Frank Tassone was on top of the world. Rising from a humble school administrator to the superintendent of the Roslyn school district in Long Island, he was loved by both his students and his contemporaries. Not only was he likable, but he knew how to get the job done.

Between his reputation and the soaring performance of Long Island schools, Tassone could do no wrong. Until he did. Soon, the truth came out that Tassone was not who he said he was. The superintendent hid behind an elaborate web of lies while he destabilized the system he worked so hard to build.

Frank Tassone was a Bronx-native and Columbia-educated professional. His doctorate made him look great on paper, but his stellar background wasn’t even his greatest strength. He knew how to connect with people.

He was involved and invested in the education of his students and the betterment of his community. Frank often took the time to eat lunch with the student body. He formed a book club with parents. He was one of the good ones, or so everyone thought.

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Tassone enjoyed an incredibly successful 12 years as superintendent of the Roslyn County school district. Roslyn High School, located on the North Shore of Long Island, was particularly thriving. During Tassone’s tenure, it became a top 10 public school.

In a 2004 New York Magazine article ranking the best public schools in America, writers dubbed Roslyn High School number six. The article explained that “a diploma from Roslyn High School is the closest you can get on Long Island to a ticket to Harvard.”

Orange County Register

Certainly, the students at Roslyn were intelligent. That was exactly what Tassone wanted — his overachieving student body made his job as superintendent even easier. Incredibly, one of those brilliant students would eventually bring his downfall.

Newsday / Karen Wiles Stabile

Rebekah Rombom was a student reporter at the Roslyn school paper when the assistant superintendent of schools, Pamela Gluckin, was fired with no explanation. Rombom’s reporter instincts activated.

Rebekahn Rombom / Youtube

Rombom got a tip that Gluckin’s firing had something to do with some budget discrepancies, and it turned out to be true. Pamela Gluckin used her position as assistant superintendent and business administrator to steal an incredible sum of money.

The school board uncovered that Gluckin had been using the district credit card for her own personal expenses. She racked up more than $250,000 in bills paid by the county. Still, the quarter of a million dollars was just the tip of the iceberg.

The Island Now / Max Zahn

When all was said and done, she stole a reported $4.3 million from the schools. Gluckin had multiple vacation homes, fine art pieces, and high-end jewelry to show for it. Her niece, Debra Rigano, who worked as a county clerk, was in on the scheme as well.

HBO

Even Gluckin’s son John McCormick used district funds to have an $83,000 spree at Home Depot of all places. Of course, the school board wanted to press criminal charges against Gluckin, but one man fought against that decision: Frank Tassone.

Huntington Now

Tassone agreed that she should be immediately fired but stressed the importance of keeping the authorities out of it. He expressed concerns over the possibility of ruining the pristine reputation of their school. But there was more to his worry.

He was less worried about the school and more worried about what the authorities would uncover if they investigated Gluckin’s crimes. Tassone was just as guilty as Gluckin; the unassuming administrator was stealing even more from the school budget.

Thanks to the reporting of Rombom and the school paper, the jig was up for not only Gluckin, but Tassone as well. The two worked together to steal over $11 million from taxpayers. Tassone financed an extravagant lifestyle with his stolen cash.

Dartmouth College

His lavish Park Avenue apartment that he shared with his partner, Stephen Signorelli; his trips to Vegas to visit his lover; a collection of expensive cars; fancy clothes; and plastic surgery — all funded by hard-working New Yorkers. His spending was almost laughable, as he blew $5,000 on Christmas cards.

In 2006, Tassone was sentenced to four to twelve years in prison. He actually got out early in 2010 for good behavior and was put on probation until 2018. The disgraced superintendent is barred from working any job that requires him to handle money.

Newsday

Today, Tassone lives in New York and amazingly still receives his $170,000 a year pension from the state, reportedly due to a loophole in pension laws. He recently guest starred on a podcast hosted by Mike Bayer, where he described the impact of his crimes.

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As HBO recently created a film based on the whole ordeal, Tassone explained it dredged up old memories. “I thought this finally was over. You know, it’ll never be over for me, because every day I feel pain,” he said. And he wasn’t the only one who claimed to make amends.

After a 2011 prison release, Gluckin also continued receiving her pension, which she allegedly promised to donate to the Roslyn school district. The former assistant superintendent worked at a nonprofit in Queens before she passed away in 2017.

Newsday / Karen Wiles Stabile

“My actions were shameful, deplorable,” Tassone said at his hearing more than a decade ago. “I am deeply sorry to the people of Roslyn, and to the children.” The children at Roslyn have since become adults, but have not forgotten the crimes of Tassone.

Sadly, the world is full of people who portray one face to the world, but have completely separate intentions. It’s far too easy to prey on the kindness of others, whether it’s robbing the school board or something else entirely. Like one New Jersey couple who planned a long con.

Kate McClure and Mark D’Amico of New Jersey were just like any other couple, except, come the weekend, you wouldn’t find them at any old bar in the neighborhood. Their usual hangout was a tad unconventional.

Richard Harbus – The New York Post

The hangout spot in question was a nearby casino. Mark had a bit of a gambling addiction, so this was the predominant reason behind their routine. On their frequent trips, they ran into someone who would change their life.

This was a man named Johnny Bobbitt, and he was a homeless veteran. The couple started to befriend him, providing the man with cups of coffee and extra dollars they’d won from the slot machines.

ABC News

Bobbitt was thankful for the kindness, but he missed something about McClure and D’Amico: Strapped for cash themselves, they were beginning to devise quite the sinister scheme — one in which he would play a crucial role.

David Swanson – Inquierer

See, over 60,000 text messages, the couple complained about their money problems, brainstorming a less-than-legal way to remedy the hungry bank accounts. That’s when they remembered the nice homeless man near the casino.

So, they let Bobbitt in on their sneaky plan, and he hastily agreed. McClure posted the made-up narrative on GoFundMe: Bobbit gave her a $20 for gas; she wanted his kindness rewarded. Donations poured in.

It was the details that won over strangers: “Johnny did not ask me for a dollar,” McClure wrote, “and I couldn’t repay him at that moment because I didn’t have any cash, but I have been stopping by his spot for the past few weeks.”

ABC News

In the meantime, however, McClure texted her friend, “Okay so wait the gas part is completely made up … But the guy isn’t. I had to make something up to make people feel bad … So, shush about the made up part.” The friend listened.

Law and Crime

As the GoFundMe went around the internet, more than 14,000 individuals donated to the made-up cause, amounting a grand total of $402,000 — money that was supposed to be helping a homeless veteran get back on his feet.

GoFundMe

McClure and D’Amico themselves even got a ton of accolades online. Hailed as good people and selfless Samaritans, after the money had been raised, Kate posted an update: “now jonny will have a roof over his head!” Soon, things would start to unravel..

GoFundMe

The first sign of trouble came when Bobbitt himself complained to local authorities that he hadn’t gotten any of the money that was owed to him. This is when investigators turned an eye to the seemingly innocent couple.

Richard Harbus / NY Post

Bobby’s attorneys claimed that out of the hundreds of thousands raised, their client had received a mere $75,000 from the fund. They accused McClure and D’Amico of spending the money that was rightfully his on luxury items, including fancy trips and handbags.

David Swanson / The Philadelphia Inquirer

Their first line of defense was to say that they’d withheld a portion of the funds from Bobbitt because they were worried that he would have spent the money on drugs, an issue he’d struggled with in the past.

David Swanson / The Philadelphia Inquirer

Little did Bobbitt know, he too would soon be implicated in the nefarious scheme. Detectives seized the couples’ cellphones, revealing texts that incriminated all three of them.

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When asked why it didn’t cross Bobbitt’s mind that complaining about his share of the money might land him in hot water as well, prosecutor Coffina simply replied that he “can’t speculate what is in Johnny Bobbitt’s mind. It certainly appears to have been a miscalculation on his part in hindsight.”

Elwood City Ledger

Marc D’Amico accepted a guilty plea, guaranteeing him five years in prison but allowing him to avoid taking full responsibility for the scheme. He also has to help pay back the stolen money.

Jose F Moreno – Inquirer

Meanwhile, Johnny Bobbitt was given five years probation and, despite being homeless, must also help to pay back the funds stolen through the scam. And as for Kate McClure? Her fate is still being decided…

Tim Tai – Inquirer

Kate continued to pinpoint her boyfriend, Mark D’amico, as the ringleader behind the entire thing, so her sentencing date was pushed back. Eventually, she pleaded guilty to conspiracy to commit wire fraud.

The Inquirer

GoFundMe has issued their own statement, writing, “We are fully cooperating and assisting law enforcement officials to recover every dollar withdrawn by Ms. McClure and Mr. D’Amico. Finally, it’s important to understand that misuse is very rare on our platform.”

David Swanson/Philadelphia Inquirer

But GoFundMe executives knew people had been leveraging online platforms for crime. In 2010, a New York City woman, Clarabelle, was called by a Mr. Tony Russo. Owner of a glasses marketplace, he said his supplier didn’t have the pair she ordered in stock, but he could offer a replacement pair of glasses. She turned them down.

Photo by Jeremy Moeller/Getty Images

“What the hell am I supposed to do with these glasses?” Tony Russo screamed back at her. “I ordered them from France specifically for you!” This was a lie. Tony had simply purchased the “replacement pair” from Ebay. Clarabelle didn’t know.

Taken aback by his outrage, Clarabelle relented. Not long after, the glasses arrived, but they were clearly counterfeit — and to make matters worse the seller, a company called DecorMyEyes, had overcharged her by $125!

The New York Times

This was when Clarabelle’s nightmare began. She told Tony Russo, below, she was going to dispute the charge, sending him into another tirade. “I know your address,” he told her. “I’m one bridge over.” Then, he threatened to sexually assault her.

William Farrington – New York Post

Alarmed but not about to go down without a fight, Clarabelle contacted her bank the next day to make a complaint about the unfair charges. They said they would get back to her within 60 days. Russo was not happy.

Rosie Nanins

“Call me back or I’m going to drag you to small-claims court,” the shameless con artist wrote. “You have one hour to call me back or I’m filing online.” She refused. Hours later, he sent her a photo that shook her to her core.

It was a photo of Clarabelle’s apartment, taken on Google Maps (the address pictured below is not hers). A clear threat and breach of privacy. Tony called her non-stop until she finally went to the police at 1am. There was little they could do.

And as the 60-day deadline for settling the bank charge dispute approached, Clarabelle received a notice informing her that she had indeed been charged for the counterfeit product. Someone had posed as her, falsely claiming to accept the charges. All signs pointed to Russo.

YouTube – Proyectos Escolares

Furious, the disgruntled customer really began to look into this guy. She was shocked to find that dozens of others around the world had gone through the same exact experience with Russo, all posting their stories on a consumer advocacy site called Get Satisfaction.

All of the sordid tales were the same: rude intimidation, scary physical threats, and blatant fraud. But why was he still able to operate so successfully? And more importantly, why was his business, “DecorMyEyes” still at the top of Google search results?

YouTube – CNBC Prime

Even worse for the victims, all the negative publicity was increasing Russo’s profits — and by a large margin. A New York Times report on the strange case questioned Google employees about this, and their responses were somewhat concerning.

Flickr – Ryan Shea

The popular search engine’s mysterious algorithm launches sites that are merely linked frequently on other respected sites to the top of the search list. Whether the links are shared in a positive or negative context does not matter.

Lucy Greider

And Russo himself, or Stanley Bolds (one of his aliases), or Vitaly Borker (his actual name) recognized this profitable yet highly immoral business tactic and capitalized on it big time. He even spoke on the issue.

Daily Mail

“I’ve exploited this opportunity because it works,” he told The New York Times. “No matter where they post their negative comments, it helps my return on investment. So I decided, why not use that negativity to my advantage?”

YouTube – CNBC Prime

This phenomenon did not bode well for Google’s reputation, and the company remained notably cryptic about how its algorithm worked to make it harder for people to exploit. The possible solution has the potential to turn dystopian.

A concept called “sentiment analysis” allows search engines to distinguish between positive and negative publicity (Russo’s site would definitely count as the latter). Utilizing sentiment analysis would be a quick way of taking scammers like Russo down, but it also could turn bad pretty quickly

Pixabay

An example shared by Danny Sullivan, an expert on Google, pointed out the negative sides to sentiment analysis with an example: If people speak negatively of a president, Googlers possibly wouldn’t find the White House page in search results. Not great.

J. Emilio Flores – The New York Times

Surprisingly enough, Russo claimed he didn’t start out using these cruel and intimidating tactics, claiming to be perfectly friendly to the majority of his customers. But he could be starting an alarming new trend.

YouTube – CNBC Prime

Given the profitability and relative lack of consequence he received for his actions, others may follow suit, giving way to a new and unprecedented form of advertising that thrives on negativity and abject rudeness to customers

Even with the controversy, Russo was living comfortably in a large brick house in Brooklyn with his wife and two daughters, happy as a clam. He knew he was safe — there were a lot bigger con artists for the police to fry.

Instagram – Sam Sorine

By 2015, Elizabeth Holmes had already reached the top of the world, but she was determined to go higher. The billionaire entrepreneur promised her company would change the world — and it did…in a way.

The New York Times

Born in 1984, Elizabeth stood out as a gifted student from a young age. She seemed destined to achieve greatness, and at age 9, she wrote a letter to her father saying she wanted to do “something that mankind didn’t know was possible.”

After mastering Mandarin in her teens, Elizabeth enrolled at Stanford University to study chemical engineering. Even such a prestigious academic setting, however, couldn’t quite keep up with Holmes’ ambitions.

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So, after less than two years at Stanford, Elizabeth dropped out to found her own consumer healthcare company. Not long after, she unveiled a revolutionary idea that took the entire world by storm.

TED

Citing a lifelong fear of needles, the budding businesswoman announced that she was about to revolutionize blood analysis. With just a finger prick, her technology could allegedly perform 50 different blood tests.

In 2004, she officially brought her company together in the form of Theranos — a portmanteau of “therapy” and “diagnosis.” Though she chose to keep the company quiet from the general public, she coaxed big spenders to support her.

The New York Times

Elizabeth found her first investor in venture capitalist and family friend Tim Draper. Soon, she brought aboard Rupert Murdoch, future Secretary of Education Betsy Devos, and the Waltons — founders of the Walmart empire.

Time Magazine

But to become an iconic CEO, Elizabeth needed more than just a lot of dough; she had to look the part. She took a page out of Steve Jobs’s book and began wearing black turtlenecks every day. According to some, she also significantly lowered her voice.

Reuters

By 2013, Elizabeth introduced Theranos to the world by inking a monster deal with Walgreen’s. Elizabeth had billions in company coffers and became the talk of the town, but she did have to deal with criticism.

The New York Times

In scientific circles, statements abounded that Holmes’ technology simply couldn’t work. While she brushed off the naysayers, the young CEO also refused to explain exactly how they were wrong. She wouldn’t tell reporters or the FDA. Not even her employees knew — save for one.

GIPHY

In her late teens, Elizabeth met entrepreneur Ramesh “Sunny” Balwani. Though he was 19 years older and married, they entered a relationship that was both romantic and professional. Sunny became the COO of Theranos and the only other soul who knew the secrets of its technology.

People

For a while, the lack of transparency didn’t bother anyone. Forbes credited her the youngest self-made female billionaire in history, and Elizabeth received honors from Time Magazine and Harvard Medical School.

Elizabeth went so far as to become an icon for the next generation. In 2015, she launched a campaign called Iron Sisters to promote women in STEM fields. That was shortly before her entire world came crumbling down.

Twitter / Elizabeth Holmes

That year, disturbing rumors started to circulate about Theranos. For instance, anonymous sources whispered that Theranos secretly used other companies’ blood tests for demonstrations, while leaving their own technology completely untested.

These theories gained traction when Theranos employee Tyler Schultz turned whistleblower. Cooperating with the Wall Street Journal, he revealed that Theranos’ technology was completely inaccurate and didn’t do what the company claimed. All eyes turned to Elizabeth.

Wall Street Journal / Jason Henry

Attempting damage control, she rebuffed the allegations on CNBC’s Mad Money. She told Jim Cramer, “This is what happens when you work to change things. First, they think you’re crazy, then they fight you, and then all of a sudden you change the world.”

Biography

However, the general public didn’t buy her disruptor narrative any longer. Without an actual product, Theranos fell apart from the inside out and saw its $9 billion worth turn to ash.

Arizona Daily Star

After the Securities and Exchange Commission began interviewing so many Theranos insiders, it was no surprise when the bell came tolling for Elizabeth. She and Sunny were charged with eleven counts of fraud. Amazingly, she wouldn’t admit anything was wrong.

People

Elizabeth continued to chat pleasantly with her scant employees, adopted a husky, and found a new love interest in Billy Evans. However, no level of denial could stop Theranos from finally dissolving in 2018.

Only time would tell exactly how Holmes would pay for her crimes, but her legacy is clear. Instead of revolutionizing technology, she innovated the 21st-century scam, wrapping up rich and poor alike in her lies.

In modern society, where success and notoriety are so intertwined, some people will tell any story to get ahead. This doesn’t just happen in the business world, either.

Anna Delvey, for instance, was the life of the party. She fit in with Manhattan’s elite effortlessly, but she certainly had secrets. Her wads of cash led people to conclude that she was very wealthy, but no one really knew how she earned her money.

Anna’s story started on February 18, 2017, when she first checked in to 11 Howard, a fancy hotel in SoHo, Manhattan. Staff noticed her right away. After all, she tipped everyone $100 every time she saw them, and it was money that would pay off…

Anna quickly befriended a concierge who was roughly her same age. She asked Neff Davis from Crown Heights, Brooklyn for restaurant suggestions, but seemed to already know of every one that Neff suggested. “This was not a guest who wanted my advice, this was a guest who wanted my time.”

Neff didn’t mind spending time with Anna since she was grateful for her generous tips. Even the bellboys literally fought to help Anna because they knew that they would get a Benjamin. Anna threw cash around wherever she went.

Anna and Neff got along well and started visiting bars, restaurants, and clubs together, even mixing with artists like Guido Cacciatori, Gro Curtis, and Giorgia Tordini. Anna seemed particularly interested and knowledgeable in the world of fashion and art.

Anna knew how to climb up the social ladder, rung by rung, and kept working hard to meet even more famous, more wealthy, more successful people. She began hosting dinners and parties until all of her friends’ friends knew her name. But she always kept Neff nearby.

One night, thanks to Anna, Neff even found herself seated next to her childhood idol, Macaulay Culkin. “Which was awkward,” she said. “Because I had so many questions. And he was right there. Still, I never got the chance to be like, ‘So, your the godfather to Michael Jackson’s kids?'”

One of the closest friends Anna collected was Michael Xufu Huang, an art collector who founded his first museum at the age of 22. They planned a trip to Europe together, but Anna asked him to put flights and hotels on his credit cards, promising to pay him back… but she never did. That’s when her secrets started unraveling.

You see, Huang had seen Anna spend money, so he figured she’d be good for it. They had a great time in Venice, but when they returned, she never offered to pay him back. It didn’t seem too big of a deal, and she got away with it — this time.

It was a few weeks before her birthday when she hired a PR firm to throw her an unforgettable b-day bash at one of her favorite restaurants, Sadelle’s. When it came time to pay up, Anna was gone. The firm even contacted Huang to see if he knew where to find her, but he was just as stumped. But he knew one thing: Anna wasn’t someone he could trust anymore.

Huang began asking around to see if anyone had a deeper insight into Anna’s life. Not only did nobody know her whereabouts they also didn’t know her origin. Some assumed she was Russian, or Polish, or German. A few thought she came from oil money while others thought she was the child of a diplomat. The only thing they were certain about was her interest in parties and art.

Truthfully, Anna wasn’t just a socialite: she had a plan. She wanted to make the right contacts in the art world to set up an exclusive club with a focus on art. She had her eyes set on 281 Park Avenue South and would call it the Anna Delvey Foundation, or ADF.

Marc Kremers was a creative director and digital designer from London whom Anna convinced to work with her on the ADF. The club would have a German bakery, restaurants, a basement nightclub, an artist residency program, and roof terrace overlooking Central Park. He said at first she was “a pleasure to work with.”

But, after several months, the bills once again piled up, and Marc saw no money. “Hundreds of painful emails followed,” Mar said, “complete with fictitious financial managers CCed, who’d muscle in every-time I threatened to seek legal action. As a small business owner, it was a grueling ride and nearly shut us down.” The project was put on indefinite hold.

It was then that Anna met Martin Shkreli, an infamous businessman and hedge fund manager. He would soon be convicted of securities fraud, but not before giving Anna some tips.

Not long after, her hotel discovered that they didn’t have a working credit card on file and locked her out. She did what Martin advised and threatened to buy web domains in all the hotel managers names; in order to use them in the future, they would have to pay her tons of money. Her dark side was starting to show…

Things had gone awry for Anna. There was little progress with the ADF and she was moving from hotel to hotel while avoiding paying for anything. She literally fled the country by taking a trip to Morocco with her personal trainer and her friend, Vanity Fair‘s Rachel Deloache Williams.

Of course, Rachel never saw a dime. “She walked into my life in Gucci sandals and Céline glasses,” Rachel recalled, “and showed me a glamorous, frictionless world of hotel living and Le Coucou dinners and infrared saunas and Moroccan vacations. And then she made my $62,000 disappear.”

By July of 2017, everything had fallen apart. Anna was arrested for three counts of misdemeanor theft of services (including a dine-and-dash) and was released without bail. Now she had nowhere to go, and no one left to turn to — not even Neff. Her old friends staged an intervention and told her the ADF was sold. With nothing left to lose, she tried to escape once again.

Using the last of her money and her tricks, Anna traveled to California, where she tried to hide in a rehabilitation center. Meanwhile, back in New York, the press got hold of her story, and slowly but certainly, the mystery that was Anna Delvey began to unravel…

The truth was: Anna Delvey didn’t exist! Anna was really Anna Sorokin, a German-Russian girl from a working-class family. She tried attending the Central Saint Martins Art School in London but dropped out. She worked at Purple Magazine in Paris before moving to New York City at the age of 25. Anna Delvey got away with everything, but Anna Sorokin couldn’t.

In October of 2017, she was arrested on six charges of grand larceny for scamming wealthy NYC business acquaintances and several hotels. According to the Manhattan District Attorney’s office, the damage was as high as $275,000. She rejected a plea deal and faced a 15-year prison sentence.

Once in Riker’s Island, Anna used her sly ways to befriend all the right prisoners. Perhaps that was how she learned how to post “throwback” pictures from jail because an old photo of her and Neff mysteriously appeared on her Instagram page.

TV producer and screenwriter Shonda Rhimes was set to produce a Netflix series detailing Anna’s scandalous New York adventures. While a couple actors have shown interest in the lead role, Anna stated she wanted Jennifer Lawrence or Margot Robbie to portray her. She actually seemed more worried about casting than her upcoming trial.

Anna conned friends and businesses out of $275,000, using falsified documents to get multiple bank loans. She floated bad checks and took out lines of credit. The plan was to pay it all back with money from the ADF, but the money never came. Still, with her skills, she could come out of prison an even smarter criminal mastermind.