The AAS portraits reveal some of the complex relationships of community life. When Isaiah Thomas, the staunch patriot, moved his business to Worcester in 1775, William Paine, a Loyalist, had already left for medical training in Scotland and would return to the colonies as a surgeon in the British Army during the Revolution. Paine and his family moved back to Worcester in 1793, and in 1812, old political sentiments set aside, this physician would join with Isaiah Thomas as one of the founding members of the American Antiquarian Society. Likewise, we learn of the regional and even national importance of some of the sitters. For example, Aaron Bancroft was the minister of the Second Parish in Worcester from 1786 to 1839, but also served as president of the American Unitarian Association from 1825 to 1836.

  Since many of the portraits came to AAS together with manuscript collections or were commissioned by the Society, we have extraordinary information about the circumstances of their production. There are occasional first-person accounts of the process of sitting for portraits as well as important documents revealing the costs of the paintings and even their frames. Newspaper advertisements found in the AAS collection provide documentation about itinerant artists who came to Worcester. In an effort to obtain commissions for one artist, Isaiah Thomas, Jr., placed an advertisement in the September 12, 1804, issue of the Worcester Spy saying that examples of Gerrit Schipper's portraits could be seen in his home or office. Other early nineteenth-century Worcester residents, such as Edward D. Bangs and Isaiah Thomas, traveled to Boston to sit for oil portraits by artists established in Boston studios; later in the century, Stephen Salisbury II went to New York for sittings with Daniel Huntington.