This letter was written by Capt. Andrew Thomas Leopole, a native of Sharpsburg, Maryland, who enlisted 20 April 1861, in Co. F, 1st Virginia Cavalry. He was then transferred to Co. D of the 12th Virginia Cavalry and promoted to lieutenant. After fighting with the 12th Virginia Cavalry and suffering three wounds at the Battle of Second Manassas, Andrew was ordered by General J. E. B. Stuart to join Capt. Redmond Burke on “detached service.” Their duty was to remain in the Potomac River area between Berryville and Shepherdstown to find conscripts, carry mail between homes and soldiers, steal horses and watch the movements of the Federal army. In carrying mail, Andrew was also abled to determine the names of, and whereabouts of, able-bodied men not enlisted in the Confederate army. After Captain Burke was killed by Unionists in late November 1862, Andrew swore vengeance on the Unionists in Jefferson county as this letter attests.

About a month after this letter was written, Andrew and a group of his men visit Shepherdstown and Sharpsburg where Andrew kills a citizen in each place, and though they escape, they are now wanted men and he was eventually captured at Castleman’s Ferry on 21 April 1863 and placed under arrest for the murders. Northern newspapers called him “a guerrilla chief and spy and murder of the blackest die.” He was held in the prison at Fort McHenry in Baltimore where he was eventually tried for the murder of the two citizens. Though he claimed he was no guerrilla, the jury rejected his defense and he was hanged on 12 May 1864, President Lincoln choosing not to overturn the sentence. He was buried in Elmwood Cemetery at Shepherdstown (see Find A Grave, “Capt. Andrew Laypole”].  While he was in irons. Lt. Leopole gave the following statement to the staff of Gen. Robert H. Milroy at Winchester, Va.:

Hometown Sharpsburg, Maryland. Enlisted in Confederate service two years ago in 1st Regiment Virginia (Rebel) Cavalry and remained  in that regiment until (J.E.B.) Stuart’s appointment as brigadier. About a month after the Battle of First Manassas, became ensign of the brigade, continued until last May (1862) when transferred to 12th Virginia Cavalry as third lieutenant. Continued until after the  Battle of Sharpsburg when promoted to first  lieutenant of Co. D. Captured 24 November at Shepherdstown. Remained prisoner until 6 January 1863 when exchanged. Reported to Gen. Stuart and until 13 January acting as  chief of couriers. On 14 January left for Castleman’s Ferry in command of 70 men and remained until captured with six of my men. My business was to observe the movement of Federal forces and report to Gen. Fitzhugh Lee. Am tired of fighting and wish to take the oath of allegiance and retire to Ohio. I have always stood high with General Stuart, enjoyed  his confidence, and when at his headquarters ate at his table. — Andrew T. Leopole.  (The statement transmitted to Maj. Gen.  C. Schenck, in Baltimore. Official Records,  Series 1, Vol. 25, Part 2, pages 252-53)

Another source spells Andrew’s surname Leopold and gives the following (long) story of his life under the title of Andrew Leopold’s Forlorn Hope on YouTube. Mary Louise Entler, the recipient of this letter, is also mentioned in this story. She corresponded with Andrew and might also have been charged with being a spy had Federal authorities elected to go after her.

[This letter is from the personal collection of Richard Weiner and is published on Spared & Shared by express consent.]

Letter

Snicker’s Ferry (in the glorious reign of Jeff Davis)
February 14, 1863

Miss Mary L. Entler

I wrote you a few lines to let you know that I am out of the reach of the invaders. They followed us to Battletown where my company was stationed at the time. When we got in camp, there was but twenty men in camp & I got them all mounted & followed them as far as Charlestown & there they had twenty more men & we was compelled to fall back to our former position on account of their reinforcements & when we got to Snicker’s Ferry we was reinforced by the rest of my squad and followed them again and captured six and killed four and wounded nine of the Yankees. And then we started for camp. We rested well there when Padda commenced talking about Shepherdstown.

Miss Mary, I heard that you showed the other letter that I sent you. Don’t show this one if you please for I don’t want the Union people to find out that I am coming back for when I come, we want to take them on surprise & I will bring a plenty of men to clean up all of the Yankees that is at Kearneysville and Duffield’s Depot.

I am living now for the avenge of Capt. [Redmond] Burke ¹ & for the ladies of the noble place of Shepherdstown & for the great and loved country of the Southern Confederacy so by the grace of God, if [I] am killed, I die in a good cause and die for the Ladies and for the country which gave birth to me so you know how I feel in this cause.

When I come to town, I will come to see you if I have time. We have plenty of money & of everything to eat and drink. That canteen of whiskey we got there we drank before we got to camp. The next time I come I will bring you that candy that I have here for you. When I come through town, I throwed a stone against Mr. Green Grant’s window & then he skedaddled from town at a double quick time.

Miss Mary, you will please remember me to Miss Emma and to all of the secesh ladies of Shepherdstown and if you get to Sharpsburg, please go to Mr. Hebb & tell him to send word to Morgan Miller’s and tell them that I am well and killing all the Yankees that lays in my power.

So I must end my few lines as you don’t like to read long letters. So give my love to all my friends but don’t forget that lady on Main Street and to Uncle Joe and to Sissa and to the rest of the family.

From Capt. Andrew Thomas Leopole

Command Burke Avengers

P. S. With many regards to your future health and happiness. I remain the most profound respect your only friend. Don’t forget to answer.

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¹ Capt. Redmond Burke led the company that Andrew served in. Capt. Burke was killed in a skirmish in Shepherdstown on 25 November 1862 and Andrew was taken prisoner by the 2nd Massachusetts Infantry. Andrew was imprisoned but a short time and then was paroled. He apparently afterward was elevated to his captain’s position.