I was thinking yesterday about writing that would build off of Lewis's essay, "Screwtape Proposes a Toast." I might, but since I was just kind of throwing around the idea in my head, I thought about names and the immediate thing that jumped into mind (though not particularly creative) was, "Wormwood Proposes a Toast." The thought being that time has passed and Wormwood has now taken his uncle's place in the Lowerarchy, while Screwtape has no doubt gone on to bigger and better things like maybe being dean of the Tempter's College.
Of course, there's a bit of a problem with the name because we don't know what happened to Wormwood after, "The Screwtape Letters." On the one hand, in Letter 22, Screwtape kindly sends Wormwood graphic pictures of the House of Correction for Incompetent Tempters, suggesting that Wormwood might end up there. That seems pretty gruesome, but I guess better than complete negation. On the other hand, Screwtape himself says in his toast, that, "Hell expects and demands that [your career] should be — as mine was — one of unbroken success," suggesting there is no second chance.
So, this then begs the question: Is there Repentance in Hell? Is repentance a mode only of good, or can one repent to evil? Or is there a mode of repentance that would not be acceptable by Heaven, but would perfectly fit Hell?
I think the answer to the latter question is, yes. In Hell repentance can be achieved via a desire for revenge.