A native of Estonia, Jacob I. Greenleaf (1887-1968) became one of the more prominent artists associated with the Cape Ann community of painters in Massachusetts, maintaining a studio on Bear Skin Neck in Rockport as well as in Boston. Greenleaf achieved consideration recognition for his work, including membership in the North Shore Arts Association, the Copley Society, and the Rockport Art Association. He exhibited widely during his career, including at the National Academy of Design in 1943.