Don Gregorio de Silva Mendoza y Sandoval was an important aristocrat in the court of Carlos II and was appointed Knight of Santiago in 1666, shortly before this portrait was painted. The scallop shell hanging on his chest and the cross that adorns his clothing are indications of that honor.

This image reflects all the rhetoric which portraiture had attained in Spain by the second half of the seventeenth century. The cape draped over his arm, the crop and sword as symbolic elements and, most of all, the two servants that accompany him, are elements alluding to his high status.

The work reveals the evolution of Spanish portraiture, which is evident in the choice of Flemish models combined with Velasquez's technique, but free of the rigidity of traditional court portraiture.

The painting was acquired from the Osuna family in 1896. They were heirs to the House of Pastrana, and the painting had almost certainly been in their hands since it was first painted.