Modern-day swindlers possess an arsenal of tactics—social media, pop psychology, and high tech—that plant them directly into their victims’ lives. And, they have the advantage that con artists have always had: They feel no guilt for ruining other people’s lives. That is a dangerous combo. Let’s take a look at these modern scammers who put their time, hard work, and ingenuity all into the pursuit of the same thing: easy money.
1. They Swiped Right
Not a lot of thought usually goes into whether you swipe right or left on your Tinder app—but what if the wrong swipe could cost you thousands of dollars? That’s exactly what happened to women who pursued dates with a man who called himself Simon Leviev. While a lot of dates you arrange through an app turn out to be duds, Leviev would turn up as that mythological creature: the perfect man.
2. He Ticked All The Boxes
Leviev was handsome—but so are a lot of men. What made Leviev stand out was what he had to offer. He was capable of taking dates to five-star restaurants and hotels, and even on trips on a private jet. But it wasn’t just about money, Leviev also spoke about having a true connection with women, which made them putty in his hands.
What made Leviev so successful as a manipulator, however, was that he understood his victims’ needs and proceeded to hand them over. The one sad thing? It was all a lie.
3. He Was Serial
But how did Leviev convince his victim’s that he was actually wealthy? Leviev’s plan was to go from one woman to another, but instead of breaking their hearts, he was breaking their bank accounts. He used the proceeds from his last mark in order to impress the new one. It was a flawless scheme that preyed on women’s desire, curiosity, and love of luxury. But how long could it last?
4. He Kept His Distance
The first thing that Leviev did was to start long-distance relationships with his victims. That way, he didn’t have to keep up the charade of wealth for long periods of time. The second thing he did was drop hints that his family was wealthy. He never actually said the name of his rich family, but he didn’t have to for one good reason: He knew how people ticked.
5. He Never Said It
The thing was: Leviev wasn’t actually Leviev. His birth name was Shimon Hayut and he changed it to Simon Leviev. When he was on a date, he would drop hints that his family was wealthy. But, what he knew was that people are curious and have loads of information at their fingertips. So when his dates checked his name on the internet, they hit a jackpot.
The Leviev family was rich in the diamond industry. It was every woman’s dream—until it became a nightmare.
6. He Had An Allure
One part of Leviev’s allure was the danger that he suggested was part of his life trading in diamonds. But this danger wasn’t just to get women’s attention; it was part of his scam. Eventually—after a few dates and countless calls and texts—the vague danger that he mentioned would surface. Leviev would suddenly need help and he’d even have a photo available of his bodyguard covered in blood.
With this proof of danger, Leviev’s victims took out loans, lines of credit, and even sent him suitcases full of money. The good news was: He always promised to pay them back. I bet you can guess the bad news…
7. He’s Still Out There
Of course, the way Leviev paid his victims back was also part of the scam. His checks and money drafts weren’t worth the paper they were printed on. In the end, it wasn’t all these false sources of income that alerted the authorities—it was a fake passport. Once behind bars, Leviev’s stay would only be a short one: He was soon out and now he’s back in the world, ready for more.
So, be careful who you swipe right for—it may be him. It’s not just online dating that can be perilous, though. What about the next festival you attend?
8. They Were Promised Supermodels
Who doesn’t want to frolic with supermodels on a white sand beach? Well, that’s what the promise was for attendees of the Fyre Festival in the Bahamas. Ticket buyers’ first clue that this was a scam should have been the, I hope, intentional misspelling of “fire”—always a giveaway. They paid anywhere from $1,200 to $12,000 for a chance to party with models, listen to live music acts, eat gourmet food, and live on the beach.
When the hordes arrived on the island, however, there was just one thing waiting for them: a complete disaster.
9. He Was The Brains
The brains—and I use this term loosely—behind the Fyre Festival was Billy McFarland. He was 27 years old when the idea of an elite festival on a Bahamian beach came to him. What didn’t come to him was how to make any of it actually happen. It’s pretty clear that McFarland was good at looking at the big picture; it was the details that took him down.
The festival started to crumble before it even began—at the Miami airport.
10. They Had A Bad Start
The private jet McFarland had promised guests was actually an ordinary plane with “Fyre Festival” written on the side—and worse still, it was late. Guests waited in the Miami airport for hours. They did eventually arrive in the Bahamas…but the VIP welcome they anticipated wasn’t there. Instead, participants were shown a very makeshift tent city and instructed to go find a tent to stay in.
Those who’d paid extra for VIP accommodation had to fight the regular folk for their special tent—which had a Persian carpet on the sand. So fancy! There was, however, an even bigger problem: They had no luggage.
11. It Was A Treasure Hunt
By the time the luggage arrived, the sun had set on the Bahamas—leaving it and the Fyre attendees in darkness. Guests, who were expecting concierge service, had to use their smartphone flashlights, probably in their mouths, to sort through countless bags in search of their own. Food was also a huge disappointment. The promise was gourmet cuisine, the reality was junk food on a Styrofoam tray.
This was an unforgivable oversight—but what happened next took this festival to a whole new low.
12. He Committed A Festival Sin
The flight had been a disaster, and the food and accommodation were looking to be the same. Young people, however, are resilient and can make a bad situation into something fun as long as they have one thing: brewskis. Sadly, McFarland also failed here. There was none: no craft brew, no IPA, not even a Bud.
When the hundreds of attendees found this out, things went a little Lord of the Flies…
13. He Didn’t Learn
In the end, the Fyre Festival was a bust and attendees started leaving in droves. At least, McFarland had learned a valuable lesson—or had he? Before he got sent behind bars for this debacle, he was already starting another—selling fake tickets to events. At his trial, it came out that one of McFarland’s major offenses was sending money through fake wire transfers.
There’s evidence that our next scammer may have learned this trick from him.
14. He Spawned A Copycat
While Billy McFarland was busy planning his failed festival, he was living in a Soho loft with another famous scammer: fake German heiress Anna Sorokin. It turned out that Sorokin was basically squatting at the Worster street home, living rent-free for up to four months. But she may have been doing more than squatting; she was also learning.
After residing with McFarland, Sorokin also began using wire transfers to pay for her luxurious lifestyle. And what a lifestyle it was…
15. She Was Fabulous
Anna Sorokin, who went by the name Anna Delvey, lived a fabulous New York City lifestyle—all on other people’s money. She partied at the best clubs, lived in luxury hotels, flew in a private jet, and, more damagingly, conned major banks into funding her Anna Delvey Foundation for artists. To do this, she used the same wire transfers that the Fyre Festival’s McFarland had.
While Sorokin didn’t quite stoop so low as to host a bogus festival for thousands of attendees, she did host a vacation for her and her friends in Morocco—and it went horribly wrong.
16. She Had Nerves Of Steel
The hotel Sorokin booked in Morocco cost a cool $7,000 a night. She somehow convinced her friend into paying for the flights, even though she’d promised the vacation would be all on her dime. Imagine the nerve a person had to have to arrive in Morocco and move into a luxury hotel—all the while knowing she didn’t have any money to pay for anything.
Sorokin did have a plan though, and that plan was gal pal Rachel Williams.
17. She Needed Someone To Pay
Sorokin had already got Williams to pay for the flights, but how could she get Williams to pay for the rest of the Moroccan vacation? When Sorokin’s credit cards all came up useless, Sorokin turned to Williams. Sorokin knew that Williams had a work credit card—from Vanity Fair no less—and she knew it had a very high credit limit.
It took some persuading, and a whole bunch of lying, to get Williams to foot the bill. Of course, Sorokin promised to pay her back as soon as they got back to the states. I hope Williams didn’t hold her breath for that.
18. She Conned The Wrong Person
The bill for the Moroccan trip ended up being a whopping $62,000. Williams was not independently wealthy—like Sorokin’s other victims—and this proved to be Sorokin’s biggest mistake. Williams worked with authorities and brought Sorokin down. The fake German heiress—who was in reality from a middle-class Russian family—was soon spending her days at Rikers.
While Sorokin used her charms to get what she wanted, our next scammers used their star power.
19. They Had It All
Actors Felicity Huffman of Desperate Housewives and Lori Loughlin of Full House seemed to have it all: fame, money, a lovely family. Well, there’s one thing they didn’t have, apparently: smart kids. Both wanted their daughters to go to Ivy League schools and both would do almost anything to get them there. Of course, when you mix motherly love and untold millions of dollars, you get one big juicy scandal.
20. They Cheated
To get their girls into college, Huffman and Loughlin got in touch with William Rick Singer, who accepted money from the two actors and used a not-for-profit charity to launder it. Singer then went to work using the money to get college administrators to do all kinds of unlawful things, including faking records, changing test scores, and even writing entrance exams for the daughters.
The whole thing eventually blew up and Huffman and Loughlin ended up with short prison sentences and hefty fines. If you think the punishment was a little light, you’re not alone. One angry parent wanted to go beyond what the court had dished out.
21. She Wanted A Fortune
A parent of a child who didn’t get into the college of his choice tried to sue everyone involved in the college cheating scandal for—drum roll please—$500 billion. Jennifer Kay Toy gave a reason for her unfathomably huge class action. Toy said that because the scam went back a few years, one million people lost their chance to enter Ivy League schools—her son Joshua being just one of them.
But in reality, who needs college? All our next scammer had was an idea—and not even an original one.
22. He Was An Original
Adam Neumann—whose wife’s cousin is scam-accused Goop founder Gweneth Paltrow—had an idea to create shared office space for individuals and start-up companies. While the idea for WeWork was hardly original, Neumann was—but for all the wrong reasons. In 2018, Neumann and his friends flew on a chartered jet from the US to Israel.
Onboard the flight, Neumann and his buddies partook in various cannabis products. When the plane landed in Israel, Neumann and the jet company were in for a big surprise.
23. They Flew High
Because Neumann and associates hadn’t consumed all the marijuana on board the flight, they had just successfully trafficked a controlled substance across an international border. The penalty for this little misstep was sizable, so the jet company sent the plane immediately back to the US—complete with a cereal box stuffed with marijuana.
Neumann obviously had a fondness for using mind-altering substances—a fondness he unscrupulously took to his workplace.
24. It Was Unlimited
There were many perks for working for WeWork, and one of them was free unlimited drinks for all employees. I’m not sure what this policy did for production, but you can guess what it did for employee morale. One new hire finally complained and even mentioned that Neumann plied her with shot after shot of spirits—during her interview.
This accusation was a downer, and Neumann was forced to reduce the beverage intake from unlimited to a lousy four per day. What a buzz kill. All this booziness on the job site led Neumann to make some disastrous financial decisions.
25. He Was A Mismanager
Besides mismanaging staff, Neumann also had no idea how to manage money. WeWork was somehow worth almost $5 billion, which attracted all kinds of new investors. By the time SoftBank stepped in, WeWork clocked in at $20 billion. So how is that a problem? In 2010 WeWork released a disclosure document exposing something shocking: financial losses.
Losses? How is that possible? What happened to the $20 billion?
26. He Was A Contradiction
At some point, Neumann purchased a personal jet for $60 million—which could account for part of the company’s financial losses. But it also pointed out Neumann’s contradictory lifestyle. Neumann had demanded that all staff eat plant-based meals in order to save the environment. At the same time, however, Neumann was a major polluter by crisscrossing the globe on his private jet.
Neumann was a charismatic and unpredictable CEO—and, as it turned out, very hard to get rid of.
27. They Bailed Him Out
By 2019, SoftBank had invested a whopping $10 billion into WeWork. After a few years under Neumann’s leadership, the company was in serious trouble. Unbelievably, Softbank offered the company over $9 billion to bail it out of the horrible state Neumann had brought it to. There was just one stipulation that came with the bailout: Neumann must leave. It looked like Softbank was finally playing hardball…except for one thing.
They gave Neumann an unbelievable parting gift: almost $2 billion. Nothing says thanks for wasting our money like a multi-billion dollar payout. Major banks seem more than willing to throw money at unscrupulous entrepreneurs, but the US government is sometimes no better.
28. There Was One Rule
David Packouz and Efraim Diveroli were just a couple of young dudes interested in selling arms when the US government offered them a contract. That was already surprising enough, but there was way more to it. The contract was for a whopping $300 million, but it came with one unbreakable rule: The arms had to come from a list of approved countries.
After some shopping around, the two young men came to a conclusion—they’d make a lot more money if that rule somehow disappeared.
29. They Went Where They Weren’t Allowed
Packouz and Diveroli knew that if they stuck to the list of approved arms-selling countries, they wouldn’t make a huge profit, so they decided to break the rule. They approached verboten Chinese arms producers and created an elaborate scheme to buy the arms from China and repackage them so they looked like they came from one of the approved countries. The pair, after going on a spending spree with the cash, got caught.
Packhouz spent time under house arrest while Diveroli received a four-year sentence. While these two bandits made their fortune running arms, our next scammer extraordinaire got into his victim’s head in the most sinister way.
30. There Was A Nosy Neighbor
In 2010, journalist Joe Nocera moved into a vacation home in the Hamptons and was excited to meet his new neighbor. Nocera assumed his neighbor was a big deal because he’d seen him throwing parties with VIP guests like Gwyneth Paltrow—hey, that’s twice she’s appeared on this list! There was another man on the property who was also around a lot and Nocera assumed, because he was serving drinks and manning the barbecue, he was some kind of employee.
That’s when Nocera learned something that made his reporter’s curiosity stand up and take notice.
31. They Were Reversed
Nocera soon realized that he had gotten the men mixed up. He found out that the guy acting like hired help was actually the owner of the house. And what about the guy living the Hampton lifestyle? He turned out to be none other than the owner’s therapist. So why was the owner of this vacation house acting like nothing more than a servant?
What had happened to create this bizarre reversal of fortune?
32. He Just Needed Help
The story goes way back to 1981, when Marty Markowitz found himself facing hardships he could no longer deal with: His parents had recently passed, his family business was in chaos, and he couldn’t handle all his responsibilities. Markowitz did what anyone with a few extra dollars would do: He saw a psychiatrist. When Markowitz entered Issac Herschkopf’s office he had no idea that, instead of getting much-needed help, he’d risk losing everything he had.
33. His Therapy Was Unique
It was clear from the beginning that Herschkopf’s therapy was out of the ordinary. Instead of the cliched couch and armchair, Herschkopf conducted sessions while the two men walked through the streets of New York. Incidentally, Gwyneth Paltrow was also a patient of his, but seems to have come out of it unscathed. For Markowitz, however, things soon took a far more sinister turn.
Herschkopf began taking control of different aspects of his patient’s life. Before long, Herschkopf had a firm grasp on Markowitz’s financial, family, and even romantic lives.
34. He Cut Her Out
Markowitz’s sister slowly started to notice that her brother was no longer making decisions for himself or their shared business. Her next move wasn’t well thought out: She took money from her brother just to get his attention. Markowitz then, on advice from Herschkopf, cut his sister out of his life. Before long, Herschkopf was Markowitz’s only friend and the only person he could trust.
In the meantime, Herschkopf was slowly taking over Markowitz’s finances. If this wasn’t bad enough, Herschkopf was keeping his patient busy with the oddest jobs.
35. He Put Him To Work
Over the many years that Herschkopf controlled Markowitz’s life, Herschkopf had his patient painstakingly type out manuscripts that the therapist had written in longhand. Herschkopf also had Markowitz handwrite invitations to his lavish parties—the ones where Herschkopf would be the host. Markowitz was paying the bill for these parties, but guests assumed he was hired help and treated him as such.
Sadly, this bizarre relationship went on for decades, until something Herschkopf didn’t do raised a red flag.
36. It Ended Abruptly
Markowitz ended up in the hospital and, when no one came to visit, had to take stock of his life. He realized two things: He had almost no friends or family, and that his one friend hadn’t even bothered to see him in the hospital. Markowitz abruptly put an end to his friendship with Herschkopf and started to rebuild his life. Markowitz is now enjoying his retirement, has reunited with his sister, and even has a girlfriend.
Herschkopf, on the other hand, had to face the New York State Department of Health, who stripped him of his license to practice medicine. Herschkopf’s was manipulative to the max—but sadly, the next scammer managed to manipulate not only his victims, but also the judge in his trial!
37. He Was Like 007
Robert Hendy-Freegard was a UK resident whose specialty was pretending to be a James Bond-type spy for M15. For 10 years, Freegard manipulated men and women out of their hard-earned cash using psychological techniques. He somehow got his victims to believe their lives were in danger, give him their money, and, in some cases, even fall in love with him.
38. He Sent Her To School
One of Freegard’s victims, Kim Adams, fell for his psychological manipulation even though she was a psychologist herself. Freegard talked her into signing up for spy school. The one hitch was that spy school was very expensive. No problem, it just so happened that Adams’ parents had recently won the lottery and could easily foot the bill.
Coincidence? I don’t think so. But that was just small potatoes. Freegard could get a lot more creative than that.
39. It Was A Long Con
One of Freegard’s most complex cons involved three young people he met in a bar. Freegard convinced the three youths that their lives were in danger and had them running across the country in fear. The con went on so long that Freegard eventually had not one but two children with one of the victims. Freegard, however, was not only cruel. He was also unusual.
40. He Was A Music Fan
Just for fun, Freegard told his victims that he had a famous relative: Duran Duran’s bassist John Taylor. Freegard apparently liked the 1980s new wave band and played them in the car—especially as they were making a nail-biting, and probably fake, getaway from unseen assassins. By the end of the ordeal, one of the victims said she couldn’t listen to “Ordinary World” by Duran Duran ever again.
Freegard, on the other hand, was about to exchange his extraordinary world for a world behind bars.
41. He Talked His Way Out
While never enjoying Duran Duran again was punishment enough for his victims, Freegard’s punishment was a life sentence. But this master manipulator managed to talk his way out of that too. The judge gave Freegard a life sentence because he abducted his victims and held them against their will. Freegard appealed the charge and said, no he did not physically hold them, he just fooled them into thinking they couldn’t leave.
In a shocking twist, the befuddled judge had no choice but to change the life sentence to time served and Freegard was free to go. It seems unfair—but luckily, there’s at least one person out there getting back at scummy scammers.
42. She Swindles The Swindlers
When Rosie Okumura discovered that swindlers had conned her mother out of $500, she vowed to get revenge. Now, Okumura takes pleasure in giving con artists some of their own medicine. Okumura is a master at imitating voices—old ladies, young children, and even Britney Spears—and she uses her voice to waste swindlers’ time and have a little harmless fun. So what’s in it for her? Okumura now makes money by uploading videos of herself in the midst of scamming the villainous swindlers.
Let’s just call her a scammer vigilante. If only there’d been one to come for Elizabeth Holmes…
43. She Dropped Out
Elizabeth Holmes started her company Theranos when she was just 19 years of age. She was attending Stanford at the time and felt she was wasting her life studying when she should be doing. Holmes’s area of development was in the health sector, and she strove to make the world a better place. In the end, she just made it a poorer place—at least for the companies she swindled, the employees she screwed over, and the people who trusted her.
44. It Started With A Turtleneck
Holmes worked tirelessly to create a piece of technology that could easily test someone for a variety of conditions, all from just one finger prick of blood. If the device worked it would be a revolution for the health industry. As she began to court investors, Holmes donned a black turtleneck which many believed she did in order to remind entrepreneurs of the late CEO of Apple Steve Jobs. Except this apple was rotten.
45. She Barely Tested
Holmes was successful at exciting investors—to the tune of $9 billion dollars. What she wasn’t successful at doing was actually testing her product. She had promised that she’d tested her technology hundreds of times. In reality, however, she’d only run around 12 tests—and even those results were not conclusive. Somehow, it was enough to fool investors like Rupert Murdoch and Walmart’s Walton family.
What Holmes did to trick more investors is a textbook definition of irony.
46. She Went Behind The Scenes
So, Holmes did test about a dozen patients and, because her machine didn’t actually work, had to come up with valid results for those patients. Holmes made a big show of testing for results on her machine and then secretly went behind the scenes and tested the blood on more traditional machines—those of her competitors.
It was a new version of the bait and switch routine, and it worked perfectly for Holmes. But what was it about Holmes that let her get away with such obvious ploys?
47. She Was A Package
What appealed to investors and members of the business community was Elizabeth Holmes’ age and her gender. It was not common to see a young woman with such fervor working in this sector. She was a bright light and it didn’t hurt that she was easy on the eyes. She was an appealing package as long as you didn’t look too deep.
Holmes’ major sin was getting more caught up in dollar signs than she did in actual scientific results—a transgression she is going to have to atone for.
48. She Blamed Him
One of the big shockers at Holmes’ trial was that she’d been having an affair with the much older Theranos COO Ramesh “Sunny” Balwani. Holmes and Balwani met in 2002 when she was an 18-year-old high school student and he was a 37-year-old MBA student. It’s not clear when the relationship started, but by 2005, the two were sharing a house together.
It was soon safe to say that the two would not be sharing anything at all in the future. At the trial, Holmes revealed some startling accusations against her ex.
49. She Was Under His Control
There are two different stories about Holmes and Balwani’s relationship. One saw them as partners in the scam—that they worked together to trick investors into handing over large sums of money. The other view, one that Holmes herself put out there, was that Balwani tried to control everything about her including what she ate and how she spoke.
Holmes also alleges that Balwani forced her to sleep with him when she didn’t want to. The jury took all this into consideration—and then the verdict came crashing down.
50. She Was Guilty
Eventually, the jury found Holmes guilty on four of the charges against her. When she is finally sentenced she could face a large and very unpleasant surprise: 20 years in prison, a huge fine of $250,000, and an order to pay restitution to each of her investors. But despite the verdict, Holmes seems to be living the good life. Well, the good life—with a scandalous side.
51. Her Boyfriend Is Footing The Bill
Elizabeth Holmes’ crimes are a horror story—so it’s kind of infuriating that she seems to be getting a happily-ever-after. In 2017 or 2018, she began dating hotel heir Billy Evans, and he proposed shortly after. But there’s a sinister dark side to their whirlwind romance. Early in their relationship, a source close to his family revealed that they thought she’d “brainwashed” Billy. Others have said that he’s helping pay for her legal bills. Some blind items have implied that she’s already cheating on him.
In July of 2021, the pair had a child—but even that had a bitter tinge to it, as many speculated that Holmes may have thought being pregnant on the stand would make her seem sympathetic. A lawyer not involved in the trial even said: “The fact that she [Holmes] is a young, new mother is going to play into any potential sentence.” I guess we’ll have to wait and see…