Theodore Winthrop was a curious young man whose literary career began late in his short life. Born on September 22nd, 1828 in New Haven, Theodore was a member of the prestigious Winthrop family of Connecticut, which included John Winthrop, the first governor of Connecticut Colony. Theodore attended Yale College where he excelled in scholarship, taking the Clark and Berkeleian scholarships. He had a great love of Greek and of philosophy, a quick mind, and a great ability to absorb and retain knowledge. In his memoir of Winthrop, George William Curtis, a close friend, describes Theodore as "thoughtful and self-criticising, he was peculiarly sensible to religious influences, and his sensitive nature grew sometimes morbid." The use of "morbid" in this description is peculiar and may indicate that Winthrop was attracted to men. After receiving his degree from Yale in 1848, he took the grand tour, returning to New York where he worked in W. H. Aspinwall's counting house.

Winthrop traveled extensively across the western hemisphere, spending time during the 1850s in Panama, California, Oregon, and the territories of the northwest. Returning to New York, he studied law and was admitted to the bar in 1855. His first position as a lawyer took him to St. Louis, but because of ill health, he returned to New York to practice. Winthrop began to write essays, stories, and novels. During this period, Winthrop, along with many artists, writers, and intellectuals, lived in the NYU University Building that provides the backdrop for Cecil Dreeme, his gothic novel about sexual ambiguity that is set in and around Washington Square and NYU. A frequent visitor to his friend Frederic Church, the noted Hudson River School painter, Winthrop came to know the intricate details of art history, painting, and bohemian culture, which also play a central role in the novel.

Winthrop was a fervent advocate for democracy and human freedom. When the South fired on Fort Sumter, Winthrop enrolled in the artillery corps of the Seventh Regiment and marched from New York in April, 1861. His first published piece followed in June, 1861 in an issue of the Atlantic Monthly Magazine where he describes the march of the Seventh Regiment from New York to Washington. Awe swept by the war, Winthrop wrote letters home that echo Walt Whitman in their use of the word "comrade." For all his enthusiasm and sentiment, Winthrop died in battle on June 10th, 1861 at Great Bethel.

Description of Cecil Dreeme

Cecil Dreeme (Boston: Ticknor and Fields, 1862) is one of the queerest American novels of the 19th century. Basically a gothic tale in the style of The Castle of Otranto , which is cited in the text, the partially autobiographical story is a combination of plots take from Shakespeare and Gautier's Mademoiselle de Maupin, and Winthrop's experiences living on Washington Square. In the story Robert Byng, a former New Yorker who has just returned from ten years abroad, takes up lodgings in "Chrysalis College" (NYU) on "Ailanthus Square" (Washington Square) in rooms unused by the fledgling school. Caught up in the strange world of artists, "bohemians," and dandies on the one hand and the stolid, respectable society of Knickerbocker New York on the other, Robert befriends a young man who has locked himself away from the world, painting by day and moving about the City at night. Their friendship deepens into love as Robert describes them as "Damon and Pythias," the famous Greek lovers. The disappearance, and presumed suicide, of a young woman Robert knew when he was a child haunts Churm, one of his other friends, who is convinced that the evil dandy, Densdeth, was in someway responsible for the girl's disappearance Densdeth was engaged to marry the girl by her father's arrangement but against her will. Densdeth, whose influence is considerable, has ruined many young men and his next conquest is to be Robert himself. Robert's attentions to Cecil, however, keep him from falling totally under Densdeth's power. As the plot unravels, scenes of life in Chrysalis College, the Square, and the Village during the period provide a backdrop for a complicated philosophical discussion about the nature of male/female, manly/unmanly, womanly/unwomanly, and effeminate and langourous behavior. Cecil Dreeme, the young artist of Robert's affection, turns out to be Clara Denman, the young woman, thought dead, who has been hiding in Chrysalis College dressed as a man. This revelation is startling to Robert who now has an explanation for his sexual attraction to the young man, but now has to confront the gender differences society places on their relations.

Two extra-texual features of this novel are important for placing it in context: 1) it was published by Ticknor and Fields, one of the most important literary publishers of the day, a publisher known for high quality American literature; and 2) the text was incredibly popular, running through several editions in the first year (it was published posthumously with a lengthy introduction by George William Curtis). The text, with its combination of New York scenes, gothic tropes, metaphorical use of Greek history and mythology, gender confusion, and sexual ambiguity provides a glimpse into the American vision of same-sex sexuality before the definition of homosexuality.