumping over a wall at Fishers Hill and luckily was not hit by one of the volley that was fired after him… Whitney and Stubbs, two of the scouts, were badly wounded and Major Young’s horse was shot dead 200 feet from the Crahill brick house, about a mile and a half south of Mauertown.

“Chrisman took Young on his horse, and Campbell and Rowand kept the enemy off until Young and Chrisman were at a safe distance. Unfortunately the cavalrymen were new recruits, although Sheridan’s order was for picked men. Whenever a Jessie Scout was captured, it meant death, either by being shot or hanged.” 

and shared it with a National Tribune reporter on November 4, 1915. McCabe outlived Arch Rowand who died on December 15, 1913, and McCabe revealed Cassidy’s pass that reveals the clever scout had managed to gain the confidence of Jubal Early’s Shenandoah headquarters as either a Union deserter or an actual Confederate volunteer. Cassidy, one of Young’s scouts, was obviously operating within Confederate lines while carrying a pass issued by Confederate General Early’s headquarters

The pass used by Cassidy, when disguised as a Confederate, was signed by S. J. C. Moore, Adjutant-General, in behalf of Gen. Early, and reads as follows:

December 1, 1864

Pass Thomas Cassidy, scout at these headquarters, through the lines at any point. By the order of:

Lieut.-Gen. Early.

S. J. C. Moore, Adj’t-Gen.

Cassidy is the only member of the Jessie Scouts who appears to have managed to become a double agent, appearing to spy for Jubal Early’s Confederate army and probably providing harmless “throwaway” information related to positions and activities of Sheridan’s Union army — along with information intended to shape Confederate understanding of potential Union operations against them. The Confederate pass displayed long after the war clearly corroborates Rowand’s assertion that Cassidy was “one of the best scouts we had.”

Rowand’s letter to his Quaker father continued:

“While we were talking a young lady of strong Southern proclivities pointed me out to Maj. Grandstaff as one of the ‘Jessie Scouts,’ and said that I had been up there the day before; she had seen me with the party. I had been there at different times. Grandstaff looked at me, and I of course said nothing. There was a Confederate soldier there whose brother was killed in our fight and he became a little obstreperous, and I pulled out my revolver and told him to step aside and we would settle it. Grandstaff stopped us both very quickly.

“Then he asked Maj. Baird if I was one of the ‘Jessie Scouts’ and I answered the question this way: ‘You know or ought to know that I belong to the 1st Va. Cavalry.’ Grandstaff said: ‘Why?’ Says I: ‘I was one of the 13 men with Lieut. Smith that charged you and ran on the top of Fishers’ Hill on April 23, ’63. We didn’t whip you fellows, but you killed two of our boys.’

“Grandstaff didn’t ask me any further questions whether I was a scout or not. But I was there to keep my eyes open.

“We didn’t get Cassidy. He was sent south as a prisoner, and after 30 days was exchanged for a Confederate Major. When he returned to Hdqrs. he refused to do any more scouting duty and very candidly told the General he had lost his nerve after looking in a noose for 30 days, and the General, with great reluctance, parted with him, and in a short time Gen. Sheridan secured him a commission.”

The title of Beymer’s subsequent book on special operations during the Civil War, “On Hazardous Service,” was an understatement. Sheridan explained the dangers these Jessie Scouts faced:

“To Major H. H. Young, of my staff, chief of scouts, and the thirty or forty men of his command, who took their lives in their hands, cheerfully going wherever ordered, to obtain that great essential of success, information, I tender my gratitude. Ten of these men were lost.”

From Gen. Philip H. Sheridan’s report of the expedition from Winchester to Petersburg, Virginia. February 27 — March 28, 1865. Official Records, Vol. 46: I: 481.