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Home Boxing

Hemingway, Fitzgerald, And The Round That Went On Too Long

February 10, 2026
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Hemingway, Fitzgerald, And The Round That Went On Too Long
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“My writing is nothing. My boxing is everything.” So said the one and only Ernest Hemingway, one of the twentieth century’s most captivating and revered writers.

Best-selling literary titan. Celebrity. Hard drinker. Womanizer. Big game hunter. Bull fight aficionado. Hemingway was a man’s man who wore many hats other than that of writer. And, to be sure, boxer was one of the roles he honed with genuine zeal. While he was by no means a professional fighter (more on that later), Hemingway was most certainly a die-hard fan who liked to lace up the gloves and climb into the ring.

Just how into boxing was Hemingway? Well, as a child, he posed for a picture as John L. Sullivan, reflecting his early passion for the sweet science. Indeed, several of Hemingway’s most revered short stories focus on boxing and boxers: “The Killers,” “Fifty Grand,” and “The Battler” quickly come to mind. Each of these works, to varying extents, are steeped in the fight game. Furthermore, Hemingway’s classic novel, The Sun Also Rises, literally starts with a description of the boxing background of Robert Cohn, one of the book’s central characters. Make no mistake, Papa, as Hemingway came to be affectionately called, was obsessed with boxing. Obsession, though, doesn’t necessarily imply skill.

While Hemingway was nothing if not brave – documented acts of courage on the battlefield attest to as much — he wasn’t exactly Gene Tunney once he slipped through the ropes. Hemingway’s skill-set as a fighter may have been suited to barroom brawls, but street fighting is a far cry from scientific boxing. Although strong and aggressive, he tended to be clumsy and consistently left himself an open target in the ring. However, to give credit where credit is due, he persisted with boxing despite his limitations. As with writing fiction though, heart and determination only go so far. One ultimately either has the goods or doesn’t.

Enter one F. Scott Fitzgerald. Yes, that F. Scott Fitzgerald, of The Great Gatsby fame. Scott, as he was known to intimate associates, was living in Paris at the same time as Hemingway, and the two would go on to develop one of the most peculiar friendships in literary history. Consider that Fitzgerald was already a best-selling author when he first met Hemingway, while Ernest, four years Fitzgerald’s junior, was struggling. Still, it was Fitzgerald who revered Hemingway. Hemingway, you see, was a far cry from most of the degenerate expatriates populating Paris at the time.

Openly masculine, swaggering and gregarious, the young World War I veteran — Hemingway had been severely wounded in combat while serving as an ambulance driver in Italy — commanded every room he entered.

Ernest Hemingway and F. Scott Fitzgerald.

Not only could Hemingway out-drink even the wildest members of the so called “Lost Generation” bohemian cohort, he also engaged in activities, like hunting and boxing, that intimidated his peers and made them appear soft in comparison. Like countless others, Fitzgerald developed a case of hero worship. Yet unlike most of the people keen to join Hemingway’s burgeoning cult-like following, Fitzgerald was at least the man’s equal as a writer.

While Hemingway was indeed on the precipice of emerging as a literary heavyweight, Fitzgerald had already found enviable establishment success and recognition. And given that Hemingway’s hyper-masculinity was always grounded in fragility, a threat to his supremacy, in any regard, could prove problematic. As such, the young author tried to assert himself by disrespecting and challenging Fitzgerald. Despite this, Scott, like so many others, largely accepted it. But such “chemistry” can lead to combustion, and feelings reportedly inflamed one especially heated afternoon in 1929.

By that time, Hemingway was beginning to surpass Fitzgerald as an artist. Not only did his first published novel, The Sun Also Rises, shake up the world of letters, his follow-up book, A Farewell To Arms, was (and still is) considered a masterpiece of war fiction. A reminder, though: Hemingway wasn’t much of a boxer. But limitations aside, he had some legitimate in-ring experience due to sparring with the likes of Canadian writer Morley Callaghan, who was a genuinely skilled fighter, on several occasions.

On that 1929 day in question, however, Fitzgerald reportedly acted as timekeeper, and he apparently let the second round with Callaghan run a minute too long. Bad enough, sure, but in those bonus sixty seconds, Callaghan put Ernest on the canvas. For a man as competitive as Hemingway, the round’s perceived length was enough to warrant outrage and suspicion. Loudly blaming Fitzgerald for wanting to see him get thrashed by Callaghan, Hemingway, as he was known to do, escalated the situation.

Hemingway cut a notorious image of masculinity.
Hemingway cut a notorious image of masculinity.

That is, of course, if one can trust this apocryphal tale of literary violence. Hemingway is said to have later claimed that Fitzgerald had let the round extend for an obscene ten minutes – an entirely ridiculous charge. Callaghan’s testimony about the incident in his autobiography, written after Fitzgerald’s death, would go on to elevate the story to the realm of literary legend. Interestingly, Fitzgerald is said to have never published a word about the fight. Perhaps he was ashamed, but it’s more likely than not that the incident was soon forgotten, only to be revisited after memories and specifics had faded, and alternative histories had taken root in the minds of each participant. And although he was volatile by nature, Hemingway’s correspondence with Fitzgerald after that infamous day remained warm and supportive.

However, if there’s a moral to this story, it’s that boxing can never escape controversy – even among its most unlikely participants.             — Sean Crose

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