After his uncle dies, lawyer Tolman informs Bobby Gillian that...
O. Henry's stories often express the romantic wish that people, who possess an inherent dignity, are essentially good and generous. "One Thousand Dollars" expresses this wish.
Here is the structure of the plot of this story:
After his uncle dies, lawyer Tolman informs Bobby Gillian that he has been bequeathed $1000.00. Tolman tells Gillian that he must render an account of how he has spent this money as soon as he has disposed of it. Without any idea of how to spend this sum, "a confoundedly awkward amount," as he calls it, Gillian decides to ask for advice.
Gillian goes to his men's club and talks to a sarcastic older man who "sequesters" himself in a winged chair. After explaining his inheritance, he asks Old Bryson what he should do with the money. Bryson sardonically offers several ideas, one of which is to purchase a diamond necklace for the chorus girl that Gillian has been seeing. He then suggests that Gillian move to Idaho. "I advise a sheep ranch, as I have a particular dislike for sheep."
Gillian departs and takes a cab. While riding, he asks the cab driver what he would do with $1000.00, and the cab driver says he would open a saloon. When he gets out of the cab, Gillian talks to a blind man selling pencils. Suddenly, Gillian decides to return to the cab and has the driver take him to the law offices of Tolman & Sharp where he asks about Miss Hayden, a ward of his late uncle, and her inheritance. The lawyers tell him that she has only received ten dollars and a ring.
Gillian returns to the cab and directs the driver to the home of his uncle. There he finds Miss Hayden, who is dressed in black, in the library, writing letters. Gillian tells her that his uncle had a codicil which left her $1000.00. Appearing faint when she receives this sum, Miss Hayden exclaims, "Oh! Oh!" Then, Gillian tells her that he loves her, but she only replies, "I am sorry." Disappointed, Gillian asks if he may write a note. On the paper he writes his account of the money he has received,
Paid by the black sheep, Robert Gillian, $1000 in account of the eternal happiness, owed by Heaven to the best and dearest woman on earth.
Then, Gillian returns to the law offices.
Gillian informs the lawyers that he has spent the one thousand and hands them the envelope; so, they bend down and pull from a safe a codicil to his uncle's will which bequeaths to Gillian $50,000.00 if he has spent the first sum unselfishly. Otherwise, the sum is to go to Miss Hayden.
As lawyer Tolman starts to open Gillian's account of how he has spent the $1000.00, the young man snatches the envelope and tears it into pieces. "I lost the thousand dollars on the races. Good-day to you, gentlemen."
Tolman and Sharp shake their heads mournfully, convinced that Gillian has continued what his uncle termed "reprehensible dissipation."
Gillian departs, whistling. He is happy in his act of love for Miss Hayden.