Union general fought slavery in Winchester
Posted: February 16, 2013
Special to The Winchester Star
On New Year’s Day in 1863, as a bright sun burned in a cloudless sky, about 8,000 Union soldiers commanded by Gen. Robert H. Milroy marched into Winchester from the west.
Since Christmas Eve, the vanguard of Milroy’s division, commanded by Gen. Gustave Paul Cluseret, had occupied the town, but Milroy’s arrival struck fear into the area’s Confederate civilian population.
By the time the “Gray Eagle” — as his men affectionately referred to him — came to Winchester in 1863 he had established a reputation as being callous toward Confederate civilians.
Mary Greenhow Lee, perhaps Winchester’s most outspoken female Confederate sympathizer, compared Milroy to Union Gen. Benjamin F. “Beast” Butler, who in the eyes of Confederates enforced brutal policies during his occupation of New Orleans in the spring of 1862.
“Milroy is only second to Butler in brutality,” Lee wrote in her journal on Jan. 1, 1863, “so we need expect no consideration from his hands.”
The general seemed to care little that some of Winchester’s civilians likened him to “a modern Nero,” as he had multiple tasks to perform in the lower Shenandoah Valley.
While his immediate superior Gen. Robert C. Schenck, commander of the Middle Department, wanted Milroy to protect the Baltimore & Ohio Railroad, Milroy also had designs of aggressively enforcing President Abraham Lincoln’s Emancipation Proclamation and making life as difficult as possible for civilians in the area who supported the Confederate war effort.
“Freedom to Slaves!”
As a fervent abolitionist from Indiana, Milroy believed that slavery needed to be ended for the war to turn in the Union’s favor.
In his eyes, emancipating slaves in areas in rebellion would not only destabilize the Confederacy’s main labor source and ultimately lead to extinguishing slavery throughout the nation, but it would also put the Union in favor with God.
Milroy explained to his wife: “President Lincoln’s immortal Proclamation has enlisted God almighty on our side and ... he will soon clear away the tempests of war occasioned by that mighty curse, slavery.”
Five days after Milroy entered Winchester, he issued his own emancipation decree — “ Freedom to Slaves!” His proclamation informed area citizens that he expected them to “yield a ready compliance with the Proclamation of the Chief Executive” and warned that any civilian who interfered would be “regarded as rebels in arms against the lawful authority of the Federal government and dealt with accordingly.”
Milroy not only had to worry about area civilians inhibiting his ability to bring freedom to those who knew none, but also had to be concerned with men in his division who did not approve of Lincoln’s transformation of the conflict into the dual purpose of preserving the Union and ending slavery.
Although some of Milroy’s soldiers, such as the 87th Pennsylvania’s Thomas Crowl, stated that emancipation “is playing hell, this is a wrong thing,” Milroy informed them that if they refused to see emancipation’s merit in bringing an end to the conflict they could suffer penalties.
The Gray Eagle “admonished and ordered” his troops “to act in accordance with said proclamation and to yield their ready co-operation in its enforcement.”
A $100,000 reward
Despite his desire to emancipate aggressively, Milroy hoped that the slaves he freed would not become idle or disruptive.
He ordered that “all persons liberated by said Proclamation, are admonished to abstain from all violence, and immediately betake themselves to useful occupations.”
“Freedom to Slaves!” created significant anger and trepidation among the area’s white residents, who feared that, despite Milroy’s directive to discourage violent behavior, the emancipation decree might spark massive insurrection.
The general told his wife that his program to free the slaves “created a great excitement and commotion among the first families of Virginia in this old aristocratic city.”
Milroy’s emancipation policy also caused enormous anxiety in Richmond among leaders of the state and the Confederate government. Gov. John Letcher branded Milroy’s edict and enforcement of the Emancipation Proclamation as a “brutal” attempt to incite a slave revolt, a crime which in Virginia carried the death penalty.
Five days after Milroy issued “Freedom to Slaves!” the state Legislature passed a resolution which declared Milroy an “outlaw” for his emancipation policy. His desire to eradicate slavery so infuriated state and Confederate leaders that the two governments combined their resources to post a $100,000 reward for Milroy’s capture — a man branded by both houses of the General Assembly as “barbarous and fiendish.”
The substantial bounty for his capture was of small concern to Milroy. As an elder of the Presbyterian Church, he undoubtedly believed that God had ordained his actions. He also thought that only an Old Testament-style scourge of the land could rid the country of slavery and end the conflict.
“In ancient times,” Milroy told his wife, “the cry of a nation of slaves went up to a God out of Egypt and He heard them and sent Moses and Aaron to reason with the slave holders and try to get them to emancipate their slaves, but all the arguments and reasoning ... were received by the slave holders with scorn and ridicule.”
He continued in biblical tone that a “long bitter cry has went up to the same God from a nation of slaves in America. He has heard that cry ... but the slave holders have met all arguments ... with scorn .... War, devastation, want, Misery, disease, terror and death are everywhere around them, but still they defy God and refuse to let their slaves to free. Hell deserving iniquity until like the Pharaoh and his host, they will overwhelm in total destruction.”
“Oppressed on every side”
As part of his program to bring freedom to thousands of slaves in the lower Shenandoah Valley and punish those area civilians who supported the Confederacy, Milroy imposed martial law in Winchester, a customary practice of any occupying force.
Throughout his occupation, the general imposed a number of measures to control the civilian population, including curfews, mail censorship and a ban on gatherings of two or more people on the streets.
Cornelia McDonald wrote of Milroy’s restrictive measures: “We are oppressed on every side, even little school girls are dispersed if more than two stop to talk on the street on their way home.”
In addition to those common martial law practices, Milroy also employed former slaves to gather information about former masters which might be used as a pretext for banishing them from Winchester.
He also hired several professional detectives to hunt down individuals who smuggled items through his lines. This system of espionage created considerable anxiety among the town’s Confederate civilian population.
“Milroy is screwing the engine tighter every day,” McDonald confided to her diary in early February. “He now employs spies to enter houses and report what the women talk about or if the children play with Confederate flags, or shout for [Confederate President] Jeff Davis.”
The Gray Eagle employed Jessie Scouts (Union soldiers who dressed and portrayed themselves as Confederate soldiers) for a variety of tasks, including gathering information about anyone who might harbor anti-Union sentiment or be stockpiling goods for the Confederate war effort.
He also used Jessie Scouts to entrap Winchester’s Confederate civilian population. On numerous occasions, the scouts went about town late at night, knocked on doors and portrayed themselves as war-weary Confederate soldiers in need of food and shelter. When the people opened their doors and expressed sympathy to what they thought truly was a beleaguered Confederate soldier, they were placed under arrest or exiled.
In early April 1863, Milroy used the mistreatment of a Jessie Scout as an excuse to evict Mrs. Lloyd Logan and her children from their house at Braddock and Piccadilly Streets (now occupied by Kimberly’s Gifts) and banish them from Winchester.
The Logan house had served as Milroy’s headquarters since his arrival, but the ill treatment of the scout coupled with the arrival of Milroy’s wife Mary, who desired not to share the home with anyone except her husband, doomed the Logans.
Without sufficient time to gather any significant number of possessions, the Logans boarded a wagon which carried them to Newtown (present-day Stephens City) beyond Union lines. As the wagon drove south, one of Mrs. Logan’s daughters pointed her finger at a Union soldier standing in the street and in a mad rage shouted: “There is a man whose brains I could blow out!”
A “Valentine” for Milroy
Despite the exile of scores of families such as the Logans throughout Milroy’s tenure, the town’s Confederate civilian population and in particular the women never lost their spirit and did whatever they could to show their disdain for general and his men.
On February 23, 1863, Milroy held a parade in honor of George Washington’s birthday. The parade, which commemorated the occasion one day late, brought Confederate women out on their porches to view the spectacle.
Mary Greenhow Lee noted that as they watched, they were “hurrahing for Jeff Davis, the Southern Confederacy, [and] Washington, the first Virginia rebel.”
One Union soldier who viewed this defiant behavior remarked simply: “Those are the damndest women I ever saw.”
Perhaps the most unique exhibition of disgust among the town’s Confederate female population came on Valentine’s Day when McDonald and several other women proposed that they make and send a card to Milroy as a result of the treatment he showed to Mrs. Robert Baldwin.
Several days before Valentine’s Day, Baldwin visited Milroy to see if she could procure food — a task which proved difficult as a result of the general’s order which forbade any farmers from outside the town and Union Army sutlers to sell produce or goods to any man, woman, or child who had not taken an oath of allegiance to the United States.
During the discussion, two African-American women desired to speak to Milroy. He promptly showed Baldwin out of his office so that the two free black women could speak to him.
McDonald marked the event with a card that depicted Milroy sitting down, greeting two free black women and throwing out a white woman (Baldwin) who was wearing a dress of red and white stripes emblematic of the Confederacy.
When Milroy received the card, he immediately ordered the search of all homes and the artist’s prosecution. Luckily for McDonald, Milroy’s men could not find any evidence that her hand produced the image.
Although Milroy sought retribution, he took a more light-hearted tone about the affair with his staff and family. He enclosed the card in a letter to his wife and wrote: “You see they have made me very amiable looking, while I am ordering one of the secesh misses out of the room .... It is pretty well got up and has made considerable fun for my staff.”
“A man of intense patriotism”
While much maligned by Confederate civilians for his occupation policies which ended in mid-June 1863 with his defeat at the Second Battle of Winchester, and even detested by some 150 years later for his boorish practices, Milroy offers a great reminder that history is about perspective.
Confederates understandably despised him. On the other hand, the approximately 10 percent of Winchester’s white Unionist sympathizers and the region’s African- Americans viewed him as a great patriot.
However Milroy is viewed — patriot, tyrant, or fanatic — none can dispute his love of the Union, hatred of slavery and role in enforcing Lincoln’s Emancipation Proclamation.
Perhaps Col. E.P. Hammond, during the dedication of Milroy’s bronze monument in Rensselaer, Ind., on Independence Day, 1910, best captured the positive qualities of a man so greatly reviled by Confederates:
“He was a man of intense patriotism. The cause for which he was fighting, his country, the integrity of the Republic, the freedom of the slaves, was constantly present in his mind. It was the advantage won or the injury suffered by his cause that made him rejoice over our victory or mourn over our defeat.”
Jonathan A. Noyalas is an assistant professor of history and director of the Center for Civil War History at Lord Fairfax Community College in Middletown.