1. Inheritance of $1,000.00
The greatest complication of O. Henry's story "One Thousand Dollars" is indicated in the title. A young man named Bobby Gillian inherits $1,000.00 from his wealthy uncle, who has always indulged him; although the uncle was a millionaire, he has allocated this specific amount to Gillian with the stipulation that he must spend the money and bring the receipts of the purchases to the lawyer's office.
2. Gillian cannot decide how to spend the $1,000.00
In his dilemma of how to spend the money, Gillian then seeks the advice of a wry friend at his club, whom he calls Old Bryson. Although reluctant to advise Gillian, Bryson finally makes the sarcastic suggestion on how to spend the money:
"Why, Bobby Gillian, there's only one logical thing you could do. You can go buy Miss Lotta Lauriere a diamond pendant with the money, and then take yourself off to Idaho and inflict your presence upon a ranch. I advise a sheep ranch, as I have a particular dislike for sheep."
So, Gillian decides to buy Miss Lauriere a necklace, but when he speaks with her, she exhibits no feeling for him and only greed for such a possession. After she has a curtain call, he departs and takes a cab. Still undecided, Gillian asks the cab driver and a blind man on the street what they would do with a thousand dollars. Something in what they say causes Gillian to return to the cab and be driven to his uncle's house.There, he tells Miss Hayden that a codicil to his uncle's will has left her $1,000.00; furthermore, he declares his love for her, but she merely says, "I am sorry" and picks up the money.
After writing a "memorandum" on the expenditure of the money, Gilliam returns to the law office and tells the lawyer that he has spent the money.
3. Gillian is told that he is to inherit $50,000.00 if he has been unselfish in his expenditure, but if he has not, Miss Hayden is to receive the fifty thousand dollars.
Because he truly loves Miss Hayden, Gillian then tears up his memorandum, telling the lawyer that he "lost it on the races," and departs, "whistling gayly."