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Portraits played a major role in the lives of the family of Chief Justice John Jay during his generation and those of his father and grandfather. Most of the surviving portraits were executed explicitly for family members before, during, or after trans-Atlantic journeys. Further, the modest character of Jay and his wife, Sarah Livingston Jay, comes across in likenesses devoid of wigs and fancy jewelry. Only after 1795, as governor of New York, did Jay begin to wear a wig (at precisely the time they were going out of fashion) to symbolize his dedication to a “Whig” republicanism that he feared the incipient Democracy (both lower and upper cases) was threatening to replace. Portraits, which began as private keepsakes, became public signifiers of political principles.