June 10: The First Union Officer to Die Fighting in the American Civil War


Today in 1861, 32-year-old Major Theodore Woolsey Winthrop, a descendant of one of the most important figures in the founding of Connecticut, died in action at the Battle of Bethel in eastern Virginia, one of the first land battles of the American Civil War. Winthop was the first Union officer to die fighting in that epochal conflict .

Born in New Haven in 1828, Theodore Winthrop was a direct descendant of both John Winthrop Sr., Puritan leader of the Massachusetts Bay Colony, and John Winthrop Jr., longtime Connecticut governor and founder of both Saybrook and New London. He graduated from Yale (where his uncle, Theodore Dwight Woolsey, was president) in 1848, and spent the next four years touring Europe and the American West. He then settled in New York City, where he studied law by day and mingled with writers and artists by night, hoping to make a name for himself as a famous author. Among his unfinished works are memoirs and travelogues of his adventures to the Pacific Northwest and several gothic-style novels portraying the vivid Bohemian-style nightlife of antebellum New York City.

A sketch of Theodore Winthrop in uniform, from Appleton’s Cyclopedia.

Though Winthrop successfully published a handful of short stories and articles in local magazines and newspapers, he put his literary aspirations on hold with the start of the Civil War in April 1861. Already a member of the New York State militia, the bright young volunteer joined the Union army, quickly earning promotion to Major and a posting as aide-de-camp to Major General Benjamin Butler in Virginia.

In early June 1861, Confederate forces around the Virginia state capitol of Richmond attempted to lure Union forces out from the strategically important Fort Monroe. That Hampton Roads installation was the last bastion of United States authority in the Virginia Tidewater region, following the military realignments that had taken place after the fall of Fort Sumter. To counteract the Confederate thrust at Fort Monroe, General Butler sent a regiment of troops, many under the command of Major Winthrop, to attack the Confederates. The two forces met at dawn on June 10, near a town known as Big Bethel, on the Virginia peninsula. Even though the Union troops outnumbered their Confederate counterparts two to one, a number of amateurish mistakes and communications breakdowns on the Union side — including several friendly-fire incidents — gave the Confederates a huge battlefield advantage. Even as things turned badly against the Union forces, many of whom were ready to flee the battlefield, Winthrop courageously attempted to rally his panicked men. He is said to have leaped on top of a tree stump and yelled, “One more charge, boys, and the day is ours.” Moments later, however, Winthrop was struck in the chest by a musket ball. The 32-year-old Connecticut-born Major subsequently died from his wounds, thus becoming the first Union officer to die in battle during the Civil War. All together, 18 Union soldiers lost their lives at Big Bethel and more than 50 were wounded, while the victorious Confederates suffered only one loss and a handful of wounded men.

The literary fame Theodore Winthrop sought during his lifetime arrived after his death, following the posthumous publication by his close relatives of many of his works. His novel Cecil Dreeme went through over a dozen editions in the late 19th century, and his memoir of travels through Washington Territory, titled The Canoe and the Saddle, was so popular that the town of Winthrop, Washington (as well as the famous Winthrop Hotel in Tacoma, Washington) was named in his honor.

Though Winthrop’s combat death made him the first Union officer to die fighting in the Civil War, he was not the first Union officer to have died in the Union cause. That distinction had gone to Colonel Ephraim Ellsworth of New York, who was shot to death by a hotel owner in Alexandria, Virginia on May 24, 1861, after Ellsworth had removed a large Confederate flag the hotelier had been flying from the roof of his establishment.

A promising young Union officer became the first to fall fighting in the American Civil War, today in Connecticut history.

Further Reading

Dave Altimari, “Maj. Theodore Winthrop Of New Haven, 1st Ranking Officer To Be Killed In Civil War,Hartford Courant

Judith Ann Schiff, “Two Months in the Civil War,Yale Alumni Magazine