Dean Jobb's 'A Gentleman and a Thief' is all about a charmer who robbed Gold Coast's rich

Dean Jobb admits he's always liked con men. Not personally, that is, but as the subjects of his books.

His 2015 book, "The Empire of Deception" followed Leo Koretz, a Chicago swindler whose Ponzi schemes made him the Bernie Madoff of the 1920s. But Koretz had nothing on Arthur Barry, the notorious yet charming jewel robber at the center of Jobb's latest, "A Gentleman and a Thief: The Daring Jewel Heists of a Jazz Age Rogue" (Algonquin Books, $32.50).

Set against the backdrop of Long Island's Gold Coast in the Gatsby era, the book chronicles Barry's robberies, arrest, prison break and more. Jobb recently spoke by phone from his home in Nova Scotia about his fascination with Barry.

How did you come to be interested in Arthur Barry's story?

My last book in 2015, The Empire of Deception," was about a Chicago swindler who actually lived out here in Nova Scotia. ... The Jazz Age is such a great era, such a great time for larger-than-life characters. So I just Googled 1920s con artists, and much to my surprise, the name Arthur Barry popped up. I’d never heard of him, but it was the link to the Life magazine feature published in the 1950s that described him as the greatest jewel thief that ever lived. So that immediately caught my attention. The article was there in full text to give me a sense of the story and I was hooked. And I just started researching from there.

How familiar are you with Long Island?

As familiar as I could be during the pandemic.

Reading about the Long Island of that period and all the mansions and society, it seems so different from the Long Island of today.

I know. So many of those mansions are now gone. Ideally I would have visited them all. The Old Westbury house is still there and a smattering of others. I had to make myself familiar with Long Island from a century ago as the setting. F. Scott Fitzgerald set "The Great Gatsby" there for a reason. It was really a millionaire's country retreat.

Arthur Barry committed all of these robberies, yet he never really amounted to much in his life. I kept thinking about Cary Grant in "To Catch a Thief" and how he lived so well on the Riviera, but this guy just blew the money so quickly.

He was very matter of fact when asked where the money went and said he’d blown it. He gambled it away, sometimes won, mostly lost. When he needed money, he’d just pull another jewelry heist. This was the 1920s, the stock market is booming and everyone wanted to live well. You have to remember the times, it was live for today. He was the epitome of a product of his times. He has served in the Great War, he was a medic, had been wounded and faced death overseas. So he just wanted to come home and have a great time.

He had this philosophy that if somebody could afford $10 million, he felt like it’s OK to rob them.

You can’t make any excuse for that. He’s bursting into people’s homes, sometimes when they’re there, and sometimes planning to have them there because he knows their jewels will be there, so they can open a safe or help him find the jewels. So he’s violating people’s safety. On the other hand, he kind of coldly set upon this enterprise in 1920 after returning from the war and he couldn’t find a job. He didn’t want to be a bank robber — too much gunplay, too many accomplices — he didn’t want to mug people, he thought it was somehow impolite.

So he really was a gentleman thief.

He did develop this persona of coming to a party in a tux and blending in with their rich invitees so he could wander upstairs and case the mansion and then come back later and steal jewels. Or if he broke into a bedroom and the occupants were awakened, he'd calm them down and say "Relax, I’m just here for the jewels." Even chitchatting with them and saying "How was the opera?" ... He was so polite, and in one famous case returning jewelry at the insistence of the woman he was robbing because it had sentimental value. The woman, Dorothea Livermore, later said, "I know he’s terrible, but isn’t he charming."

Not only was he a master thief, he was also a master when it came to escaping from prison.

In 1927 he was caught and sent to prison for 25 years. And within a couple of years, he planned and executed this dramatic breakout. ... He manages to stay on the lam for three years and there's a love story at the heart of this, which is the reason he breaks out. He meets and marries Tammany Hall political worker Anna Blake. ... He ultimately pled guilty to save her from any charges as an accomplice. ... She falls ill with cancer and that’s why Barry feels he has to break out of prison in order to be with her.

She claimed that she knew nothing about Barry's career as a thief. Do you believe she was telling the truth?

There were firsthand accounts by the arresting detective Harold King of the Nassau County police force and the local DA who gave blow-by-blow descriptions of the arrest and their interrogations of Barry and Blake and her reactions when she finally realized what Blake did. It’s all so in the moment and real that it seems hard to think that she put this on as an act. And the police and district attorney believed she was an innocent party. I have readers ask, "If there was one person in the book who you could interview, who would it be?" For me it would be Anna Blake, and I would ask, "Did you really have no idea?"