I doubt Major General Robert Milroy (above) had any doubts when the sun rose on that muggy Monday, 15, June, 1863. Even the first volley from 3,500 rebel muskets and the blasts from the single cannon failed to shake the confidence of the “Grey Eagle", as Milroy liked to call himself. I doubt even then Millroy believed he was responsible for the disaster into which he had lead his soldiers.
Sitting at the northern entrance to the Shenandoah Valley, Winchester, Virginia (above) had already changed hands twice in this war. Most professional soldiers considered it indefeasible. Despite this, and even after General-in-Chief Halleck had ordered him to retreat to Harpers Ferry, and even after being warned about the approach of a Confederate horde, the Grey Eagle remained in Winchester, confident his earthen forts would withstand any attack by the despised Confederate army. As Hoosier farm boy Robert Milroy dreamed of being a soldier. When his father refused to recommend the boy for West Point, he paid his own admission to a private military academy in Vermont. But after graduation, the U.S. Army rejected his application to be an officer, and only then did he bow to his father's will and enter law school. But for the rest of his life the lawyer and judge scorned the "...selfish, bigoted, supercellious, incompetent West Pointers" whom he blamed for killing his dream. He saw the American Civil War as a chance to get even.
As a captain of Indiana militia Milroy proved a brave and competent leader, rising quickly through the ranks thanks to his courage and his deep hatred of slavery. Twice in the first two years of the war the aggressive "Gray Eagle" managed to throw Confederate General Stonewall Jackson off balance, something damn few Federal commanders ever did. With his "...piercing black eyes...aquiline nose..." and "... white, shocky, stiff
hair" Milroy was loved by his men, despite "...an ever present pomposity..."
But as the occupier of Winchester, Virginia (above), Milroy was perhaps the most hated Yankee in the nation. Under his regime, only farmers who signed a loyalty oath were allowed to buy grain to feed their dairy cows. He forbade gatherings of two or more people, even harassing school girls walking home together. After 8:00pm no townspeople were allowed outdoors. And his troop of paid informers insured that anyone who said anything which might be construed as pro-Confederate was immediately expelled from the town. He admitted, "I feel a strong disposition to play the tyrant among these traitors." He did this so well, the rebels offered a $100,000 reward for his capture.
It was not until he was ducking shot from rebel artillery from the surrounding hills that Milroy realized by retreating into the 3 earth forts he had built, he had merely concentrated his 9,000 men, making them easier targets. After the capture of the West Fort he finally ordered his shell shocked troops to slip out of their fortifications at 1:00 am. on 15 June and belatedly begin their retreat 30 miles north to Harpers Ferry on the Potomac River.
The cork holding Milroy in the bottle was the single cannon on a wagon bridge over the destroyed tracks of what had once been the Winchester and Potomac Railroad.
In his panicked response Milroy launched two unprepared flailing attacks which killed all but one of the brave rebel gun crew, but failed to silence the cannon or remove the supporting infantry. Just as Milroy launched a third assault another 1,300 rebel infantry appeared – the brigade once led by Thomas “Stonewall” Jackson. And under their combined fire the federal regiments began to surrender.
The next day the “debris of Winchester” stumbled into Harpers Ferry. The Hoosier Milroy (above) had lost half his men - killed, wounded and more than 2,500 taken prisoner. But he saved himself.
By order of Brigadier General Halleck (above) General Milroy was relieved of his command and arrested. As the overall Union Commander explained, “We have had enough of that kind of military genius.”
Thanks to Major General Robert Milroy's arrogance and stupidity the road “down” the valley, meaning to the north (above), was now wide open, and the entire 75,000 man rebel Army of Northern Virginia under the feared Robert Edward Lee was free to invade Maryland and Pennsylvania, with it's supply line back to Virginia secure. It was the idiot Milroy who made the battle of Gettysburg possible.
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