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Historical Profile: Major Theodore Woolsey Winthroop
By Nancy E. Sheppard

TWW ImageHe lived a colorful life and left his enduring legacy in a clumsy death upon the muddy battlefield at Big Bethel; one of the first ranking officer deaths of the Civil War. But who was Major Theodore W. Winthrop?

Theodore Winthrop was born into a prominent New England family. He was a decedent of Puritan governor of the Massachusetts Bay Colony, John Winthrop. He graduated from Yale in 1848 and set out on a quest to see as much of the world as he could. From the Puget Sound to Panama to the British Isles, Winthrop saw so many things and wrote down his experiences in manuscripts.

After returning home at 32 years old, he settled in Greenwich Village in New York City, joining the avant-garde artists and literary types that lived there. When the South began to secede from the Union, Winthrop enlisted in the 7th Regiment of the New York’s "silk stocking” state militia; one of the earliest regiments to respond to Lincoln’s call to duty. He found himself a position as a military war correspondent for the popular magazine, The Atlantic, and began to pen an essay entitled, "Our March to Washington,” regarding this unique experience.

Unlike many of his fellow soldiers, Winthrop did not foresee a quick end to the war and knew that, once the war had ended in favor of the Union, the South would need their aid for policing and reconstructing the remains of the land beneath them. He was soon appointed to the rank of Major and assigned as aide-de-camp to Union Major General Benjamin F. Butler at Fortress Monroe. At Butler’s side, Winthrop, an ardent abolitionist, witnessed Butler’s declaration of slaves as contraband, setting into motion emancipation.

On June 10, 1861, Winthrop joined other Union troops in the failed and frazzled attempt at the Battle of Big Bethel; the first planned land engagement of the Civil War. As his comrades fell beside him one by one, in a romantic gesture, Winthrop leapt upon a fallen tree stump, waved his sword in the air while screaming, "One more charge, boys, and the day is ours!” Within moments, an enemy musket pierced his body, killing the 33- year-old soldier. The battle was a solid victory for the Confederacy and Winthrop was buried where he fell; his belongings pillaged by Southerners. A week later, his brother arrived in Virginia to retrieve his corpse for burial in New Haven, Connecticut.

It wasn’t until after his death that Winthrop’s literary prowess became known. Two of his essays appeared in the Atlantic, several of his manuscripts published, and his sister had a collection of his poetry printed. Nearly a month after his death, Major General Butler received a package from Confederate Commander D.H. Hill containing Winthrop’s pocket watch and a note stating, "Sir, I have the honor herewith to send the watch of young Winthrop, who fell while gallantly leading a party in the vain attempt to subjugate a free people.”

In the years after his death, Major Winthrop’s predictions of war proved true as his writings gained popularity and his essays gave invaluable insight to the early days of the Union Army. However, there is no great marker commemorating his original grave. In a somewhat fitting twist of irony, the off-base housing for Langley Air Force Base now stands on the land that was once soaked by Winthrop’s blood.


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