Frederick Douglass, the abolitionist, the civil rights advocate and the great rhetorician, has been the focus of much academic research. Only more recently is Douglass work on aesthetics beginning to receive its due, and even then its philosophical scope is rarely appreciated. Douglass’ aesthetic interest was notably not so much in art itself, but in understanding aesthetic presentation as an epistemological and psychological aspect of the human condition and thereby as a social and political tool. He was fascinated by the (...) power of images, and took particular interest in the emerging technologies of photography. He often returned to the themes of art, pictures and aesthetic perception in his speeches. He saw himself, also after the end of slavery, as first and foremost a human rights advocate, and he suggests that his work and thoughts as a public intellectual always in some way related to this end. In this regard, his interest in the power of photographic images to impact the human soul was a lifelong concern. His reflections accordingly center on the psychological and political potentials of images and the relationship between art, culture, and human dignity. In this chapter we discuss Douglass views and practical use of photography and other forms of imagery, and tease out his view about their transformational potential particularly in respect to combating racist attitudes. We propose that his views and actions suggest that he intuitively if not explicitly anticipated many later philosophical, pragmatist and ecological insights regarding the generative habits of mind and affordance perception : I.e. that we perceive the world through our values and habitual ways of engaging with it and thus that our perception is active and creative, not passive and objective. Our understanding of the world is simultaneously shaped by and shaping our perceptions. Douglass saw that in a racist and bigoted society this means that change through facts and rational arguments will be hard. A distorted lens distorts - and accordingly re-produces and perceives its own distortion. His interest in aesthetics is intimately connected to this conundrum of knowledge and change, perception and action. To some extent precisely due to his understanding of how stereotypical categories and dominant relations work on our minds, he sees a radical transformational potential in certain art and imagery. We see in his work a profound understanding of the value-laden and action-oriented nature of perception and what we today call the perception of affordances (that is, what our environment permits/invites us to do). Douglass is particularly interested in the social environment and the social affordances of how we perceive other humans, and he thinks that photographs can impact on the human intellect in a transformative manner. In terms of the very process of aesthetic perception his views interestingly cohere and supplement a recent theory about the conditions and consequences of being an aesthetic beholder. The main idea being that artworks typically invite an asymmetric engagement where one can behold them without being the object of reciprocal attention. This might allow for a kind of vulnerability and openness that holds transformational potentials not typically available in more strategic and goal-directed modes of perception. As mentioned, Douglass main interest is in social change and specifically in combating racist social structures and negative stereotypes of black people. He is fascinated by the potential of photography in particular as a means of correcting fallacious stereotypes, as it allows a more direct and less distorted image of the individuality and multidimensionality of black people. We end with a discussion of how, given this interpretation of aesthetic perception, we can understand the specific imagery used by Douglass himself. How he tried to use aesthetic modes to subvert and change the racist habitus in the individual and collective mind of his society. We suggest that Frederick Douglass, the human rights activist, had a sophisticated philosophy of aesthetics, mind, epistemology and particularly of the transformative and political power of images. His works in many ways anticipate and sometimes go beyond later scholars in these and other fields such as psychology & critical theory. Overall, we propose that our world could benefit from revisiting Douglass’ art and thought. (shrink)