"Fifty Grand" was first published in the Atlantic Monthly in July 1927 and later the same year in Men Without Women. It is about the collusive world of gambling and the humanity/compromising of aging boxing champ Jack Brennan during his last fight with Jim Walcott. The fight is likely based on the Jack Britton/Mickey Walker fight in Madison Square Garden on November 1, 1922, although Carlos Baker (author of Hemingway: A Life Story) asserts it was the fight between Britton and Benny Leonard on June 26, 1922, at the New York Hippodrome. Recently, omitted pages from original drafts of the story indicate that the Leonard fight was referred to in retrospect, making it a near certainty that the Britton/Walker fight is the basis for the Brennan/Walcott fight in the story. It is also likely that the foul and "double-cross" was inspired by the Siki/Carpentier fight in Paris on September 4, 1922.

The aging hero, a common figure in Hemingway's work, is Jack Brennan, aged 37, trained by Jerry Doyle, the narrator, at Hogan's health ranch. Dwelling on his age, his insomnia and how much he misses his wife, Jack decides this will be his last fight. The day before the fight, he is visited by his manager, John, and two strangers—Steinfelt and Morgan, referred to as "wise boys" and "sharpshooters." John asks Jerry to leave the room, so the reader does not know for sure what John, Steinfelt and Morgan, and Jack talk about. After the meeting, Jack gets drunk and tells Jerry that he is going to bet $50,000 against himself. Jack says that since he knows he cannot win against a younger, stronger fighter, he may as well make some money on the deal: losing intentionally will be easy. He tells Jerry to bet on Walcott. Most initial interpretations of this secret meeting assume that Steinfelt and Morgan conspire with John to bribe Jack to fix the fight. Following this interpretation, Jack makes a good showing and almost loses his bet when Walcott throws him a low blow. Walcott would have been disqualified, making Jack the winner of the fight and loser of his bet. (This is the double-cross" John later refers to: Walcott's low blow might be evidence that Walcott intended to fix the fight.) Jack stays on his feet to save his bet, inevitably loses the bout, and saves some integrity by making it to the final round. John apologizes for asking Jack to lose intentionally.

There is another interpretation. James Tackach's article "Whose Fix Is It Anyway?: A Closer Look at Hemingway's 'Fifty Grand,'" states that Jack never decided to throw the fight (until the last round). Either Steinfelt and Morgan offered to pay Jack to lose intentionally and he refused; or, Jack had his manager summon Steinfelt and Morgan (as bookies), so that Jack could place his $50,000 bet. If this interpretation is correct, Jack genuinely tried his best but was absolutely sure he would not win, so decided to bet on Walcott and make some money. Jack controls the beginning of the fight, eventually tires (as he, Jerry, and John seem to have anticipated), and Walcott takes over. Walcott hits Jack below the belt, Jack survives, then fouls Walcott and is disqualified. John apologizes because Jack is so beaten and it is the end of his career.

In either scenario, Jack is not simply in this for monetary reasons. He gives a good fight by going the distance and struggling through Walcott's foul (which may or may not have been evidence of Walcott's own fix). Jack's foul is probably intentional. In any case, by fouling Walcott in the last round, Jack does eventually cause his own defeat.

Fifty Grand Synopsis

Right jabs and double-crosses abound in "Fifty Grand," Ernest Hemingway's short story about boxing, gambling, and the lure of big money. "Fifty Grand" was published in Hemingway's short story anthology Men Without Women (1927) by Charles Scribner's Sons. Hemingway apparently based his tale on the real life welterweight title fight between champion Jack Britton and Mickey Walker on November 1, 1922, in Madison Square Garden. The aging Britton was a 3-1 favorite early, but the betting switched to the young Walker's favor shortly before the fight. Later known as the "Toy Bulldog," Walker went on to handily defeat the former three-time world champ.

Although there was no actual suggestion of a fixed fight in the real Britton-Walker bout, Hemingway creates the major conflict of his story by introducing two shady "wise boys" who hold a mysterious meeting at the protagonist's training camp. It appears initially that the two gamblers have succeeded in their mission, and that a fix is on, but Hemingway has several twists to deliver before the fight and story end.

Hemingway barely disguises the names of his fictional pugilists from the real men. Jack Brennan is the veteran brawler who realizes he is on his last legs and has little expectations of defeating the up-and-coming blonde youngster, Jimmy Walcott. (Interestingly, Hemingway shows an uncanny prescience by choosing for his challenger a name that will later become famous when Jersey Joe Walcott becomes the oldest world heavyweight champ ever when he wins the title in 1951.) The author intersperses other real characters within his fictional story, referring to Ted "Kid" Lewis as a "sore" spot to Brennan (in fact, Britton fought the real Ted Lewis an incredible 20 times); "Willard" (the "Great White Hope," Jess Willard); "Corbett" (1920s oddsmaker Tom Corbett); and "Lardner" (famed sportswriter Ring Lardner).

"Fifty Grand" is classic Hemingway, with short, realistic dialogue laced with vivid period slang that tells the story of a subject he knows so well. Hemingway spins his tale through the eyes of Jerry Doyle, Brennan's friend and trainer. During Brennan's lethargic preparation for the fight, Doyle remains hopeful that his charge can pull off one more win, though another insider assures him that "He's stale as poorhouse cake...He'll (Walcott) kill him." Following the visit of the two "wise boys," Brennan gets drunk and reveals to Doyle that he has bet $50,000 on Walcott and advises Doyle to do the same. As the fight unfolds, Brennan takes control early, but he begins to fade after the seventh round. However, this is standard fare for Brennan, and he appears to be giving his all. Then, in the 11th round, with Walcott giving Jack "an awful beating," the youngster suddenly delivers Brennan a deliberate low blow "five inches below the belt."

It is a shot that would end most fights, and Brennan "walked as though all his insides were going to fall out." Walcott's punch is meant to be the finale of the match—a fight that will end in his disqualification and a victory for Brennan. But with $50,000 riding on the outcome, Brennan begs the referee to continue. "It wasn't low," he said. "It was a accident."

So the fight goes on. Walcott "didn't know what to do....He never thought Jack could have stood it." Brennan continues punching, swinging wildly while Walcott covers up. Brennan's body is beaten, but his mind reacts quickly. Without warning, Brennan delivers a devastating left-right combination—directly to Walcott's groin. This time, the referee stops the fight. The victory goes to "Walcott on a foul."

The fix is on, all right, but it is meant to be a double-cross. Only Brennan's quick thinking saves him from winning the fight and losing his bet.

"It's funny how fast you can think when it means that much money," Jack says.
"You're some boy, Jack," John says.
"No," Jack says. "It was nothing."

The implication of mob interference and a fixed fight is never perfectly clear, however, since Hemingway chooses to keep his narrator, Doyle, outside the closed-door meeting between Brennan and the two gangsters. The reader is never sure what is said, and no payoff is mentioned, so the question remains as to why Jack needs to be bribed to take a fall when it is highly unlikely that he can go the distance against the younger, stronger Walcott. Jack is never knocked down—even with the low blow—and he remarks to his corner men late in the fight that "I don't want this bohunk to stop me." Does Jack agree to lose? Does he take money from the mobsters? Or does he decide to place the bet on Walcott on his own? The reader is never quite certain, but the low blows that decide the outcome are a complete surprise, and Jack Brennan is yet another example of Hemingway's vision of the flawed hero.