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Roads of Destiny

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An adventure story.

312 pages, Hardcover

First published January 1, 1902

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About the author

O. Henry

2,913 books1,863 followers
Such 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.

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Displaying 1 - 30 of 30 reviews
Profile Image for Madhulika Liddle.
Author 22 books547 followers
April 4, 2025
A collection of 22 short stories by one of the masters of the craft.

The stories in this collection are fairly varied, but there are some settings and tropes that appear in more than one story. The soldier of fortune, for instance, generally going to some impoverished South American country to help start off a revolution. Or a tramp, a man with no fixed address and nobody by way of family, who ends up in some adventure. Several stories are set in South America (or in Texas or other states that border Mexico), some in New Orleans. There are stories of love and ambition, of fortune and the way we humans often cannot control our destinies—or, in some cases (the well-known story A Retrieved Reformation, for example) how it is up to us to decide what path we will take.

I have to confess that I didn’t like all of these stories equally. Some, like A Retrieved Reformation, A Double-Eyed Deceiver, Friends in San Rosario and The Enchanted Profile I had read before and loved even now. Others, like The Guardian of the Accolade, Phœbe and On Behalf of the Management, were new to me but stories which I enjoyed immensely. Several others, however, I found a little tiresome: too wordy, too meandering, without the crispness and the zing I generally associate with O Henry’s writing. In this category, the stories I especially found a bit tedious were The Fourth in Salvador (I saw the twist coming in this story), Whistling Duck’s Christmas Stocking, The Halberdier of the Little Rheinschloss, A Departmental Case and Cherchez La Femme. Compared to the others, these were a little ho-hum, but not terrible.

On the whole, though, a readable collection, and of course the best thing about short stories is that you can dip into them a little at a time: good for a quick bit of reading before bedtime.
Profile Image for Manuel Alfonseca.
Author 80 books214 followers
August 31, 2025
ENGLISH: In this collection of 22 stories by O.Henry, I liked three of them specially, besides the story that gives title to the collection:

"The discounters of money" about an ornithological millionaire (a millionaire through inheritance, i.e. because of the stork) who wants to marry a young lady who despises money.

"A retrieved reformation" about a safe-cracker who reforms when he falls in love.

"Friends in San Rosario," a tale of two friends, worthy of comparison to famous stories about great friends, as that by Don Juan Manuel in Spanish literature, or as the old story about Damon and Pythias, in the time of the tyrant Dyonisius of Siracuse. For me, this was the best story in this collection.

ESPAÑOL: En esta colección de 22 cuentos de O.Henry, además del que da título a la colección, me gustaron especialmente los tres siguientes:

"Los que no tienen en cuenta el dinero" sobre un millonario por herencia que corteja a una joven que desprecia el dinero.

"Una reforma recobrada" sobre un ladrón de cajas fuertes que se reforma cuando se enamora.

"Amigos en San Rosario", la historia de dos amigos, digna de compararse con historias famosas de grandes amigos, como la de Don Juan Manuel en literatura española, o la antigua sobre Damon y Pitias, en la época del tirano Dionisio de Siracusa. Este fue el cuento que más me gustó.
Profile Image for Paul Groos.
Author 6 books8 followers
February 14, 2017
A collection of short stories, some funny, with twist endings. O.Henry's style is witty, but sometimes difficult to understand. He often introduces his stories with his view on American history and society, which is not always easy to understand for the modern reader. The stories are inventive and creative. A nice discovery.
Profile Image for Scoats.
311 reviews6 followers
August 26, 2018
Jeez O. Henry could write. So many thoughts. Please forgive any misspellings or words that are mistyped.


O. HENRY THE MAN, THE WRITER
For those who don't know about O. Henry, he was a short story writer at the start of the 20th century. His stories often had a surprise twist. Like an early M Night Shyamalan but without the sucky stretch. O Henry's most famous story is the Gift of the Magi with the hair combs and the watch chain.

O. Henry was a pen name. He lived quite a life (including being a pharmacist, ranch hand, bureaucrat, publisher, fugitive and convict) before becoming O. Henry the famous short story writer living in New York City aka The Four Million.

If you have never read any O. Henry, check out After Twenty Years https://americanenglish.state.gov/fil... . It should only take 5 to 10 minutes to read the whole thing. A grade school teacher read it to our class 40 years ago and I became a fan.

When enough short stories were published in magazines, they were released in book form. Roads of Destiny is one of those.


ROADS OF DESTINY THE BOOK
The unrelated stories take place all over. France, New Orleans, South America, New York City, Texas, and are all places where O. Henry lived at some point.

The stories that take place in NYC are my favorites. They are densely packed with jokes and references, most of which are lost to the ages. It's like listening to a Dennis Miller monologue back in the 80s or a Highway 61 Revisited era Bob Dylan song. The man could put words together.

These stories are over 110 years old, and some things are dated, but unlike Charles Dickens, some of which can a chore to plow through, remain wonderfully readable. And most of the stories did have a twist. It was an enjoyable ride.


ABOUT THE EDITIONS I HAVE
Edition 1
Somewhere along the line at a thrift store or similar, I picked up 3 of the novel length short story collections, all with matching bindings. The book I have was published in 1919 and features a stupid illustration at the beginning with a line from one of the stories. The line contains the N word. For better or worse, it is captured here https://archive.org/details/roadsdest...

Was O. Henry a racist? Did I have to reconsider liking him? The few instances of the N word are all spoken by characters not by the narrator. The story in question is near the end and among the weakest of the lot. Unlike Ian Flemming who's voice as a narrator comes off as the racist he was, O. Henry remains likeable.

Sign of the times, oh the irony - so the book has the N word but when it came to printing "damn", they printed it as "d--n". We've come a long way as a country. Thank God.

Edition 2: Masters Library Edition
Way before ebooks and the Worldwide Web, in the 1980s Masters Library would give old time American authors the big leather bound treatment. Sort of a CD box set, but for books. Stamped on the back, in gold, is "BONDED LEATHER". I guess I should look up what the bonded part of that means.

When I was in college, after reading about it in the Sunday paper, I asked for the just released O. Henry edition for Xmas. I expected someday I would read it. It only took 30+ years for me to get to it. This edition has most but not all of the book length collections.

After starting the 1919 printed book, I realized it was in BONDED LEATHER so I switched.

BONDED LEATHER omits the offensive illustration but keeps the N word and the original printing of d--n.

Edition 3: Free eBook
I was in the middle of reading this when I headed out of town. Rather than lug the big leather book with me, I downloaded the in public domain eBook onto my tablet. I switched back the BONDED LEATHER when I got home, mostly because the tablet stays on the other floor of our house.

While at it, I downloaded rest of O. Henry's books. I have set aside the trio of matching books for donation to the used book store. I'm keeping the BONDED LEATHER version and will read the rest of the books in it over the next year or so, while mixing up my reading with other writers.
Profile Image for Brenda.
769 reviews158 followers
August 15, 2015
4.5
SO SO SO GOOD! I loved it!
I was a bit lost at the beginning but when I understood the branches and those things I was absolutely hooked.
Profile Image for Pallavi Kamat.
212 reviews77 followers
June 13, 2016
Ah, the eternal 'What, if' question. Also, the 'Two roads diverged in a wood' conundrum explained in a brilliant fashion. I bow to you O'Henry!
3,480 reviews46 followers
September 7, 2023
3.9⭐

Roads of Destiny is a story collection by O. Henry, published in 1909. There are twenty-two short stories in this collection.

Roads of Destiny 5⭐
The Guardian of the Accolade 4.25⭐
The Discounters of Money 4.75⭐
The Enchanted Profile 3.5⭐
"Next to Reading Matter" 3.25⭐
Art and the Bronco 4⭐
Phoebe 4⭐
A Double-dyed Deceiver 3.5⭐
The Passing of Black Eagle 3.25⭐
A Retrieved Reformation 5⭐
Cherchez la Femme 3.75⭐
Friends in San Rosario 5⭐
The Fourth in Salvador 4⭐
The Emancipation of Billy 4⭐
The Enchanted Kiss 3.5⭐
A Departmental Case 4⭐
The Renaissance at Charleroi 3.25⭐
On Behalf of the Management 3.5⭐
Whistling Dick's Christmas Stocking 4.25⭐
The Halberdier of the Little Rheinschloss 3.25⭐
Two Renegades 3.5⭐
The Lonesome Road 3⭐
Profile Image for Classic reverie.
1,852 reviews
April 21, 2024
O. Henry's "Roads of Destiny" is a collection of 26 stories varies with romance, Westerns, mysteries, soldiers of fortunes and tramps. I just wish I could watch the silent film and wonder what direction they took. Love O. Henry's stories!

Highlights and synopsis from Delphi collection of his works
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O. Henry’s sixth short story collection was first published in 1909 and contains 26 tales, mostly based in New York, following the same format as his successful The Four Million collection. The title story was made into a 1921 silent film, produced and distributed by Goldwyn Pictures, directed by Frank Lloyd and starring actress Pauline Frederick.


Short stories from collection below

ROADS OF DESTINY -All the branches - David fights with his girlfriend and leaves home.
THE LEFT BRANCH -David helps a young niece is this a good choice?
THE RIGHT BRANCH -David takes another road but ends up in trouble with the King?
THE MAIN ROAD - David has another fate on this road.
THE GUARDIAN OF THE ACCOLADE- Is the bank owner embezzling?
THE DISCOUNTERS OF MONEY -Can money buy you love?
THE ENCHANTED PROFILE -Is Ida's boss rich woman?
“NEXT TO READING MATTER” -Will the ugly or handsome man win the girl?
ART AND THE BRONCO -Political barter at its best?
PHŒBE -Is a star the cause of bad luck?
A DOUBLE-DYED DECEIVER - Is a kid a scoundrel?
THE PASSING OF BLACK EAGLE -Is the the terror really that?
A RETRIEVED REFORMATION - A safe cracker falls in love with a bankers daughter.
CHERCHEZ LA FEMME - A detective and mystery are combined.
FRIENDS IN SAN ROSARIO -Troubles when a bank examiner comes to town.
THE FOURTH IN SALVADOR - July 4 adventures in another country.
THE EMANCIPATION OF BILLY -Is Billy always just the governor's son?
THE ENCHANTED KISS -Sam is in love but very shy.
A DEPARTMENTAL CASE -An old friends daughter is in trouble.
BENTON SHARP MEETS HIS MATCH -Finishing up "A Departmental Case" short story.
THE RENAISSANCE AT CHARLEROI -A sister waits for a long lost brother to return.
ON BEHALF OF THE MANAGEMENT -Election troubles
WHISTLING DICK’S CHRISTMAS STOCKING - Christmas with bandits
THE HALBERDIER OF THE LITTLE RHEINSCHLOSS -A love story concerning a restaurant
TWO RENEGADES - When abroad and your government gives you no hope.
THE LONESOME ROAD- A hen pecked husband and bachelor friend go out


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ON BEHALF OF THE MANAGEMENT
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I had it from Sully Magoon, viva voce. The words are indeed his; and if they do not constitute truthful fiction my memory should be taxed with the blame.
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“‘I’ve been manager here for a year,’ says Denver, as we drew nigh. ‘When I took charge,’ says he, ‘nobody nor nothing ever stopped at the Brunswick. The clock over the clerks’ desk used to run for weeks without winding. A man fell dead with heart-disease on the sidewalk in front of it one day, and when they went to pick him up he was two blocks away. I figured out a scheme to catch the West Indies and South American trade. I persuaded the owners to invest a few more thousands, and I put every cent of it in electric lights, cayenne pepper, gold-leaf, and garlic. I got a Spanish-speaking force of employees and a string band; and there was talk going round of a cockfight in the basement every Sunday. Maybe I didn’t catch the nut-brown gang! From Havana to Patagonia the Don Señors knew about the Brunswick. We get the highfliers from Cuba and Mexico and the couple of Americas farther south; and they’ve simply got the boodle to bombard every bulfinch in the bush with.’ “When we got to the hotel, Denver stops me at the door.
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Sully,’ says he, with seriousness and levity, ‘I’ve been a manager of one thing and another for over twenty years. That’s what I was
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cut out for — to have somebody else to put up the money and look after the repairs and the police and taxes while I run the business. I never had a dollar of my own invested in my life. I wouldn’t know how it felt to have the dealer rake in a coin of mine. But I can handle other people’s stuff and manage other people’s enterprises. I’ve had an ambition to get hold of something big — something higher than hotels and lumber-yards and local politics. I want to be manager of something way up — like a railroad

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or a diamond trust or an automobile factory. Now here comes this little man from the tropics with just what I want, and he’s offered me the job.’
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“‘He’s no ‘coon,’ says Denver. ‘He’s General Rompiro — General Josey Alfonso Sapolio Jew-Ann Rompiro — he has his cards printed by a news-ticker. He’s the real thing, Sully, and he wants me to manage his campaign — he wants Denver
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C. Galloway for a president-maker. Think of that, Sully! Old Denver romping down to the tropics, plucking lotus-flowers and pineapples with one hand and making presidents with the other! Won’t it make Uncle Mark Hanna mad? And I want you to go too, Sully. You can help me more than any man I know.
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“‘Wasn’t I just giving you his rating?’ says Denver. ‘His country is one of the few in South America where the presidents are elected by popular ballot. The General can’t go there just now. It hurts to be shot against a wall. He needs a campaign manager to go down and whoop things up for him — to get the boys in line and the new two-dollar bills afloat and the babies kissed and the
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machine in running order. Sully, I don’t want to brag, but you remember how I brought Coughlin under the wire for leader of the nineteenth? Ours was the banner district. Don’t you suppose I know how to manage a little monkey-cage of a country like that? Why, with the dough the General’s willing to turn loose I could put two more coats of Japan varnish on him and have him elected Governor of Georgia.
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“Before the three days was up I decided to join Denver in his campaign. Denver got three months’ vacation from his hotel owners. For a week we lived in a room with the General, and got all the pointers about his country that we could interpret from the noises he made.
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When we got ready to start, Denver had a pocket full of memorandums, and letters from the General to his friends, and a list of names and addresses of loyal politicians who would help along the boom of the exiled popular idol. Besides these liabilities we carried assets to the amount of $20,000 in assorted United States currency.

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Here is moneys,’ says the General, ‘of a small amount. There is more with me — moocho more. Plentee moneys shall you be supplied, Señor Galloway. More I shall send you at all times that you need. I shall desire to pay feefty — one hundred thousand pesos, if necessario, to be elect. How no? Sacramento! If that I am president and do not make one meelion dolla in the one year you shall keek me on that side! — valgame Dios!’
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“In a few more days the campaign managers from the other towns came sliding into Esperitu. Our
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headquarters was a busy place. We had an interpreter, and ice-water, and drinks, and cigars, and Denver flashed the General’s roll so often that it got so small you couldn’t have bought a Republican vote in Ohio with it.
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“Denver went ahead and worked things smooth. He dealt out money on the quiet to his lieutenants, and they were always coming after it. There was free drinks for everybody in town, and bands playing every night, and fireworks, and there was a lot of heelers going around buying up votes day and night for the new style of politics in Espiritu, and everybody liked it. “The day set for the election was November 4th. On the night before Denver and me were smoking our pipes in headquarters, and in comes
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Hicks and unjoints himself, and sits in a chair, mournful. Denver is cheerful and confident. ‘Rompiro will win in a romp,’ says he. ‘We’ll carry the country by 10,000. It’s all over but the vivas. To-morrow will tell the tale.’ “‘What’s going to happen to-morrow?’ asks Hicks. “‘Why, the presidential election, of course,’ says Denver. “‘Say,’ says Hicks, looking kind of funny, ‘didn’t anybody tell you fellows that the election was held a week before you came? Congress changed the date to July 27th. Roadrickeys was elected by 17,000. I thought you was booming old Rompiro for next term, two years from now. Wondered if you was going to keep up such a hot lick that long.’ “I dropped my pipe on the floor. Denver bit the stem off of his. Neither of us said anything. “And then I heard a sound like somebody ripping a clapboard off of a barn-roof. ’Twas Hicks laughing for the first time in eight years.”
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Sully Magoon paused while the waiter poured us a black coffee. “Your friend was, indeed, something of a manager,” I said. “Wait a minute,” said Sully, “I haven’t given you any idea of what he could do yet. That’s all to come. “When we got back to New York there was General Rompiro waiting for us on the pier. He was dancing like a cinnamon bear, all impatient for the news, for Denver had just cabled him when we would arrive and nothing more.

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“‘Am I elect?’ he shouts. ‘Am I elect, friend of mine? Is that mine country have demand General Rompiro for the president? The last dollar of mine have I sent you that last time. It is necessario that I am elect. I have not more money. Am I elect, Señor Galloway?’ “Denver turns to me. “‘Leave me with old Rompey, Sully,’ he says. ‘I’ve got to break it to him gently. ’Twould be indecent for other eyes to witness the operation. This is the time, Sully,’ says he, ‘when old Denver has got to
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make good as a jollier and a silver-tongued sorcerer, or else give up all the medals he’s earned.’ “A couple of days later I went around to the hotel. There was Denver in his old place, looking like the hero of two historical novels, and telling ’em what a fine time he’d had down on his orange plantation in Florida. “‘Did you fix things up with the General?’ I asks him. “‘Did I?’ says Denver. ‘Come and see.’
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“He takes me by the arm and walks me to the dining-room door. There was a little chocolate-brown fat man in a dress suit, with his face shining with joy as he swelled himself and skipped about the floor. Danged if Denver hadn’t made General Rompiro head waiter of the Hotel Brunswick!” “Is Mr. Galloway still in the managing business?” I asked, as Mr. Magoon ceased. Sully shook his head. “Denver married an auburn-haired widow that owns a big hotel
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in Harlem. He just helps around the place.”


*** A manager of a hotel, who is able to sell which made the hotel prosper, is selected by a General from South America to help elect him in his country but he cannot go back until elected for fear of being imprisoned. He gives his money to Denver who has his friend Sully help him elect the General, who gave the money to his manager but after the manager comes back empty handed after trying to win votes but the election was a week before they came and the man that knew of this when they came left laughing after he learned it was not for the election 2 years later.
Profile Image for Preetam Chatterjee.
6,833 reviews367 followers
November 24, 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’s something about Roads of Destiny that makes you want to sit a little straighter, breathe a little slower, and listen as though someone has just lowered their voice to confide a secret that stretches beyond the strict boundaries of time. Among O. Henry’s many stories, this one stands apart—not because it is louder or more dramatic, but because it glimmers with the quiet, nerve-tingling awareness that life is a vast branching map and each step we take is a wager against infinity. Perhaps that’s why reading it during Covid felt like entering a hall of mirrors: every choice mattered, every hesitation mattered, every recalibrated plan mattered. The world itself felt like a set of diverging paths, each leading to a different shape of survival.

O. Henry, usually the master of grounded urban comedy, pulls off something surprisingly metaphysical here. Without being preachy, without donning philosophical robes, without so much as shifting his narrative posture, he steps into the territory that modern theorists would label “multiverse thinking.” But he does it with charm, with storytelling ease, with that effortless magician-voice that makes the extraordinary feel domestic and the speculative feel inevitable. It is a story built on a single human impulse: the desire to flee one’s present moment and seek something better—but with the sting of knowing that possibility and regret always share a pillow.

The frame is deceptively simple: a young man, a burst of impulsive emotion, a fated crossroads. But O. Henry is not concerned with the melodrama of the moment. What he cares about is the shimmering tension of the “what if.” That tiny hinge on which the entire machinery of destiny pivots. And because he writes from inside that tension rather than outside it, the story feels uncannily modern—as if the author had swallowed Netflix multiverse dramas whole before spitting out a pared-down, elegant, pocket-sized version in 1909.

COVID was, in many ways, the global version of that crossroads. Every cancelled plan felt like a fork. Every health decision felt like one possible universe closing and another reluctantly opening. People reimagined their lives in whispered fragments: “If I had gone home earlier,” “If I hadn’t gone to that wedding,” “If I hadn’t taken that flight.” Reading Roads of Destiny in such a moment was like watching your own anxieties acquire literary ancestors. Choice became a story. Regret became an echo. Fate became a quiet background hum.

O. Henry’s protagonist isn’t a tragic hero. He’s not a philosopher-king. He’s simply a young man who wants something other than what he has, and this desire propels him into the lattice of destiny. His innocence is part of his appeal, but so is his earnestness. COVID-19 reminded us that earnestness—this vulnerable wanting—can become both a compass and a trap. Everyone, during that period, tried to chart new roads: baking, gardening, relocating, divorcing, reconciling, quitting jobs, starting side-hustles, or simply examining their lives with a severity they’d previously avoided. In that sense, O. Henry’s character becomes a patron saint of the human impulse to rewrite one’s life.

The story’s experimental structure marks it as O. Henry at his most ambitious. He dares to explore cause and effect not with lectures but with narrative fragments. Each path becomes a small self-contained world, each revealing something about not only the protagonist but the nature of chance itself. In a way, the story reads like a proto-postmodern gesture—an early exploration of the idea that identity is not a fixed point but a constellation of unrealised possibilities, each with its own internal logic. That multiplicity, that refusal to present a single authoritative reality, feels intensely contemporary.

And yet, O. Henry keeps the tone intimate. Warm. Human. There’s always a little smile hiding in the folds of the sentences. Even when the story leans toward the eerie, it never loses its gentle humour. Covid-era readers clung to humour like a life raft—memes about banana bread, jokes about Zoom fatigue, ironic commentary about how every day felt like a VGA-resolution loop. Roads of Destiny feels like a literary cousin of that coping mechanism. The humour is subtle, but it serves the same function: a way to endure the immensity of uncertainty without succumbing to it.

That’s where O. Henry’s genius glints. He knows that the idea of multiple destinies can be terrifying if left in the hands of a grim storyteller. Instead, he frames the whole philosophical conundrum as an unfolding curiosity. A narrative experiment that invites you to lean forward and trace the seams of possibility with your fingertip. It is the literary version of standing in front of a mirror maze—not to panic, but to marvel.

The emotional heart of the story lies in its exploration of agency. O. Henry suggests, in the sweetest, most mischievous undertone, that human beings are always dancing between autonomy and fate. Our choices matter, but their outcomes do not always belong to us. Our desires shape our actions, but the world has its own set of unpredictable counter-moves.

COVID hammered this into collective consciousness: you could plan everything down to the minute, and the universe would still shrug you into lockdown. The protagonist’s branching roads embody this tension. Each path reflects a different form of agency, but each also reveals the limits of what agency can accomplish.

The lyrical quality of O. Henry’s writing here deserves praise. He paints landscapes—not lushly, not indulgently, but with a kind of careful brushwork that lets you feel the dust on the road, the shift of light across the horizon, the emotional weather inside the protagonist’s heart. And this spareness, this refusal to over-describe, is what gives the story its dreamy, timeless quality. It feels like a tale whispered under lamplight, not pinned down by era or geography.

It also carries the hint of the tragic—not the tear-soaked kind, but the fate-tinged kind found in ancient storytelling. A kind of modern-day myth-making. O. Henry doesn��t belabour the tragedy; he simply lets it hover. Covid made us hyper-aware of the fragility of human aspiration, the thinness of the membrane separating what we want from what we must accept. Roads of Destiny taps directly into that emotional register.

The philosophical core of the story can be read through a postmodern lens as well: the idea that no narrative is definitive, that each telling is merely one angle among many. If life is a text, then choices are simply edits. And O. Henry’s story is a demonstration of how easily meaning fractures when subjected to even slight shifts in circumstance. It aligns beautifully with the idea that identity is a perpetual drafting process, never finished, never stable. COVID-19 accelerated that process for many people. It cracked open assumptions about careers, relationships, family, and priorities. It forced everyone to see themselves on different possible paths, even if they didn’t choose them willingly.

One of the most enduring qualities of the story is its tenderness toward human folly. The protagonist’s impulsiveness isn’t condemned—it’s tenderly contextualised. O. Henry doesn’t punish his characters for wanting too much or too quickly. He simply acknowledges that longing is part of the human engine.

It drives us into mistakes, but it also propels us into adventures. That balanced generosity makes the story feel comforting even as it probes heavy themes.

Above all, Roads of Destiny is a meditation on narrative structures themselves. The story becomes a self-aware investigation into how stories are shaped by the roads they choose not to take. What makes a plot “the plot”? What makes a life “the life”? In giving the protagonist multiple paths, O. Henry exposes the artificiality of narrative inevitability.

And because he does this, decades before postmodernism formalised its theories, the story feels lightly prophetic.

That prophetic quality hits differently after Covid. Everyone has a “road” they didn’t take in those years. A relationship that didn’t happen. A job that was lost. A move that never occurred. A reunion that remained a floating wish. Reading O. Henry from within that emotional landscape makes the narrative feel less like fiction and more like catharsis. It becomes a space to acknowledge that life is indeed a set of branching possibilities—some realised, some lost, some imagined, some mourned.

O. Henry’s storytelling voice remains one of his greatest strengths. He never overplays. He never moralises. He never draws attention to the philosophical weight of what he’s doing. Instead, he lets the story unfold with the gentle pace of a wandering tune—comforting, rhythmic, quietly profound. Even the emotional peaks are delivered with a soft hand, as though the story itself respects the reader’s fragility.

And this fragility matters. COVID made fragility visible—not as weakness but as truth. People became softer, or harsher, or both. Everyone was quietly negotiating the emotional consequences of too many possibilities collapsing too quickly. In that sense, Roads of Destiny reads like a parable for the age: a reminder that every life contains multitudes, and every moment contains the seed of an alternate life running parallel to the one we inhabit.

The story’s structure—one character, three possible paths—also resonates because it mirrors the mental rehearsal of modern anxiety. We are constantly imagining alternate outcomes, alternate beginnings, alternate futures. O. Henry gives that anxious mental habit a narrative body. And he does it without ever letting the structure overshadow the soul of the story. The emotional throughline remains steady, graceful, and unbroken. It is one man’s yearning, refracted through the prism of circumstance.

By the end of the story, what lingers is not the mechanics of the plot but the texture of its emotional and philosophical fabric. You feel the presence of fate as a kind of soft pressure, but you also feel the stubborn glow of human agency. You feel the branching paths as both opportunities and traps. You feel tenderness where you expected irony.

You feel irony where you expected certainty. You feel O. Henry smiling just off-stage, aware of the cosmic joke but never cruel about it.
3,480 reviews46 followers
August 27, 2023
This is the title story of the volume Roads of Destiny a collection of short stories. It is an allegorical story in nature, one which suggests that the choice is not so much among different fates as among different versions of the same fate. This story explores three different versions of David's fate, ultimately leading to his unescapable destiny.

David Mignot is a shepherd from Vernoy, a small village in France who wants to be a poet. When he quarrels with his fiancé Yvonne, he decides to leave home and look for "fame and honor in the great world outside". Davd is a poet, which greatly affects his personality making him romantic and easy going. David comes to the first fork and sees three roads. This is the first serious choice on his way. Further, in the story, David will have to choose the path each time and this will lead him to new adventures and unexpected acquaintances. On his first choice he chooses the left branch. He meets an aristocrat the Marquis de Beaupertuys, who promised to marry his daughter off to the first man they came across. And this is just the beginning of David's journey as he comes back to the fork in the road to choose another branch and another adventure.
Profile Image for Margarita.
429 reviews3 followers
April 21, 2018
I loved this story. The message is a little bit "discouraging" but really interesting.
It's a story about our Destiny. Can we fight against our fate?
________

Me ha encontado esta historia. El mensaje es un poco "descorazonador" pero realmente interesante. Es una historia sobre nuestro destino. ¿Podemos luchar contra nuestro destino?
Profile Image for Helen.
3,654 reviews82 followers
August 16, 2018
Of the several O. Henry short story books I have read, this is one of the best! It seems to be works he wrote during the prime of his career. Most are more "masculine" stories about accomplishments, rather than love stories.
86 reviews1 follower
November 4, 2010
I really liked these short stories of ordinary American life. I'm not really a short story person so I didn't read them all but got about half way through.
Profile Image for Naiara Lew.
15 reviews1 follower
Read
May 24, 2013
I think this srory it´s really diferent from the ones i´m accostume but it´s classic reading, and it has a great final
Profile Image for Calvin Moalosi.
5 reviews
August 15, 2017
One of the best short stories I've ever read. You cannot escape your destiny.
Profile Image for Scoats.
315 reviews
September 5, 2025
Jeez O. Henry could write. So many thoughts. Please forgive any misspellings or words that are mistyped.


O. HENRY THE MAN, THE WRITER
For those who don't know about O. Henry, he was a short story writer at the start of the 20th century. His stories often had a surprise twist. Like an early M Night Shyamalan but without the sucky stretch. O Henry's most famous story is the Gift of the Magi with the hair combs and the watch chain.

O. Henry was a pen name. He lived quite a life (including being a pharmacist, ranch hand, bureaucrat, publisher, fugitive and convict) before becoming O. Henry the famous short story writer living in New York City aka The Four Million.

If you have never read any O. Henry, check out After Twenty Years https://americanenglish.state.gov/fil... . It should only take 5 to 10 minutes to read the whole thing. A grade school teacher read it to our class 40 years ago and I became a fan.

When enough short stories were published in magazines, they were released in book form. Roads of Destiny is one of those.


ROADS OF DESTINY THE BOOK
The unrelated stories take place all over. France, New Orleans, South America, New York City, Texas, and are all places where O. Henry lived at some point.

The stories that take place in NYC are my favorites. They are densely packed with jokes and references, most of which are lost to the ages. It's like listening to a Dennis Miller monologue back in the 80s or a Highway 61 Revisited era Bob Dylan song. The man could put words together.

These stories are over 110 years old, and some things are dated, but unlike Charles Dickens, some of which can a chore to plow through, remain wonderfully readable. And most of the stories did have a twist. It was an enjoyable ride.


ABOUT THE EDITIONS I HAVE
Edition 1
Somewhere along the line at a thrift store or similar, I picked up 3 of the novel length short story collections, all with matching bindings. The book I have was published in 1919 and features a stupid illustration at the beginning with a line from one of the stories. The line contains the N word. For better or worse, it is captured here https://archive.org/details/roadsdest...

Was O. Henry a racist? Did I have to reconsider liking him? The few instances of the N word are all spoken by characters not by the narrator. The story in question is near the end and among the weakest of the lot. Unlike Ian Flemming who's voice as a narrator comes off as the racist he was, O. Henry remains likeable.

Sign of the times, oh the irony - so the book has the N word but when it came to printing "damn", they printed it as "d--n". We've come a long way as a country. Thank God.

Edition 2: Masters Library Edition
Way before ebooks and the Worldwide Web, in the 1980s Masters Library would give old time American authors the big leather bound treatment. Sort of a CD box set, but for books. Stamped on the back, in gold, is "BONDED LEATHER". I guess I should look up what the bonded part of that means.

When I was in college, after reading about it in the Sunday paper, I asked for the just released O. Henry edition for Xmas. I expected someday I would read it. It only took 30+ years for me to get to it. This edition has most but not all of the book length collections.

After starting the 1919 printed book, I realized it was in BONDED LEATHER so I switched.

BONDED LEATHER omits the offensive illustration but keeps the N word and the original printing of d--n.

Edition 3: Free eBook
I was in the middle of reading this when I headed out of town. Rather than lug the big leather book with me, I downloaded the in public domain eBook onto my tablet. I switched back the BONDED LEATHER when I got home, mostly because the tablet stays on the other floor of our house.

While at it, I downloaded rest of O. Henry's books. I have set aside the trio of matching books for donation to the used book store. I'm keeping the BONDED LEATHER version and will read the rest of the books in it over the next year or so, while mixing up my reading with other writers.
Profile Image for Jefferson Fortner.
272 reviews2 followers
March 30, 2021
One of the official collections of O. Henry’s short stories. Several are somewhat atypical from his usual compositions. There are fewer stories that have the surprise twist at the end (although some do), and the humor less frequently relies on the malapropisms of the teamless semi-educated hobos, although once again such characters do appear in some stories. There are a significant percentage of straightforward stories with a vein of literary realism, which I believe elevates his overall craftsmanship to consideration with the great realists of he era, such as William Dean Howells and Mark Twain. This collection reminded me of one of his other collections, Heart of the West, and many of the stories do take place in Southern and Western settings.
Profile Image for Jeff Hobbs.
1,087 reviews32 followers
Want to read
September 25, 2021
Read so far:

*Roads of Destiny --
*The Guardian of the Accolade --
The Discounters of Money --
*The Enchanted Profile --
*Next to Reading Matter --
Art and the Bronco --
Phoebe --
*A Double Dyed Deceiver --
*The Passing of Black Eagle --
A Retrieved Reformation --3
*Cherchez la Femme --
*Friends In San Rosario --
*The Fourth in Salvador --
The Emancipation of Billy --
*The Enchanted Kiss --
A Departmental Case --
*The Renaissance At Charleroi --
On Behalf of The Management --
*Whistling Dick's Christmas Stocking --
*The Halbardier of the Little Rheinschloss --
*Two Renegades --
The Lonesome Road --3
79 reviews1 follower
July 23, 2023
Nice collection of O. Henry stories

Roads of Destiny provides an entertaining collection of O. Henry stories with some good ones and some not so great ones. You won't find many of the heavily anthologized classics in here, but there are some real gems scattered around especially later on.

However, many of the stories do date very badly, especially in terms of racial matters. There are a lot of jarring references, stereotypes and racial epithets used for the Black and Hispanic characters and idealizations of the antebellum South that all but ruin a number of the stories. With that warning in mind, this is a pretty good collection, especially for O. Henry fans.
Profile Image for Robin K.
485 reviews3 followers
October 2, 2019
So interesting. Henry essentially writes long, drawn out jokes ending with a one-line punchline. He’s obviously talented, uses lots of big words and educated references, and at times writes in the vernacular. Yet this book became tedious for me to read. There is a fair amount of casual racism indicative of the era in which he wrote, and wading through a story was often not worth the surprise ending. So, there you go.
1,681 reviews
April 15, 2019
More great stories from the master of the short story, these all featured sweet and honest con men getting the better of a situation by sheer luck or clever shenanigans. Not a page turner but a solid collection.
Also wouldn’t these stories make a good TV anthology with one charming character (think Zachary Levi) experiencing all these close calls?
Profile Image for aldana.
131 reviews
June 12, 2022
4.5⭐
I really enjoyed this story, it's short but so interesting!
Profile Image for Dystopian Mayhem  .
683 reviews
July 23, 2022
Each story has a deep message, and ends with a gasp or a sweet surprise, or an involuntary “aww Henry” or a smile and sometimes a laugh.
Profile Image for Antacq.
41 reviews
April 21, 2024
Interesante. Atrapante. Invita a leer y conocer al escritor estadounidense O’Henry.
Profile Image for S. Wilson.
Author 8 books15 followers
March 6, 2020
A collection of short fiction by O. Henry. This is my first direct exposure to O. Henry's work, and I can definitely see the appeal of his writing style. Henry's more humorous pieces remind me of Mark Twain in their ability to fill the gaps with subtle humor of a wise-crack variety, while the more preachy plot-twists feel more heavy-handed. I can definitely see my self reading more of his work. In this collection:

Roads of Destiny - Told in four parts (the other three being The Left Branch, The Right Branch, and The Main Road), a metaphorical tale about the inability to escape one's destiny. One of Henry's less than uplifting tales. Themes: Fate, Art (Poetry)

The Guardian of the Accolade - A misunderstanding results in the right outcome, albeit for the wrong reasons, with some rather unfortunate dialogue.Themes: Vice/Virtue, Misunderstanding, Banks

The Discounters of Money - A rich young man learns what money can't buy. Themes: Money, Romance

The Enchanted Profile - A stenographer becomes the unwitting obsession of a miserly spinster for all of the wrong reasons. Themes: Money, Romance

Next to Reading Matter - A sort of retelling of Cyrano de Bergerac as a cough drops ad, more or less. This one was a tad underwhelming. Themes: Con Artists

Art and the Bronco - Artistic aspirations and political manipulations come to blows. One common thread popping up in many of these stories involves individuals with artistic aspirations that lack the talent to follow their muse, usually with the message being that common folk shouldn't try to be artists; a strange position for a writer to come from. Themes: Art (Painting), Bureaucracy

Phoebe - The story of Bad-Luck Kearny, born under an unlucky star. Themes: Fate, Revolution

A Double-Dyed Deceiver - A con-job goes wrong. Or does it? Themes: Con Artists, Fate

The Passing of Black Eagle - A Rags to Riches story, of sorts, regarding the sudden arrival and mysterious disappearance of an outlaw legend. Themes: Con Artists, Derelicts

A Retrieved Reformation - A notorious safe-cracker takes a stab at the straight and narrow. Themes: Redemption, Criminals

Cherchez La Femme - Two reporters attempt to find the woman behind a dead man's missing fortune. Themes: Misunderstanding, Money

Friends in San Rosario - A bank examiner is treated to a tale of friendship upon finding a shortfall. Themes: Loyalty, Bureaucracy, Banks

The Fourth in Salvador - An Independence Day celebration by a handful of patriots in a banana republic gets a little out of hand. Themes: Patriotism, Bureaucracy, Revolution

The Emancipation of Billy - A father/son story, Themes: Community, Family

The Enchanted Kiss - Another story about romance and fate, feels very similar to Roads of Destiny. Themes: Fate, Romance

A Departmental Case - An aging cowboy turned federal employee tries to cut through the red tape to help an old friend's daughter. Themes: Loyalty, Bureaucracy

The Renaissance at Charleroi - A weird little parable about fading royalty and lost family, the ending is a bit too predictable. Themes: Romance, Family, Derelicts

On Behalf of the Management - A tale of third-world politics and the management of men. Themes: Bureaucracy, Business, Revolution

Whistling Dick's Christmas Stocking - A Hobo's Christmas Eve adventures. Themes: Derelicts, Redemption

The Halberdier of the Little Rheinschloss - A "Prince and the Pauper" type story, this one is probably more entertaining than it should be due to the main narrator, Waiter Eighteen. Themes: Rich/Poor

Two Renegades - A converted confederate explains to an old friend why he left the North for the South. Cute story. Themes: Revolution, Military, Bureaucracy

The Lonesome Road - A yarn about committing matrimony in the old west. One of my favorite in this collection.
Profile Image for Tinquerbelle.
535 reviews9 followers
Want to read
August 5, 2012
Henry, O.
The Complete Works of O. Henry

In compilation only.

1) Roads of Destiny
2) The Guardian of the Accolade
3) The Discounters of Money
4) The Enchanted Profile
5) "Next to Reading Matter"
6) Art and the Bronco
7) Phoebe
8) A Double-Dyed Deceiver
9) The Passing of Black Eagle
10) A Retrieved Reformation
11) Cherchez la Femme
12) Friends in San Rosario
13) The Fourth in Salvador
14) The Emancipation of Billy
15) The Enchanted Kiss
16) A Departmental Case
17) The Renaissance at Charleroi
18) On Behalf of the Management
19) Whistling Dick's Christmas Stocking
20) The Halberdier of the Little Rheinschloss
21) Two Grenades
22) The Lonesome Road
Profile Image for Sayed.
155 reviews
August 7, 2017
رغم سوء الترجمة التى قام بها شخص يدعي نور الدين الزرارى ، فالمجموعة القصصية رائعة وسامح الله المترجم
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