William Sydney Porter, better known as O. Henry, published “One Thousand Dollars” in his 1908 collection of short stories The Voice of the City: Further Stories of the Four Million. The stories explore New York City at the turn of the 20th century. Believing every person had a story to tell, O. Henry wrote about the poor and the rich and the shared experience of being human. This study guide references the 1908 edition of “One Thousand Dollars,” published in The Voice of the City by Doubleday, Page, and Company.

The story begins with two men meeting in an attorney’s office. The younger, Young Gillian, is the nephew of the late Septimus Gillian, while the older man, Lawyer Tolman, serves as the executor of Septimus’s estate. Upon his uncle’s death, Gillian was left $1,000. Gillian, surprised by the specificity of the amount, notes the oddity of the sum. If the gift had been $10,000, he would celebrate but, he says, even “$50 would have been less trouble” (75). Gillian is then reminded by Tolman that, upon spending the $1,000, he must give a true account and report his expenditures per the stipulations of Septimus’s will.

Upon receiving the money, Gillian goes to his social club where he sees Old Bryson, an older and solitary club member, reading in the corner. When Bryson sees Gillian he sighs and places his book in his lap, annoyed by Gillian’s presence. Upon hearing Gillian has another story to share with him, Bryson bids him go and tell it to someone in the billiard room. Gillian ignores Bryson and shares the story of his inheritance. Bryson, surprised by the amount, notes that he thought Septimus was worth at least half a million. Gillian explains that most of his uncle's money was left for scientific research and building a hospital, but that his butler and his ward, Miss Hayden, both received $10 and a seal ring.

Gillian asks Bryson what he can do with $1,000, and Bryson sarcastically suggests several ways to use it, noting that it could save a life, buy a home, or feed hungry babies. It could educate a child, buy a genuine Corot painting, or as he suggests in the end, he could buy his girlfriend, actress Lotta Lauriere, a diamond necklace and then fund the purchase of a ranch in Idaho.

Gillian leaves and takes a cab to the Columbine Theatre, where he finds Lauriere backstage. He asks if she would like a necklace that costs $1,000. She tells him of one she likes that costs $2,200, and then she goes on stage for her performance. Gillian leaves the theater and asks a cab driver what he would do with $1,000. The driver tells him he would open a saloon. When he gets out of the cab, Gilliam asks a blind man selling pencils what he would do with $1,000, but after looking at his ledger book learns he already has that amount.

He asks the driver to take him back to Tolman’s office, where he inquires whether Miss Hayden was left anything more than the seal ring and $10. Tolman tells him she received nothing more. Gillian takes the cab to his late uncle’s house, where he finds Miss Hayden in mourning. He tells her the lawyers found that his uncle left her an additional $1,000. After doing so, he tells her he loves her. However, Miss Hayden does not share his affection.

Gillian writes a note of account for the $1,000, places it in an envelope, and returns to Tolman’s office to tell him he has distributed his inheritance. Before he can give him the envelope, however, Tolman shares an additional stipulation in the will. If Gillian uses the money unselfishly, he will inherit an additional $50,000, but if he wastes it, as would fit his past behavior, the money will go to Miss Hayden. Hearing this, Gillian tears up the envelope, says that he lost the money gambling, and quickly exits, whistling as he makes his way down the hallway.