On a night in May 1927, at a 29-room mansion on Long Island Sound — Gatsby country — two men dressed in elegant grey suits and matching fedoras entered through a second-floor window to snatch the jewelry of the home’s owners, a Wall Street tycoon and his wife. Armed with pistols and impeccable manners, the thieves made off with an $80,000 strand of pearls and a $20,000 diamond ring (valued at about $1.5 million today). But at the request of the lady of the house, one of the burglars, Arthur Barry, returned a pair of $60,000 pinky rings before politely saying goodnight and taking his leave.

Barry’s irresistible story is told in Dean Jobb’s A Gentleman and a Thief. Much like in the author’s prior book, The Case of the Murderous Dr. Cream, which was the page-turning chronicle of a Victorian-era physician who just happened to be a serial killer, Jobb once again plunges into a real-life, forgotten tale of an audacious criminal and emerges with a story that supports the cliché that truth is stranger than fiction.

Not one to victimize the needy, Barry described how he picked his Jazz Age targets: “If a woman can carry around a necklace worth $750,000, she knows where her next meal is coming from.” But unlike Sir Robin of Locksley, Barry didn’t rob from the rich to give to the poor. He took from the rich to line his own pockets. In the end, crime did not pay, and Barry suffered a hard fall; the man who, in 1924, partied in evening wear with Edward, the prince of Wales, ended up doing hard time in drab prison garb in a 48-square-foot cell. After years behind bars in New York’s harshest prisons (minus time on the lam following a bold escape), Barry was paroled to a humble life waiting tables for $50 a week at a roadside diner in Worcester, Massachusetts, the proceeds of his long, successful crime spree long gambled away.

Barry began life in as a petty thief in a shabby New England industrial town. He was drinking alcohol by the time he was 7. At 16, he was convicted of discharging a firearm. His parents — at their wits’ end — had him put under the supervision of the court under the Massachusetts Stubborn Child Law, to no avail. Following a stint in a reformatory, he lied about his criminal record so he could enlist and serve in World War I. When he came home, he headed to New York City to find his fortune, which he did in the boudoirs of the wealthy.

Jewel heists were big business in the Roaring Twenties — everyone was in the money and wanted to look the part. Bootleggers who needed to launder their illicit profits were eager fences for jewel thieves. Barry approached his profession seriously. “Burglary is about 80 percent preparation and about 20 percent luck,” he said. He studied the society pages to see which wealthy families were wintering in Palm Beach or summering in Europe. He dressed up to crash cocktail parties and flirt with maids to ascertain their employers’ habits. He donned a workman’s uniform and pretended to be the alarm-system repair man, snipping wires so he could return undetected later. He even brought red meat and occasionally a female dog to the manors he intended to burglarize as distractions for the fierce male guard dogs that homeowners relied on for protection.

After carefully casing a joint, as an ace “second-story man,” either alone, or with his childhood friend and sometime accomplice, James Francis Monahan, Barry climbed in and out of a window in his stylish attire and cloth gloves and made off with thousands of dollars in gems within minutes; often, the homeowners slept just feet away or dined with guests on the floor below. His bejeweled victims, recounted by Jobb in playful detail, included Lord Louis Mountbatten and his wife, Edwina, while they stayed at the Long Island home of oil-refinery magnate Joshua Cosden, as well as a Rockefeller cousin, composer Irving Berlin’s mother-in-law, and an heiress to the Woolworth fortune. Ironically, he even struck at the home of the publisher of the upscale Town & Country magazine, which celebrated the rarified lives of the same rich and famous who were Barry’s targets.

After a good seven-year run, Barry was captured, convicted, and imprisoned, only to escape from the Auburn Correctional Facility in 1929 and survive nearly three years on the run with his long-suffering and devoted wife, Anna. Considered Public Enemy No. 1 while he was at large, he was briefly eyed as a suspect in the Lindbergh Baby kidnapping. Barry was eventually returned to prison, where he served a total of 19 years before being paroled in 1949 as a new man.

In his dotage, besides waiting tables, Barry became a beloved uncle and grandfather figure to his sister’s children and something of a media star. He was the subject of profiles in LIFE and Hearst’s American Weekly magazines, and author Neil Hickey wrote a well-received biography of him in 1961, The Gentleman Was a Thief. He was interviewed on television by legendary journalist Mike Wallace, and on November 16, 1964, he was a guest on Johnny Carson’s “The Tonight Show” along with singer Rosemary Clooney.

After his 15 minutes of fame, Barry retreated to a quiet life. He died in his sleep at the age of 84 and would be all but forgotten if not for Jobb’s outstanding book. Nonetheless, the erstwhile thief offers sound advice from the grave for women lucky enough to own important and expensive jewels: Don’t leave them in the top right-hand drawer of your dressing table. “Nine out of ten times,” Barry noted, “that’s the spot where I’ve found the whole haul.” Instead? “Hide your jewels in the kitchen.”

Diane Kiesel is a former judge of the Supreme Court of New York. She is an author whose next book, When Charlie Met Joan: The Tragedy of the Chaplin Trials and the Failings of American Law, will be published in February by the University of Michigan Press.

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