Moses Small (1790–1861) was a free Black man who sold the Baltimore Patriot newspaper in Baltimore, Maryland. He worked as a news vendor for most of his adult life and had accumulated fifty years of experience by the time Thomas Waterman Wood painted this portrait. According to Maryland tax lists, Small donated money to help fund the private education of Black children.

A local celebrity, he was remembered fondly in The Chronicles of Baltimore (1874): “Perhaps there was no person better known in Baltimore than Moses Small: he was universally respected and esteemed.” Small’s newspaper profession is notable, as many states had laws that prohibited teaching enslaved people to read and write. Accordingly, literacy was viewed as a tool that could undermine the slavery system and lead to both liberation and enlightenment.