It is interesting to compare the three characters in Saki's "Dusk" with the three characters in Dahl's "The Umbrella Man." In "Dusk" all three characters-- Gortsby, the young con man, and the elderly gentleman--are males. In plotting "The Umbrella Man," Dahl, for his own reasons, decided to make two of the characters females, one of them the young girl who is narrating the story, and the other her mother. We might wonder why the Umbrella Man tries to sell his stolen umbrella to a woman. Dahl probably decided to use females for the sake of contrast. It is easy to visualize the three characters in Dahl's story because they are all so different. Two are female, but one is only a girl. The con man in "Dusk" is a young man about the same age as the viewpoint character Norman Gortsby. It is not easy for the reader to visualize them as different persons. But Dahl has to get the reader to accept the premise that a con man would go up to a strange woman on the street in England, a country where people are known for their diffidence and standoffishness, and try to sell her a hot umbrella. Dahl must have decided to make his swindler an old man in order to avoid any suspicion on the mother's part that he is a masher who is trying to pick her up. Dahl also must have decided to have the mother accompanied by a girl who is also the narrator. So in avoiding having a story in which a young grifter approaches a strange woman standing on the sidewalk by herself, Dahl ends up with a story in which an elderly grifter approaches two women with his offer. This old grifter is obviously not interested in flirting with women; he is interested in getting a triple shot of good Scotch whisky. But is it reasonable for a man selling hot umbrellas to try to peddle them to women? If so, why? One wonders whether this old man, who obviously makes a habit of stealing umbrellas, also makes a habit of trying to sell them to women. There must be plenty of men who are caught in the rain without their umbrellas. In fact, there must be many more times as many men on the streets as women in that time and place. Does the Umbrella Man think it would be easier to sell an umbrella to a woman? The only reason I can see for having the Umbrella Man approach a woman is that it provides for an "orchestration" of characters. He has three very distinct and different figures: an elderly, well-dressed gentleman, a suburban housewife approaching middle age, and a twelve-year-old girl who exists as a character in the story mainly to provide protective companionship for her mother as well as to give her someone to exchange thoughts and observations with and thereby enable Roald Dahl to create dramatic dialogue and avoid tedious description and exposition. Looking at Saki's "Dusk," we can see that it would have been impossible for a young con man to approach a woman who was sitting all alone on a park bench in the growing darkness.
The trickster in "Dusk" is a young man who seems to be something of an amateur who is trying to become a professional con artist. He has invented or appropriated a complicated story about losing his hotel after going out to buy a cake of soap. His intended victim, Norman Gortsby, listens to his hard-luck story skeptically, and then:
"Of course," said Gortsby slowly, "the weak point of your story is that you can't produce the soap."
This incident will be a learning experience for both Gortsby and the trickster. Gortsby has learned that you can't trust anybody and that you should look out for yourself in this cold, cruel world. The trickster has learned that he can make his story more effective by the simple ploy of carrying a wrapped cake of soap in his overcoat pocket.
The trickster in "The Umbrella Man" is an elderly man who isn't trying to make a living out of his scam but only to get a few drinks on a rainy day. He is offering something for the money he takes from his victims, unlike the young con man in "Dusk." The real victim is not the woman who buys the umbrella for one pound but the man in the pub who owned the umbrella.
"Dusk" was intended to be a serious story with a moral. "The Umbrella Man" was intended to be purely humorous. The opening paragraph of "The Umbrella Man" sets the tone.
I'm going to tell you about a funny thing that happened to my mother and me yesterday evening. I am twelve years old and I'm a girl.
She prepares the reader for an amusing tale by calling the incident "a funny thing." Unlike her mother, she seems to feel sympathy for the old man who satisfies his craving for Scotch whiskey by stealing umbrellas. The reader does not feel as much disapproval for this old man as for the young con man in "Dusk" who seems to be starting off on a life of crime which could lead to far more serious offenses and land him in prison.
There is another character in Saki's "Dusk" who might also be a con artist.
On the bench by his side sat an elderly gentleman with a drooping air of defiance that was probably the remaining vestige of self-respect in an individual who had ceased to defy successfully anybody or anything.
After Gortsby finds the cake of soap and chases the young man to give him a sovereign and the soap, he finds out that the soap really belonged to the elderly gentleman who had been sharing the bench with him before. Could both the young man and the old man have been working the same scam? How could the old man be so sure he lost the soap by the bench if he hadn't left it there purposely, intending to go away and then come back and use the soap as a pretext for starting a conversation with Gortsby? But Gortsby had found his soap and had run off with it. If the elderly gentleman was also a con artist, then he was a more experienced one than the young amateur.
The trickster in "The Umbrella Man" is just an amusing "character." The girl-narrator of the story thinks he is funny, and the reader thinks her story is funny. The young trickster in "Dusk" is a cold-blooded crook who wants to prey on generous, gullible people in order to avoid having to go to work. If the elderly gentleman who owned the cake of soap is also a con artist who happens to be using the same hard-luck story of a lost hotel, then he only serves to emphasize Saki's serious moral with political overtones: that you shouldn't feel sorry for people, that you shouldn't trust strangers, and that the world is full of parasitical types.