Arthur Barry: The Gentleman Thief Who Dazzled the Jazz Age and Robbed Its Richest with a Smile
- U I Team
- Jun 26
- 12 min read
If you ever find yourself romanticising the glitzy outlaws of the 1920s, spare a thought for Arthur Barry, a polite burglar whose life seemed lifted from a crime caper novel but was all too real. Dubbed The Gentleman Thief by admiring newspapers, Barry spent the Roaring Twenties slipping in and out of mansions, mingling with high society and departing unseen with jewellery worth millions.
Yet for all the diamonds, champagne and scandals, his story is one of squandered genius, missed chances and an oddly admirable moral code, as moral as a jewel thief’s code can be.
From a Humble Irish Household to High Society Heists
Arthur Barry was born in 1896 in Worcester, Massachusetts, into a bustling Irish immigrant family. One of twelve siblings, his early years were far removed from stolen pearls and silk gloves. His family were ordinary working folk, earning their bread honestly, expecting Arthur to do the same.
But young Arthur matured too quickly for his own good and soon found himself unable to stomach the notion of fair trade. A restless mind and sticky fingers pulled him into the orbit of Lowell Jack, a notorious safecracker known for brewing up nitroglycerine in backrooms. As a boy, Arthur’s job was to ferry this volatile cargo to accomplices in nearby towns. It was an education in danger and dishonesty, and he took to it with worrying ease.
By fifteen, he’d graduated to full-time robbery, netting a tidy $100 on his first ‘hit’. But the life of rough stick-ups and grimy pawn shops quickly bored him. If he was going to steal, he reasoned, he’d steal elegantly, from the people who would feel it least.
A Master of Manners and Floor Plans
What set Barry apart from the usual hoodlum with a crowbar was his remarkable self-discipline and flair for disguise. Experts later concluded he could have been a formidable Wall Street baron if only he’d put his mind to it. Instead, he used that sharp mind to plan burglaries down to the last doorknob.
He dressed well, spoke better and carried himself like a gentleman. Dressed informally enough to blend in yet sharp enough to be noticed for all the right reasons, he would stroll through lavish lawn parties in Long Island or mingle at society galas. Between polite chit-chat and a discreet drink with the host, he memorised floor plans, noted where jewellery was stashed and spotted every possible alarm and exit.
Then, under moonlight, Arthur Barry returned, so softly that, on many occasions, homeowners did not stir until he flicked a torch beam across their eyes.
Champagne, Crowns, and the Perfect Crime
In an era known for its extravagance, Arthur Barry had a knack not only for getting into the party — but for stealing the silver on his way out. And sometimes, the silver wore a crown.
One evening in the mid-1920s, Barry was walking along 59th Street in Manhattan when he struck up conversation with a man whose tailored attire and polished accent stood out even in New York’s wealthiest quarter. It was none other than the Prince of Wales — the future King Edward VIII — in town on one of his regular, low-profile visits to the United States. With his usual ease and disarming charm, Barry introduced himself as Arthur Gibson and found in Edward a willing companion for the night.
Before long, the unlikely pair were sipping cocktails and sampling the nightlife of Prohibition-era Manhattan. Barry led the prince on a tour of the city’s speakeasies, including the infamous El Fey Club, where showgirls danced on tables and rules were suspended in favour of pure fun. At one point, Edward was spotted laughing as a dancer balanced his top hat jauntily on her bobbed curls.
For the Prince, it was a glittering memory of youth. For Barry, it was something else entirely — reconnaissance.
Not long afterwards, the Long Island estate of Edward’s cousin, Lady Edwina Mountbatten, was robbed during the early morning hours. Three rings, a platinum bracelet with 30 square-cut rubies, and a host of black pearl adornments belonging to Edwina and fellow guests were taken — a haul later estimated at $150,000 (well over $2 million today). Lady Mountbatten’s husband, Lord Louis Mountbatten, stirred briefly in his sleep during the theft. But Barry, crouched silently behind the bedroom curtains, waited until he drifted back off before making his exit.
He left no mess, no trace. Only empty jewellery boxes, and later, a perfectly polite note to the press declining to confirm or deny involvement.
The Woolworth Heiress and the Hotel Plaza Job
If Barry’s evening with Edward VIII was daring, his next big operation was audacious.
In 1925, he set his sights on the Plaza Hotel, that marble edifice overlooking Central Park, the kind of place where robberies simply did not happen. Yet one afternoon, in broad daylight, Barry walked calmly through its revolving doors, passed the reception with the air of a guest, and made his way to the six-room suite of Jessie Woolworth Donahue.
Donahue was the daughter of F. W. Woolworth, whose fortune came from five-and-dime retail stores that were now dotted across the continent. She was the kind of heiress for whom jewellery was worn like a second skin.
While Mrs Donahue soaked in the bath, only a few feet away, and her maid flitted about in the next room, Barry crept through the suite in complete silence. He ignored the obvious decoys, five ropes of pearls, of which four were good-quality imitations. He took only the real ones, worth $450,000 at the time. Then he slipped out as quietly as he came in.
By evening, the jewels had already been fenced, and the heiress, upon discovering the theft, refused to cooperate with the police out of embarrassment.
A Gentleman Among Thieves
Perhaps the most peculiar thing about Arthur Barry wasn’t the value of what he stole, but how he stole it, and how he treated those he robbed.
Barry never liked violence. It was inefficient, unpredictable, and messy. He preferred diplomacy, even charm. When he did wake homeowners mid-robbery, it was with the cool composure of a maître d’. A quiet “Good evening,” a cut phone line, and a calm request: “Please hand over the jewellery and no one gets hurt.”
One of his more famous encounters was with Mrs Livermore, a society matron startled awake by torchlight in her bedroom. Her voice shook as she asked, “Who is it?”
Barry’s reply was as smooth as silk: “Good evening, J.L., just don’t move. The phone lines are cut. Just hand over the jewellery and let us go.”
He helped her into her robe when he noticed she was shivering, struck a match and lit her cigarette to steady her nerves, and gently emptied the drawers of her dressing table. When Mrs Livermore begged him not to take a pinky ring given to her by her husband, Barry paused, then placed it delicately on her nightstand. As he exited, she could only whisper: “You are a real devil.”
Jewels Over Gold, and a Strange Disposal Habit
Barry’s eye was for precision and liquidity. He wasn’t interested in cumbersome silver candelabras or heavy heirloom brooches set in antique gold. He wanted gems, easy to fence, light to carry, hard to trace.
After each job, he would separate the stones from their settings and discard the metal in New York Bay. He’d hire a small motorboat, sail out just beyond the docks, and casually toss gold clasps and platinum mountings into the water as though feeding ducks.
It was wasteful, certainly. But for Barry, efficiency and escape always outweighed excess.
A Class Act, With a Curious Code
There’s something inherently contradictory about Arthur Barry. He was, at once, a criminal and a courtier, a thief and a performer. He robbed the rich not out of revenge, but because he believed they wouldn’t suffer. And while he took millions, he did so with an odd air of civility that even his victims struggled to resent.
In his own words years later:
“If a woman can carry around a necklace worth $750,000, she knows where her next meal is coming from.”
To the police, he was maddening. To the press, magnetic. And to the high society whose safes he emptied, he was — somehow — unforgettable.
The Bane of Detectives, the Darling of the Press
Detectives fumed at his uncanny ability to walk in and out of the most secure estates. Once, he balanced an 80-kilogram safe on his shoulders, carried it out of a Duchess’s bedroom and left without so much as creaking a floorboard.
He also knew the value of inside information, tracking wealthy ladies from casinos or department stores, calling the police posing as a patrolman to obtain their addresses, and following wedding announcements to time his raids.
His cleverness cost insurance companies dearly. Often, detectives would ‘recover’ some of Barry’s loot and return it to insurers for a fraction of its claimed value, a racket Barry cheekily hinted was more crooked than his own thieving.
Betrayal, Prison, and the Great Escape
By 1927, Arthur Barry was at the height of his infamy. His heists had grown more daring, more elegant, and more lucrative. The police were always a step behind. The society pages whispered about him in half-admiration, and detectives could do little but speculate as to who might be next.
But it wasn’t a dog, an alarm system, or even a misstep that brought Barry’s golden run to an end. It was jealousy.
Barry was a ladies’ man in the most classic sense, polished, flirtatious, and generous with his stolen spoils. Among his many romantic liaisons was a New York showgirl, a performer on the fringe of Broadway’s busy circuit. She had been seeing Barry for some time, but grew increasingly frustrated by his dalliances with other women, particularly his taste for actresses and chorus girls. Eventually, hurt turned to fury.
In a moment of anger, or perhaps calculated revenge, she tipped off the police, passing along details that connected Barry to the recent Livermore robbery, where $95,000 in jewels had vanished as the couple slept. It was the break the authorities needed.
Barry was swiftly arrested and convicted. At sentencing, the court showed little mercy. A judge handed him 25 years in Auburn Prison, upstate New York. It was a harsh sentence, but Barry had eluded justice for so long that few believed he’d stay put.
They were right.
Auburn, 1929: The Birthday Cake Breakout
Prison did not suit Barry — not the grim monotony, nor the constant surveillance. But what rankled most was the waste. Here was a man whose crimes were executed with the finesse of a stage magician, now reduced to making socks in a workhouse. He began observing routines, memorising guard movements, and identifying weaknesses.
He discovered one in particular: the prison's ammunition store was unusually housed within the walls, a design flaw. Only two guards manned it, and on Sundays, the yard was teeming with nearly 1,700 inmates enjoying their allotted ‘free time’. All Barry needed was a diversion.
On 28 July 1929, he baked a birthday cake in the prison bakery, more symbolic than celebratory, and persuaded one of the guards to deliver it to a fellow inmate. When the door to the ammunition store opened, Barry was waiting. He hurled laundry ammonia in the guards’ faces, seized their keys and firearms, and sounded the alarm, not for help, but for chaos.
Within moments, a full-scale riot erupted across the prison yard. Inmates ran, screamed, and fought. Guards scrambled to contain the outbreak. Amid the frenzy, Barry and an accomplice slipped away, scaling the outer wall, dodging searchlights and bullets. One slug grazed his head, showering his face with glass splinters. Partially blinded and bleeding, he landed on the far side — free.
A Fugitive Life
Outside the prison gates, Barry and his accomplice hijacked a nearby car and vanished into the countryside. But the vehicle ran out of petrol, forcing them to hide in a disused garage and flee on foot. In the confusion of the escape, Barry’s companion disappeared, likely caught or killed. Barry stumbled on alone.
He later recalled limping along back roads, bloodied and nearly blind in one eye, his face seared with pain. He forced one eyelid open manually to navigate and hijacked another car. He drove half-blind and without headlights to avoid detection. That night, as he found temporary shelter and dressed his wounds, he made a vow to himself: If I live, I will never go back to that life again.
The following morning, nobody seemed to notice the limping man in dishevelled clothes as he ate breakfast in a roadside diner. They assumed he was just another drunk, rough around the edges. He made it to Albany, where old friends sheltered him and arranged treatment for his injuries.
Barry spent the next three years living under the radar in rural New Jersey, near Flemington, with his wife Anna. They kept to themselves. He grew quieter. The roaring, jewel-hunting thrill of his former life seemed to recede.
The Slip of the Tongue
But the law, like time, rarely forgets.
In 1932, FBI agents and local police began conducting background checks on new arrivals to the area. Barry, while no longer listed as a wanted man in headlines, still attracted the attention of detectives who hadn't forgotten the Auburn breakout.
One day, under casual but persistent questioning, a detective pressed Barry for an opinion:
If you were to rob Percy Rockefeller’s estate — two ferocious dogs, locked gates and all — how would you do it?
Barry smiled, deflecting at first. But his pride got the better of him. He began to talk — hypothetically, of course.
He described lowering a female dog on a rope to distract the guard dogs. He’d enter the house, grab what he needed, and leave the same way, hoisting the decoy back up as he made his escape. The officers listened silently. Then one leaned back, laughed, and promised to send him a box of cigars.
What arrived instead was a fresh arrest warrant.
A Legend, But No Longer a Fugitive
That confession, unintended, spontaneous, and entirely self-inflicted, ended Barry’s second run of freedom. But this time, the legend of the Gentleman Thief only grew. Not many prisoners orchestrate a riot with a birthday cake, hijack cars while half-blind, and then hide in plain sight for years.
He was returned to custody, but even his captors couldn’t help admiring the man’s wit and resolve. If Barry had been born in different circumstances, or made a few different decisions, he might’ve led a bank, not robbed its customers. Even the police chief, upon confirming Barry’s fate, chuckled and said: “He’s the best we ever had.”
From Jewel Thief to Community Man: Barry’s Second Life
After nearly two decades behind bars, years marked by riot, escape, re-arrest and introspection, Arthur Barry was released from prison in 1949. He was 53 years old. The dazzle and drama of the Jazz Age were long gone, buried under the weight of the Great Depression, a second world war, and a very different America than the one he’d once tiptoed through in patent leather shoes.
But unlike so many career criminals who returned to the only life they knew, Barry kept a promise he had made to himself on a night of desperation and pain, glass splinters in his eyes, blood drying on his clothes: if he lived through it, he would change. And this time, he did.
Back in Worcester, Massachusetts, where it had all begun, Barry made no effort to hide who he had once been. He settled into a modest house and took an honest job earning $50 a week — not a fortune, not even enough to pretend, but enough to live. He worked in a local restaurant and later at a newsstand, quietly dependable, turning over the day’s takings without question. His employers trusted him. More importantly, his neighbours did too.
In a surprising but deeply telling twist, Barry was elected commander of his local Veterans of Foreign Wars post. It wasn’t a ceremonial gesture. Despite his criminal past, his wartime service — and more importantly, his humility and honesty in his later years — had earned the community’s respect. He didn’t apologise for what he’d done, but he didn’t excuse it either. He simply lived better.
In interviews given not long after his release, Barry was reflective but without self-pity. He admitted the waste of it all — not just the money squandered, but the years lost to shadowy streets, high fences and prison cells. “There was no nobility in what I did,” he once said. “I robbed the rich, but not for some cause. I did it for me. That’s the truth. But I tried to do it my way.”
The Final Curtain
Barry lived quietly for the next three decades. He never returned to crime. The newspapers eventually stopped calling. The stage girls, society columnists, and Pinkerton detectives of his youth had all moved on or passed away.
He died in 1981, at the age of 85, not in hiding, not on the run, but peacefully and with dignity. There were no headlines this time. No editorials. Few today remember that he once terrified the East Coast elite more than any gangster, yet never fired a shot, never left a body, and rarely provoked anything more than grudging admiration.
Arthur Barry never pretended to be Robin Hood. He stole from the rich, and kept the spoils. But unlike most crooks, he had charm without menace, precision without cruelty, and a code, however flawed, that made even his victims hesitate to hate him.
There’s something oddly enduring about a man who could steal $450,000 in pearls while the owner bathed nearby, and still be remembered with a smirk rather than scorn.
Barry didn’t live a perfect life. But he eventually lived an honest one. And in that quiet second act, he pulled off perhaps his greatest feat of all — redemption.
Sources
Jobb, Dean. Empire of Deception and biographical features
New York Times crime archives, 1920s
FBI historical case notes on Arthur Barry
Contemporary newspaper interviews with Barry (1949–1950)
