When Larry defends his friends, Hickey declares that Larry's form of pity leaves a man worse off by sustaining dreams that can only consume him with guilt. Larry himself must recognize his pose as the "grandstand foolosopher" as his own pipe dream. Larry is an old man who fears life and fears death even more. Moreover, he is certain that Larry is the only one who can help Parritt. Parritt needs punishment so he can forgive himself. Hickey is certain a woman is involved somehow.


As midnight approaches, it becomes clear that Hickey's work has unraveled the group's relations of sociability and fragile web of pipe dreams. Irritably they lash out at each other, the former co-conspirator in the pipe dream becoming a witness who laughs behind their back, a judge who can call them out on their illusions. The anxiety Hickey inspires lies precisely in his messianic call to judgment.

Hickey does not so much speak of judgment here as pity. He distinguishes between a pity that colludes with the pipe dreamer and condemns him to guilt when he fails to realize it and the other, his own, that would force the dreamer to confront himself apart from his fantasy of tomorrow. As he implies with regard to Parritt, this pity might require the dreamer's punishment. In some sense, Hickey's pity includes the notion of judgment as well.

The proximity of pity and punishment suggest how, in this play, pity is closely tied to aggressive intentions. The subtle patterns in the play's fabric make this dialectic, that of a fundamentally ambivalent, love/hate relationship with the other, abundantly clear. There is something nasty in the way the residents of Harry Hope's warmly collude with each other's pipe dreams, as if bent if keeping their closest friends at rock bottom with them. Similarly, as Larry continually point out, Hickey's pity for the dreamer—a pity which, again, explicitly includes that dreamer's punishment—is often quite cruel. The reversible relation between pity/aggression and love/hate will find lethal articulation in Hickey's murder of his wife. Hickey will justify this murder to himself as his wife's salvation. Only the final scene will reveal it as an act of revenge as well.

We will return later to the dreamer's ambivalence toward the beloved, and more specifically, the beloved woman. Note here how Hickey's fantasy of his wife's salvation is a crucial element of his own pipe dream. This inability to admit his ambivalence toward his wife, the mixture of love and hate impulses, recalls Hope's own relation to his sentimentally enshrined Bess. Arguably, one of the defining features of the pipe dream is an inability to tolerate one's ambivalence toward the beloved.

At the same time, along with this aggressiveness, there is something inexorably masochistic about Hickey's sales pitch. This masochism partially explains the messiah-like fascination he exerts over Larry and the other residents. Hickey has destroyed his dreams and, through his self-torments, is reborn. As Rocky observes, it is as if tonight is his birthday. More precisely, we sense, particularly in his identification with Parritt, that Hickey's demystification of his fantasies function as a sort of punishment or atonement, a delivering of himself up to judgment. As Larry notes, however, Hickey has yet to make the "great revelation" to both his friends and himself. Only in the final scene will we learn how Hickey's scripture of judgment, punishment, and salvation colludes in the denial of his own sense of guilt.