In this essay, I am concerned with fleshing out the complex mesh of politico-cultural significations that inscribe Banksy’s installation of an inflatable doll dressed as a Guantánamo Bay detainee in Disneyland. In particular, I want to bring into focus the systems of relation that hold between subjects and sites that might otherwise appear to stand in absolutely incommensurable positions: Guantánamo Bay detainees and inflatable dolls, Guantánamo Bay military prison, Cuba and Disneyland, California. Driving this analysis of seemingly untenable systems of relations between graphically dichotomous subjects (real prisoners and inflatable dolls, an entertainment theme park and a military prison) is a desire to address what I think is magnetised and brought to the surface through Bansky’s provocative guerrilla gesture of installing the simulacrum of a Guantánamo detainee within a site that is charged with an iconic cultural status. In the course of my analysis, I proceed to read Banksy’s tactical intervention in terms of the rhetorical figure of the apostrophe. As an apostrophic gesture, Banksy’s Guantánamo detainee in Disneyland disrupts the narrative fabric of the site in order to broach a number of critical questions. In the latter part of this essay, I proceed to examine these questions by focusing on the ongoing incarceration of a juvenile, Omar Khadr, in Guantánamo. Khadr, I argue, at once embodies the violent effects of Banksy’s apostrophic intervention, precisely as he dramatises the unsettling figure of the Muslim prisoner as contemporary Muselmann.