Steve French, author, tells the factual story of the winding road in Andrew Thomas Leopold’s life.

2880 words

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With support from American Public University System ( (The sentiments expressed do not in any way reflect modern-day policies of APUS, and are intended to encourage fact-based exchange for a better understanding of our nation’s foundational values.


French, Steve. (2012). “Rebel Chronicles: Raiders, Scouts and Train Robbers of the Upper Potomac.” New Horizons Publishing Company. Print.

In May of 1864, when Andrew Leopold was taken to Baltimore under guard to be taken to be transferred to Fort McHenry a Baltimore Sun reporter noted “he is a guerilla chief and spy and murderer of the blackest die.” Now whether all that was true or not remains to be seen. But Andrew Leopold was born in Sharpsburg, Maryland in 1841. His father was Mathew Leopold and his mother, Polly Leopold. His father soon died and later his mother would marry John Zittle of Sharpsburg. The boy grew up in the town; later on, he worked on farms – local farms along the C&O Canal. He was a friendly boy who knew people on both sides of the river, especially in Shepherdstown where he knew quite a few people and traveled over here quite a bit. Probably at this time during his teenaged years he met Thomas Hipsley, who lived over near Moler’s Crossroads, who was an especially close friend of his and served in the Confederate Army later on with him. In 1861, he would join the first Virginia Cavalry.

Some of his first actions in the Civil War would be right here when militia men from Virginia would fire across at union guards, guarding the C&O Canal. The Entlers who lived across the river at that time running the ferry, commented later on, especially Luther about gunshots ringing out and bullets flying in the ferry house on the far side. But he served in the 1st Virginia Cavalry until April of 1862. Then he joined the 12th Virginia Cavalry along with his friend, Thomas Hipsley. During that time he participated in the Valley Campaign with Stonewall Jackson. He wrote a letter home to his mother about his experiences during that time, attacking the Union camp. Later on, he’ll fight in the Battle of Second Manassas, and he’ll be wounded three times towards the end of that battle. And his brigade commander, Gen. Beverly Robertson, will mention in the official reports of the battle how brave a man Leopold was. But once again, he was wounded three times at the Battle of Second Manassas. He has a long recovery but about October, 1862, he is headquartered with Stuart, at Stuart’s headquarters at The Bower, not far from here in Jefferson County. Towards the end of October, he is dispatched with Capt. Redmond Burke with a small band of men and they come to Shepherdstown, and are in this area scouting and rounding up conscripts for a two or three-week period.

On November 19th, there is a skirmish along the river at Guard Lock 4. And at this time a civilian named Mortimer Cookus is shot and killed by Leopold, as he is trying to escape across the river. On the night of the 24th and 25th of November, Leopold, Burke, Burke’s sons are surrounded in a house in Shepherdstown by soldiers from the 2nd Massachusetts Infantry. Burke is killed. Leopold and two of Burke’s sons are captured, Hipsley and a soldier named John O’Brien also. The next day they are taken to Sharpsburg. The Union soldiers come back to Shepherdstown to arrest Daniel Rentch, a noted Shepherdstown resident. They are taken to Fort McHenry. The soldiers who are captured – they’re released very soon afterwards, paroled.

And by January the first, 1864, they’re all back with Stuart at his camp near Fredericksburg, Virginia. That winter, as soon as he is exchanged and the others are exchanged, they’re back in the service – dispatched service – operating once again in the Shepherdstown/Berryville area, carrying mail back and forth between the citizens and armies, scouting and so on. On the night of March the 6th, he comes into Shepherdstown with John O’Brien, and he’s hunting for a man named Jacob Hudson. He finds Hudson caring for his uncle at his house at Shepherdstown. And he knocks on the door with O’Brien. Evidently he doesn’t know Hudson, but Hudson has been talking about him around town. When Hudson opens the door, Leopold asks for Hudson -“Is Hudson in the house?” – Hudson immediately becomes scared and he runs toward the back door and he is shot down. George Brantner, who was a former Confederate soldier, he’s seated right in that room, cannot tell whether it was Leopold or O’Brien who shot the young man, but he sure identifies him later on, because Leopold met Brantner at the door and (Leopold) told him he had mail for him. Leopold will come down the street that night. He will tell one resident here in the town that he did shoot a man up the street and then they will leave the mail here and head back for camp.

Ten days later, on the night of March 15th & 16th, Leopold and a group of men go to Sharpsburg, Maryland, and, in Sharpsburg that night they steal six horses from an oyster wagon, parked outside of a local tavern. After midnight on the 16th, they return to try to get across the river. They go to Bridgeport where the ferry is, directly behind me, and they knock on the door. They say they have a dispatch to take to Harper’s Ferry to (Federal) General Stevenson. The young man, Charles Entler and his friend Samuel Jones, that are in the office that night, sleeping in the office, refuse to answer the door. Finally, Leopold starts tearing the shutters off the windows and Charles decides to come out. Samuel Jones would later say he knew it was Leopold at the door, but he was too scared, too frightened to say a word. As Charles comes out the door, his brother, Luther, who is in the ferry house himself, walks outside; and, as soon as he gets outside, he hears a man shout at his brother: “By God, I’m Captain Leopold and I’ve been looking for you a long time.” Immediately the gunshot goes off, Luther turns, makes haste into his house to get his revolver. His brother, Charles, nineteen-years-old, runs off and dies in the road, going up towards Ferry Hill. Leopold and his men escape. Now, they’re wanted men. The Middletown Valley Register over in Maryland, a few days later, comes out with a long article about Leopold and his band and at the end of it says: “Leopold deserves a hempen collar.” So he’s a wanted man, not only by the authorities in Maryland, but by Union soldiers, especially Major General Robert Milroy, the famous “Grey Eagle,” who was headquartered at that time in Winchester.

Towards the end of April around April 21st, Union forces are sent out of Berryville and they go to Castleman’s Ferry. That night, they will capture Leopold, and, once again, some of the Burkes – Hipsley and some other men when they surround the house, and they threaten to burn it down, if the Confederates don’t come out. They’re taken to Winchester and put in the Clarke County jail. While in that jail, one of Milroy’s citizen spies named Michael Graham from Woodstock, Virginia, talks to Leopold and finds out what he wants. Leopold wants to either join the Union Army or be allowed to get out of jail and go to Ohio. In return he will tell Milroy who the scouts and spies are in the lower Shenandoah Valley. He will meet with Milroy, and Milroy will listen to all this, but Leopold plays his hand too fast, and tells Milroy what he needs to know beforehand. So Milroy won’t agree to give him his freedom or allow him to switch sides and join the Union Army, but he will pack him to the prison at Fort McHenry. The inner fort was where only the most notorious Confederate guerrillas and partisans are held.

Now over in Sharpsburg at this time, Polly Zittle will hear of her son’s dire circumstances, and she will ask daughter, Sally Zittle, who is Andrew’s half-sister to come to Shepherdstown and meet with Mary Louise Entler and convince her to take her south – for Entler to take Zittle south – and meet with J.E.B. Stuart and try to arrange some sort of deal where(by) Andrew can get out of prison. So, at this time, Andrew is already at Fort McHenry. The girls meet here and they head south. Now, Entler was a – maybe we’d call spy today – but she was mostly concerned with delivering the mail between – once again this mail system between the army and the citizens. The girls get as far as Berryville. They’re taken into custody one morning at the Berryville hotel and sent to Winchester. Here they are going to meet – once again – General Milroy, who is in a big argument with a lot of women there. It’s over a cow. All of the sudden, the girls come in. He turns around and sees them and says: ”What do you want?” They tell him and he shouts out: “By God, I wouldn’t have any trouble here if it wasn’t for the women!” The women in Winchester. So, he listens to them, talks to them a while, then he will pack them off to Harper’s Ferry. At Harper’s Ferry, they are put under guard there, kind of loose guard – the Stipes Boarding House. They’ll stay probably close to six weeks there under sort of a house arrest. Mary Lou Entler will even meet her future husband Walter Herrington, who is a telegrapher for the Union Army at Harper’s Ferry. The girls are eventually sent to Baltimore and, while there, they will take the Oath of Loyalty to the Union, although the girls would say: “We really didn’t mean it. We dropped the Bible on the floor. So we didn’t swear to it on the Bible.” When, especially Miss Entler, gets back to Shepherdstown, she’s met right at this location as she comes across the ferry by hundreds of people and she’s a very gracious local hero for a long time afterward. (Back to Leopold).

He’s in the prison at the inner fort. He’s with a number of noted desperadoes, including William Boyd Compton (Belle Boyd’s cousin), who had been captured behind the Union lines in Fairmont, West Virginia. Captain Joel Baker, the guard, comments that most of the prisoners of the group – there’s about eight or nine in the guard room – most of the prisoners are cultured gentlemen, but not Leopold. Baker would write that Leopold is not trusted by the other prisoners. They think he would sell them out for just a few cents. Leopold is held in prison until mid-December, 1863, when he is put on trial by a military tribunal. He’s charged with a number of crimes, of being a guerrilla, murderer, violating an act of war, and being a spy. The tribunal is led by Col. W. W. Bates of the 8th New York heavy artillery. The Judge Advocate is Lieutenant Roderick Baldwin. Leopold will represent himself, but he will have the help of a local, Baltimore attorney, Milton Whitney Esq. who was well-known in Baltimore for many years. The trial opens up. A lot of local residents come from here to Fort McHenry to testify, including Daniel Rentch, Luther Entler, Samuel Jones, other men from Shepherdstown and also General Milroy will appear. The trial will go – on and off – for probably three, almost four, weeks. They break for Christmas a while; they break for different witnesses to arrive.

Finally, two charges are dropped, but he is still charged with being a guerilla and murderer, both capital offences. His defense rests on that he wasn’t a guerilla, that he was a Confederate soldier, especially dispatched into this area by J.E.B. Stuart. Also, he refused to admit that he had murdered Charles Entler. He said he didn’t have anything more to do with the murder of that young boy than any of the judges on the tribunal; and, he said the shooting of Cookus was just part of a local skirmish. So he denied being a guerilla; he denied being a murderer. In his summation, Lt. Baldwin, the Judge Advocate, would say: we owe something to the people of the border who have been hounded from their home, who have been murdered at their doorstep. We need to protect them. The verdict comes back. He is convicted of murder: the murder of Entler, the murder of Cookus – and he is convicted of being a guerrilla. Afterwards, the verdict and the results of the trial – goes up through the chain of command.

Finally, they reach that April, Judge Advocate Joseph Holt. Holt reviews all capital cases for Abraham Lincoln. In a four-page review, Holt will say this man has been convicted of these crimes and he deserves the death penalty. In late April, 1864, Abraham Lincoln will sign off on that. At that time, Leopold is taken from the guard room, shackled. He’s put in a cell, still in the inner fort, but not with the rest of the men on death row. During that month, there is a big escape from the guard room at Fort McHenry. William Boyd Compton leads the rest of the men in the escape and they all eventually get back to the Confederate lines. On the evening of April the 22nd, Leopold will be informed by his chaplain, Doctor Reese, that his execution will be the next morning. He will meet with Reese that evening for prayer and communion. During the winter, Leopold would become a committed Christian. He studied the Bible frequently. He had another small book that he would study. They had prayer. Reese left for a while.

About, five-thirty, he would return. Once again, they would talk of the afterlife. Then he (Leopold) would go out under guard, get on the wagon atop his coffin, and he would ride to the execution site right outside the walls. Captain Robert Baylor of Charlestown was also a prisoner at Fort McHenry at the time. He was out on the grounds of the fort and as he passed Baylor, Leopold would wave to Baylor and said: “Tell the boys I remain true to the cause.” As they neared the execution site, he could see the soldiers of the fort lined up on three sides of the gallows. The gallows there could have four executions at the time. (Federal) Major General Lew Wallace was there, later on the author of “Ben Hur.” He was the commander-in-chief of the Eighth Corps Middle Department, and Brig. General W. W. Morris, the sixty-six year old commander of Fort McHenry was also there. He was helped off the wagon. The reporter for “The Baltimore American” said that “Leopold went up the steps firm and undaunted.” Once atop the scaffold, he was asked for any last words and Leopold pointed to Gen. Morris and said: “Old man, you’re the reason I’m here. But I’ll forgive and I’ll meet you in Heaven.” After that, he stepped back. The hood was put on his neck by Private Elijah Brown, and then the rope put around his neck. Just afterwards, Morris gave the signal, and then – Leopold dropped into eternity. He would hang there for about twenty minutes before the soldiers took him down. There were friends there in Baltimore, some of Leopold’s friends.

They brought him back to Sharpsburg, where he was prepared for burial. A few days later, he was going to be brought to Shepherdstown to bury in the Soldier’s Cemetery. His plot will be right beside Redmond Burke, his old Captain. But he’s going to be brought across here by the undertaker, (with) of course his mother and sisters are with that group. They’re going to ride up this hill. At the Entler Hotel, there is a group of Unionists shouting at the undertaker to go back. Beforehand these same people had (gone) to the cemetery and warned the over four hundred mourners there to leave, but they ignored them. They go to the cemetery – once again – there’s a big crowd there. Lots of girls crying and so on. He is buried. Although maybe a year before, Leopold had been a hated person by most Confederates in this area because they heard that he was going to switch sides. By this time, he totally redeemed himself.

His conversion to Christianity, his bravery on the scaffold had turned him into a local hero. Later on, that same day, the Unionists would strike. They would come back and would steal the undertaker’s hearse and his horses and ride away with them. Whether he was really guilty of every crime that he was accused is questionable. He wasn’t a guerilla. He was a member of the regular Confederate Cavalry and there’s some question, on the murder of Entler that it might have O’Brien did the shooting.