Law360 Canada (September 15, 2026, 11:28 AM EDT) --

John L. Hill

I was recently approached by email and asked to be interviewed about my latest book on a Zoom call that would reach more than 800 viewers. What troubled me was that the Zoom call was to originate in Dubai. I checked the company before accepting. The Winnipeg Free Press had reported on the venture and labelled it a scam intent on pushing authors to make sizable donations.

There was a time when a con artist needed something that technology can now provide in abundance: personal contact.

The classic swindler was a performer. He had to look the part, tell a convincing story and persuade another human being to surrender money, property or trust. The great con artists were, in effect, actors operating without a stage.

Frank Abagnale Jr., whose exploits inspired the movie Catch Me If You Can, became famous for impersonating airline pilots and engaging in cheque fraud. Anna Delvey, the fake German heiress whose story became the Netflix series Inventing Anna, worked the social circles of New York’s wealthy and influential.

Their stories are fascinating because they involve personal deception. The victim met the fraudster, listened to the story and, in some sense, participated in the deception.

That world is rapidly disappearing. As Vikram Nijhawan observes in The Walrus, the modern scammer is less likely to be a charismatic individual than a technician operating behind a screen. Phishing emails, romance scams, investment fraud and cryptocurrency schemes have replaced much of the face-to-face artistry of the traditional con.

The irony is that the disappearance of the traditional con man has not meant the disappearance of the con. It has meant its proliferation.

According to the Canadian Anti-Fraud Centre, digital fraud continues to impose enormous losses on Canadians. Investment fraud, spear phishing and relationship scams are among the most financially damaging forms of fraud. Artificial intelligence, deepfakes and increasingly sophisticated digital platforms are making deception easier to manufacture and harder to detect.

This presents a profound challenge for the criminal justice system. The traditional fraudster had a location. There was usually a victim, a suspect and some physical evidence connecting the two. The investigation might involve bank records, documents, witnesses and eventually an accused person sitting in the courtroom.

Today’s fraud can be almost entirely virtual. A scammer can communicate with a victim from another country, use a false identity, employ artificial intelligence to create a convincing voice or image, transfer the proceeds through multiple financial institutions and disappear before the victim realizes what has happened.

The criminal law has not suddenly become irrelevant. Fraud remains fraud whether it is committed across a desk or across a computer network. Enforcement becomes much more difficult when the crime has no meaningful geographic boundary.

That raises familiar but increasingly difficult questions about jurisdiction, identification, disclosure of electronic evidence and extradition. It also raises questions about whether the institutions responsible for investigating and prosecuting fraud are equipped for a world in which a single offender can potentially target thousands of victims simultaneously.

There is another important change. The traditional con artist had to persuade people one at a time. Technology permits fraudsters to industrialize persuasion.

An email can be sent to thousands of people. A fake investment website can be designed to look entirely legitimate. A romance scammer can maintain relationships with multiple victims. Artificial intelligence can generate convincing communications at a speed no human con artist could match.

The result is a disturbing transformation: fraud has become scalable. That scalability changes the nature of the harm. If one person loses $50,000 to a traditional swindler, the loss is devastating. But a digitally operated fraud can produce hundreds or thousands of victims, each suffering what may appear to be an individual loss but collectively represents millions of dollars.

Unlike the fictionalized con men of Hollywood, the modern fraudster may never need to know anything about the victim. The machine does much of the work.

There is an obvious temptation to regard these victims as responsible for their own losses. Why would anyone send money to a stranger? Why would someone believe an unbelievable investment opportunity? Why would anyone give personal information to an unknown caller?

That response misses an important point about modern fraud. Sophisticated scams are designed to exploit ordinary human instincts. They exploit trust, fear, greed, loneliness, urgency and the desire to help another person. Artificial intelligence can make the deception extraordinarily convincing.

A telephone call apparently from a family member may no longer sound suspicious if the caller’s voice has been convincingly reproduced. An investment adviser may have a professional-looking website, photographs and credentials that exist only in cyberspace. A romantic partner may appear to have a complete digital life manufactured solely to extract money.

The question for the legal system therefore cannot simply be: Why did the victim fall for it? It must increasingly be: How did the system permit the deception to occur at such scale? That question moves the discussion beyond criminal law.

Banks, telecommunications companies, social media platforms, cryptocurrency exchanges and technology companies all occupy positions between the fraudster and the victim. The more sophisticated the scam becomes, the greater the pressure will be to determine what responsibility these intermediaries should bear.

That inevitably raises difficult legal questions about negligence, consumer protection, privacy, regulation and the allocation of losses.

There is also a problem of deterrence. Traditional criminal sanctions depend upon identifying an offender and bringing that person before a court. But if the person responsible is thousands of kilometres away, operating under a false identity and using technology designed to conceal the source of the crime, imprisonment may be a theoretical rather than practical deterrent.

Canada’s legal system may therefore face an uncomfortable reality: the law can punish the fraudster only after the fraudster has been found. Prevention becomes equally important. The Canadian Anti-Fraud Centre, police agencies, financial institutions and technology companies all have roles to play. So does public education. But education alone cannot reasonably be expected to solve a problem in which the technology available to the fraudster may be more sophisticated than the technology available to the victim.

There is, however, one Canadian exception to the disappearance of the traditional con artist. The Walrus recounts the story of Allan Rothschild, dubbed the “Yorkville Swindler,” whose alleged activities over four decades represent something closer to the old-fashioned confidence game. His story reminds us that the human con artist has not entirely disappeared.

But perhaps that is precisely why such a figure is now so fascinating. The old con artist needed charm, patience and an understanding of human nature. The new one may need little more than a computer, an internet connection and access to artificial intelligence.

The great irony is that technology has not killed the con. It has democratized it for the criminal justice system, that may be the most troubling development of all. The problem is no longer finding the occasional clever individual who can talk his way into someone’s confidence. The problem is confronting an industry capable of producing deception cheaply, anonymously and on a global scale.

The con man may be disappearing. The con is just getting started.

John L. Hill practised and taught prison law until his retirement. He holds a JD from Queen’s and an LLM in constitutional law from Osgoode Hall. He is also the author of Pine Box Parole: Terry Fitzsimmons and the Quest to End Solitary Confinement (Durvile & UpRoute Books) and The Rest of the (True Crime) Story (AOS Publishing). Contact him at johnlornehill@hotmail.com.

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