A man on vacation in Jamaica decides to buy a beer and sit on a deck chair by a swimming pool. The garden surrounding him is filled with azaleas and tall coconut palms, and several sunburnt people on deck chairs surround the pool, while three or four English girls and a dozen American boys, likely naval cadets, splash around in the pool. The man sits back with a beer and a cigarette and watches as the American boys and English girls interact.
Then, the man spots a small, oldish man in a white suit and a large Panama hat walking briskly to the edge of the pool. The old man asks to sit next to the narrator. The old man is around 68 or 70, and the narrator cannot place whether he has an Italian or Spanish accent, but feels fairly sure that the man is South American. The man complains that the group of American sailors is too loud.
One of the American cadets, a boy of about 19 or 20, sits near the old man and offers him a cigarette, but the old man refuses, preferring to smoke a cigar. The young cadet offers to light the man's cigar, and the old man insists that the light will not work. The young man says that his lighter always works, so the old man proposes a big bet to see if the young man's claim holds true. The young cadet replies that he cannot bet more than a dollar.
The old man agrees to go up to a hotel room with the cadet, and bets that the cadet cannot light his lighter ten times in a row without missing once. The cadet agrees to this bet, and the old man puts up his Cadillac for his bet. In exchange, the old man wants the cadet's left pinky finger. The cadet refuses, and the old man offers to drop the whole thing.
The narrator asks the cadet for a light, and the cadet walks over to him, lighting his cigarette. The cadet sits very still, clearly disturbed by the old man's proposal. He reconsiders taking the bet as he shifts in his seat, rubs his chest, strokes the back of his neck, and taps on his kneecaps with his fingers. The cadet agrees to bet his finger for the Cadillac and the man insists on tying the cadet's finger to a table so he can cut the finger off with a knife in case the lighter fails.
The old man asks the narrator to be the referee, and the narrator and the English girl denounce this bet as crazy and ridiculous. But, the narrator follows the old man and the cadet up to the old man's room. The old man insists they all have Martinis, and rings the maid, requesting a chopping knife, a nail, and a hammer. The narrator and the English girl continue to try to dissuade the cadet from taking the old man's bet, but the cadet continues on with the bet.
The old man produces the keys and papers for his car, and begins to hammer the nails meant to hold the cadet's hand in place into the table. The narrator realizes that the old man must have done something like this before given his immense precision, and worries about the boy's well-being. The old man puts the boy's hand in place and prepares the chopping knife. The boy lights the lighter eight times, until a woman storms into the room screaming "Carlos," the old man's name.
She grabs the old man by his suit and starts violently shaking him and yelling at him. She explains that the man has taken 47 fingers and lost 11 cars. The old man bets the woman's Cadillac, as he has no car, and she tells the group that she won everything from the old man. As the cadet hands her the keys, the woman reveals a hand with only one finger and a thumb.
In "Man from the South," money rules, as the old man's extreme bet—a car if you win, a finger if you lose—does not deter a young naval cadet. Though the naval cadet initially refuses to take the old man's bet, he eventually grows restless, and agrees to take the bet.
This story is fundamentally about what people are willing to give up for the chance to win some money. Over time, the old man has accumulated 47 fingers and lost 11 cars. By putting up their fingers as collateral in their bet, the bettors prove that they are willing to give up a literal and metaphorical part of themselves for the chance to win a car, a simple, disposable material possession.
Carlos, who runs the bet, seems to relish in the cruelty of his game, as he collects fingers over time. Here, Carlos seems to represent established wealth which proudly announces its depravity. Even though the old man has lost all of his possessions to the two-fingered woman, he thirsts for the excitement of his bets, and he sets the young naval cadet up for possible failure just to experience the rush of the bet and the possibility of cutting off one of the boy's fingers.
The old man's false bet underscores the difficult nature of the bet, and the metaphorical implications of this betting. This story suggests that nothing is truly a safe bet, and that any bet can be faulty. It also suggests that the search for wealth involves losing some part of the self.
The woman who loses several fingers best exemplifies this loss of self, as she loses almost all of her fingers in the process of winning and acquiring all of the old man's riches. But, despite this wealth, the old man still travels with her, hanging over her like a shadow. The old man's lingering presence symbolizes the inescapable nature of the past, as well as the haunting quality of past endeavors, both successful and failed.