Abstract: This essay addresses three specific moments in the history of the role played by intuition in Kant's system. Part one develops Kant's attitude toward intuition in order to understand how ‘sensible intuition’ becomes the first step in his development of transcendental idealism and how this in turn requires him to reject the possibility of an ‘intellectual intuition’ for human cognition. Part two considers the role of Jacobi when it came to interpreting both Kant's epistemic achievement and what were taken to be the outstanding problems of freedom's relation to nature; problems interpreted to be resolvable only via an appeal to ‘intellectual intuition’. Part three begins with Kant's subsequent return to the question of freedom and nature in his Critique of Judgment. With Goethe's contemporaneous Metamorphoses of Plants as a contrast case, it becomes clear that whereas Goethe can embrace the role of an intuitive understanding in his account of nature and within the logic of polarity in particular, Kant could never allow an intuition of nature that in his system would spell the very impossibility of freedom itself.