Pickaninny (also picaninny, piccaninny or pickinniny) is an American-slang term which refers to a depiction of dark-skinned children of African descent. It is a racist and derogatory caricature, whose meaning and usage grew to fruition in the antebellum American south, where race-based slavery was legal. It is a pidgin word form, which may be derived from the Portuguese pequenino (a diminutive version of the word pequeno, "little"). In modern sensibility, the term implies a caricature which can be used in a derogatory and racist sense. According to the scholar Robin Bernstein, who describes the meaning in the context of the United States, the pickaninny is characterized by three qualities: "the figure is always juvenile, always of color, and always resistant if not immune to pain". These three qualifiers demonstrate the dehumanizing nature of the pickaninny caricature and are reflective of the predominantly colonial society in which its use was popularised, where Portuguese values predominated.
Although the Oxford English Dictionary quotes an example from 1653 of the word "pickaninny" used to describe a child, it may also have been used in early African American vernacular to indicate anything small, not necessarily a child. In a column in The Times of 1788, allegedly reporting a legal case in Philadelphia, a slave is charged with dishonestly handling goods he knows to be stolen and which he describes as insignificant, "only a piccaninny cork-screw and piccaninny knife — one cost six-pence and tudda a shilling..." The anecdote goes on to make an anti-slavery moral however, when the black person challenges the whites for dishonestly handling stolen goods too - namely slaves - so it is perhaps more likely to be an invention than factual. The deliberate use of the word in this context however suggests it already had black vernacular associations. In 1826 an Englishman named Thomas Young was tried at the Old Bailey in London on a charge of enslaving and selling four Gabonese women known as "Nura, Piccaninni, Jumbo Jack and Prince Quarben".
In the Southern United States, pickaninny was long used to refer to the children of African slaves or (later) of dark-skinned African American citizens. While this use of the term was popularized in reference to the character of Topsy in the 1852 book Uncle Tom's Cabin, the term was used as early as 1831 in an anti-slavery tract "The History of Mary Prince, a West Indian Slave, related by herself" published in Edinburgh, Scotland. The term was still in some use in the United States as late as the 1960s.