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Catherine Sickles (circa 1778-1855) married American naval commander Isaac Chauncey (1772-1840) around 1794. The couple lived in Fairfield, Connecticut and had three children, Charles W. Chauncey, John S. Chauncey, and Peter S. Chauncey. Isaac Chauncey served during the Franco-American War, both Barbary Wars, and the War of 1812, where he famously commanded all naval forces on both Lake Ontario and Lake Erie. Following his accomplishments on the Great Lakes, Isaac was named commodore and was given command of the New York navy yards.

Around 1818, Gilbert Stuart painted a distinguished portrait of Isaac on panel, and he likely executed this portrait of Catherine at the same time. Isaac’s portrait was given to Secretary of the Navy Robert Smith, thence to the Lyceum of the Brooklyn, New York Navy Yard in 1842. It was later transferred to the U.S. Naval Academy in Annapolis, Maryland, as discussed in Lawrence Park’s Gilbert Stuart: An Illustrated Descriptive List of his Works, Vol. 1 (1926, New York), number 150, page 229. Catherine’s portrait, by contrast, remained in the family, passing from her son Peter Schermerhorn Chauncey (1810-1866) to his daughter Augusta Chauncey Anderson (1835-1919) and then to her son, Peter Chauncey Anderson (1868-1933). Peter’s two surviving children, Elbert Chauncey Anderson (1903-1941) and Olive Yale Anderson Wood (1907-1987), inherited the painting and shared in its ownership. While in their possession, Catherine’s portrait was exhibited twice, first at the Union Club in 1934 and again at the Newport, Rhode Island gallery of M. Knoedler & Company in 1936. 

The associated Newport exhibition catalogue, Portraits by Gilbert Stuart, contains a brief essay: “Mrs. Chauncey was the wife of Commander Isaac Chauncey, who was acting Captain of the Chesapeake in 1802, and later Commander of New York Navy Yard; from 1833 to 1840 he was the President of the Board of Navy Commissioners. . . [The painting] was inherited by Mr. E. Chauncey Anderson, who was the great-great-grandson of the sitter; and it is owned jointly with Mrs. Horatio C. Wood. III, who is also the present owner of the crescent pin worn by the subject of the picture.” (Portraits by Gilbert Stuart (1936, Newport), number 5, pages 4—5). Most recently, the painting was owned by direct descendants of Olive Yale Anderson Wood and Horatio C. Wood III.