Rousseau’s political thought is commonly understood as his prescriptive attempt to restore, recreate, or replicate the natural goodness of man in society. In contrast to this prevailing view, I argue for a reorientation that sees Rousseau’s political thought as a diagnostic project, primarily concerned with discovering what Man is and to what extent this image of Man is still present in men. The political problem facing Rousseau and us, his readers, is the gap between the naturally good Image, Man, and His corrupted image-bearers, men. To investigate this problem, Rousseau utilizes portraiture. Portraiture is Rousseau’s explicit and intentional methodology that approaches the problem of Man and men through figures—of natural man, Emile, Sophie, Julie, and Jean Jacques—from the relational perspective that arises between the interplay of the author of the portrait, the nature of the subject, and the impact on the audience of both the author and his work of art. On my reading, the framework of portraiture allows us to approach the metaphysical and moral concept, Man, apart from his phenomenal likenesses and historical development in men through the imaginative portraits of Rousseau. Rousseau thus can be seen as providing a much richer philosophical groundwork for his moral and political system than has previously been appreciated. The dissertation explains Rousseau’s diagnostic attempt to see Man as he truly is and save men as they are through his portraits and by way of portraiture.