Despair calls her brother Dream into a contest, initially he refuses but she provokes him, the contest is to see if he can pull "Joshua Abraham Norton" from her realm before their elder sister comes for him. Reluctantly he does accept the challenge, and to do so he gives Joshua a dream, and Joshua proclaims himself Emperor of these United States. When Death comes to inquire of her brother what he is doing, he tells her he has given Joshua the one thing most men strive for but never achieve, he has made him a King.
Next we see Joshua dressed an Emperor and eating with Samuel Clemens (better known as Mark Twain), who implicitly accepts Joshua's Imperial status. While the two men are dining together, Delirium comes to Dream about a challenge she seems to remember. She tells her brother that she is pleased to see him and he tells her that perhaps he is pleased to see her too. They talk about how Joshua should be in her realm, but eventually she comes to the conclusion that his madness is what keeps him sane and she too departs as her sister Despair had done before.
As expected, another year passes and once again Norton is tested, this time when he goes to a bar (the Cobweb Palace) and a dead man, the King of Pain, comes to him and offers him to be a real Emperor, to have anything and everything he ever wanted, including women, all the women he could ever want. Yet Joshua retains his dignity and refuses the offers, saying he is content ruling his city of St. Francis, that he has all he needs. Back at the carriage outside, Pain tells Desire of his failure and she asks Dream how he did it, how he resisted her, and he tells her that Joshua has his dignity, after all, he is an Emperor. Finally he leaves, telling her of how her lack of subtlety disappointed him, and than the two part ways.
Finally the story ends, with the death of Joshua Abraham Norton, Despair comes to see his corpse lying in the gutter, regretting that he did not return to her, that although he was one of the most pitiful of men and he died in a gutter, that he never despaired. Dream comes to the man as well, giving Despair a statuette of the man as a gift, to remind her of the lesson she learned from all this. Finally, Death comes and she and Joshua walk off into the night, with her telling him that of all the Kings, and Emperors, and Heads of State she has met in her time, he is probably her favorite.