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.
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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 person deceiving you. Of all the losses in our AI-ridden world, one of the strangest might be the decline of the flesh-and-blood fraudster. Soon, they may go the way of the dodo. Should we mourn them?
Rosenberg’s canonical forerunner is hard to pin down, but he was known to some as Samuel Thompson. Dubbed the original “Confidence Man” by a New York Herald headline in 1849, Thompson was once just a hapless petty thief, described by one local rag as “more audacious than adroit.” He spent two and a half years in prison after a failed robbery of a lace store, and after his release, he took up a more promising trade in New York City. He would convince at least three different well-heeled strangers to lend their pricey watches to him for safekeeping by posing as an old acquaintance. Their confidence in him was evidently misplaced—they would likely never see him or their watches again. But so was Thompson’s confidence in his own ability. One of his victims happened to spot him on the street shortly after their meeting, leading to Thompson’s arrest.
He died imprisoned, but his influence lived on. Avarice is as old as civilization, but “confidence men,” wrote linguist David Maurer, weren’t “crooks in the ordinary sense of the word.” Anyone can relieve a stranger of their valuables; convincing them to hand them over, through sheer guile, is another thing altogether.
While Charles Dickens depicted wily pickpockets roaming London streets, Herman Melville and Edgar Allan Poe wrote about a new class of criminal in America who relied less on sticky fingers than a silver tongue. This new archetype was gifted, entrepreneurial, and moulded by the evolving commercial age. They weren’t so different, in principle, from their higher-ups in the world’s emerging centre of capital. “The Confidence Man,” reads a satirical Herald editorial in 1849, “has obtained half a dozen watches,” while Wall Street financiers “have pocketed half a million dollars.” The latter just made for less compelling characters—and were far less likely to be caught.
The “con man” was a people’s criminal and became part of the cultural lexicon. He is what Jia Tolentino has described as “a uniquely American folk hero—a logical endpoint of our national fixation on reinvention and spectacular ascent.” One of the best known might be Frank Abagnale Jr., of Catch Me If You Can fame. He spent years touting his sensational history of swindling, in which he recounted flying across the country disguised as a commercial airline pilot and racking up millions of dollars in fraudulent cheques. It got him talk shows, a 1980 book deal, and, eventually, a 2002 biopic directed by Steven Spielberg.
Like all uniquely American things, a diluted version inevitably cropped up in Canada. The Yorkville Swindler’s origins are hazy. He is both “hero and misfit,” according to the title of a book he claims to have written, pre-ChatGPT. Rosenberg grew up as the son of a mid-century boutique owner in Toronto’s old-money neighbourhood. In the documentary, he recounts an unhappy childhood, a gilded cage he escaped with an intimate knowledge of polite society that would serve him well in his jet-setting lifestyle of serial impersonation.
It was a criminal path perfect for the analog age, when multiple identities could be donned without leaving a digital trace. But can such a calling exist in the information age, when biographical legerdemain is easy to spoil with a concerted Google search? Intrepid reporting has since revealed that Abagnale embellished, if not outright fabricated, most of his publicized criminal history; a scammer’s life story aptly turned out to be the biggest scam of all.
The Rosenbergs and Abagnales feel like silent film actors on the eve of the talkies. But the end of con artistry isn’t just a question of style. As that mid-nineteenth-century New York Herald article alluded to, it’s also a question of scale.
