From Elizabeth Holmes to Samantha Azzopardi, who are the most astonishing female con artists?

Fake German heiress Anna Sorokin: I’m trying to fix what I’ve done wrong (Richard Drew/AP) (AP)
Fake German heiress Anna Sorokin: I’m trying to fix what I’ve done wrong (Richard Drew/AP) (AP)

Australian Melissa Caddick went missing during a run in November 2020, then three months later her foot washed up on a beach hundreds of miles away.

This was only the beginning of the astonishing story surrounding the high-flying businesswoman, as investigations into Caddick’s disappearance revealed that she had allegedly been running a lucrative Ponzi scheme.

Now this shocking tale is being retold in two upcoming ITVX projects: a three-part drama, A Vanishing Act, which, according to ITVX “tells the story of this charismatic con-artist” and The Real Vanishing Act: Missing Millionairess, a documentary about Caddick’s life, business activities and the revelations that followed her apparent death. The documentary includes conversations with her husband, hairdresser Anthony Koletti, as well as with others close to the investigation.

With both dramas landing on the streaming site on August 3, here we take a further look at some of the most astonishing con women of all time.

Anna Sorokin (b.1991)

After Elizabeth Holmes, Anna Sorokin is without a doubt the world’s most famous living con woman. The New York socialite, who went by Anna Delvey, gained a reputation in the city for her lavish lifestyle (which involved living at several upscale hotels), funded, she claimed, by her ultra-rich father who would wire her money from her trust fund, and her big plans to create a private members club in one of New York’s most exclusive buildings. But her life was a lie and the house of cards quickly came crashing down as unpaid bills started to pile up.

In an interview before her 2019 sentencing, Sorokin famously said: “I’d be lying to you and to everyone else and to myself if I said I was sorry for anything.” After being sentenced to four to twelve years in jail she made a $320,000 deal with Netflix for her story, which she used to pay her legal fees and restitutions to different banks. Shonda Rhimes’ Inventing Anna, which starred Julia Garner as Anna, was released in February 2022 and became a huge hit. Something about Anna’s wreckless ambition spoke to people and the con woman gained as many fans as critics.

Samantha Azzopardi (b.1988)

Australian Samantha Azzopardi was sentenced to two years in prison in 2021 for conducting a series of scams in Australia, Ireland and Canada. They reportedly involve Azzopardi pretending that she was Dakota Johnson and applying for two schools in Brisbane and posing as a student, when she was at least 21. In 2013, in Dublin, she spent weeks in a children’s hospital after being found outside a museum in Dublin and indicating that she was a young teen.

Then, in 2014 in Canada, she pretended she was someone called Aurora Hepburn who was a victim of sexual assault and abduction. In 2016, when she was 28 years old, she enrolled in another school pretending to be a 13-year-old girl. And so the cons go on.

What’s fascinating about Azzopardi’s many exploits is that, unlike other con artists on this list, it’s more difficult to comprehend her motivations, which don’t seem to be particularly financial or social. Her story was investigated in a four-part documentary from Paramount+, Con Girl, which one reviewer called “quite possibly the most astonishingly outlandish story ever told”.

Elizabeth Holmes (b.1984)

Elizabeth Holmes in November 2022 (Getty Images)
Elizabeth Holmes in November 2022 (Getty Images)

The jury is still out over whether Elizabeth Holmes deserves to be on this list. Some believe Holmes was a genius who only did what any entrepreneur would do on their way to the top in the ever-competitive Silicon Valley. Others – including the American justice system, which successfully convicted her for conspiracy and wire fraud in 2022 – see her as a fraudster and liar who put hundreds of lives at risk through promising biomedical technology that her company could not provide.

Holmes’ company Theranos was once worth $9 billion. It claimed to have devised simple blood tests that would provide users with a range of results from a very small amount of blood. The idea was to cut out the middleman: imagine how much cheaper it could be, and how many lives could be saved, if people could do their own blood tests for a range of issues illnesses including cancer, kidney disease and diabetes. Undoubtedly an inspired proposal, the issue was that Theranos was not able to create the technology.

Melissa Caddick (b.1971)

Businesswoman Melissa Caddick went on a run near her Sydney home in November 2020, and then disappeared. Three months later, her foot – detached from her body, and still wearing a trainer – washed up on a beach 250 miles away.

The mystery surrounding Caddick’s apparent death didn’t stop there: after she vanished, the truth about her business practices started to come out. Millionaire Caddick seemed to have an accomplished career, but it quickly became clear that she had allegedly been secretly running some sort of elaborate Ponzi scheme which, according to ITVX, involved dozens of victims and millions of dollars.

Linda Taylor (1926-2002)

Linda Taylor is best known as a scammer who cheated the American welfare system. She became so famous for her extensive frauds that Ronald Reagan even used her in his 1976 presidential campaign as an example of the flaws of the system, which he criticised.

In order to con people, Taylor changed her ethnicity, job role and age and went under a dozen different names including Linda Jones, Constance Loyd, Linda Lynch, Linda Mallexo and Linda Ray. She used her multiple identities to receive multiple welfare payments. When she was finally arrested, she’d reportedly created as many as 80 different aliases, and she’d received as much as $100,000 in welfare payments.

Amy Bock (1859-1943)

Bock is not only New Zealand’s most famous con woman, but was also described by writer Fiona Farrell as the country’s “most unusual and energetic con artist”. She spent her entire life trying to scam people out of money and her frauds varied in grandeur and success. In the most outrageous case, she pretended to be a man in order to marry the daughter of a wealthy family. She nearly pulled it off, too: she did indeed marry Agnes Ottaway, but was arrested three days later and the marriage was annulled. Ottaway’s father apparently said: “Well, it might have been worse.”

Over the course of her life Bock spent 16 years in prison. She would employ every trick in the book to be given money and property and then abscond. But most often, once she was caught she would admit everything and return her takings. She was also a school teacher, but even then got up to mischief, doctoring how many kids were in attendance (which boosted her salary) and taking constant sick days.

Elizabeth Bigley (1857-1907)

Elizabeth Bigley, who is best known by her con name Cassie Chadwick, was a Canadian fraudster who astonishingly managed to scam banks out of between $800,000 and $1.3 million by pretending to be the illegitimate daughter of Andrew Carnegie. A newspaper article published in 1955 said she had used a letter from ‘an attorney in London’ which said she had been bequeathed $1,800. She lived on credit provided by merchants (very Sorokin, or rather, Sorokin was very Bigley) until she was eventually found out and arrested. The newspaper said: “At her trial, she made faces at the witness. The jury, convinced she was insane, acquitted her.”

She married a doctor, but he chucked her out only 11 days later after debt collectors came round to collect money for expensive wedding gifts she had been buying. Bigley’s stories go on and on, each as incredible as the next: one scam involved worthless notes and a clairvoyant; she spent lavishly, under one guise buying eight grand pianos; one bank was even forced to close after its president had lent her $240,000 – four times the bank’s capital stock. By the time of her trial, she was incredibly famous. She was sentenced to 14 years in prison, but died two years into her sentence.

Jeanne de Valois-Saint-Rémy (1756-1791)

Although Jeanne de Valois-Saint-Rémy, who went by Comtesse de la Motte, did not conduct any frauds on the scale of Theranos, or Bigley’s exploits, she deserves to be on the list because of her involvement in one of France’s biggest scandals, the Affair of the Diamond Necklace. The scandal is often named as one of the factors that led to the downfall of King Louis XVI.

Like so many of the con women on this list, Comtesse de la Motte’s main initial aim was raising her social status. She was born into an impoverished family but managed to marry Nicholas de la Motte, who claimed to be a nobleman (though it’s not clear that he actually was). She started hanging around the palace in the hope of speaking to Marie Antoinette to ask for a more generous royal pension, but the Queen, who had been warned about Jeanne, avoided her.

Jeweller Charles Auguste Boehmer was trying to sell a necklace that was so expensive that only the King was able to buy it. But the King didn’t want it. Jeanne saw an opportunity to make some money so asked her lover, Rétaux de Villette, who happened to be a master forger, to write letters from ‘The Queen’ to the ‘Comtesse’ saying that she wanted the necklace but that the King wouldn’t buy it for her. In the letters ‘The Queen’ asked the Cardinal to lend her money so she could secretly purchase it and said that Jeanne was her agent.

The cardinal, believing the letters to be true, purchased the necklace and gave it to Jeanne who then took off with it and started selling the diamonds. She, her husband and her lover, all of whom were in on the scam, were eventually found out and arrested, but the damage had been done at court.

Marie Antoinette’s reputation was on the rocks, and the public trial of the con artists (a decision made by the King and Queen to try and reinstate their honour) in the end only reinforced preconceived ideas about the royal family and their lavish spending. People felt sorry for Jeanne, and had a kind of admiration for her chutzpah, as centuries later people have sympathy for Sorokin and Holmes.

Barbara Erni (1743-1785)

It’s hard to work out where the legend around Erni starts and her real-life story ends. Sounding like a character from a Celtic legend rather than one of the world’s greatest con women, the story goes that Erni was strong with red-blonde hair and apparently carried a large treasure chest on her back. At night a man popped up out of the chest, would steal all the objects in the room and off Erni and the man would go again.

In truth, she was a skilled thief, who would steal from inns across Lichtenstein and Western Europe using a confidence trick. She and her accomplice – who history has not remembered – were arrested and trialled in 1784. She was sentenced to death and beheaded in 1784 in front of approximately 1,000 spectators. She was the last person ever executed by the Liechtenstein state.

A Vanishing Act and The Real Vanishing Act: Missing Millionairess are both streaming on ITVX from August 3