New York City in the early 1900s, the period when this story is set, was a bustling metropolitan center of 4 million people. There was a huge divide between the poor and the wealthy. While millions struggled to survive, the wealthy few lived luxuriously and at leisure. In 1908, O. Henry published a collection of short stories set against the backdrop of New York City, The Voice of the City: Further Stories of the Four Million, with the belief that all the people who resided in New York City, rich or poor, had a story to tell.

Gambling, which plays a central role in “One Thousand Dollars,” was mostly illegal in New York at that time. As Gillian’s behavior and reputations suggest, however, gambling was prevalent across the city and not only among the upper class. Poor people played card and dice games in small gambling parlors, while the rich gambled in expensive private clubs. While the existence of these clubs was well known, the owners bribed local police and judges to avoid prosecution. The city’s middle class, by contrast, generally opposed gambling and wished to see the laws enforced. In “One Thousand Dollars,” Septimus’s

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