O. Henry's short story “One Thousand Dollars” opens with a brief and polite conversation between a young man and a lawyer. The lawyer offers the young man one thousand dollars, his apparent inheritance from a recently deceased uncle. “Young Gillian,” the young man in question, chuckles at the peculiar and specific amount of his inheritance. He marvels that, had his uncle bestowed a much larger or a much smaller amount of money upon him, he would better understand the bequest. As it stands, however, he is puzzled and stunned by the legacy of one thousand dollars exactly.

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Mr. Tolman, the lawyer, gives young Gillian the money and further explains the conditions of his uncle’s will. The will stipulates that the young man must spend the money and bring receipts of his purchases to the lawyer’s office. In fact, he must account for the manner in which he spends every penny of the inheritance. The young man, still astonished by his uncle’s final bequest, leaves the lawyer’s office and goes to his club.

Upon entering the club, young Gillian approaches a fellow member, Old Bryson, and asks him for advice. He explains that his uncle, who was reportedly worth nearly half a million dollars, left him only a one thousand dollar inheritance. He asks Old Bryson for advice on exactly how to spend the money.

Old Bryson questions him about the remainder of his uncle’s fortune. Young Gillian explains that his uncle left a sizable portion of his fortune to science, particularly the study of bacteria. He also states that his uncle’s servants, “the butler and the housekeeper,” will each inherit $10 and a ring. His uncle’s ward, a Miss Hayden, will inherit an identical legacy. Old Bryson reminds him that his uncle always indulged him financially and that he had never before been a cautious spender. Young Gillian acknowledges the truth of the statement, referring to his uncle as “the fairy godmother” of generous allowances. Still, he is dismayed by the pittance of an inheritance that he receives from his uncle’s estate. In his dismay and disbelief, he again asks Old Bryson how he should spend the one thousand dollars.

Old Bryson sarcastically offers several possible uses for the money. For instance, he suggests that young Gillian could purchase a home and live a modest life. He could also purchase enough milk to supply one hundred hungry babies for a month. He could quickly waste it in half an hour at “one of the fortified art galleries” or by leasing Madison Square Garden for the evening. Finally, he recommends that young Gillian spend the money on the purchase of a diamond pendant for “Miss Lotta Lauriere.” Young Gillian observes that this final request is just silly enough and just expensive enough to remedy his problem. He leaves the club with the intention of purchasing the diamond pendant for the full one thousand dollars. In this manner, he reasons, he will have solved the problem quickly and finally.

Young Gillian calls for a cab and instructs the driver to take him to the Columbine Theatre, where he hopes to see Miss Lotta Lauriere. When he arrives, however, she is hurriedly preparing for her entrance onto the stage. He asks her to pause and offers to give her a pendant. She replies that Della Stacey, an associate, had recently worn a Tiffany’s necklace that cost “twenty-two hundred dollars.” Young Gillian realizes the senselessness of his offer to Miss Lotta Lauriere, and, as she is called to the stage for the opening chorus, he again enters the cab and departs he theater.

Once inside the cab, he asks the driver how he would spend one thousand dollars. The driver immediately launches into a plan (that he has apparently...