The story begins just before Christmas with a small sum of money: $1.87 to be exact, 60 cents of which was in pennies. For the writer O. Henry, the pittance was enough to launch his most famous work, a fable about poverty, love, and generosity, and also likely covered the drinks he plied himself with as he crafted the tale at Healy's, the neighborhood bar.

In “ The Gift of the Magi, ” first published in 1905, two down-on-their-luck lovebirds Della and Jim make sacrifices well beyond the cost of a boozy beverage to share their Christmas spirit with each other. The beloved tale tells of Della cutting off her gorgeous past-her-knees hair described in the story as, “rippling and shining like a cascade of brown waters” for $20 to buy her man the perfect gift: a platinum fob watch chain, “simple and chaste in design, properly proclaiming its value by substance alone and not by meretricious ornamentation.” Later on that fateful Christmas Eve, Jim offers his present in kind, combs for Della’s beautiful locks, purchased after he sold his watch. The timeless, ironic twist, emblematic of O. Henry’s oeuvre, reminds readers of the oft-repeated “true meaning of Christmas.” The sentiment is tiresome and trite, but the story’s soul endures.

First published by the New York World in 1905, and then to a wider audience in the 1906 collection Four Million (named for the NYC population, it was the number of stories O. Henry, whose real name was William Sydney Porter, believed existed in his adopted city), the 2,163-word masterpiece has become a holiday standard, a slim mix of pain and joy sitting on a fireplace mantel with other redemptive Yuletide perennials like A Christmas Carol , It’s A Wonderful Life , and “Fairytale of New York.”

The mixture of sadness and sentimentality in “Gift of the Magi” befits a man whose life was marked by repeated human tragedies. Porter was born in Greensboro, North Carolina, in September 1862, the same month as the Civil War battles at Antietam and Harpers Ferry. His father was a prominent doctor and inventor whose life unraveled after his wife died of tuberculosis when William was only 3. His father retreated into a private world of tinkering with machinery— a perpetual-motion machine, a steam-driven horseless carriage, a device for picking cotton —and drinking away his troubles. The diseases of alcoholism and tuberculosis would haunt Porter throughout his life.

At 20, in hopes of relieving his own perpetual cough, the “family curse,” Porter left North Carolina for the dry air of Texas and livedwith a sheep herder who had Greensboro ties. William worked the ranch on the Nueces River near San Antonio for two years, apparently becoming a proficient broncobuster while also learning Spanish and memorizing the dictionary. Two years later, he went to Austin where he took various jobs including cigar store clerk, pharmacist, bookkeeper and draftsman for the state’s General Land Office. He also played the guitar and sang baritone for the Hill City Quartette and met and fell in love with 17-year-old Athol Estes, who he wooed by helping with her homework. They eloped and were married two years later on July 5, 1887. Athol gave birth to a son in 1888, who died hours after birth; the following year, the couple had a daughter, Margaret.

Porter’s life was rife with sorrow, but outwardly, at least, he was seen as a good-natured raconteur with a sharp wit, especially after a few belts. On the ranch, he’d begun jotting down stories, mainly with a Wild West theme, but not doing anything with them. In Austin, with Athol’s encouragement, he upped his literary output and began submitting stories to the Detroit Free Press and Truth , a New York-based magazine featuring the likes of Stephen Crane. Along the way, he took a job as a teller at First National Bank and 1894, borrowed $250 from the bank (with a note signed by a couple of drinking buddies), bought a printing press and started self-publishing a weekly magazine. The Rolling Stone . Featuring stories, cartoons, and humor pieces, it found a local audience with print runs of more than 1,000. For a hot second, times were good.

“The little cottage [Potter] rented and lived in with his wife and children is now a museum. It’s in the middle of downtown Austin’s skyscrapers and looks even more modest and sweet than it did before the city grew,” says Laura Furman , a fiction writer who served as the series editor for the O. Henry Prize stories from 2002-19 . “The house doesn’t have many authentic O. Henry possessions but there’s enough in it to give you a sense of what his brief-lived family life might have been like. It’s widely believed that he was his happiest in that house. The happiness of family life didn’t last long for him.”

The Rolling Stone never made much money or made it beyond Austin, so Porter shut it down in 1895, later telling the New York Times that it had all the hallmarks of getting “mossy.” He decamped to Houston to write columns for the Daily Post, but was called back to court in Austin. The First National Bank, which had been freewheeling and informal in its lending practices, accused him of embezzling $5,000. Instead of facing the charges, Porter fled the country, eventually landing in Honduras, which had no extradition treaty with the United States. (It’s where he coined the term “ banana republic, ” in his story “ The Admiral,” which appeared in his first book, Cabbages and Kings .)

It was a short stay. After seven months, Porter returned to Texas to care for Athol who was suffering from tuberculosis. She died in July 1897. (In 1916, C. Alphonso Smith, a childhood friend of O. Henry’s, wrote that Della was modeled on Athol.) This time, he stayed in the Lone Star state and faced the music. In February 1898, William Sydney Porter was found guilty of embezzling $854.08 and sentenced to five years in federal prison at the Ohio Penitentiary. Various biographers , including Smith , have long held the evidence of serious criminal intent was flimsy and that while Porter kept haphazard records, bank mismanagement was more to blame, and he was actually punished for going on the lam. Porter who was never good with money and routinely walked the line of being dead broke, always maintained his innocence. From the North Carolina History Project :

“ When confronted with his crime, William would write his mother-in-law and claim, ‘I am absolutely innocent of wrongdoing in that bank matter…I care not so much for the opinion of the general public, but I would have a few of my friends still believe there is good in me.’ The Ohio Penitentiary was a harsh life for prisoners, but William received partial treatment due to his skills as a pharmacist. Allowed a higher status than the normal prisoner, William was given more free time, and it was during these long night hours that William adopted the pseudonym O. Henry and penned some of his best short stories.”

The official reason behind “O. Henry” as a pen name has never been fully established. An Inkwell of Pen Names links it to a cat from his childhood named “Henry the Proud,” a verse from a cowboy song called “Root, Hog, or Die.,” while the writer Guy Davenport , who wrote introductions to multiple collections believes it was a twist on “Ohio Penitentary” while also keeping his true identity safe in prison—the stories O. Henry wrote doing time were sent to the wife of an incarcerated banker in New Orleans to be sent out to editors—but the author himself claimed it was simply easy to write and say. The pseudonym may be a mystery, but his success was not. The first story published as O. Henry was “Whistling Dick’s Christmas Stocking.” Appearing in McClure’s magazine in December 1899, it tells the tale of a “professional tramp,” a fateful gift from a passing surry, and a good night’s sleep on Christmas Eve.

Released after three years for good behavior, O. Henry moved to Pittsburgh where Margaret, now 12, lived with her grandparents. She was never told of his being incarcerated, only that dad was away on business. (Tragically, Margaret too would die at 37 from tuberculosis, three days after getting married from her deathbed.) O. Henry didn’t stay long. He headed to the heart of the publishing world, New York City, the crowded relentless cosmopolitan polyglot he fell in love with and nicknamed “Baghdad-on-the-Subway.” The streetlife of New York would be a major inspiration for O. Henry as he penned some 380-some-odd stories while living in the Gramercy Park area. The nightlife, however, would exact a bigger toll as O. Henry drank himself to an early grave at the countless number of joints just like Healy’s. On June 5, 1910, at the age of 47, O. Henry died from cirrhosis of the liver and other health complications. (Many years later, his second wife from a short marriage, Sarah Lindsey Coleman, would emphatically proclaim he died from diabetes, not the bottle.)

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Nestled away on 18th St. near Gramercy Park, just a couple blocks from the bustling Union Square holiday markets, Pete’s Tavern welcomes tipplers with an awning reading “The Tavern O. Henry Made Famous.” The writer lived across the street at 55 Irving Place in a first floor apartment featuring three large windows where he could look out at his second home across the street, which was then named Healy’s Cafe . (First opened in 1864, the bar would be renamed Pete’s in 1922 after Peter Belles purchased the establishment, which today claims itself as the longest continuous tavern in New York City. During Prohibition, the flower shop in front led to the booze in the back, likely protected from police raids by its nearby proximity to Tammany Hall.)

The hard-drinking Henry became a regular at Healy’s and was said to consider it an extension of his office at the New York World , who hired him for $100 a week for a single story. Healy’s even made it into O. Henry’s story ‘The Lost Blend,’ but in disguise as “Kenealy’s,” perhaps to keep his favorite watering hole to himself.

According to biographer David Stuart, in late autumn 1905, a new World editor decided Henry’s salary far exceeded his output and ordered him fired. Unbeknownst to Henry, the World still wanted him to write up until his contract expired in December. So it came as a shock to Henry when, shortly before the World ’s big Christmas special edition came out on December 10, an office boy knocked on his apartment door looking for a contribution. The lackey wasn’t leaving without a story so O. Henry sat down and banged out “Gift of the Magi” in “two feverish hours” according to the faded plaque outside his apartment building. It fit Henry’s pattern of writing overnight, on deadline , and delivering at the last minute, but usually with pristine copy that didn’t require much editorial heavy lifting.

On the whole, “Gift of the Magi” encapsulates the best of what O. Henry stories accomplish, a brief lived-in human experience. One that is often, for good, bad, or in-between, given over to an unwanted fate, only to be rescued through a combination of sentimentality and his patented surprise ending.

“O. Henry had a strong sense of form; if you read a story of his blind, you’d be able to identify it as an O. Henry story by the movement of the action, leading up to his famous trick—the twist at the end,” says Furman. “The twist is really a wringing out of the plot elements and revealing something that was there all along but the reader hadn’t noticed. He was less interested in style than in getting a reaction from his reader. That performative aspect of his stories and his relationship to the reader as audience has appeal to writers now.”

Despite the plaque on 55 Irving Place, the question of where O. Henry scribbled down his masterwork remains an open one. Folklore handed down from generations of the tavern’s owners claims it was authored inside Pete’s—a sacred booth includes multiple pictures and a handwritten letter O. Henry wrote as William Sydney Porter deferring on a dinner invitation—but at least one dissenter claims it was authored in Henry’s apartment. Written in 1936, The Quiet Lodger of Irving Place is a series of reminisces about O. Henry’s time in New York City by his friend and colleague William Wash Williams. In it, Williams says “Gift of the Magi” was written in the room O. Henry rented. No official documentation exists either way, but what truly matters is the story has become synonymous with Pete’s Tavern, the New York City holiday season, and the wonderfully brighly festooned intersection of the two.

“Some of the decorations we have are over 50 years old, so I’d say the Christmas season has always been important to us here at Pete’s,” says general manager and tavern historian Gary Egan , who started working there as a waiter and bartender in 1987. “Every year, five of us put up all the lights and decorations. We close early and go from midnight to eight in the morning for three weeks straight. And at home, I make gallons and gallons of eggnog and bring it in. It’s brutal.”

Egan means the holiday stretch, of course, not the egg nog, which is delicious. Made with brandy, a glass runs $13, which could’ve probably bought a quality timepiece and a full-length wig in O. Henry’s day, but late on a Tuesday afternoon, with a wintry mix flurrying about the setting sun, before the boisterous crowds shuffled in, it wasn’t hard to be transported to Christmases past and to toast the spirit of Della and Jim in the reflected glow of a sea of red lights.

“[O. Henry’s] such an American character and it’s too bad an ‘O. Henry’ story has become somewhat of a cliche,” says Amanda Vaill , a writer and former book publisher who edited a 1994 collection of his works. “His other works deserve a bigger audience, but I also still vividly remember reading Magi at age 10 in a holiday anthology and thinking, ‘Oh, my gosh. Oh, no . No! NO!’ I was struck by the cruelty of the universe and the kindness of the characters within it.”

Furman has a similar recollection, saying, “I have fond memories of reading ‘Gift of the Magi’ as a child and thinking hard about the misfortune of the two main characters. It bothered me that they both failed in their presents. That’s how I saw it then. Later, I had an appreciation of the story’s cleverness and how tightly constructed it was—and I understood that it really didn’t matter if the presents weren’t the right ones since, in O. Henry’s view, their sacrifice was a sign of their love. I was more focused as a child on the presents than love.”

One reason the “Gift of the Magi” has had a longer time in the spotlight than any of the estimated 600 other stories O. Henry wrote over his lifetime--which were extremely popular, by 1920, a decade after his death, some five-million copies of his books had been sold in the United States —is that its seasonal message and framework has been paid homage for years.

The first one, The Sacrifice , was a silent film directed by D.W. Griffith in 1909. Later versions include O. Henry’s Full House , a 1952 quintet of his stories tied together by on-screen narrator John Steinbeck in his lone acting credit , a 1999 animated riff featuring the famous Disney mice and a harmonica in Mickey’s Once Upon A Christmas , and a tender 2014 Greek short film set during the country’s recent financial crisis. It’s also been a staple television plot, be it in a 1955 “ Honeymooners” episode in which Ralph Kramden pawns his beloved bowling ball, a 1988 “ Saturday Night Live” parody lampooning a future president impersonated by Phil Hartman and a gold-plated jewel-encrusted golf club door, and the one that introduced many a young Gen-Xer, myself included, to the O. Henry classic. In the 1978 special “ Christmas Eve on Sesame Street ”, Bert and Ernie follow the formula with a rubber duckie-for a cigar box/paper clip collection-for a soapdish trade. (In the end, Mr. Hooper shows up in the fuzzy roommates bedroom, returns their original items, and tells his Muppet pals they gave him the best gift of all.)

$1.87 might not buy a cup of holiday cheer anymore, but it remains holiday central at Pete’s Tavern, thanks to O. Henry’s deadline masterpiece, be it written with a stiff drink in a booth or not. The holidays are Egan’s craziest time, yet, given a chance to reflect on the Della, Jim, and the dewy-eyed scribe who made his tavern famous, the insanity of the season slips away, for a moment anyway.

“‘Gift of the Magi’ is heartwarming, a beautiful story with a hint of sadness,” he says. “It’s Christmas.”