After an opening editorial about President Theodore Roosevelt, Thanksgiving proclamations, and the state of “tradition” in America, the story proper begins with Stuffy Pete, a homeless man who occupies a bench in New York’s Union Square. There, as has happened annually for nine years on Thanksgiving Day, he is met by an elderly gentleman, who escorts him to a restaurant and treats him to a lavish dinner, which the old gentleman watches him eat. But this year, while Stuffy is en route to his park bench, he passes the mansion of two old ladies of ancient family, who have their own tradition of feasting the first hungry wayfarer that comes along after the clock strikes noon. The servants of the elderly sisters take Stuffy Pete in, and banquet him to a finish. So he is well stuffed by the time he reaches his bench. When the old gentleman appears as usual, Stuffy Pete doesn’t have the heart to disappoint the kindly old man, whose “eyes were bright with the giving pleasure.” He goes with him to the traditional table at the traditional restaurant, and like a valiant knight consumes a second huge Thanksgiving Day meal. As soon as the men go their separate ways, Stuffy Pete, now dangerously overstuffed, collapses and is taken by ambulance to the hospital. An hour later, the old gentleman is brought in, and, as the story’s surprise final sentence tells us, he is discovered to be near starvation, not having had anything to eat for three days past.

Two Thanksgiving Day Gentlemen is a story that links the spirit of giving and the impulse to charity with the development of tradition and the holiday of Thanksgiving. But the “twisty” ending shows us that good intentions may have bad consequences, and, more specifically, that generous impulses toward our less fortunate fellow-citizens do not always yield genuine benefaction. Indeed, the ending seems to support the view— encouraged by the narrator’s ironic and mocking tone throughout—that the entire story is intended to expose the hollowness or foolishness of gentlemanly generosity, American traditions, and the holiday of Thanksgiving in particular.

William Sydney Porter (September 11, 1862—June 5, 1910), known by his pen name O. Henry, was an American writer. O. Henry's short stories are known for their wit, wordplay, warm characterization and clever twist endings. The best known ones are A Service of Love, The Cop and the Anthem, The Furnished Room, The Gift of the Magi and The Last Leaf, which help him win fame abroad.

O. Henry's stories are gems of their kind; mellow, humorous, ironic, ingenious and shot through with that eminently salable quality known as 'human interest.'" —Bennet Cerf and Van Cartmell