In their collection Milton in Popular Culture (2006), Laura Lungers Knoppers and Gregory M. Colón Semenza have established the importance of Miltonic intertextuality in popular culture, while recognizing the importance of William Blake to the field. Blake’s definition of Milton as “a true Poet and of the Devils party without knowing it” in The Marriage of Heaven and Hell (1793) lies at the centre of a main concern of Milton criticism since the poem’s original publication. The debate between Satanists and anti-Satanists goes back even further than Blake and the Romantics, and this central ambivalence is representative of the “discontinuities” and “irresolvable complexities” which Peter C. Herman and Elizabeth Sauer (2012) argue are the focus of interest of the New Milton Criticism. Following this strand of critical thought, this article proposes to show how the introduction of Miltonic intertext into Neil Gaiman’s The Sandman, in issues 21–28, serves to structure the series’ theme of change and death — which involve questions of freedom and teleology, free will and damnation — through a critical dialogue with, and creative rewriting of Miltonic theodicy in the epic poem. Gaiman draws upon the ambivalent theological dimensions of Paradise Lost not to present his own concept of good and evil but rather to discuss the freedom to change and the damnation inherent in the inability to change as part of the human condition.