This is a difficult question. In the two stories being analyzed, the Umbrella Man is more successful, but he is taking many risks. He does not seem to have a long career ahead of him. First of all, men will begin complaining to the pub owners about losing their valuable umbrellas. Employees will be warned to keep an eye on the umbrella rack, and they will begin to suspect a certain elderly gentleman from walking off with other people's umbrellas. They might set a trap for him. Furthermore, exchanging stolen umbrellas for triple whiskies seems more like a hobby than a viable career. How many such straight shots can an old man hold. Isn't he ruining his health by drinking all that Scotch and running around in the rain? He is essentially just a thief and not a trickster. He is selling stolen umbrellas. What he does with the money is inconsequential. He could use it to buy anything. He is not really tricking the woman who buys the umbrella, since she is getting a silk umbrella worth twenty pounds for one pound.

"It's a lovely umbrella," the little man said.

"So I've noticed," my mother said.

"It's silk."

"I can see that."

"Then why don't you take it, madam," he said. "It cost me over twenty pounds, I promise you. But that's of no importance so long as I can get home and rest these old legs of mine."

The trickster poses as a wealthy gentleman, but why doesn't he have money for a cab. He has to use that age-old excuse:

"My wallet," he said. "I must have left it in my other pocket."

The trickster in Saki's "Dusk," on the other hand, only succeeds in getting a pound from Norman Gortsby by the purest luck. Gortsby finds a cake of soap by the park-bench and naturally assumes it belongs to the man who has just been telling him a hard-luck story about losing his hotel and having left all his money in his room. The trickster is described as being young. He is a sort of apprentice at the game. He has perfected his story but overlooked one important detail.

"Of course," said Gortsby slowly, "the weak point of your story is that you can't produce the soap."

The young man sat foward hurriedly, felt rapidly in the pockets of his overcoat, and then jumped to his feet.

"I must have lost it," he muttered angrily.

"To lose an hotel and a cake of soap on one afternoon suggests willful carelessness," said Gortsby.

But obviously this is only a temporary embarrassment, an emotion which con men must learn to expect. The incident will be a learning experience for both these young men. The apprentice trickster will not only be prepared for his next victim by carrying a cake of soap, but he won't even have to buy it, since Gortsby has already provided it along with his sovereign. The trickster will go on to greater heights in what Edgar Allan Poe calls "diddling" in an amusinig essay with that title in which he writes:

Diddling, rightly considered, is a compound, of which the ingredients are minuteness, interest, perseverance, ingenuity, audacity, nonchalance, originality, impertinence, and grin.

So the young trickster in "Dusk" is more successful than the old Umbrella Man because he will perfect his craft and live comfortably without working, whereas the elderly gentleman will either drink himself to death or die of pneumonia. The insurance company actuaries would not give him a life expectancy of more than a few years at best--and he is only accelerating his demise by drinking large quantities of straight whiskey and running around in the pouring rain.