June 10: Theodore Winthrop Becomes First Union Officer to Die in the Civil War


Today in 1861, 32-year-old Major Theodore Woolsey Winthrop of the Union Army was killed during the Battle of Bethel in eastern Virginia, during one of the first land battles of the American Civil War.

Winthrop was a direct descendant of John Winthrop Sr., Puritan leader of the Massachusetts Bay colony, and John Winthrop Jr., longtime Connecticut governor and founder of New London.  Born in New Haven in 1828, he graduated from Yale (where his uncle, Theodore Dwight Woolsey, was president) at age 20 and toured Europe and then the western United States for several years before settling in New York City.  There, he studied law by day and mingled with writers and artists by night, hoping to one day make a name for himself as a famous writer.  Among his unfinished works were memoirs and travelogues of his adventures to the Pacific Northwest and several gothic-style novels that portrayed the vivid Bohemian-style nightlife of antebellum New York City.

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

While Winthrop managed to publish a handful of short stories and articles in local magazines and newspapers, he was forced to put his long-term plans for literary fame aside once the Civil War broke out in April 1861.  Already a member of the New York state militia, the bright young volunteer was quickly promoted to Major once he joined the Union Army, and was soon serving as the aide-de-camp to Major General Benjamin Butler in Virginia.

In early June 1861, Confederate forces around the Virginia state capitol of Richmond devised a plan to lure out Union forces from nearby Fort Monroe.  General Butler sent a regiment of troops,  many of them under the command of Major Winthrop, to attack the enemy 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 communication breakdowns on the Union side — including a number of friendly-fire incidents — gave the Confederates a huge advantage on the battlefield.  Major Winthrop tried his best to rally his panicked men, allegedly leaping on top of a tree stump and yelling, “One more charge, boys, and the day is ours” — only to be struck in the chest by a musket ball moments later.  The thirty-two-year-old Connecticut-born Major, who later died from his wounds, thus became the first Union officer to died in the Civil War.  The Union soldiers ultimately lost the battle, losing 18 men and sustaining over 50 casualties while the Confederates only suffered one loss and a handful of wounded men.

Ironically, the literary fame Theodore Winthrop sought during his lifetime arrived after his death, following the posthumous publication of many of his works by his close relatives.  His novel Cecil Dreeme went through over a dozen editions in the late 19th century, and his memoir of his 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.  A promising young man’s life cut tragically short by 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