15 Scams People Almost Pulled Off That Will Leave You Impressed And Appalled

There's a reason Hollywood loves these stories.

1. Selling the Brooklyn Bridge

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This classic of scam artistry was supposedly first attempted by 19th-century conman George C. Parker, who also sold "the Metropolitan Museum of Art, the Statue of Liberty, and Grant's tomb." It became such a popular trick that it's the origin of the saying, "If you believe that, I've got a bridge I can sell you."

2. The Original Ponzi Scheme

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A Ponzi scheme can best be summed up with the idiom, "borrowing from Peter to pay Paul." According to Smithsonian Magazine, the man who lent his name to the con was Charles Ponzi, who "raked in an estimated $15 million in eight months by persuading tens of thousands of Bostonians that he had unlocked the secret to easy wealth." Needless to say, he hadn't.

3. The Fake Archduchess(es)

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Unlike her animated counterpart in the 1997 musical Anastasia, Czar Nicholas II's real life daughter was executed with the rest of her family in 1918. However, the movie's plot is based on a kernel of truth. Following the execution, a handful of imposters came forward over the years, claiming to be one of the five deceased Romanov children. They hoped to claim some imperial riches or fame. The most famous of them was a woman named Anna Anderson, who spent decades posing as Anastasia.

4. 1950s Quiz Show Scandals

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In the 1950s, rigging the outcome of these popular programs was its own genre of fraud, with producers and contestants collaborating to make a more entertaining show. Perhaps the most famous perpetrator was Charles Van Doren, a champion of Twenty-One who was forced to resign from his teaching position at Columbia when the deception was revealed. His downfall was chronicled in the 1994 film Quiz Show. Following the scandals, public trust in game shows was so low that Jeopardy's iconic "answer in the form of a question" format was specifically designed to be scam-proof.

5. The Many Identities of Frank Abagnale, Jr.

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If he ever heard it, Frank Abagnale, Jr. never took the advice "just be yourself" to heart. At the age of 16, Abagnale began an illustrious career as an imposter, posing as a pilot, a doctor, and an attorney, becoming an expert at forging checks and other documents. After being arrested at age 21, he was eventually released from prison early, on the condition that he assist the FBI in catching other fraudsters. The remarkable story was adapted in the 2002 film Catch Me If You Can.

6. The Real Wolf of Wall Street

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The "pump-and-dump" schemes of Jordan Belfort were first exposed by Forbes magazine back in 1991, when it described him as, "a twisted version of Robin Hood, who robs from the rich and gives to himself and his merry band of brokers." Belfort would go on to spend 22 months in prison for his crimes. In 2020, he sued the filmmakers of his biopic for $300 million, the same amount the movie made at the box office.

7. Stephen Glass's Journalistic Deception

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A 1998 Vanity Fair article described the deceptions of rising star reporter Stephen Glass as, "the most sustained fraud in modern journalism." He went to great lengths to fake his sensational stories, creating false websites and documents like business cards, and even tricking fact checkers by inserting purposefully incorrect details as a red herring. The New Republic, where Glass was employed full-time, would eventually find fabrications in 27 out of the 41 pieces he wrote for them. In 2014, after Glass attempted to pivot to the legal profession, the California Supreme Court refused to admit him to the state bar, arguing that "the disgraced former journalist had failed to rehabilitate himself."

8. "McMillions" Scam

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If you've ever laid eyes on the Golden Arches, then you're familiar with McDonald's yearly Monopoly promotion. But what you may not know is that for a significant chunk of its history, an ex-cop named Jerome Jacobson fixed the game so that he and his network "won almost every prize for 12 years, until the FBI launched Operation 'Final Answer.'" The tale is so elaborate and unbelievable that HBO adapted the Daily Beast article about it it into a six-episode docuseries called McMillions. Apologies to anyone who lovingly peeled those little tiles off of your fries and Coke prior to 2001 — you never had a chance.

9. Who Wants To Be A Millionaire? Cheating Scandal

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Society didn't leave game show cheating in the '50s, though this time, the show itself had nothing to due with the fraud. On the British edition of this mega-popular program, Major Charles Ingram scammed his way to the top prize by reading each answer out loud and waiting for an audience plant to cough. When Ingram heard the cough, he'd know that was the correct choice. Following his 2001 victory, the producers were immediately suspicious. An investigation revealed the fraud, with all three perpetrators — Ingram, his wife Diana, and accomplice Tecwen Whittock — eventually being found guilty in court. Quiz, a mini-series about the scandal, aired in April 2020.

10. Bernie Madoff's Ponzi Scheme

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In 2009, Bernie Madoff was sentenced to 150 years in prison for, "the largest, longest, and most widespread Ponzi scheme in history." Apparently, the $65 billion fraud makes him "one of the biggest thieves of all time." The judge pointed out that while multiple victims testified about the devastating impact of his crimes, no friends or family of Madoff had come forward to offer a positive perspective on his life or work. The Wizard of Lies, a 2018 HBO made-for-TV movie, dramatizes the collapse of the scam. It is extremely stressful.

11. Corruption at FIFA

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In 2015, the Justice Department announced "a 47-count indictment against 14 defendants" involved in soccer's governing body, for crimes including "racketeering, wire fraud, and money laundering." If you want a primer on FIFA's history of legal troubles, check out John Oliver's 2014 segment on them here.

12. Theranos

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It was always too good to be true. Founded by 19-year-old Stanford dropout Elizabeth Holmes, Theranos (as in, "therapy" and "diagnosis") promised to revolutionize medical testing. At its height, it was worth $9 billion. But a bombshell exposé by Wall Street Journal reporter John Carreyrou stated outright what those in the scientific establishment had long suspected: The technology simply did not work. Holmes and the former president of the company, Ramesh “Sunny” Balwani, were later indicted on eleven counts of fraud and conspiracy. In September 2018, the company shut down. The following March, HBO released a documentary about the scandal, The Inventor: Out For Blood In Silicon Valley.

13. Fyre Festival

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The world watched the 2017 Fyre Festival disaster unfold in real time. Attendees of the festival arrived hoping to document the best weekend of their lives on social media. Unfortunately, instead of parties and musical acts, they ended up tweeting pics of disaster tents and an infamous cheese sandwich. Promoted by models and influencers, Fyre Festival was supposed to be an exclusive, luxurious experience. Maybe it would have been, if founders Billy McFarland and Ja Rule knew how to plan an event that even sort of approximated what the slick advertisements had promised. Alas, they didn't, and McFarland was eventually sentenced to six years in prison for the fraud. In January 2019, Hulu and Netflix each released a documentary about the disaster: Fyre Fraud and Fyre: The Greatest Party That Never Happened, respectively. Naturally, I watched both.

14. Anna Sorokin (aka Anna Delvey)

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Anna Sorokin (known as Anna Delvey to those she conned) was not an heiress like she claimed to be, though for a brief period of time she lived the life of one: Anna stayed in boutique hotels, dined at award-winning restaurants, and carefully manipulated her circle of friends and the businesses themselves into fronting the bill for it all, claiming forgetfulness or difficulties with accessing her $60 million trust fund while abroad. She would eventually spend nearly four years in prison for "cheating friends, banks and businesses out of more than a quarter million dollars." If you want to know more, this exposé by The Cut lays out the timeline and details of the scam, and this Vanity Fair essay was written by one of her victims. Multiple Hollywood adaptations of the story are currently in the works.

15. Operation Varsity Blues

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In 2019, federal prosecutors announced charges against 50 people for a scheme that sounded like a parody of rich kid privilege: These parents had paid fraudster Rick Singer tens of thousands of dollars, if not more, to guarantee their child admission to elite universities. Applicants posed with athletic equipment to con admissions into thinking they were competitive in sports they never even played. And one of the perpetrators was Aunt Becky! Operation Varsity Blues (the name of the FBI investigation that caught the scam) is a story full of infuriating details, from the fake photos to the flippancy of the parents cutting a check for a good score on the ACT. Most frustrating of all? Singer's "side door" may be closed, but the "back door" — donating a ton of money in exchange for an acceptance letter — remains open for whoever can access it.