“I regret that fate thrust such a duty upon me…” Mosby, Custer and the Black Flag in the Shenandoah Valley Part II

part two of two

Since the execution of Mosby Ranger Albert Willis at Flint Hill on October 14, 1864, Mosby sought revenge for what he considered to be the unlawful execution of seven of his men.   Though he was not directly involved in each execution, Federal Maj. Gen. George Custer was blamed by Mosby as being behind the retributions against Mosby’s men. It was known that Custer and others in the Federal high command did not step in to stop the execution of Mosby’s men at Front Royal.

Mosby returned to his “Confederacy” in late September (he spent the previous weeks recovering from a wound) and learned the details of what had happened. On October 29^th, Mosby wrote a letter seeking permission to “hang an equal number of Custer’s men whenever I capture them.” By November 4^th, Gen. Robert E. Lee and Secretary of War James Seddon agreed with Mosby’s plan.

On November 6^th, Mosby gathered his partisans at Rectortown in northern Fauquier County. Nearly 500 of his men reportedly made the rendezvous, all wanting to be part of the spectacle. Present also were 27 Federal prisoners that were captured during the previous weeks from Mosby’s various raids, most from Custer’s command. To pay retribution for the seven of his executed men, Mosby called out for the 27 prisoners to draw a slip of paper out of a hat, with marks on seven of them. This method randomly selected seven men to be executed in kind. As the hat was passed down the line of prisoners, a drummer boy selected a marked slip. One of Mosby’s officers let Mosby know, and it was determined that they would redraw for the last slip and spare the life of the young man.

Once seven were selected, Mosby ordered a small detachment of his Rangers to take the selected prisoners towards the Union lines near Winchester. Along the way one of Mosby’s most trusted officers, Capt. Richard Montjoy, pardoned one of those condemned to die. Recently, Montjoy was inducted as a Freemason and was wearing a Masonic pin on his uniform. One of the Federal prisoners slated for execution, Lt. Disosway, was also a Freemason and recognized the pin. He flashed Montjoy a secret Freemason distress signal, which Montjoy recognized. Montjoy pardoned the man and selected another prisoner from Custer’s command to take his place. This act of mercy did not sit well with Mosby and reminded Montjoy that the Masons and his command were two different organizations with different objectives.

Arriving in Berryville at 4:00am on the November 7^th, a hill on the western end of town was selected.   The area, known as Grindstone Hill, was on the road to Winchester. Mosby was not with the detachment, but he made specific instructions that four should be shot and three hanged (to match how his men were executed).   The executions did not go as planned with many of the Rangers dreading their tasks for executing the men. Two men who were to be shot escaped (one by getting loose from his rope and another after a misfire). Two other men were shot in the head and left for dead, though miraculously they both survived their wounds. Finally, three men were hanged and left dangling from the tree with the note “These men have been hung in retaliation for an equal number of Colonel Mosby’s men hung by order of George Custer, at Front Royal. Measure for measure.” Local residents discovered the two wounded men and three dead later that morning. Mosby was not bothered that some of the executions were botched, he argued the point was to call to question the policy of executing prisoners.

On November 11^th, Mosby wrote directly to Federal commander Gen. Phil Sheridan and called for a “truce.” Both commanders agreed to stop the “black flag” tactics and treat captured men as prisoners of war, with all the rights that prisoners of war are afforded. Though the war moved south and never returned to the lower Valley, Mosby continued to operate in the area until the end of the war. After the war, Mosby defended his actions in November at length:

“I determined to demand and enforce every belligerent right to which the soldiers of a great military power were entitled by the laws of war. But I resolved to do it in the most humane manner, and in a calm, judicial spirit…I regret that fate thrust such a duty upon me; I do not regret that I faced and performed it.”

The legendary actions between Mosby, Custer and Sheridan that fall are still told in lore today. One of the ugliest episodes of the war is considered today another facet of how destructive the Civil War was on the region and nation.

Stay tuned for an ECW Weekender post focusing on the events at Rectortown