Benjamin “Beast’ Butler was not the only Union commander who imposed harsh discipline on Southern civilians beneath his boot. Robert Huston Milroy was the Southerner’s worst nightmare. His brand of abolitionism was fanatical. Certainly, today, we can appreciate his zeal for freeing persons who had long been enslaved. Burt, his zeal also marked him as an extremist in his time period. Milroy, raised in Indiana, graduated from Norwich Military Academy in Vermont. The young Robert Milroy’s earnest desire was to attend West Point. But, his farther would not support his goal. Even though the Milroys had for two generations been involved in the military, they had served in volunteer or militia units. Robert’s father may have had an aversion to a professional military. Norwich University still exists today as a military college. 
Robert Milroy served in the Mexican war without particular distinction. Although, even at this early stage, he demonstrated a zeal for combat and a strong irreverence toward authority. After the Mexican war, he returned home to Indiana, practiced law, became a judge and became an ardent abolitionist. 
“Known” Confederate Sympathizers
In early 1861, Milroy started recruiting a regiment. He was gung-ho for the war from the very start. By 1862, he was serving under Gen. McClellan, In 1862, he was now a Brig-General overseeing the war in West Virginia. In that new state, the Southern partisans were very active. It was a closely divided state. Unable to catch the partisans, Milroy devised a new strategy. Focusing on the “known” Confederate sympathizers. He decided that Union supporters who suffered from the partisan raids would present a bill for the value of lost property. Local commanders would then apply that bill to “known” Confederate supporters in their area. If the Confederate supporter failed to pay, the sympathizer’s house would be burned and the Confederate supporter shot. Thus, one West Virginian had to pay $1,000. Another 82 year old German immigrant – who was crippled and infirm – had to pay $285. Brig-Gen. Milroy’s scheme order produced some $6,000 within just a few months.
So, the Virginia government sent a protest through Gen. Robert Lee to General-in-Chief Henry W. Halleck. Halleck found Milroy’s order to violate the rules of war and that Milroy lacked the authority for such measures. Thus began long antagonism between Brig-Gen.Milroy and Halleck. Milroy had little patience for military etiquette or for West Point officers. 
Brig.-Gen. Milroy was promoted to Maj.-Gen. and to command of the Second Division, Eighth Army Corps headquartered in Winchester, Virginia. It has been estimated that the town of Winchester changed hands some 70 times during the war. But, for many months in 1863, it was held by one ardent abolitionist, Maj.-Gen. Robert Milroy. The Emancipation Proclamation had just been issued in January, 1863. But, it had not yet been enforced in Winchester. Milroy rectified that oversight immediately. Even on the road to Winchester on Jan. 1, 1863, he would excitedly proclaim to the marching troops that today was “Emancipation Day, when all slaves will be made free.” 
But, like any fanatic, he did more than just enforce this critical Presidential decree. Milroy also ruled the city with an iron fist. As he said to his wife, his will was “absolute law” in Winchester. He required Winchester citizens to swear a loyalty oath if they wished to buy supplies from the Union Army sutlers. They had to swear an oath if they simply needed a pass with which to leave town. He exiled Winchester families for violating his rules. He exiled folks who provided goods or information to Confederate forces. And, he also exiled folks who simply voiced support for the Confederate forces in which their sons, fathers and neighbors served. He exiled folks who wore a ribbon for the deceased Stonewall Jackson in May, 1863. Stonewall was from the nearby town of Lexington and was much mourned throughout the Shenandoah Valley. But, Milroy did not care. He exiled “scores” of families. 
In practical terms, exile meant the Union soldiers would transport a Winchester family with little notice in a wagon to some place 20 miles south of town. The family would then be deposited by the side of the road, sometimes in bad weather.
Maj.-Gen. Milroy exiled the Logan family at the corner of Braddock and Picaddilly streets because they harassed a “Jessie Scout” – a Union soldier dressed as a Confederate. But, the Winchester residents say he exiled the Logans mainly because his wife wanted their house. He saw himself as fulfilling the role of an Old Testament prophet ending slavery and he would brook no opposition. 
The Rules of War
Serving under Maj.-Gen. Milroy was Brig.-Gen. Gustave P. Cluseret. French-born, Cluseret objected to “fighting for Negroes.” But, he also objected to arresting women. And he believed that it violated the rules of war to refuse to feed prisoners – in which belief he was correct. And, he believed that maintaining some accommodation with the locals would assist in the Federal occupation. Milroy reversed Cluseret’s more accommodating policies. Cluseret would eventually resign. While, at the same time, Milroy was seeking leave to relieve Cluseret. 
In June, 1863, one Confederate Corps advanced upon Winchester. Gen. Halleck told Milroy to withdraw. But, Maj.-Gen. Milroy persuaded his superiors that he had built fortifications which would withstand any invasion. Milroy, ever sure of himself, said it was not possible for Lee to have moved so many troops to Winchester in such a short time. But, on June 13, a key defense was seized by Dick Ewell’s troops. And, on June 14, 1863, Milroy finally realized he was virtually surrounded by Gen. Jubal Early. He ordered an evacuation back to Harper’s Ferry. Leaving behind artillery and wagons, they started moving that night. But, his forces were ambushed during the retreat by Confederate forces. The surprise was complete. Milroy, ever brave in combat, rushed to the scene of the worst fighting and held his men together. Still, some 3,300 Union soldiers were captured. His army essentially ceased to exist. 
Milroy was relieved of command and arrested. It was not entirely his blunder. He was later found not guilty of malfeasance. And, he even obtained a new command later in the war. But, through that long process, Gen. Halleck for one always viewed him as an inferior officer – starting with those reckless orders in West Virginia.
 Cary C. Collins, “Grey Eagle: Major General Robert Huston Milroy and the Civil War,” Indiana Magazine of History, vol. 90, No. 1 (March 1994), p. 51-52.
 Collins, “Grey Eagle,” p. 53-55.
 Collins, “Grey Eagle,” p. 60-63.
 Collins, “Grey Eagle,” p. 64; Jonathan A. Noyalas, Slavery and Freedom in the Shenandoah Valley during the Civil War Era (Gainesville: University of Florida Press, 2021), p. 88.
 Collins, “Grey Eagle,” p. 64; Shenandoah Valley Battlefields National Historic District website, at https://www.shenandoahatwar.org/robert-milroy, accessed Jan. 8, 2023; National Park Service website at https://www.nps.gov/articles/000/occupied-winchester-1863.htm, accessed Jan. 8, 2023.
 Shenandoah Valley Battlefields National Historic District website, accessed Jan. 8, 2023.
 Collins, “Grey Eagle,” p. 65.
 Collins, “Grey Eagle,” p. 66-67.