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America's Civil War

Yale’s Theodore Winthrop once rivaled Oliver Wendell Holmes, Jr., as the Ivy League’s most prominent Civil War veteran.

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Supreme Court Justice Oliver Wendell Holmes, Jr., by virtue of his long and distinguished legal career, may have been the most famous Harvard College graduate to take part in the Civil War, but his fame was eclipsed at the outset of the war by that of another Ivy League alumnus–Theodore Winthrop of Yale, who fell in battle at Big Bethel, Virginia, on June 10, 1861.

Winthrop, like Holmes, came from a distinguished New England family. His father was a direct descendant of John Winthrop, the first governor of Massachusetts, and his mother was the great-granddaughter of the famous theologian Jonathan Edwards. Seven presidents of Yale were also in the family background. Winthrop himself was born and raised in New Haven, Conn., within sight of the Yale campus. He graduated from the college in 1848, ranked second in his class academically.

With the aid of a family inheritance, Winthrop traveled widely in the decade preceding the Civil War. Driven by a stern Puritan sense of duty, he was an intense devotee of the abolitionist cause, and in 1856 he took an active role in the presidential campaign of John C. Frémont, the first Republican, anti-slavery candidate.

Following Frémont’s surprisingly close defeat, Winthrop withdrew to Long Island, where he wrote two travel books and three novels. None of the volumes found a publisher, but Winthrop did manage to sell a charming little short story, “Love and Skates,” to Atlantic Monthly in early 1861. His future as a writer seemed assured.

Before the story appeared, however, the war began, and Winthrop enlisted in the 7th New York Zouaves. He subsequently detailed the regiment’s hasty trip to Washington in two magazine articles, “Our March to Washington” and “Washington as a Camp.” When his initial enlistment expired, Winthrop secured a post on the staff of Maj. Gen. Benjamin Butler, who commanded the Union garrison at Fort Monroe, on the Virginia Peninsula.

Confederate troops were menacing Fort Monroe from all sides, and Butler was determined to destroy the enemy camps. With the help of Winthrop, a military neophyte, Butler devised an elaborate and ambitious plan to capture the main Rebel position at Big Bethel, a crossroads village 12 miles west of the fort.

On the morning of June 10, Butler’s troops attacked the Confederate position in two columns. Lacking experience, the troops predictably failed to coordinate their attack. Winthrop, who did not need to be at the front–Butler, in fact, had pointedly warned him to be careful–attempted to stem the growing tide of defeat by leaping onto a log and exhorting his retreating soldiers. “One more charge and the day is ours!” he yelled. A Confederate sharpshooter immediately sent a bullet crashing into Winthrop’s chest. He died instantly, “a meaningless casualty of a day already lost.” He was 33. Winthrop’s best friend, fellow writer George William Curtis, noted, “Theodore Winthrop fell at Big Bethel on a summer morning and those who loved him learned that the war had begun.”

Winthrop was widely mourned, and the coincidence of his articles and short story appearing in national publications immediately after his death created an enormous public demand for his writings. His sister Elizabeth found his earlier rejected manuscripts scattered on the desk of his old room at home, and all five of the books were published in the two years immediately following Winthrop’s death. Thousands of loyal Northern readers purchased copies of Life in the Open Air, The Canoe and the Saddle, Cecil Dreeme, John Brent and Edwin Brothertoft. Winthrop’s works remained constantly in print for 40 years, making him one of the best-selling–if now largely forgotten–authors of the late 19th century.

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