The dominant reception of Kant accords him the view that our capacity for feeling and our capacity for self-determination are essentially independent of one another: feelings, therefore, are essentially un-free. The negative aim of the dissertation is to argue against this standard interpretation; the positive aim is to offer an alternative. ,I demonstrate that the standard interpretation is not only alien to our ordinary ways of self-understanding but that it moreover threatens the internal coherence of the Kantian account itself. I develop an alternative by examining Kant’s account of how reason motivates the agent: first, in the account of the feeling of moral respect, and, second, in the account of moral character. I argue that moral respect does not name one particular feeling among many but that implicit in Kant’s account is the previously unrecognized idea that human feeling is a unique mode of self-consciousness—disclosing the subject to herself as rational and efficacious, i.e., as a moral agent. The distinctively human capacity for feeling emerges as the form of self-consciousness constitutive of practical agency, i.e., of freedom. This understanding of feeling allows us to reevaluate Kant’s account of moral character. Drawing on an Aristotelian understanding of the logical structure of capacities and activities I argue that character is the activity of maintaining one’s identity as a practical agent—an activity that consists in maintaining the agent’s structure of motivation. I then attend to the apparent tension between Kant’s rigorism—the claim that an agent is of either wholly good or wholly evil character—and his nuanced account of the grades of moral imperfection. In addition to good and bad character, I claim, we must find room for moral immaturity, or the partial acquisition of moral character. To do this we must recognize the acquisition of moral character as a form of rational accomplishment: the development and determination of our rational capacities for feeling. Thus, on this alternative interpretation of Kant’s account, feeling and character do not oppose, but are rather the constitutive conditions of freedom.