Velázquez's evocative Portrait of the Jester Calabazas, earlier known as Le Fou, shows the possible influence of Caravaggio and became one of many portraits that inspired the later work of Francisco de Goya.

Archival evidence suggests that the father of the artist descended from conversos, Jews who converted to Christianity in order to survive the persecution and eventual expulsion of the Jews from Spain. The outward conversion of Jews living under the political dominion of Christian and Islamic regimes did not always indicate an inner spiritual acceptance of the doctrine of the dominant faith. On the contrary, in the 12th century, before the expulsion of the Jews from Spain, a Spanish Jew who left Spain for Egypt and became one of the greatest medieval philosophers, Rabbi Moshe ben Maimon (רבי משה בן מימון), defended the choice of Jews living under Islam to convert, rather than become martyrs, arguing that such people were still Jews and deserved equal respect within the community. With such a background, Velazquez and his family occupied a liminal space, living in the former Jewish quarter of Seville, and this liminality of his identity gave him a heightened consciousness of others who lived on the margins, as he depicted in his portraits.

In those days of feudal Spain, few people understood the difference between physical and psychological disabilities, and people with disabilities had very few rights aside from the advocacy of family and, in the case of the portrait's subject, nobility. The Americans with Disabilities Act, which afford federal protections for disabled people in the United States, has made an impact which we cannot overstate: it has altered the protection of the rights, dignity, and autonomy of disabled people around the world. A significant portion of the literature on the Portrait of the Jester Calabazas, also named Calabacillas, is speculation regarding the medical nature of the condition of Don Juan de Calabazas. Psychologist Jerónimo de Moragas argues that Calabazas did not have an intellectual condition but cerebral palsy, which affects the coordination of the brain and the body, and perhaps a condition of the facial features. Calabazas was "not stupid," Moragas adds. The fact that a journal of medicine would print such words three centuries after the portrait was made is evidence of the ignorance of the society itself.

The realism and starkness of the portrait, the matter-of-factness and the artist's lack of commentary on the subject, suggests that Velázquez recognized that the feudal system would not survive much longer, that its decadence would catch up with it. The fact that Michel Foucault and many other 20th century writers would dedicate their energy to analyzing the work of Velázquez indicates that although the artist was forced to practice with only two possible patrons, the Catholic church and the Crown, he was able to express a great brilliance within his restricted environment.