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Whatever Happened to the Good Old-Fashioned Con Artist?

The silver-tongued swindler has given way to phishing links and industrial-scale fraud

In May of 2019, Allan Rothschild walked into an art gallery in Midtown Toronto. He wore aviator sunglasses, a bomber leather jacket, and black Valentino combat boots with red laces—odd attire for a man in his seventies and for the purported heir to a billion-dollar Swiss fortune, no less.

As reported by the Toronto Star, Rothschild told the gallery owner that he was in the market for some valuable pieces. He offered to write a cheque for three paintings, overpay slightly, and get back the difference in cash (about $5,000). As the gallery owner would soon realize, Rothschild wasn’t there to buy anything—according to one report, he couldn’t even tell you the difference between Lucian Freud and Sigmund Freud. He possessed a very different kind of expertise—and was prolific in it.

He was “Albert Rosenberg” legally, but somewhere along the way, he adopted other noms de plume. “I kind of felt like he was making the story up as we went along,” says the filmmaker Barry Avrich in his 2022 documentary The Talented Mr. Rosenberg. The man he was profiling had been doing that for most of his observable life. The titular subject had played many roles: socialite, doctor, author, tennis champion. But his only real career was conning.

Across four decades, Rosenberg, later dubbed the “Yorkville Swindler,” had become to Toronto’s high society what Anna Delvey would be for New York’s. His list of marks included art dealers, corporate bigwigs, and ex-wives. His twenty-five fraud convictions spanned continents. He’d been imprisoned three times and finagled millions of dollars from a variety of phony investment schemes. He left a trail of tears, broken hearts, and empty chequing accounts. As many an unfortunate victim could attest, it was hard not to love him.

For as long as con men have dominated our imaginations, they have defied an easy understanding, at once reviled but also revered through glamorous big-screen portrayals. Leonardo DiCaprio, in Catch Me If You Can, forging uncanny cheques, or Amanda Seyfried as Theranos founder Elizabeth Holmes, sporting black turtlenecks and dropping her voice to a baritone. Much like the actors who inevitably play them, these swindlers slipped between different personas like outfits—and they didn’t lack star charisma either.

Albert Rosenberg, in his Sunday best or luxury casual wear, felt comfortable in any room. Those who knew the man (or at least thought they did) called him “mischievous” and “magnetic,” per an in-depth Toronto Life feature in 2015. The way he glided through his world masked his commitment to the craft, and like any master, he made the difficult look easy. As Moisés Naím and Quico Toro write in their 2025 book Charlatans, there was once a time when Rosenberg’s kind had to “identify marks one by one, woo them one by one, and even then, many might walk away. It was exhausting, painstaking work.” In other words, it was an art.

Scams still flourish, just not in the same way. The classic meet-cute of the confidence trick—a chance chat on a train platform, an encounter in a corner store or at any of the so-called third spaces where charming strangers once struck up conversation—feels rarer. The increasingly streamlined paths of daily life don’t allow for the same chances to be drawn in by someone’s story and fall into their web. Instead, from the comfort of your couch, you can fall for deepfakes, cloned voices, or phishing emails without ever meeting the........

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