For Kant, poetry is the freest, finest art of all. Music and painting depend on sensuous charms. Poetry offers the most direct presentation of "aesthetic ideas". As Kant's critique subjects reason to reason, so too does the poet try to best language via language. However, the poet's license is not absolute. The poet must create a new sense, not nonsense, lest he slide into the intractable privacy of delirium or evil. Using Hannah Arendt's reading of the Third Critique, and excerpts from one of Kant's favorite poets, Milton, I examine the extent of the free play poetry allows.