We all know that the world of business isn't strictly black or white, but there is a clear line between making a mistake and committing deliberate fraud against people's life savings.

In the realm of high finance and business, few topics capture the public imagination like the tales of fraudsters and their elaborate scams. These individuals have orchestrated some of the most audacious and financially devastating frauds in history. This article delves into some of the most notorious fraudsters and their scams, ranking them in terms of financial impact and societal shock value. We also explore some recent shocking scam cases that have rocked the financial world.

I collected the most important cases and ranked them starting with the most shocking ones:

What Are The Biggest Money Scams of All Time?

Sam Bankman Fried ‘SBF' (FTX Crypto Scandal) · $10 billion (2023)

Sam Bankman-Fried, the founder of FTX, was found guilty on all seven criminal fraud counts linked to the collapse of crypto exchange FTX and its sister hedge fund, Alameda Research. Despite pleading not guilty, he was convicted of wire fraud, conspiracy to commit wire fraud, securities fraud, commodities fraud, and money laundering, with prosecutors labeling his actions as “one of the biggest financial frauds in American history.”

Going Infinite: The Rise and Fall of a New Tycoon, by Michael Lewis (2023)

When Michael Lewis first crossed paths with Sam Bankman-Fried, he was meeting more than just the world's youngest billionaire. Bankman-Fried, a figure straight out of a modern-day financial drama, had CEOs and even heads of states lining up for a slice of his attention and investment. Despite his financial clout, he looked every bit the ordinary guy, often seen in cargo shorts and white socks, half-focused on video games during Zoom calls.

Going Infinite is where Lewis tells us the story of Bankman-Fried, a character whose quick rise to the top and even faster fall shook the pillars of high-frequency trading and cryptocurrency. The book isn't just about the numbers and the crashes—it paints a human picture of a man who played by his own set of rules until the reality of the financial world hit back hard. Lewis captures this journey without losing the grip on the stark reality of ambition colliding with the limits of the system.

Elizabeth Holmes (Theranos) · $7 billion (2022)

Theranos, once a high-flying startup valued at $9 billion, promised to revolutionize healthcare with its groundbreaking blood-testing technology. However, it came crashing down when it was revealed that its technology was essentially a fraud. Elizabeth Holmes, the charismatic CEO of Theranos, was at the center of this scandal. She was accused of massive fraud for misleading investors, patients, and doctors about the capabilities of Theranos' technology.

Bad Blood: Secrets and Lies in a Silicon Valley Startup, by John Carreyrou (2018)

In 2014, Elizabeth Holmes was riding high, likened to tech giant Steve Jobs. She had dropped out of Stanford and was at the helm of Theranos, a company that shot to a $9 billion valuation. Her claim? A device that needed just a drop of blood to do what took labs a vial to do. Big names with deep pockets, like Larry Ellison and Tim Draper, bought into the hype, and Holmes's stake was said to be worth $4.5 billion.

But behind the scenes, the tech didn’t deliver. People were getting wrong test results, leading to a host of medical mishaps. Holmes and her second-in-command, Sunny Balwani, did everything they could to keep critics quiet, from journalists who got too close to employees who started asking tough questions.

Bernie Madoff (Investment Ponzi Scheme) · $65 billion (2008)

Bernie Madoff orchestrated the largest known Ponzi scheme in history, defrauding thousands of investors out of tens of billions of dollars over several decades. His fund, which promised unusually steady and high returns, was nothing but a facade for a massive fraud operation.

The Wizard of Lies: Bernie Madoff and the Death of Trust, by Diana B. Henriques (2011)

Henriques's book, which has also been adapted into an HBO film starring Robert De Niro and Michelle Pfeiffer, provides a thrilling narrative of Madoff's ascent to the pinnacle of Wall Street and his subsequent rapid downfall. The Wizard of Lies delves into the personal and financial devastation left in the wake of Madoff's scheme, including suicides, ruined businesses, split families, and closed charities. Beyond the engrossing story, the book also extracts critical lessons for regulators, financial professionals, and the general public, highlighting the implications of Madoff’s scheme on various facets of society.

Ivan Boesky (Insider Trading Scandal) · $100 million (1986)

Ivan Boesky was a prominent figure in the 1980s Wall Street, but his name became synonymous with insider trading. He was implicated in a vast insider trading scandal and was fined $100 million, marking one of the biggest cases of insider trading in history.

Den of Thieves, by James B. Stewart (2012)

James B. Stewart's Den of Thieves brings to light the story of how four major players on Wall Street in the 1980s—Michael Milken, Ivan Boesky, Martin Siegel, and Dennis Levine—almost succeeded in pulling off the biggest insider trading scam in financial history. These men were on the verge of making off with billions when a group of dogged detectives managed to outsmart their high-priced lawyers and bring them to justice. Stewart's account is built on a foundation of hard evidence, including secret grand jury transcripts, interviews, and trading records.

The book offers a narrative that's both detailed and engaging, showing the human side of a business saga that rocked the financial world. It presents the intricacies of greed and corruption, set against the backdrop of the glitzy 80s finance era. Stewart gives us a story that's about more than just the facts, it's about ambition, the seduction of power, and the tireless efforts of those who worked to set things right.

Jan Marsalek (Wirecard) · $4 billion (2020)

Wirecard, once a darling of the fintech world, collapsed in a spectacular scandal when it was revealed that nearly €2 billion supposed to be held in trustee accounts probably did not exist. Jan Marsalek, Wirecard's COO, became a central figure in this scandal which is considered one of the most notable corporate collapses in the post-war German history.

Money Men: A Hot Startup, A Billion Dollar Fraud, A Fight for the Truth, by Dan McCrum (2022)

Money Men is the gritty account of Wirecard's spectacular implosion, penned by Dan McCrum, the journalist who sniffed out the rot within what was once a fintech powerhouse. McCrum started with a hunch that something was off about the company that had swiftly climbed the ranks to overshadow the likes of Commerzbank and Deutsche Bank. Wirecard's success story seemed improbable, especially with a CEO who blatantly mimicked Steve Jobs. McCrum's initial skepticism led him down a rabbit hole of financial deceit.

As McCrum picked at the seams of Wirecard's glossy exterior, what he found was not just unsettling but outright dangerous. His investigation drew him into a shadowy world where the lines between legal and criminal enterprises blurred. He found himself a target, followed by strangers and bombarded with legal threats, all while being pegged as a criminal himself. His book promises a raw look into how he connected the dots to expose Wirecard's massive fraud, involving everything from phantom bank accounts to possibly staged deaths.

Jordan Belfort (Stratton Oakmont) ·  (1990s)

Stratton Oakmont, under the guileful helm of Jordan Belfort infamously dubbed as the ‘Wolf of Wall Street’, orchestrated a colossal securities fraud scheme that shook the financial echelons of Wall Street. Jordan Belfort, the charismatic yet fraudulent genius behind Stratton Oakmont, became the emblem of stock market maleficence that the early 90s is often remembered for.

The Wolf of Wall Street, by Jordan Belfort (2011)

The Wolf of Wall Street is a brazen narrative by Jordan Belfort himself, delving into the tumultuous world of high-stakes trading, the allure of insatiable greed, and the unforgiving descent into infamy. Belfort began his brokerage journey with a veneer of legitimacy, only to swiftly veer into a nefarious realm of financial chicanery. As his firm Stratton Oakmont soared to notoriety, so did the tales of wild office antics and a corporate culture steeped in excess.

As Belfort navigated the treacherous waters of Wall Street, his empire built on deceit grew, but at a harrowing moral cost. His book lays bare the machinations behind the massive securities fraud, the relentless pursuit of wealth, and the egregious violations of trust that led to his eventual downfall. His raucous tale is not just a portrayal of his audacious ventures, but an odyssey of self-reckoning as he came face to face with the consequences of his unbridled avarice.

Others Noteworthy Fraudsters

Bernard Ebbers (WorldCom) · $11 Billion Accounting Fraud (2002)

WorldCom, once a titan of the telecommunications industry, plummeted into disgrace when an $11 billion accounting fraud came to light. At the center of this financial maelstrom was Bernard Ebbers, the company's CEO, whose tenure saw one of the largest bankruptcies in U.S history. The scandal was a stark revelation of the widespread accounting malfeasance under Ebbers' regime.

Kenneth Lay & Jeffrey Skilling (Enron) · $74 Billion Accounting Fraud (2001)

Enron’s tale is synonymous with one of the most notorious corporate frauds in history. Under the leadership of Kenneth Lay and Jeffrey Skilling, a labyrinthine network of accounting deceit was spun, causing a cataclysmic loss of approximately $74 billion for investors. The scandal unraveled a tale of hubris, greed, and an audacious disregard for ethics.

Final Thoughts About The Most Prominent Fraud Cases

The impact of these fraudsters and their scams extends beyond financial losses. They erode trust in financial systems and institutions, necessitate tighter regulatory scrutiny, and often result in lasting changes to laws and industry practices. Yet, as the recent cases of Bankman-Fried and others illustrate, the lure of vast wealth continues to tempt individuals into committing acts of fraud, with the consequences reverberating through society.

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Joel Stafford

My profession is online marketing and development (10+ years experience), check my latest mobile app called Upcoming or my Chrome extensions for ChatGPT. But my real passion is reading books both fiction and non-fiction. I have several favorite authors like James Redfield or Daniel Keyes. If I read a book I always want to find the best part of it, every book has its unique value.