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Partita a scacchi (1555), one of Anguissola’s most famous paintings, has often been analysed with regard to worldly power structures of gender roles and familial relations. However, no critic has noted the real artistic depth of this work which in fact should be considered the climax of Anguissola’s career due to the complex thoughts on meta-painting and metaphysics contained therein. Based on Michel Foucault’s concept of power which rests upon the controlling function of the gaze, I argue that the sequence of gazes in Anguissola’s painting plays a similar role in relation to dynamics of power. In particular, unlike existing criticism, this paper takes a closer look at previously undiscovered details on the chessboard, which will reveal an unprecedented perspective on profound conceptions of art, reality, illusion, and power — notions that anticipate key ideas of the Baroque period — and thereby demonstrate the true power of Anguissola’s art.