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The Gentle Crafter
"The Gentle Grafter" looks at business from a distinctly shady angle, with its stories about cool-headed, sharp-dressing trickster Jeff Peters.
O. Herny was a supreme story teller, drawing his material from the lives of ordinary people - clerks, city dwellers, exiles and drifters.
O. Henry was the pseudonym for William Sydney Porter, master of the short story. His empathy ran deep and he wrote in the language of the man in the street.
In March of 1898 he was sentenced to five years in the federal penitentiary. During his term he began his serious writing. He would use a score of pseudonyms in his career to this point, but his favorite was borrowed from Orrin Henry, a prison guard.
O. Henry's popularity reached its height after his death. His writing was seen as straightforward and simple, written in the plain vernacular of his readers. His stories may rely on a sameness of plot, but the sharp, unexpected twist at the end is still his distinctive trademark today. Critics have singled out O. Henry as one of the greatest American short story writers - describing him as a "writer's writer" who also possesses universal appeal. A critic traveling early in the century fell into a conversation with a Midwest farmer. When asked if he ever read O. Henry, the farmer replied, "Professor, that's literature, that's real literature."
287 pages, Hardcover
First published January 1, 1908
108 people are currently reading
348 people want to read
About the author
O. Henry
2,913 books1,863 followersSuch volumes as
Cabbages and Kings
(1904) and
The Four Million
(1906) collect short stories, noted for their often surprising endings, of American writer William Sydney Porter, who used the pen name O. Henry.
His biography shows where he found inspiration for his characters. His era produced their voices and his language.
Mother of three-year-old Porter died from tuberculosis. He left school at fifteen years of age and worked for five years in drugstore of his uncle and then for two years at a Texas sheep ranch.
In 1884, he went to Austin, where he worked in a real estate office and a church choir and spent four years as a draftsman in the general land office. His wife and firstborn died, but daughter Margaret survived him.
He failed to establish a small humorous weekly and afterward worked in poorly-run bank. When its accounts balanced not, people blamed and fired him.
In Houston, he worked for a few years until, ordered to stand trial for embezzlement, he fled to New Orleans and thence Honduras.
Two years later, he returned on account of illness of his wife. Apprehended, Porter served a few months more than three years in a penitentiary in Columbus, Ohio. During his incarceration, he composed ten short stories, including A Blackjack Bargainer , The Enchanted Kiss , and The Duplicity of Hargraves .
In 1899, McClure's published Whistling Dick's Christmas Story and Georgia's Ruling .
In Pittsburgh, Pennsylvania, he sent manuscripts to New York editors. In the spring of 1902, Ainslee's Magazine offered him a regular income if he moved to New York.
In less than eight years, he became a bestselling author of collections of short stories. Cabbages and Kings came first in 1904 The Four Million, and The Trimmed Lamp and Heart of the West followed in 1907, and The Voice of the City in 1908, Roads of Destiny and Options in 1909, Strictly Business and Whirligigs in 1910 followed.
Posthumously published collections include The Gentle Grafter about the swindler, Jeff Peters; Rolling Stones , Waifs and Strays , and in 1936, unsigned stories, followed.
People rewarded other persons financially more. A Retrieved Reformation about the safe-cracker Jimmy Valentine got $250; six years later, $500 for dramatic rights, which gave over $100,000 royalties for playwright Paul Armstrong. Many stories have been made into films.
His biography shows where he found inspiration for his characters. His era produced their voices and his language.
Mother of three-year-old Porter died from tuberculosis. He left school at fifteen years of age and worked for five years in drugstore of his uncle and then for two years at a Texas sheep ranch.
In 1884, he went to Austin, where he worked in a real estate office and a church choir and spent four years as a draftsman in the general land office. His wife and firstborn died, but daughter Margaret survived him.
He failed to establish a small humorous weekly and afterward worked in poorly-run bank. When its accounts balanced not, people blamed and fired him.
In Houston, he worked for a few years until, ordered to stand trial for embezzlement, he fled to New Orleans and thence Honduras.
Two years later, he returned on account of illness of his wife. Apprehended, Porter served a few months more than three years in a penitentiary in Columbus, Ohio. During his incarceration, he composed ten short stories, including A Blackjack Bargainer , The Enchanted Kiss , and The Duplicity of Hargraves .
In 1899, McClure's published Whistling Dick's Christmas Story and Georgia's Ruling .
In Pittsburgh, Pennsylvania, he sent manuscripts to New York editors. In the spring of 1902, Ainslee's Magazine offered him a regular income if he moved to New York.
In less than eight years, he became a bestselling author of collections of short stories. Cabbages and Kings came first in 1904 The Four Million, and The Trimmed Lamp and Heart of the West followed in 1907, and The Voice of the City in 1908, Roads of Destiny and Options in 1909, Strictly Business and Whirligigs in 1910 followed.
Posthumously published collections include The Gentle Grafter about the swindler, Jeff Peters; Rolling Stones , Waifs and Strays , and in 1936, unsigned stories, followed.
People rewarded other persons financially more. A Retrieved Reformation about the safe-cracker Jimmy Valentine got $250; six years later, $500 for dramatic rights, which gave over $100,000 royalties for playwright Paul Armstrong. Many stories have been made into films.
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Displaying 1 - 30 of 37 reviews
August 29, 2025
Published early in the 20th century, this is a collection of 14 short stories about the schemes and projects of grafters, grifters, con men and swindlers - guys looking to make a quick buck (or more) at someone else’s expense. It’s light entertainment from the late 19th century with a focus on the shady side of the American dream. The stories are written in a folksy, conversational style, filled with street-wise slang, malapropisms and a particular humour of the times that may be missed by today’s readers. In keeping with O. Henry’s trademark style, all of the stories conclude with an unexpected, ironic or humorous twist.
I found these stories fun and entertaining. Each dealt with a different kind of grift, graft or swindle and there was something to be learned about the inner workings of some of these con games. This is a light and humorous look at America in “the Gilded Age”, starring likeable swindlers who aren't really bad guys, at all. 3.5 stars
I found these stories fun and entertaining. Each dealt with a different kind of grift, graft or swindle and there was something to be learned about the inner workings of some of these con games. This is a light and humorous look at America in “the Gilded Age”, starring likeable swindlers who aren't really bad guys, at all. 3.5 stars
April 30, 2022
The Gentle Grafter is a typical O Henry collection in that each story has something of a trick ending. It is atypical in that the stories are all connected by the character of Jeff Peters, the gentle grafter of the book’s title. Each story is a tale of his cons, bunks, grafts, and other crimes, and each trick ending reveals the con sprung, the con gone awry, or occasionally, the double cross con turned back on Peters. Jeff Peters is an affable rascal with his own unique code of conduct, and you will enjoy the time spent reading his tales, no bunk!
August 26, 2025
ENGLISH: 14 short stories by O.Henry, all of them related to grafters, swindlers, hustlers. The protagonist of twelve of them is Jeff Peters, frequently accompanied by young Andy Tucker. Apart from this book, Peters appears in two more stories, one of them quite good, but where he doesn't act as a swindler: Cupid à la carte in Heart of the West.
This is the first time I've read this book. The most original (for me) was The exact science of matrimony.
In one of the stories (The man higher up) Jeff Peters explains that there are three kinds of grafters: a) Common burglars (labor); grafters like Peters that give something in exchange for money (traders); and speculators (capital).
ESPAÑOL: 14 relatos cortos de O. Henry, todos ellos relacionados con estafadores y sinvergüenzas. El protagonista de doce de ellos es Jeff Peters, acompañado a menudo por el joven Andy Tucker. Aparte de en este libro, Peters aparece en dos relatos más, uno de ellos bastante bueno, donde no desempeña el papel de un sinvergüenza: Cupido a la carta en El corazón del oeste.
Esta es la primera vez que leo este libro. El relato más original (para mí) fue La ciencia exacta del matrimonio.
En uno de los relatos (El hombre de más arriba) Jeff Peters explica que hay tres tipos de estafadores: a) Ladrones comunes (mano de obra); estafadores como Peters que dan algo a cambio de dinero (comerciantes); y especuladores (capital).
This is the first time I've read this book. The most original (for me) was The exact science of matrimony.
In one of the stories (The man higher up) Jeff Peters explains that there are three kinds of grafters: a) Common burglars (labor); grafters like Peters that give something in exchange for money (traders); and speculators (capital).
ESPAÑOL: 14 relatos cortos de O. Henry, todos ellos relacionados con estafadores y sinvergüenzas. El protagonista de doce de ellos es Jeff Peters, acompañado a menudo por el joven Andy Tucker. Aparte de en este libro, Peters aparece en dos relatos más, uno de ellos bastante bueno, donde no desempeña el papel de un sinvergüenza: Cupido a la carta en El corazón del oeste.
Esta es la primera vez que leo este libro. El relato más original (para mí) fue La ciencia exacta del matrimonio.
En uno de los relatos (El hombre de más arriba) Jeff Peters explica que hay tres tipos de estafadores: a) Ladrones comunes (mano de obra); estafadores como Peters que dan algo a cambio de dinero (comerciantes); y especuladores (capital).
June 24, 2018
There is a wonderful irony in O Henry’s short story collection, The Gentle Grafter (Kindle edition). Almost every American has read The Gift of the Magi. It has become a cultural meme. A warm hearted story of loving and gifting. These are also warm hearted stories of con men and grafting. Think of Damon Runyoun’s Nathan Detroit on the road. There is humor in grafting and O Henry manages a light touch even has his heart-of-gold thieves touch their marks, ever so lightly. No violence and no bad language, although do not be alarmed if some of the period jargon makes its way into your child’s vocabulary.
To address sensitivities not or barely on a popular writer’s mind in the closing years of the 19th century: Women are rarely spoken of with respect and such females as make their way to these pagers are less than fully developed characters. On the other hand most of them are equals in the art of selling gilt edge stock certificates and other cons. African American get very little in the way of respect. There is some humor at the expense of Christians and almost no mention of Jews. New Yorkers seem to get the most pointed barbs although it is assumed that farmers were made to be the God given place for an honest con artist to refill his wallet.
These are fun stories about men who take, but who feel constrained about leaving something behind and never wiping out widows or the truly poor. They want their action to be at the expense of the ‘excess’ cash of which this or that citizen may be seeking to unburden themselves. And always the famous O Henry Twist.
The slang, argot and malapropism can get a tad thick. Usually one can guess the intended meaning given the context, but Henry lacks the balance that made Runyon a master of (in his case) mostly made up Broadway street talk. Of course Mark Twain was always better at using the local voice.
Read this too fast and the stories can get to be too much. Relax, pace yourself a few at a time. The Gentle Grafter is going to be fun.
To address sensitivities not or barely on a popular writer’s mind in the closing years of the 19th century: Women are rarely spoken of with respect and such females as make their way to these pagers are less than fully developed characters. On the other hand most of them are equals in the art of selling gilt edge stock certificates and other cons. African American get very little in the way of respect. There is some humor at the expense of Christians and almost no mention of Jews. New Yorkers seem to get the most pointed barbs although it is assumed that farmers were made to be the God given place for an honest con artist to refill his wallet.
These are fun stories about men who take, but who feel constrained about leaving something behind and never wiping out widows or the truly poor. They want their action to be at the expense of the ‘excess’ cash of which this or that citizen may be seeking to unburden themselves. And always the famous O Henry Twist.
The slang, argot and malapropism can get a tad thick. Usually one can guess the intended meaning given the context, but Henry lacks the balance that made Runyon a master of (in his case) mostly made up Broadway street talk. Of course Mark Twain was always better at using the local voice.
Read this too fast and the stories can get to be too much. Relax, pace yourself a few at a time. The Gentle Grafter is going to be fun.
December 28, 2014
Alright book with stories of different scams at the beginning of the 20th century in the USA.
Whole book can be found here: http://www.gutenberg.org/ebooks/1805
Some nice quotes:
"that in all my illegitimate inroads against the legal letter of the law the article sold must be existent, visible, producible. In that way and by a careful study of city ordinances and train schedules I have kept out of all trouble with the police that a five dollar bill and a cigar could not square."
"There are two kinds of graft," said Jeff, "that ought to be wiped out by law. I mean Wall Street speculation, and burglary." "Nearly everybody will agree with you as to one of them," said I, with a laugh. "Well, burglary ought to be wiped out, too," said Jeff;
"In my line of business," said Jeff, "the hardest thing is to find an upright, trustworthy, strictly honorable partner to work a graft with. Some of the best men I ever worked with in a swindle would resort to trickery at times.
Whole book can be found here: http://www.gutenberg.org/ebooks/1805
Some nice quotes:
"that in all my illegitimate inroads against the legal letter of the law the article sold must be existent, visible, producible. In that way and by a careful study of city ordinances and train schedules I have kept out of all trouble with the police that a five dollar bill and a cigar could not square."
"There are two kinds of graft," said Jeff, "that ought to be wiped out by law. I mean Wall Street speculation, and burglary." "Nearly everybody will agree with you as to one of them," said I, with a laugh. "Well, burglary ought to be wiped out, too," said Jeff;
"In my line of business," said Jeff, "the hardest thing is to find an upright, trustworthy, strictly honorable partner to work a graft with. Some of the best men I ever worked with in a swindle would resort to trickery at times.
November 26, 2025
O. Henry discovered at some early point in his career that an unexpected twist in a short story would make it more memorable, and as a result further his career as a writer. This does, though, present a problem (not unknown to M. Night Shyamalan), that you may have difficulty regularly coming up with such twists. One device that he uses, is to have as the narrator (or often the person who is telling a tale to the narrator) a con-man (since the con usually involves something unexpected, which can be revealed at the end). This collection brings together over a dozen of such tales, involving a recurring character named Jeff Peters.
It should be acknowledged that O. Henry, while he was not himself (as far as I know) a con-man, was in fact convicted of bank fraud, and probably knew at least something about confidence schemes from personal experience. He also enjoys having the shyster in question, Jeff Peters, express moral disapproval of financiers, considering their schemes to be too deceitful and unfair for his own tastes. O. Henry is not, primarily, a political writer, but that makes his occasional jibes at the ruling elite all the more cutting.
O. Henry spent time in South Carolina, Texas, central America, and New York City, and all of these backdrops make appearances in his writing. There are (especially in the 21st century) many writers who appear to mostly have learned about people by reading fiction, and therefore to have little ability to write about anyone outside of their own bubble. O. Henry was forced by circumstances (and his own actions) to spend a great deal of time living among and talking to people of many different classes, races, and cultures. It gives him an ability to write about human nature with neither innocence nor cynicism, neither ill will nor an excess of sentiment. His characters are mostly sympathetic, but not particularly noble. They lie, they are neither well educated nor (in most cases) particularly wise, and yet they are mostly people who we can like well enough to root for, most of the time.
But, if you should ever run into someone in life who reminds you of O. Henry, hold on to your wallet.
It should be acknowledged that O. Henry, while he was not himself (as far as I know) a con-man, was in fact convicted of bank fraud, and probably knew at least something about confidence schemes from personal experience. He also enjoys having the shyster in question, Jeff Peters, express moral disapproval of financiers, considering their schemes to be too deceitful and unfair for his own tastes. O. Henry is not, primarily, a political writer, but that makes his occasional jibes at the ruling elite all the more cutting.
O. Henry spent time in South Carolina, Texas, central America, and New York City, and all of these backdrops make appearances in his writing. There are (especially in the 21st century) many writers who appear to mostly have learned about people by reading fiction, and therefore to have little ability to write about anyone outside of their own bubble. O. Henry was forced by circumstances (and his own actions) to spend a great deal of time living among and talking to people of many different classes, races, and cultures. It gives him an ability to write about human nature with neither innocence nor cynicism, neither ill will nor an excess of sentiment. His characters are mostly sympathetic, but not particularly noble. They lie, they are neither well educated nor (in most cases) particularly wise, and yet they are mostly people who we can like well enough to root for, most of the time.
But, if you should ever run into someone in life who reminds you of O. Henry, hold on to your wallet.
March 5, 2021
The Gentle Grafter is one of the collections of O. Henry’s short stories. Officially, O. Henry only wrote one novel, entitled Cabbages & Kings, which consisted of a series of interconnected short stories, and is considered a novel due to the interconnected nature of the stories and the thematic unity. Usually, O. Henry’s other collections of stories are simply that—collected stories. In this case, there could be a strong argument for considering this collection as tending to the same type of unity. All of the stories feature one particular con-man, Jeff Peters, and frequently also feature his occasional partner, Andy Tucker. The stories are not interconnected, so the collection fails to hit novelistic status, but are brief episodes of the various cons that Peters—or Peters and Tucker—become involved in pulling off. The “Gentle” part of the title is due to the fact that Peters is a con-man with a moral code. He refuses to con “widows” or “shop-girls” or to take the hard earned nickels of working boys. He also refuses to simply try to con someone without a perceived exchange in value. In one story, he has been traveling from town to town in a medicine-show wagon selling a secret life-giving elixir from the Choctaw Indian Tribe that is nothing more than a concoction of well water and alcohol mixed with herbs; however, he maintains that his customers believe that it works, so there is value for the exchange. From there, he frequently moves on to more elaborate cons, but once again, he refuses to con anyone who cannot afford the loss and who must be someone who is simply asking to be taken; in such instances, the value is in the education that he is providing to the target. As in all O. Henry stories, the twist at the end of the story is important, and the malapropisms in the conversation of the main character develop the humor. I have been working my way through the collections of stories because they are ideal audio stories for the car. Most of them are between fifteen to twenty minutes listening time and do not require intense concentration. Instead, they are a fun and light bit of pleasure.
January 7, 2023
A free read for Kindle from Amazon.
What a clever idea! O. Henry takes apart grafts (scams) of the early 1900s and shows not only how they work but how double scams or the "rubes" take the scammers! I wonder how many readers saw this and thought, oh no, I've done that before! Could you imagine a short story collection now of people doing the Nigerian prince scam, or the "I'm your grandson and I'm in jail, can you send bail money in the form of Amazon gift cards to this number?"
Clever quotes as always from O. Henry--
"There are two kinds of graft," said Jeff, "that ought to be wiped out by law. I mean Wall Street speculation, and burglary." "Nearly everybody will agree with you as to one of them," said I, with a laugh. "Well, burglary ought to be wiped out, too," said Jeff.
What a clever idea! O. Henry takes apart grafts (scams) of the early 1900s and shows not only how they work but how double scams or the "rubes" take the scammers! I wonder how many readers saw this and thought, oh no, I've done that before! Could you imagine a short story collection now of people doing the Nigerian prince scam, or the "I'm your grandson and I'm in jail, can you send bail money in the form of Amazon gift cards to this number?"
Clever quotes as always from O. Henry--
"There are two kinds of graft," said Jeff, "that ought to be wiped out by law. I mean Wall Street speculation, and burglary." "Nearly everybody will agree with you as to one of them," said I, with a laugh. "Well, burglary ought to be wiped out, too," said Jeff.
July 21, 2023
Humorous, and almost instructional, tales of graft and slickery.
December 15, 2013
A great disservice has been done to O. Henry by anthologists who seem incapable of reading beyond his most hackneyed, sentimental pieces. In his best pieces, his colorful use of vernacular and his ability to capture the spirit of his times is wonderfully entertaining.
If your opinion of O.Henry is based on the horribly saccharine "Gift of the Magi", read some of these stories and see why he was so appreciated in his time.
If your opinion of O.Henry is based on the horribly saccharine "Gift of the Magi", read some of these stories and see why he was so appreciated in his time.
May 23, 2019
ENTERTAINING SHORT STORIES.
“ ‘Drink,’ says Andy, ‘always drives me to oratory.’ ” —The Octopus Marooned, (p. 6).
O. Henry has long been my go to guy whenever the bill of fare calls for highly entertaining, terrifically well written short stories. The Gentle Grafter is a collection of fourteen such short stories in tribute to the art of the scam.
Recommendation: Very entertaining way to while away the hours.
“I bit off a chunk and sits down on a pile of ties by the track to recogitate my sensations of thought and perspicacity.”—The Man Higher Up, (p. 62)
Open Road. Kindle Edition, 109 pages
“ ‘Drink,’ says Andy, ‘always drives me to oratory.’ ” —The Octopus Marooned, (p. 6).
O. Henry has long been my go to guy whenever the bill of fare calls for highly entertaining, terrifically well written short stories. The Gentle Grafter is a collection of fourteen such short stories in tribute to the art of the scam.
Recommendation: Very entertaining way to while away the hours.
“I bit off a chunk and sits down on a pile of ties by the track to recogitate my sensations of thought and perspicacity.”—The Man Higher Up, (p. 62)
Open Road. Kindle Edition, 109 pages
May 23, 2019
ENTERTAINING SHORT STORIES.
“ ‘Drink,’ says Andy, ‘always drives me to oratory.’ ” —The Octopus Marooned, (p. 6).
O. Henry has long been my go to guy whenever the bill of fare calls for highly entertaining, terrifically well written short stories. The Gentle Grafter is a collection of fourteen such short stories in tribute to the art of the scam.
Recommendation: Very entertaining way to while away the hours.
“I bit off a chunk and sits down on a pile of ties by the track to recogitate my sensations of thought and perspicacity.”—The Man Higher Up, (p. 62)
Open Road. Kindle Edition, 109 pages
“ ‘Drink,’ says Andy, ‘always drives me to oratory.’ ” —The Octopus Marooned, (p. 6).
O. Henry has long been my go to guy whenever the bill of fare calls for highly entertaining, terrifically well written short stories. The Gentle Grafter is a collection of fourteen such short stories in tribute to the art of the scam.
Recommendation: Very entertaining way to while away the hours.
“I bit off a chunk and sits down on a pile of ties by the track to recogitate my sensations of thought and perspicacity.”—The Man Higher Up, (p. 62)
Open Road. Kindle Edition, 109 pages
December 11, 2023
я дуже люблю оповідання О"Генрі, саме до них я повертаюся раз за разом, вони мене втішають, покращюють мій настрій, можу читати їх безліч разів, весь час знаходячи нові моменти, або згадуючи, як я сміялася минулого разу. Ця збірка про справжніх шляхетних злодіїв, які намагалися уникнути чистого криміналу, а займалися аферами та обманом довіри, але мали свій суворий кодекс честі і не дурили бідних, молодих дівчат, які планують одружитися, удовиць, старих та дітей. Інколи дурили їх самих :)
November 23, 2025
O’ Henry Revisited
’Is O. Henry still relevant today?’ It’s a question that three friends — I the youngest by nearly two decades, they the seasoned veterans — decided to test during the strange stillness of Covid. On May 1st, 2021, we set ourselves a rather reckless mission: to reread every word O. Henry ever wrote, slowly, deliberately, over the course of a year. And we did. What follows are the reflections and reviews born from that long, unusual experiment — an O. Henry revisited, re-examined, and re-imagined for a modern age.
There is something wickedly therapeutic about reading The Gentle Grafter during a time when the world outside feels like an instruction manual on How To Be Confused.
The book is a sequence of stories, yes, but also a sequence of masks: moral masks, economic masks, emotional masks, the whole carnival of self-presentation that we humans keep switching between like teenagers swapping phone cases.
What O. Henry does here is eerie—he turns the grifter into a kind of philosopher, not a moral monument but a cracked mirror, and in the reflection you see a world where trust is a negotiable currency and sincerity a limited-edition collectible. Perfect Covid-reading, really: at a time when frauds, scams, half-truths, and official announcements were part of the daily menu, returning to O. Henry’s con-men feels less like nostalgia and more like anthropology.
The book moves through the American early-20th-century underbelly with a skip in its step. His swindlers are not merely criminals; they’re performers of a weirdly spiritual craft, tricksters who understand that the world is not built on foundational truths but on shared illusions. Money changes hands, goods change hands, trust changes hands, but the real commodity is narrative—who tells it, who sells it, who gets to rewrite it.
Reading this in 2021 or 2025 feels uncanny because our age, too, is overrun with narrative-dealers: content creators, politicians, influencers, all of them peddling stories the way O. Henry’s grafters peddle schemes. The grifter as artist. The artist as grifter. The line dissolves.
Covid taught us how thin the membrane is between certainty and improvisation. That’s why the book slaps so hard now. O. Henry’s characters survive not because they’re villains, but because they’re agile. They think on their feet, live by wit, adapt faster than systems can catch them.
They’re entrepreneurs of chaos. If 2020-2023 taught us anything, it’s that life is mostly improv theatre with a bad backstage manager. We learned to negotiate shortages, misinformation, shifting rules, digital fatigue, and economic weirdness. So going back to these stories feels like revisiting a previous generation of hustlers—people who navigated uncertainty with charm, audacity, and the occasional burst of philosophical flair.
The postmodern flavour hits hardest when you realize that the binary between “honest work” and “dishonest hustle” is already dissolving at the edges.
O. Henry whispers, very softly but very cheekily:
1) Are the grafters wrong, or are they merely playing the same game as everyone else, just with better jokes?
2) In our era of start-ups and side-hustles, of passive income hacks and crypto-chaos, who exactly is the grafter?
3) Who gets to define legitimacy?
The stories feel like they’re winking at us across a century: Look around, sweetheart, everyone’s running a scheme. Some just write cleaner invoices.
And through all this, there is warmth. A strange tenderness. O. Henry is famously sentimental, but never saccharine. His con-artists stumble into situations where their schemes collide with something softer—human vulnerability, unexpected affection, flashes of generosity. And this tension between mischief and humanity is what gives The Gentle Grafter its glow.
Even during the pandemic, when everything felt abrasive, people were still doing tiny acts of kindness—overpaying the vegetable vendor, supporting a friend’s tiny online business, tipping the delivery guy more than usual. Survival and compassion danced together. In O. Henry’s universe too, the grifters might cheat you, but they won’t crush your spirit. They might bend the rules, but they still follow a personal, weirdly sacred code.
There’s also the unmistakable charm of the American frontier mythos—a world in flux, a world still self-inventing. The characters are restless, mobile, shape-shifting. No one stays one thing for too long. Identity is fluid not because the author is making a grand philosophical statement but because that was the nature of life then: people were reinventing themselves as fast as trains could take them from one town to another.
But reading it today, in a world where online avatars, curated feeds, and digital personae let us reinvent ourselves daily, the stories feel like early drafts of everything we currently experience.
The contemporary self is a curated myth; the grafter just got there early.
O. Henry’s humour still lands, surprisingly hard. A kind of deadpan mischief runs through the narration, like the narrator keeps nudging you in the ribs, whispering, “You see what I’m doing here, right?” It’s that slyness that makes the book sing. He isn’t mocking the grafters; he’s admiring their creativity. They’re flawed, yes, but never dull. And because the stories are filtered through this mischievous narrative tone, they acquire the rhythm of a campfire conversation—confessional, exaggerated, but emotionally true.
During Covid, when human connection felt strangely pixelated, these stories brought back a sense of conversational warmth: the feeling of sitting with a storyteller who knows exactly when to lean in, when to pause, when to drop the line that makes you grin into your mask.
What’s most striking, perhaps, is how deeply the book understands American capitalism—not the corporate giant we know now, but the raw, improvisational capitalism of individuals hustling for survival. The grafters treat the world as a marketplace of narratives, values, and opportunities.
They know that the real economy runs on confidence, not cash. They know that persuasion is a form of currency, and belief is an investment with high risk and high return. Postmodern theory—Baudrillard, Lyotard, Derrida—arrives decades later to tell us that society runs on simulacra, that authenticity is a cultural performance, that meaning is constructed through language. O. Henry’s grafters shrug and say, “Yeah, we knew that.”
And then there’s the loneliness underneath. The drifting. The sense that these characters are always standing on the edge of belonging but never quite stepping into it. They form alliances, yes, but never homes. They share bottles but not roots. They travel together, but not toward stability.
This nomadic emotional landscape hits harder in a post-pandemic world where dislocation—physical, psychological, moral—became a shared human experience. The grafters invent stories because they have no permanent stories of their own; they create schemes because permanence eludes them. It is both comedy and ache.
O. Henry does something rare in these tales: he humanizes the hustler without romanticizing the hustle. He shows the absurdity of human desire—the desire to get ahead, to outwit the system, to find shortcuts to dignity or comfort. But he also shows the fragile, stubborn humanity underneath all that scrambling. The grafters are not villains; they are dreamers with questionable methods. They’re not predators; they’re improvisers. They’re not immoral; they’re morally flexible. The difference matters.
Reading The Gentle Grafter in the digital age adds yet another layer. Today’s world is full of grifters operating at institutional scale—fake news empires, algorithmic manipulation, corporate schemes hiding behind pastel-coloured branding. Compared to them, O. Henry’s con-men feel almost wholesome, artisanal even. Handmade scams.
Ethically sourced deceit. Small-batch trickery. In a time when deception has become industrialized, these little stories feel like a reminder that the personal, human-scale trickster is not an enemy but a comic reflection of ourselves.
The postmodern undercurrent lies in the book’s refusal to privilege any single truth. Every scheme has multiple versions. Every con has shifting motivations. Every character believes their own performance.
Truth becomes something negotiated rather than discovered. And because the stories stay light, funny, and conversational, this philosophical slipperiness lands softly. You don’t feel lectured; you feel invited into a game where everyone is improvising the rules as they go.
What also endures is O. Henry’s deep affection for storytelling itself. The way each tale feels like it has been told in a bar, or under a tree, or during a lull in travel—half performance, half confession.
He captures the social life of narrative: how stories create community, how they mask insecurity, how they soothe the restless mind. During Covid, when narratives were our lifelines—messages, calls, books, memes—this felt especially urgent. Storytelling became a survival instinct, a way to connect across distance. O. Henry’s grafters tell stories because it is their livelihood. We told stories to ourselves because it was our way of navigating fear.
The charm of The Gentle Grafter lies not in its plots but in its worldview: a world where people are flawed but rarely cruel, where every trick contains a joke, where survival is a creative art, and where the line between fiction and strategy dissolves into the soft haze of human absurdity.
It is a book about making do, making up, and making sense—all skills we honed during lockdown. And because the stories are episodic, you can dip into them the way you dip into conversations—no pressure, no linearity, no demand to remember every detail.
During a time when attention felt scattered, this was exactly what the mind needed.
What stays with you long after the stories fade is the feeling that the world O. Henry builds is strangely optimistic.
Not naïve.
Not blind.
Just quietly trusting in the idea that humans—even shady, scheming humans—carry an ember of goodness that refuses to die.
And if that isn’t the most pandemic-era lesson ever, I don’t know what is.
Most recommended.
’Is O. Henry still relevant today?’ It’s a question that three friends — I the youngest by nearly two decades, they the seasoned veterans — decided to test during the strange stillness of Covid. On May 1st, 2021, we set ourselves a rather reckless mission: to reread every word O. Henry ever wrote, slowly, deliberately, over the course of a year. And we did. What follows are the reflections and reviews born from that long, unusual experiment — an O. Henry revisited, re-examined, and re-imagined for a modern age.
There is something wickedly therapeutic about reading The Gentle Grafter during a time when the world outside feels like an instruction manual on How To Be Confused.
The book is a sequence of stories, yes, but also a sequence of masks: moral masks, economic masks, emotional masks, the whole carnival of self-presentation that we humans keep switching between like teenagers swapping phone cases.
What O. Henry does here is eerie—he turns the grifter into a kind of philosopher, not a moral monument but a cracked mirror, and in the reflection you see a world where trust is a negotiable currency and sincerity a limited-edition collectible. Perfect Covid-reading, really: at a time when frauds, scams, half-truths, and official announcements were part of the daily menu, returning to O. Henry’s con-men feels less like nostalgia and more like anthropology.
The book moves through the American early-20th-century underbelly with a skip in its step. His swindlers are not merely criminals; they’re performers of a weirdly spiritual craft, tricksters who understand that the world is not built on foundational truths but on shared illusions. Money changes hands, goods change hands, trust changes hands, but the real commodity is narrative—who tells it, who sells it, who gets to rewrite it.
Reading this in 2021 or 2025 feels uncanny because our age, too, is overrun with narrative-dealers: content creators, politicians, influencers, all of them peddling stories the way O. Henry’s grafters peddle schemes. The grifter as artist. The artist as grifter. The line dissolves.
Covid taught us how thin the membrane is between certainty and improvisation. That’s why the book slaps so hard now. O. Henry’s characters survive not because they’re villains, but because they’re agile. They think on their feet, live by wit, adapt faster than systems can catch them.
They’re entrepreneurs of chaos. If 2020-2023 taught us anything, it’s that life is mostly improv theatre with a bad backstage manager. We learned to negotiate shortages, misinformation, shifting rules, digital fatigue, and economic weirdness. So going back to these stories feels like revisiting a previous generation of hustlers—people who navigated uncertainty with charm, audacity, and the occasional burst of philosophical flair.
The postmodern flavour hits hardest when you realize that the binary between “honest work” and “dishonest hustle” is already dissolving at the edges.
O. Henry whispers, very softly but very cheekily:
1) Are the grafters wrong, or are they merely playing the same game as everyone else, just with better jokes?
2) In our era of start-ups and side-hustles, of passive income hacks and crypto-chaos, who exactly is the grafter?
3) Who gets to define legitimacy?
The stories feel like they’re winking at us across a century: Look around, sweetheart, everyone’s running a scheme. Some just write cleaner invoices.
And through all this, there is warmth. A strange tenderness. O. Henry is famously sentimental, but never saccharine. His con-artists stumble into situations where their schemes collide with something softer—human vulnerability, unexpected affection, flashes of generosity. And this tension between mischief and humanity is what gives The Gentle Grafter its glow.
Even during the pandemic, when everything felt abrasive, people were still doing tiny acts of kindness—overpaying the vegetable vendor, supporting a friend’s tiny online business, tipping the delivery guy more than usual. Survival and compassion danced together. In O. Henry’s universe too, the grifters might cheat you, but they won’t crush your spirit. They might bend the rules, but they still follow a personal, weirdly sacred code.
There’s also the unmistakable charm of the American frontier mythos—a world in flux, a world still self-inventing. The characters are restless, mobile, shape-shifting. No one stays one thing for too long. Identity is fluid not because the author is making a grand philosophical statement but because that was the nature of life then: people were reinventing themselves as fast as trains could take them from one town to another.
But reading it today, in a world where online avatars, curated feeds, and digital personae let us reinvent ourselves daily, the stories feel like early drafts of everything we currently experience.
The contemporary self is a curated myth; the grafter just got there early.
O. Henry’s humour still lands, surprisingly hard. A kind of deadpan mischief runs through the narration, like the narrator keeps nudging you in the ribs, whispering, “You see what I’m doing here, right?” It’s that slyness that makes the book sing. He isn’t mocking the grafters; he’s admiring their creativity. They’re flawed, yes, but never dull. And because the stories are filtered through this mischievous narrative tone, they acquire the rhythm of a campfire conversation—confessional, exaggerated, but emotionally true.
During Covid, when human connection felt strangely pixelated, these stories brought back a sense of conversational warmth: the feeling of sitting with a storyteller who knows exactly when to lean in, when to pause, when to drop the line that makes you grin into your mask.
What’s most striking, perhaps, is how deeply the book understands American capitalism—not the corporate giant we know now, but the raw, improvisational capitalism of individuals hustling for survival. The grafters treat the world as a marketplace of narratives, values, and opportunities.
They know that the real economy runs on confidence, not cash. They know that persuasion is a form of currency, and belief is an investment with high risk and high return. Postmodern theory—Baudrillard, Lyotard, Derrida—arrives decades later to tell us that society runs on simulacra, that authenticity is a cultural performance, that meaning is constructed through language. O. Henry’s grafters shrug and say, “Yeah, we knew that.”
And then there’s the loneliness underneath. The drifting. The sense that these characters are always standing on the edge of belonging but never quite stepping into it. They form alliances, yes, but never homes. They share bottles but not roots. They travel together, but not toward stability.
This nomadic emotional landscape hits harder in a post-pandemic world where dislocation—physical, psychological, moral—became a shared human experience. The grafters invent stories because they have no permanent stories of their own; they create schemes because permanence eludes them. It is both comedy and ache.
O. Henry does something rare in these tales: he humanizes the hustler without romanticizing the hustle. He shows the absurdity of human desire—the desire to get ahead, to outwit the system, to find shortcuts to dignity or comfort. But he also shows the fragile, stubborn humanity underneath all that scrambling. The grafters are not villains; they are dreamers with questionable methods. They’re not predators; they’re improvisers. They’re not immoral; they’re morally flexible. The difference matters.
Reading The Gentle Grafter in the digital age adds yet another layer. Today’s world is full of grifters operating at institutional scale—fake news empires, algorithmic manipulation, corporate schemes hiding behind pastel-coloured branding. Compared to them, O. Henry’s con-men feel almost wholesome, artisanal even. Handmade scams.
Ethically sourced deceit. Small-batch trickery. In a time when deception has become industrialized, these little stories feel like a reminder that the personal, human-scale trickster is not an enemy but a comic reflection of ourselves.
The postmodern undercurrent lies in the book’s refusal to privilege any single truth. Every scheme has multiple versions. Every con has shifting motivations. Every character believes their own performance.
Truth becomes something negotiated rather than discovered. And because the stories stay light, funny, and conversational, this philosophical slipperiness lands softly. You don’t feel lectured; you feel invited into a game where everyone is improvising the rules as they go.
What also endures is O. Henry’s deep affection for storytelling itself. The way each tale feels like it has been told in a bar, or under a tree, or during a lull in travel—half performance, half confession.
He captures the social life of narrative: how stories create community, how they mask insecurity, how they soothe the restless mind. During Covid, when narratives were our lifelines—messages, calls, books, memes—this felt especially urgent. Storytelling became a survival instinct, a way to connect across distance. O. Henry’s grafters tell stories because it is their livelihood. We told stories to ourselves because it was our way of navigating fear.
The charm of The Gentle Grafter lies not in its plots but in its worldview: a world where people are flawed but rarely cruel, where every trick contains a joke, where survival is a creative art, and where the line between fiction and strategy dissolves into the soft haze of human absurdity.
It is a book about making do, making up, and making sense—all skills we honed during lockdown. And because the stories are episodic, you can dip into them the way you dip into conversations—no pressure, no linearity, no demand to remember every detail.
During a time when attention felt scattered, this was exactly what the mind needed.
What stays with you long after the stories fade is the feeling that the world O. Henry builds is strangely optimistic.
Not naïve.
Not blind.
Just quietly trusting in the idea that humans—even shady, scheming humans—carry an ember of goodness that refuses to die.
And if that isn’t the most pandemic-era lesson ever, I don’t know what is.
Most recommended.
February 15, 2016
It took me the longest time to finish this, even though every time I picked it up to read a chapter, I enjoyed it.
As a fan of Jerome K Jerome I would recommend this. Entertaining and funny, I shall look out for more of his work. And hopefully it won't take me as long to finish.
As a fan of Jerome K Jerome I would recommend this. Entertaining and funny, I shall look out for more of his work. And hopefully it won't take me as long to finish.
October 10, 2013
A collection of short stories about grafters who travel, peddle and swindle in the South. Those grafters have different business ethics and moral senses, and their artistic plots lead them to an unsuspected but comic ending.
September 19, 2015
Many great short stories
July 5, 2016
The master of the surprise ending tells tales of grifters Jeff and Andy and their "Scams Across America" tour...perfect reading for this political season!
April 11, 2018
I never saw so much double talk in my life. It’s a work of art.
November 9, 2024
3 stars, Metaphorosis reviews.
Summary
A collection of stories about intermittently honest con artist Jeff Peters and his compatriots.
Review
On this fifth collection of stories, O. Henry tries again to give the collection a theme – as he did with his western stories. This time, retired con man Jeff Peters is relating his experiences – invariably the story of a grift that didn’t always go right.
The stories are pleasant, but the conceit doesn’t really work here. I never felt as engaged by Peters and his cohort as I’d have liked. There’s also necessarily a sameness to the stories that palled fairly quickly. While each con is different, the general approach and tone is often the same. O. Henry applies his trademark fun with vocabulary and the occasional twist ending, but it’s not enough to make the collection stand out.
While I enjoyed this well enough, and the stories are all short and easily digested, I was never really eager to pick the book up.
Summary
A collection of stories about intermittently honest con artist Jeff Peters and his compatriots.
Review
On this fifth collection of stories, O. Henry tries again to give the collection a theme – as he did with his western stories. This time, retired con man Jeff Peters is relating his experiences – invariably the story of a grift that didn’t always go right.
The stories are pleasant, but the conceit doesn’t really work here. I never felt as engaged by Peters and his cohort as I’d have liked. There’s also necessarily a sameness to the stories that palled fairly quickly. While each con is different, the general approach and tone is often the same. O. Henry applies his trademark fun with vocabulary and the occasional twist ending, but it’s not enough to make the collection stand out.
While I enjoyed this well enough, and the stories are all short and easily digested, I was never really eager to pick the book up.
January 15, 2021
I love witty wordplay presented in 'The Gentle Grafter'. I'd recommend to listen to an audio book, because it gives a better understanding of jokes based on similar pronunciation of words. Honestly speaking, I found the last quarter of the book not as interesting as the beginning.
Being a learner of English, I'd also like to rate the comprehensibility of the book. It has a lot of rarely used words, neologisms ('octopusing' got me confused at first) and sometimes the grammar is a little bit difficult. So I rate it 3/5.
Being a learner of English, I'd also like to rate the comprehensibility of the book. It has a lot of rarely used words, neologisms ('octopusing' got me confused at first) and sometimes the grammar is a little bit difficult. So I rate it 3/5.
August 14, 2018
Sometimes the swindler gets swindled, which adds to the charm of these stories.
Warning: Story 12 or 13 (I cannot remember which) has some racial attitudes and terminology that is not acceptable today. It is towards the beginning of the story, describing how Jeff hooked up with his partner for their latest adventure.
Warning: Story 12 or 13 (I cannot remember which) has some racial attitudes and terminology that is not acceptable today. It is towards the beginning of the story, describing how Jeff hooked up with his partner for their latest adventure.
June 19, 2021
Reading O'Henry is like taking a trip through turn-of-the-century America with a tour guide who enjoys the average person and has an above-average appreciation of the absurd. I love his use of language, his often homely and decent main characters, and his hallmark twist at the end of each story.
November 7, 2022
The first story was very profligate and I thought O. Henry missed the quarry with the impassible twist denouement. But what the hay might as well imbibe another bunch of blather which was much the renovation. Note: malapropisms proliferate in this opus minimus.
March 10, 2018
This was not my favorite of O. Henry's short story books. All of the stories were about grafts (swindles) that were either effective or not. Most were okay, but not as great as other stories of his.
April 30, 2021
Even though I didn’t like the plot, the humor and the storytelling style was enjoyable. I liked the writing style of the stories and the surprising end of each one of them.
July 26, 2021
Some of the references were dated; lots of allusions to Bryan, for instance. A shocking racist section in "A Tempered Wind" (p. 164). Not O Henry at hi best.
January 31, 2023
From the author of the gift of the magi. This is a dated book with early americana references and prejudice.
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