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From Cuckold to Killer to Civil War General: The Strange Odyssey of Daniel E. Sickles

A look at a colorful figure from guest writer Matthew A. Perry

General Sickles portrait
Portrait of General Daniel Sickles.

One of the most distressing and agonizing aspects of active service is the distance between significant others. The dreaded “Dear John” letter to a jilted soldier is as old as organized armies, and the worry about cheating spouses has run rampant in armies throughout the ages. In this article, we will explore a different twist on the cheating spouse, and the extraordinary story of an ambitious New Yorker who exacted revenge on his wife’s lover and later went on to be one of the most fascinating military personalities of the Civil War.

Daniel (“Dan”) Sickles was born in 1819 in New York City. His father was a patent lawyer and politician, and he followed in his father’s footsteps by entering the legal profession in 1846 and being elected to the State Assembly in 1847. In 1852, Sickles married the fifteen-year-old (the 19th century was a different era) Teresa Bagioli against the wishes of her family. Dan didn’t care what Teresa’s family, (or anybody for that matter) had to say about their marriage, and he flaunted his young bride around the city.

Dan was not satisfied with just one woman, like many gentlemen of the 19th century, keeping many women as mistresses and even being censured in the New York State Assembly when he brought a known prostitute into the chambers. Eventually, Dan was elected to the United States House of Representatives, and he and Teresa moved to Washington D.C. It was in Washington that Dan’s carousing reached epic proportions, keeping multiple mistresses within walking distance of his home.

Victorian society was in some ways defined by double standards. While Dan was socially free to keep as many women on the side as he wished, his wife Teresa was expected to keep house and stay loyal to Dan. Teresa was no fool and knew Dan was sleeping around, and she also was angry about the lack of attention that Dan showed her at home. As they say, hell hath no fury like a woman scorned, and Teresa began a relationship with a U.S. District Attorney by the name of Philip Barton Key. Key was rich and well to do, and was the son of the author of the Star Spangled Banner, Francis Scott Key. Philip Key became Teresa’s lover in Washington while Dan was out with other women or attending to his official duties. Dan was completely oblivious about the adultery until 1859 when an anonymous letter detailing the affair was sent to him. Sickles was told to go to the address that Key had rented out for the purpose of having romantic encounters with Teresa, and he would see a dapper gentleman waving a handkerchief on the corner. When this man waved, per the letter, Teresa would appear in the window and the two would then meet for their their tryst.

What happened next made Sickles a nationwide celebrity.

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