Life magazine hailed him as “the greatest jewel thief who ever lived.”
In Jazz Age New York City, Arthur Barry hobnobbed with millionaires and celebrities as he planned his heists. He befriended Harry Houdini and led the Prince of Wales, Edward VIII, on a late-night tour of Manhattan speakeasies. He raided the mansions of the elite and scooped up diamonds, pearls, and other precious gems worth tens of millions. On the rare occasions he awakened his victims as he crept into their bedrooms, Barry soothingly assured them he was only there to steal their jewelry. “I know he’s terrible,” said one socialite he robbed. “But isn’t he charming?”
I’ve written plenty of true-crime stories about 1920s con artists and rogues. I was searching the Internet for more tales of Jazz Age ne’er-do-wells when I spotted the Life profile of Barry, published in the mid-1950s.
Why had I never heard of this man? I was hooked.
Barry collaborated with journalist Neil Hickey on a biography published in the early 1960s, which gave him some late-life fame. Mike Wallace put him on television and asked him to reveal the secrets of his success. Barry sat beside singer Rosemary Clooney on The Tonight Show as Johnny Carson quizzed him on what had become of his loot.
Then he disappeared.
Arthur Barry befriended Harry Houdini and led the Prince of Wales, Edward VIII, on a late-night tour of Manhattan speakeasies.
Re-creating the life and crimes of a man who worked in the shadows was a challenge. While the six-decade-old biography was peppered with insights, it told only part of the story. Barry revealed little about his scrapes with the law as a teenager in Worcester, Massachusetts, and the stints he served in a reformatory. He portrayed himself as a lone wolf, even though he teamed up with a thuggish childhood friend, James Monahan, for many of his burglaries.
When he was finally caught, in 1927, Barry was sent to prison for 25 years. But he confessed to only one of his many robberies, the most bizarre of all. After confronting Wall Street investor Jesse Livermore and his wife in their bedroom and forcing them to hand over their jewels, he gallantly returned expensive rings that Dorothea Livermore claimed had sentimental value.
Barry waited decades—until there was no longer a threat of prosecution—to reveal his most daring and lucrative heists. In 1924, he broke into oil tycoon Joshua Cosden’s Long Island estate and swiped jewelry belonging to a guest, Lady Edwina Mountbatten. The following year he slipped into the Plaza Hotel suite of Woolworth-five-and-dime-store heiress Jessie Donahue and made off with an exquisite strand of pearls. Driving past financier Percy Rockefeller’s palatial mansion in Greenwich, Connecticut, one evening in 1926, he decided on a whim to sneak inside and help himself to thousands of dollars worth of gems.
He was a suspect in scores of other burglaries. When I pieced together 1920s press reports of unsolved robberies and surviving court records, patterns emerged. Barry robbed estates on Long Island until his bold forays attracted too much police attention, then moved his operations to Westchester County, targeting homes from Yonkers to Rye. When authorities there became more vigilant, he returned to his Long Island hunting grounds. He went back and forth several times, staying a step ahead of the police and private detectives on his trail.
In the 1930s, Barry granted exclusive interviews to the New York Daily News that filled in many of the blanks. Barry’s wife, Anna Blake, published a syndicated tell-all series of her own. (Ever the gentleman, he confessed and cut a deal to ensure she was not charged as an accessory to his crimes.) These firsthand accounts not only made it possible to hear their narratives but are also crucial to re-creating Barry’s dramatic escape from a New York State prison, in 1929, and the three years the couple lived as fugitives.
This forgotten master of the break-in was just as adept at breaking out.
Dean Jobb is the author of several books, including The Case of the Murderous Dr. Cream and Empire of Deception
