Vignetted bust portrait of Oscar Winship in uniform, sporting sideburns and shoulder straps indicating the rank of major. (Tarnishing to edges, minor spotting and imperfections; retains original seals.) Housed in a fully separated leatherette case (full separation, significant surface wear). Brass mat stamped "M. A. & S. Root / 363 Broadway N.Y."

Oscar Fingal Winship (1817-1855) entered the United States Military Academy at West Point in 1836, graduating in 1840. He was appointed a second lieutenant, 2nd Dragoons that same year, receiving a promotion first lieutenant in 1844. He was brevetted a captain for gallantry at Palo Alto and Resaca de la Palma in 1846, and appointed assistant adjutant general that same year. The following year he was brevetted a major for gallantry at Churubusco, and promoted to assistant adjutant general (with the rank of major). In 1851, he was made captain of the 2nd Dragoons. He served as chief of staff for Major General Wool and later General Harney before taking a temporary leave for health and family reasons. In 1854 he married Mary Bulkeley Pierson (daughter of New York Congressman Job Pierson), with whom he had one child. While on leave, he contracted a severe cold which developed into brain congestion, and he died suddenly on 13 December 1855 at the home of his father-in-law. He was remembered in The New York Express as "a brave officer and an accomplished gentlemen."