This essay reads Antonio’s mysterious sadness psychoanalytically but bypasses overfamiliar, and potentially reductive, translations of early modern melancholy into Freudian melancholia. Instead, Antonio’s sacrificial longing to enter into the contract with Shylock and surrender the pound of flesh on behalf of Bassanio is read as a form of masochistic fantasy (via Deleuze, Silverman, Krafft-Ebbing, and Torok). The structure of subjection and desire at work within Antonio’s melancholy and his masochism bears a wider family resemblance to the buried contradictions that drive the turning worlds of Venice and Belmont. The extraction of the pound of flesh is not Antonio’s masochistic fantasy alone, but the political and ethical fantasy of subjection at the heart of the playtext that surrounds him. Articulating fault lines between Christian and Jew, master and bondsman, Venice and Belmont, letter and spirit, Antonio’s simultaneously melancholic and masochistic cry—"Let me have judgment, and the Jew his will"—breaks open the economic and political conflicts at the core of The Merchant of Venice.