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November 27, 2025

The Awkward Thanksgiving of O. Henry’s ‘Two Gentlemen’

Each Thanksgiving, a lonely New Yorker escorts a homeless man to a restaurant and watches with pleasure as he eats a grand feast.

Of all the Thanksgiving stories in American literature, O. Henry’s “Two Thanksgiving Day Gentlemen,” first published in 1907, may be the most subversive. It begins as an anecdote about the warm tradition of holiday charity. It ends in the hospital.

The plot is easily summarized: Each Thanksgiving, a lonely New Yorker, identified only as the Old Gentleman, approaches Stuffy Pete, a homeless man in Union Square. He delivers a little speech, almost liturgical in its formality: “I am glad to perceive that the vicissitudes of another year have spared you to move in health about the beautiful world,” the Old Gentleman begins. To celebrate that blessing on “this day of thanksgiving,” he offers to treat Stuffy Pete to a holiday meal. “If you will come with me, my man,” he says, “I will provide you with a dinner that should make your physical being accord with the mental.” He then escorts the vagrant to a restaurant and looks on with pleasure as his guest consumes a sumptuous feast.

For nine years, the Old Gentleman’s words of invitation had “always … been music in Stuffy’s ears.” But this year, Stuffy isn’t hungry. He has already been fed to bursting by two elderly Fifth Avenue ladies who have their own tradition of selecting a hungry passerby and giving him a feast. By the time Stuffy reaches his customary park bench, he is not merely full but on the verge of rupture.

Then the Old Gentleman appears and makes his familiar speech, his eyes so “bright with the giving-pleasure” that Stuffy Pete can’t bear the thought of disappointing him. So he accepts the invitation and forces himself to choke down a second gargantuan dinner.

Afterward, Stuffy collapses on the sidewalk and is hauled to the hospital. An hour later, another ambulance arrives with the Old Gentleman — who, it turns out, is suffering from “almost starvation,” not having eaten for the last three days.

Thus one man goes without food so he can afford to keep his Thanksgiving ritual of feeding a beggar. The beggar eats himself into a coma to preserve another’s joy in giving. The result is ridiculous, heartbreaking — and strangely beautiful.

On the surface, O. Henry seems to be lampooning the mechanical generosity of ostentatiously feeding the poor for one day per year. Plenty of food is involved, but there is no connection, no community, no real conversation. The Old Gentleman is so intent on sustaining a tradition that he doesn’t even notice that his usual beneficiary is already stuffed. It is a parody of giving: all performance, no understanding.

But maybe we are meant to see here not a ludicrous satire but a tradition that is sweet and graceful despite its awkwardness. On this particular Thanksgiving, to be sure, it’s a tradition that ends in fiasco. But O. Henry calls the men Thanksgiving Day gentlemen for a reason: because in the small moral choices they make — to spare another man embarrassment, to honor a promise, to put someone else’s comfort above their own — they rise, however briefly, above the claims of appetite and circumstance. Their generosity is clumsy and misdirected, but it’s real. It costs them something — and in that cost, O. Henry finds a glimmer of nobility.

That paradox touches on something I was raised to believe.

I grew up watching my father put a little money in a charity box every single day. He didn’t do it as a flourish or when the spirit moved him; it was as much a part of his morning routine as getting dressed or going to work. It helped form him, training him in habitual generosity. Long before I had words for it, I understood that daily giving was part of what made him the man he was.

I don’t sneer at ritualized, imperfect generosity, and O. Henry didn’t either. Habitual acts of giving — even when they fall short of what they should be — are shapers of character. They train the heart in directions the head may need years to follow. Of course generosity should be thoughtful. Of course we should strive to ensure that charity helps rather than harms. Judged strictly by outcomes, the Old Gentleman’s fast-and-feast routine is indefensible. But if I had to choose between a society in which thousands of people imitate his impulse, however awkwardly, and one in which everyone waits for perfect circumstances and guaranteed outcomes before lifting a finger, I know which one I’d rather live in.

The lesson from “Two Thanksgiving Day Gentlemen” isn’t to mock holiday charity or abandon tradition. It is to deepen both. Ritual can ossify into empty performance, as O. Henry shows with mischievous wit. But ritual can also become the quiet discipline out of which genuine virtue grows. The difference is whether we let the habit push us toward seeing the person in front of us, not just the role we’ve assigned him. Stuffy Pete and the Old Gentleman got that wrong. But in their stubborn, self-forgetting impulse to do right by someone else, they showed how a gentleman — even one in rags — begins to be made.

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