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Financial Cons that Became Hit Hollywood Movies



Con man actually is actually shorthand for “confidence man” – and that element turns out be an important one when it’s time to pull off outrageous crimes beyond imagination. These characters have been around since the dawn of time, but we now know a lot more about them with modern investigation techniques and an organized FBI to catch them!


Naturally, the best of these stories have been made into Hollywood movies. It’s hard to constantly come up with original material for scripts in the film industry, but these criminals seem to be doing the work for us! Let’s take a look at some of the most dastardly financial thieves in recent memory. Do you think you would have been fooled?

Bernie Madoff – The Wizard of Lies

Bernie Madoff is a name you’ve probably heard of by now, but he is certainly more infamous than famous. The former investment advisor and non-executive chairman of NASDAQ shocked the world when he turned out to be the perpetrator of the largest ponzi scheme in history. Just how large was the fraud? Bernie managed to rip off investors to the tune of $64.8 billion, affecting around 4,800 clients. But how did he manage to hoodwink these people for so long and for so much?

Although Bernie had become a legitimately successful investment portfolio manager in New York, the respect he had from this accomplishment didn’t seem to be enough. At some point during his normal business operation, he switched into the new scheme quietly on a separate floor. The company went on as usual, but he had a new project.

Bernie relied on the community respect he had earned to encourage widows at funerals and friends at cocktail parties to invest large sums into a low risk but very high reward fund. According to him, anyway. And he used some pretty unique methods to keep it all going for years and years. For example, he would intentionally reject some investors to maintain an air of exclusivity. The rumors were used to build demand for his services – but of course, there was no fund at all. He was merely pocketing the money, buying boats and houses, and laughing all the way to the bank. Bernie cleaned out charities, including holocaust survivor Elie Wiesel’s foundation. Nothing was off limits, and no one has been able to pinpoint his motivations to this day. After all, he was already a successful and respected multimillionaire!

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Bernie was eventually turned in by his own sons when they realized that the family’s entire lifestyle was illusion. Where is Bernie now? Serving a life sentence, of course. And it’s probably in his interest, because he had run out of normal, everyday American customers at that point and was starting to feed in Chinese and Russian mafia money to keep it all going. His victims have been able to recoup small amounts of their losses, but lives remain destroyed by the affair. Naturally, several documentaries and movies have been made based on this outrageous tale of greed, including a recently released TV movie starring Robert Deniro as the conman himself. People remain truly irked by this story. If you can’t trust the head of NASDAQ in the world of finance, who can you trust?

Elizabeth Holmes Bad Blood 

Elizabeth Holmes is currently in the news, and for very good reason. Gracing the covers of major magazines in recent years, Holmes was hailed as the next Steve Jobs for her company Theranos. The Stanford dropout claimed to have developed a miracle product that could analyze a tiny pinprick of blood with hundreds of tests in an instant. This would eliminate the need for expensive lab tests out of the house, and people were genuinely excited about the innovation. Celebrations over a female entrepreneur making it big in Silicon Valley were loud! Elizabeth convinced some very famous people to invest in her product, including Education Secretary Betsey DeVos, Rupert Murdoch, and Walmart heirs, to name a few. Even Carlos Slim, the richest man in Mexico! The problem was, the product never really existed.

Elizabth Holmes was an utter fraud, and it took a very long time for people to notice. Those close to her described her as mesmerizing, a woman who spoke in a baritone voice with almost cult-like persona on stage. We now know that even her voice was fake!

A lot of people were genuinely taken in, and she managed to assemble a board of military and diplomatic figures to give the company further clout in the investment rounds. It seems she really tricked former U.S. Secretary of State George P. Shultz, and this connection introduced her to a whole range of personalities on a trusted basis. The board of directors quickly comprised former U.S. Secretary of Defense William Perry, former U.S. Secretary of State Henry Kissinger, as well as a general, a senator, and an admiral. Whew! With a lineup like that, it’s no wonder that investors poured in millions without too many questions.


Along with her boyfriend Sunny Balwani, Elizabeth operated a fraudulent scheme to the tune of $9 billion. The product that she showed investors was not real at all. It could do a few tests inaccurately, but certainly not hundreds of accurate tests. It was worthless, and employees started to notice the problems she was carefully hiding. Elizabeth intimidated those who questioned her and strategically fired developers who started to show confusion over the product. She made sure there was no one around who could ever blow the whistle, but this trick didn’t last forever. Journalists exposed her in 2015, and she has been charged with criminal counts for which she is currently standing trial.

During recent depositions she answered “I don’t know” hundreds of times when asked about the accuracy of her product. This is a far cry away from the confident persona giving Ted Talks about the future of technology just a few short years ago. A hated figure at this point, Jennifer Lawrence has been recruited to play her in an upcoming film about the multi billion dollar fraud scheme. Do you think it’s a pretty close resemblance? Jennifer’s voice is pretty low, too! The film is production currently, and it’s sure to be another con(woman) blockbuster for Hollywood.

Jordan Belfort – The Wolf of Wall Street

Jordan Belfort’s scheming inspired the very popular movie The Wolf of Wall Street starring Leonardo DicCaprio, directed by Martin Scorsese. Everyone knows that Martin is very selective about his scripts, so this has to be a pretty good con story! Who is Jordan Belfort, and what exactly was his money game? This happens to be another case of investor fraud, and he did this in the 1980’s when he discovered he was an exceptional penny stock salesman. After opening his own firm, Jordan proceeded to defraud thousands of clients with the help of a few good friends he met along the way. Could things have turned out differently for Jordan? He had a decent start in life, but it seems some characters are just destined for dirty dealings.

Born in 1962 in the Bronx neighborhood of NYC, Jordan became an entrepreneur early on. Legitimate ventures included selling treats at the beach from a cooler with a friend, and he did pretty well – $20,000 from Italian ice back then was even more money than it sounds! He graduated from a DC university with a BA in biology, and wanted to continue on to dental school. But after learning that business was declining in this sector, he changed his plans. Married young, Jordan started to struggle financially. The stock business changed it all, but authorities caught him after a successful run with boats, cars, and houses to the max.

CryptoCurrency Times

The result was the slammer, but Jordan spent only 22 months in prison after turning on his co-conspirators. He wrote a memoir, claimed personal reform, and moved to Australia to start a new life. Unfortunately, this didn’t last long! Despite his opportunity for personal rehabilitation and newfound fame through an autobiographical film, Jordan has been caught again running scams abroad. He has also been avoiding restitution payments to victims in America! Some people never change, and it looks like the Australian government may have some questions for Jordan in the near future. What a shame!

Frank Abagnale, Jr. – Catch Me if You Can

Frank Abagnale Jr. was the subject of another Leonardo DicCaprio film, and it’s sure starting to look like Leo has a passion for a good con man story! This case involved fraud, of course. But it also had some memorable antics that not every thief goes so far to employ in their schemes. What did Frank do, exactly?


Born in 1948, Frank started some cons at the very young age of 15. His scams involved check forgery early on after he discovered how easy it was to manipulate this form of payment during the low-tech era of the 1960’s. To escape detection – and perhaps for a little excitement – Frank became an expert impostor. It is estimated that he had 8 identities, but no one can be sure! His fake personae included doctor, an airline pilot, and even a prison agent. He also found other ways to steal during these roles, like collecting payment bags being dropped off at big businesses. With these unusual skills of manipulation, he escaped police custody on more than one occasion. Frank was eventually caught, as most criminals are in the end. But what happened to this super thief? Surely life in prison!

Wall of Celebrities

In fact, Frank had a very unusual ending for a criminal at his level. Because he was truly the national expert on check forgery at that time, the US government cut a deal with him to reduce his penalties. What was the agreement? Frank was put in charge of analyzing other scam cases the FBI could not solve, and he did very well with this role. Indeed, he knew a lot about how criminals operated – and might have been the best of the best at the time. Today, Frank is actually a fraud consultant with a successful business in this line of work. You can listen to his public lectures, and compare him to his movie portrayal. Sometimes the truth is stranger than fiction, isn’t it?

Steven Jay Russell – I Love You Phillip Morris

Steven Jay Russell is another con artist that managed to escape custody on several occasions. The crimes that put him there were definitely financial, but his impersonations are probably what really inspired actor Jim Carrey to sign up to play him on screen. It’s quite a wacky tale, and this case doesn’t involve a rehabilitation or a happy ending.  I Love You Phillip Morris shows viewers a bit about his crimes, starting when he convinced an insurance company to make him their CFO with fake credentials. He began embezzling $800,000 to finance a glamorous life with a gay lover named Phillip Morris. They enjoyed rolex watches, luxury cars, and plastic surgery during the height of their fraud. 

During his reign of crime, he had many aliases. Like Frank Abagnale, he posed as various professionals to escape detection and conduct more fraud. There 14 fake names known at this time, and his jobs included judge, doctor, and even an FBI agent! While imprisoned for some criminal activity along the way, he managed to escape four times from prison using his world class manipulation skills. But eventually, it all came to an end.

Matt Rainwaters

Steven was sentenced to 144 years in jail after his final capture. He has since been put in a maximum security facility because of his many escapes! He actually sits on death row, despite not receiving that penalty. It’s simply more secure over there! He describes his days as mostly hotdog meals, and has been interviewed periodically on his story and current events. Today, he says he regrets his life of crime. But it’s hard to say if someone like Steven could ever live a straight arrow lifestyle! Can real con men ever change for good?