Four prominent portraitists were active in New York City between 1790 and 1825: Gilbert Stuart, John Vanderlyn, John Trumbull, and John Wesley Jarvis. Despite working in the same geographic location, these four artists received different artistic training, developed distinct aesthetics, and often worked for distinct groups of patrons.

Upon returning to the United States in 1793 Stuart quickly established himself as the preeminent portraitist in New York City. This coincided with a moment of particular political harmony in the United States, a harmony that was broken by the vitriolic debates over the ratification of the Jay Treaty in 1795. Although Vanderlyn briefly studied with Stuart, Vanderlyn received most of his training in Paris in the studio of Vincent, a prominent French neoclassicist. When Vanderlyn returned to New York City, Democratic-Republicans--politicians who wished to tie the diplomatic future of the United States to France--quickly embraced Vanderlyn's decidedly French aesthetic. This artistic style is characterized by an emphasis on linearity, a muted use of color, and compositions in which the artist places compositional focus on the sitter rather than objects around him. Conversely, Federalists who wished to further tie America to Great Britain preferred Trumbull and his English style: the energetic brushstrokes, colorful palette, and compositions that often contained ancillary elements that allude to the sitter's occupation, education, and wealth. In contrast to both Vanderlyn and Trumbull, Jarvis did not received European training. As a result, he developed an aesthetic that was quickly embraced by individuals who did not wish their portrait express political alignment. Indeed, this political neutrality--both social and stylistic--was one of the reasons members of the military preferred Jarvis over his politically inclined competitors.