What are the character sketches of Norman Gortsby in "Dusk" and the mother in "The Umbrella Man"? What makes them similar?

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In several ways, Norman Grotsby of "Dusk," and the mother in"The Umbrella Man" are similar, yet there are some differences.

Norman Grotsby 

While Norman Grotsby considers himself among the "defeated" who gather at twilight to walk in the shadows and sit on the benches of the park, on the other hand, he takes "a certain cynical pleasure" in judging others who come near him. When a young man sits down after an old gentleman leaves, complaining of the quandary that he is in, Grotsby is skeptical of his truly needing money as he points out the flaws to the young man's story. Angered, the youth leaves, but Grotsby mistakenly thinks he finds evidence to support the youth's story. So, he runs after the young man and loans him money after all. However, upon his return to his bench, Grotsby sees the old gentleman looking for something; it is the supposed evidence for the youth. Grotsby has been the victim of a canard.

The mother

After she and her daughter leave the dentist and are caught in the rain, the mother, who prides herself upon being a good judge of character, is very skeptical of the older gentleman who approaches her in the rain holding a silk umbrella.  Like the youth of "Dusk," he requests a favor.  But, the mother is suspicious, and she is disinclined to grant the older man any favors.  However, he offers her his umbrella if she will give me a pound so that he can hire a taxi to take him home because he has already walked too far. The mother refuses the trade since her daughter watches her; however, when the man will not take any money unless she accept the umbrella, the mother feels justified and hands the man a one-pound note, thinking she has the better part of the deal, as he is no "trickster" and she possesses a silk umbrella.  But, she, too, is the victim of a canard:  the old man scurries to a pub and drinks a large stein of whiskey. After happily downing the drink, he grabs an umbrella and departs from the tavern rushing to another person with another umbrella.

Although she and Gortsby are both fooled, the mother herself is somewhat of a trickster herself as she considers taking the umbrella in trade for only a 1 pound note. So, her being duped is somewhat deserved.

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