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El Greco most likely painted this in the spring of 1600, when the cardinal came to Toledo with the court of the young King Philip III. The sitter was Fernando Nino de Guevara, and just the year before he had been made inquisitor general of Spain, the head of the Inquisition. El Greco dresses him in a blaze of red silk and seats him with apparent ease, yet nothing here is quite at rest. The left hand grips the chair arm, the drapery breaks into sharp angles, and behind the round spectacles the eyes flick to one side rather than meeting ours. It is a portrait of power that seems to be listening for something. The painting stayed with the cardinal's family in Spain for roughly three centuries before an American collector finally pried it loose and carried it to New York.