Winchester is of No Importance

June 11, 1863 (Thursday)

Milroy: I am obnoxious and disliked, that cannot be denied.
Milroy: I am obnoxious and disliked, that cannot be denied.

The pompous and generally unlikeable Robert Milroy had occupied Winchester, Virginia since January with his Federal troops. Though he was hardly an inspired military commander, he seemed to have a knack for destroying the hopes and aspirations of the Confederate sympathizers in the town. This was partly due to his abolitionist rhetoric, calling the emancipation of the slaves “the most important event in the history of the world since Christ was born.”

After receiving a copy of the Emancipation Proclamation, Milroy released his own, localized edict freeing all the slaves of Winchester (which, as of 1860, numbered around 700). Virginia’s governor, John Letcher, was infuriated, and demanded execution for any white man aiding in the freedom of a black man. He, along with Richmond, put a price of $100,000 (Confederate) on Milroy’s head. But Milroy cared not at all. He believed that he was doing the Lord’s work in freeing the slaves, and used the Bible to support his views (much like the slave owners used the Good Book to support theirs).

Militarily speaking, Milroy ordered harsh raids into neighboring towns, as he did what he could to fortify Winchester, even if it meant taking apart the town piece by piece. He and his men destroyed many buildings, using the lumber as firewood or building materials. Though he ordered his men out of town by 6pm every evening, and forbade the use of alcohol, Milroy won few converts in Winchester.

Throughout the spring, life continued in this way, peppered here and there by Confederate cavalry attacks upon Milroy’s pickets and the railroad bridges throughout the surrounding area. The mail to and from Winchester was read and many people (mostly women) were arrested for even a breath of anti-Union sympathies. And if one of these women were to insult a Union soldiers, she was either imprisoned or sent packing.

He ruled harshly and with an iron fist. His will was law and he believed the citizens of Winchester should be punished for taking part in the Rebellion. Part of this punishment including quartering his men in the homes of Confederate sympathizers.

Big map for a big day.
Big map for a big day.

As spring slid into summer, and General Hooker was defeated at Chancellorsville, Milroy grew concerned that the Confederates might try to take back Winchester. He sent out countless scouts and spies to try to figure out what the Rebels might be about. Through all of this, General-in-Chief Henry Halleck, who personally despised Milroy, thought that Winchester was worthless and that all troops in the area ought to be consolidated at Harpers Ferry.

Halleck first expressed this in April, but by late May, Milroy was still in Winchester. Rumor had it that Confederates were planning to assault Milroy’s defenses on June 10. He had several weeks to prepare, and greatly improved his fortifications. All the while, Halleck was wiring General Robert Schenck, Milroy’s superior, based out of Baltimore, urging Winchester to be let go.

Schenck hasn't quite had his say yet.
Schenck hasn’t quite had his say yet.

June 10th arrived and ended with no Confederate attack. Milroy was somehow convinced that since there wasn’t an attack on the 10th, there wouldn’t be any attack at all in the foreseeable future. In preparation for the attack, General Schenck had dispatched a staff officer to inspect Milroy’s defenses. At first, the officer was completely convinced, asserting that the Federals “can whip anything the rebels can fetch here.”

Milroy, of course, couldn’t agree more. “I can and would hold it, if permitted to do so against any force the rebels can afford to bring against me,” he wrote to Schenck, “and I exceedingly regret the prospect of having to give it up….”

General-in-Chief Halleck, however, was not at all a believer. Late that night (the 10th), he ordered Milroy to take steps to remove his command to Harpers Ferry. The message was received around noon on this date.

“Harpers Ferry is the important place, Winchester is of no importance other than as a lookout,” wrote Halleck. “The Winchester troops, except enough to serve as an outpost, should be withdrawn to Harper’s Ferry.” Schenck’s staff officer, who relayed it to Milroy, added: “It must be considered an order, and obeyed accordingly. Take immediate steps. You understand this.” This emphasis should have been enough to put Milroy on the road.

The tiny, disembodied head of Robert Rodes takes the lead.
The tiny, disembodied head of Robert Rodes takes the lead.

And, for a time, it was. When Milroy received the order to leave Winchester, he wasn’t exactly thrilled. “I have sufficient force to hold the place safely,” Milroy tried to impress upon Schenck, “but if any portion is withdrawn the balance will be captured in forty-eight hours.” He believed that all of his men should go, or none of them should go. He asked General Schenck how many men he should leave behind. This bought him more time to hold onto his precious Winchester.

Time was something that was in short supply for the cantankerous Robert Milroy. Confederate General Richard Ewell’s entire Corps of 13,000 men were skirting the easter edges of the Blue Ridge Mountains, just outside the Shenandoah Valley.

The day’s march had been a tough one. Rutted roads and washed out paths held up all three of Ewell’s Divisions. But it amounted in only a little confusion, and placed Robert Rodes’ Division well in the lead at Flint Hill, while Jubal Early’s and Allegheny Johnson’s Divisions rested around Little Washington. They were between forty and fifty miles south of Milroy’s confident and somehow unsuspecting men. As Halleck and even President Lincoln tried to get Milroy to fall back to Harpers Ferry, Ewell would only draw closer.1



  1. Sources: Official Records, Series 1, Vol. 27, Part 2, p125, 161-162; “‘My will is absolute law’ General Robert H. Milroy and Winchester, Virginia” by Jonathan A. Noyalas, written as his Masters Thesis; Gettysburg by Stephen W. Sears; Here Come the Rebels by Wilbur Nye. []
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4 thoughts on “Winchester is of No Importance

  1. Although Milroy does not make it to the top tier of military leaders was it really such a bad idea to have a fortified advance post to warn about a major Confederate attack? This could certainly give Washington more time to decide what to do about Harpers Ferry and avoid a repetition of the defeat in 1862. Delaying the Confederate advance, even for a day or two might be worth the loss of Milroy and his men. But “Brains” Halleck was not much of a military leader himself.

    And so the Confederates were upset that Milroy was an Abolitionist. And Rebel Governor Lechter was angry! Well I guess they and he did not get the memo that slavery was history.

    1. Was it a bad idea? Well, 4,000 of his men were captured, so I think it was – at least the way he did it. There should have been (and were) outposts.

      But I totally agree about Gov. Lechter. Hard to feel sorry for the guy.

      1. One of the nice things about Civil War Daily Gazette, among many, is viewing the war as it happened, as a contingent experience. So how was Milroy to know that Ewell’s entire army corps was going to descend upon him, if Hooker and Halleck did not know? And if he could have bought the Union a few days it might have been worthwhile. Given the information he had it wasn’t so far fetched. Granted, he does not come across as someone who had the imaginative ability to imagine that Ewell’s army corps might descend on him…Congratulations on your marital status change and have a great road trip and a great time.

        1. Milroy couldn’t know for sure (unless he had sent scouts out ahead like he probably should have). But he did have direct orders to vacate Winchester that he not only chose to ignore, but convinced his superior to ignore them too. As with many fiascoes, there’s definitely more than enough blame to go around.

          Thanks! We’re heading out in a handful of hours. I’m all nerves and excitement.

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