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Financier Martin R. “Marty” Frankel created a fake European trust in the 1990s, acquired struggling life insurance companies in its name, and looted more than $200 million from their reserves.

How smart were insurance regulators in Arkansas, Mississippi, Missouri, Oklahoma and Tennessee where he operated? Not smart enough.

They believed what they were told: That something called the Thunor Trust represented wealthy European aristocrats who preferred to remain anonymous.

It didn’t.

It was controlled by Frankel, who had been in trouble before.

In the late 1980s, went to Florida and began attracting wealthy Palm Beach investors to his previous investment firm, Frankel Funds. There, he sometimes used astrology to guide his trades. It didn’t win big and it didn’t predict his future.

In the early 1990s, regulators froze Frankel Funds and accused Frankel of misleading investors. He settled the case and agreed to leave the securities industry.

Then he went into the insurance industry.

He’d discovered that if he controlled insurance companies, he could also control their investment portfolios.

Between 1993 and 1995, the trust acquired controlling stakes in eight insurance companies using the fake trust, aliases and other people’s names.

Then, through a slew of complex schemes, he routed assets into a company he controlled, “Liberty National Securities,” which was also little more than a mail drop.

The money funded Frankel’s eccentric lifestyle. To cultivate the image of a secretive international financier, he purchased a castle in Germany, yachts, private aircraft, and luxury homes, including a Connecticut mansion.

His world grew increasingly insular and strange. He turned his properties into armed camps, posting gun-toting guards and erecting 6-foot metal fences with cameras and flood-lights.

His personal life was equally bizarre. He often met women through personal ads and lived with some of them for a time. In 1997, one woman was found hanging from a noose at his Greenwich, Conn., property. Authorities ruled it a suicide.

All the while, Frankel was building false credibility.

In an attempt to leverage the Roman Catholic Church, he founded the St. Francis of Assisi Foundation in the British Virgin Islands. He even got Monsignor Emilio Colagiovanni, an official of the Roman Curia, to sign a letter falsely stating that the foundation received Vatican funding.

Frankel also solicited other high-profile people to join the foundation’s board, including the “most trusted man in America,” retired CBS Evening News anchorman Walter Cronkite.

Cronkite declined the offer, but the fake foundation used his name anyway.

For the most part, Frankel stayed hidden behind the corporate curtains that he had so delicately hung. Few people dealt with him directly. Associates handled many of the transactions and reinforced the mystique of the Thunor Trust.

The arrangement worked for years partly because insurance regulation is fragmented. Each state insurance regulator saw only the local company Thunor controlled and assumed the trust was legitimate.

By 1999 though, regulators finally started comparing notes. They discovered the assets backing the insurers’ policyholders were disappearing. Then Frankel disappeared, too.

Suddenly, his Greenwich, Conn., mansion caught fire under suspicious circumstances and he was no where to be found, triggering an international manhunt.

Frankel rambled through Europe using false identities until German authorities arrested him in Hamburg on Sept. 4, 1999.

In May 2002, he pleaded guilty to 24 federal counts of securities fraud, wire fraud, racketeering and conspiracy. Fifteen of Frankel’s associates, including Colagiovanni, also pleaded guilty to related crimes.

Prosecutors said he had looted at least $208 million from the insurers he secretly controlled. The wreckage in his wake forced several insurers into receivership and triggered years of litigation to recover stolen assets.

At sentencing, Frankel said his fraud had taken on a life of its own, explaining that once he began faking financial statements, he had to keep forging documents to keep the scheme from collapsing.

“Everybody looks at me as if I’m an evil genius,” he told the judge, NBC News reported. But he was only trying to help his girlfriend’s children, who he said were abused.

He then urged the judge to show mercy, according to a report in The New York Times.

“If somebody is mentally ill,” he said, “you shouldn’t punish them because it won’t stop other mentally ill people from doing it.”

He was sentenced to more than 16 years in prison on Dec. 10 2004 and is remembered as one of the most notorious insurance fraudsters of all time.

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Read More:

Fraud Suspect Hoped Expanding His Empire Would Protect Him From Authorities (The New York Times)

Phantom Insurance Empire Was Built on Trail of Aliases (The New York Times)

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Richard Whitney, New York Stock Exchange president from 1930 to 1935, was known as the “White Knight of Wall Street” until he was sent up the river in 1938 for grand larceny.

“Wall Street could hardly have been more embarrassed if J.P. Morgan had been caught helping himself from the collection plate at the Cathedral of St. John the Divine,” wrote The Nation magazine wrote at the time.

Whitney wasn’t just some bucket-shop penny stock peddler. He was old-guard Wall Street royalty – Groton School, Harvard University, tailored suits, club ties – the embodiment of establishment finance at a time when the public desperately wanted to believe in it.

“Not Dick Whitney!” President Roosevelt cried upon hearing the news about his fellow Groton grad. “Dick Whitney – I can’t believe it.”

Whitney achieved hero status in October 1929 when strode onto the NYSE floor and bid $205 a share for 25,000 shares of U.S. Steel – well above the market price. It was a dramatic show of confidence meant to halt a looming panic.

Newspapers dubbed him Wall Street’s White Knight. But his valiant effort didn’t hold off the crash for long. The Great Depression was inevitable following the financial follies of the 1920s, just as similar economic crises befall us today.

Whitney was one of the NYSE’s most vocal defenders during the push for federal securities regulation. He opposed outside oversight, insisting the Exchange could police itself. The institution, he argued, did not need Washington minders.

But what it needed was someone minding him.

Behind its mahogany doors Richard Whitney & Co., was unraveling. Whitney speculated heavily. He borrowed constantly. When losses mounted, he turned to the one asset he had in abundance: trust.

Whitney began misappropriating securities and funds entrusted to him in fiduciary roles. He dipped into family trusts. He used securities from the New York Yacht Club, where he served as treasurer. He tapped the NYSE Gratuity Fund – a pool meant to aid the widows and families of deceased Exchange members. The man defending Wall Street’s honor was quietly pawning it.

By early 1938, the facade cracked. Whitney’s brokerage firm was insolvent. Customer securities had been improperly pledged as collateral for his personal loans. In March 1938, his firm was suspended from the NYSE. Bankruptcy followed. A grand jury indicted him on charges of grand larceny.

He was sent up the Hudson River to Sing Sing in Ossining, N.Y., in April 1938, after pleading guilty to grand larceny.after pleading guilty to grand larceny.

Crowds gathered to watch the fallen aristocrat depart for prison. The White Knight was now inmate No. 37896. He served a little more than three years before getting paroled, but he was barred from the securities industry for life.

Whitney’s fall wasn’t just a personal disgrace. It was institutional humiliation. For years he had argued that the Exchange was a perfect self-governing body. Yet one of its most prominent leaders had been siphoning funds under its nose.

The scandal reinforced the case for federal oversight and strengthened confidence in the newly formed Securities and Exchange Commission.

After prison, Whitney worked on a dairy farm in Massachusetts, milking cows instead of the people who once trusted him.

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Commodities trader Anthony “Tino” De Angelis nearly toppled a pillar of American finance in 1963 with an audacious stunt that went down in history as “The Great Salad Oil Swindle.”

De Angelis ran Allied Crude Vegetable Oil Refining Corp. out of Bayonne, New Jersey. His company purportedly controlled vast quantities of soybean oil stored in tanks along a grimy waterfront.

He put up the oil as collateral for huge loans from banks and trading houses eager to finance the booming commodities trade.

There was nowhere near as much oil as he claimed.

He fooled Wall Street with simple physics: Oil floats, water sinks.

He filled massive storage tanks mostly with water, then layered a few feet of oil on top. Inspectors dipped their measuring rods and never realized that beneath the surface sat millions of gallons of H2O.

He claimed to control roughly 1.8 billion pounds of soybean oil. Investigators later found only a fraction of that amount.

He also pledged the same watered-down tanks multiple times. Lenders extended credit based on warehouse receipts and inspection certificates that were, in reality, little more than stage props.

His creditors and investors should have known better. De Angelis had previously been involved in a scam involving the National School Lunch Act and the Adolph Gobel Co. He overcharged the government and delivered over 2 million pounds of uninspected meat. Once the debacle was discovered, he ended up filing bankruptcy.

Nevertheless, he was able to move on to the next thing. His Great Salad Oil Swindle allowed him to take out $150 million to $180 million in bogus loans, or up to as much as $2 billion in today’s dollars.

De Angelis used the money to buy as much soybean oil and as many soybean oil futures contracts as possible.

He wanted to corner the soybean market amid talk of a U.S. trade deal with Russia that would boost exports. But so much for the Russian dressing. Those talks collapsed.

When soybean prices plunged, inspectors reexamined his tanks and the illusion was gone. De Angelis’ company was forced to file bankruptcy in November 1963.

His scheme bilked more than 50 banks and trading firms, but the biggest loser was a subsidiary of American Express called American Express Field Warehousing Corp. When the fraud came to light, its stock lost half its value.

A young investor named Warren Buffett studied the wreckage and decided the scandal had wounded Amex’s reputation less than its share price. He purchased a 5% stake in the company, a bet that became one of the early triumphs of his career. For Buffett, at least, it was like Thousand Island.

The collapse of De Angelis’ company triggered panic on the New York Stock Exchange and in commodity markets. But the scandal broke in November 1963, just days before the assassination of President John F. Kennedy and was quickly pushed off the front pages.

De Angelis was convicted of fraud on March 1, 1965. He spent several years in federal prison, but not long enough to cure him of ambition.

By the mid-1970s, he resurfaced in the Midwest pork business, where dealers alleged he ran a rolling payment scheme that left Indianapolis livestock sellers out roughly $7 million.

The Great Salad Oil Scandal forced lenders to reassess how they secured inventory-backed loans. It also led to tighter controls in warehouse financing and inspection procedures. Yet reckless lending continues today with the subprime auto loans and bogus account receivable financing embarrassing major banks and their genius financiers.

De Angelis pulled one of the most absurd schemes in American financial history and gave us a reminder that sometimes the market isn’t built on solid fundamentals.

Sometimes, it’s built on a thin layer of oil floating right on top of a whole lot of nothing.

Read More:

• Crime: The Man Who Fooled Everybody (Time)

• Great frauds in history: Tino De Angelis’ salad-oil scam (MoneyWeek)

• Salad Oil Scandal: Fraud Scheme, Market Impact, and Precursor (Investopedia)

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The self-styled Millennial disruptor had become the face of pharmaceutical greed. And in 2018, he was sentenced to seven years in prison for a multimillion-dollar fraud scheme.

Shkreli’s company, Turing Pharmaceuticals, acquired the rights to Daraprim in 2015, and within days, its price jumped from $13.50 per pill to $750. The price hike proved indefensible. This was a decades-old drug used to treat toxoplasmosis, a potentially deadly infection that particularly affects AIDS and cancer patients.

Shkreli wrapped the flag of capitalism around the move, arguing the drug had been underpriced and that revenues would fund research. Critics called it extortion. Lawmakers called hearings. The public called him something else entirely: “Pharma Bro.”

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Shkreli’s parents were Albanian immigrants who worked as janitors. He was raised in Brooklyn, N.Y., went to Catholic schools and got his first job at a hedge fund at age 17.

In 2007, Lehman Brothers won a $2.3 million default judgment against Shkreli and a hedge fund he’d started for failing to cover an options trade that went sour, but Lehman collapsed before it could collect.

Despite his checkered history, Forbes put Shkreli on its 30 Under 30 list in 2012, a decision it came to regret. The publication lauded him for killing a proposed merger of Amag Pharmaceuticals and Allos Therapeutics with his own hostile takeover bid and for antagonizing Pfizer to remove former CEO William Steere from its board.

Read More: Making A List, Checking It Twice

Shkreli seemed to relish his notoriety. When summoned before Congress in 2016, he smirked, pleaded the Fifth repeatedly, and later tweeted that lawmakers were “imbeciles.” If arrogance was a pharmaceutical, he might have cornered that market too.

Extorting dying patients through price hikes on a life-saving drug somehow isn’t a federal crime. For many people in this industry, capitalism means capitalizing on the sick and dying. And Shkreli was not charged in for anything the Daraprim price hike.

Instead, federal prosecutors charged him with securities fraud tied to two hedge funds he’d founded – MSMB Capital Management and MSMB Healthcare Management – well as his tenure at another drug company, Retrophin.

Prosecutors alleged he misled investors about fund performance, used new investor money to pay off old investors and illegally used Retrophin assets to settle personal hedge-fund debts. The Securities and Exchange Commission filed a parallel civil action.

His antics knew no bounds. In 2017, while out on bail, Shkreli put up a Facebook post offering $5,000 for a strand of Hillary Clinton's hair. He told the judge it was satire. The judge called it a solicitation to assault the former First Lady and revoked his bond.

In 2017, a jury convicted Shkreli on securities fraud and conspiracy counts.

“Martin Shkreli was notoriously ambitious, seeking to enrich himself at the expense of those who unwittingly invested in his lies,” said FBI Assistant Director-in-Charge Sweeney in a press release.

The judge called him a “danger to society.”

Shkreli, who fancied himself some kind of hip-hop hipster, purchased the one-of-a-kind Wu-Tang Clan album Once Upon a Time in Shaolin for $2 million. It was later seized by the U.S. government as part of asset forfeiture proceedings and ultimately sold to help satisfy judgments against him.

Nothing says “legacy” like having your rare rap album confiscated by federal marshals after trying to beat the rap. The court also seized a Picasso painting he’d purchased and $5 million he’d put up for bail.

Shkreli was released from federal prison in 2022 after serving about four years, receiving credit for good behavior.

In 2022, a federal judge also barred him from participating in the pharmaceutical industry for life and ordered him to pay $64.6 million in disgorgement in a civil antitrust case related to Daraprim pricing.

He has since attempted to reinvent himself throuh crypto commentary, live streams, and social media provocations, but the “Pharma Bro” label remains welded to his misanthropic public persona.

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As a 28-year-old derivatives trader Nick Leeson accomplished something Napoleon, two world wars, and the Great Depression could not. He bankrupted Barings Bank, Britain’s oldest merchant bank.

The “star trader” could not admit a mistake and managed to hide more than $1 billion in losses, which was more than the 233-year-old bank’s entire capital.

Barings had essentially handed Leeson the unchecked power to police himself, far away from headquarters. The bank employed Leeson in Singapore to run its futures trading operation on the SIMEX exchange.

When his early trades went bad, Leeson hid the losses in an internal error account numbered 88888. The account was set up to reconcile minor discrepancies. But it swiftly became a financial black hole.

No matter how bad his trades went, Leeson kept doubling down, placing highly leveraged bets on Japanese market movements. When the Kobe earthquake struck in January 1995, markets moved against him and his losses exploded.

In February 1995, Nick Leeson finally came clean, but not in person. He sent a fax to Barings’ London headquarters admitting the scale of the disaster. Then he tried to disappear.

He left Singapore with his wife, traveling through Malaysia and Thailand before surfacing in Europe. His flight from justice only lasted for about six days.

On March 2, 1995, German authorities arrested him at Frankfurt Airport, acting on an international warrant. He was extradited to Singapore, where he pleaded guilty to fraud. He was sentenced to six and a half years in Singapore’s Changi Prison and served just over four.

His story was later recounted in the 1999 film Rogue Trader. Today he’s a keynote speaker on risk management and corporate governance. He reportedly still trades, but with his own money, and he hosts a podcast.

In his 2015, book, Rogue Trader: The Original Story Of The banker Who Broke The System, Leeson laments that he became a victim of his ambitions.

“Success can be easily derived from putting food on the table for your children to eat as it can from running a Fortune 500 company,” he writes. “Unfortunately, it too me too long to learn that.”

Barings, founded in 1762, is gone. ING paid exactly one nominal pound to take over what was left.

The bank’s collapse became a case study in the worship of star traders, the lethal mix of ego and leverage, and most of all, failed oversight.

What bank gives unfettered access to its vault to a 28-year-old kid?

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Was Ghislaine Maxwell’s father an international spy? Could she have brought Jeffrey Epstein and his global sex trafficking ring into this shadowy fold?

There’s plenty of speculation, and not a lot of evidence … but then why would there be? The spy business is supposed to be finger-print free.

What’s certain is that Robert Maxwell and Jeffrey Epstein were both wealthy thugs with powerful connections, who died under mysterious circumstances – and they both had Ghislaine Maxwell in common.

Apples don’t fall far from trees, as the old cliché goes. Especially, rotten ones.

The truth is out there, but it’s trickling out slowly with the Trump administration delaying the release of the Congressionally ordered Epstein files at every turn.

For now, please welcome Robert Maxwell to the Business Blunders Hall Of Shame.

Robert Maxwell – Mirror Group Newspapers

He left behind one of Britain’s ugliest scandals. Then his daughter got uglier with Jeffrey Epstein.

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Robert Maxwell was a swaggering media titan who stole from his employee’s pensions, drowned at sea, and left behind one of the most notorious financial scandals in British corporate history.

He also spoiled his daughter, Ghislaine Maxwell, the imprisoned co-conspirator with Jeffrey Epstein and his pedophilic sex-trafficking network.

He died falling from a four-story super yacht that he’d named “Lady Ghislaine.” In the end, neither his boat nor his daughter proved to be a lady any more than he proved to be an upstanding businessman.

Unlike most Business Hall Of Shame inductees, Maxwell was never charged with a crime. He died before investigators discovered that he had systematically plundered hundreds of millions of pounds from his own companies’ pension funds to prop up his sprawling, debt-ridden empire.

Perhaps there’s some irony in running scandal rags like the Daily Mirror and the New York Daily News, and then spawning scandals even juicier than most tabloid headlines. Or perhaps it’s par for the course. Maxwell was commonly described as a shameless narcissist who would do anything in his bitter rivalry with Rupert Murdoch.

When accountants, regulators and Parliament pulled back the curtains, they found that at least £500 million had been diverted from Mirror Group pension funds into Maxwell-controlled companies.

His financial downfall came after he grossly overpaid for media properties, particularly, the Macmillan publishing house for $2.6 billion in 1988.

He’d borrowed with abandon from 44 different banks and financial syndicates. To cover his over-leveraged bets, he shifted assets, pledged pension money as collateral and manipulated financial statements.

Years of litigation, bankruptcy proceedings and recovery efforts followed. The UK Department of Trade and Industry later concluded Maxwell’s misconduct was “systematic and extensive.”

More than 500 pensioners were left wondering how a billionaire could treat their futures like a personal credit line.

Two of Maxwell’s sons – Kevin and Ian – were charged with fraud. Both were ultimately acquitted in 1996.

Then there’s Maxwell’s youngest daughter, Ghislaine.

She moved comfortably through London and New York high society, financed in part by her father’s borrowed and stolen wealth.

After his death, she had to turn somewhere to maintain the lifestyle her father provided. She reinvented herself in the United States and eventually hooked up with Epstein.

In 2020, a federal jury in New York convicted her of sex-trafficking minors, ensuring that the Maxwell name carried a second, darker legacy. She was sentenced to 20 years in prison in 2022.

The Trump administration and his enablers in Congress have consistently hindered the release of the Epstein files that the Department of Justices has gathered. But slowly, powerful politicians, business tycoons and celebrities are being exposed as having embarrassing relationships with the world’s most notorious sex offender.

Read More:

• Networking With A Pedophile (Business Blunders)

• Meditations With A Sex Offender (Business Blunders)

• Winter Is Coming For Summers (Business Blunders)

• Too Big To Jail (Business Blunders)

In a vacuum of information, speculations abound, including a spy theory and unproven claims that Epstein was running a honey pot operation. The game was to get powerful people in compromising positions and blackmail them into compliance – or so the theory goes.

Adding to this intrigue are similar allegations around Robert Maxwell. For decades, reporters and biographers have explored, and debated, Maxwell’s proximity to intelligence services.

Several investigations have suggested he cultivated relationships with Mossad, MI6, and even Soviet officials, using his media holdings and political access as leverage in the Cold War world of favors and information.

In 2003, journalists Gordon Thomas and Martin Dillon published “Robert Maxwell, Israel’s Superspy: The Life and Murder of a Media Mogul.” The book promo describes him as “ruthless, volatile, defiant; a man of gargantuan appetites, for food, wine, women, power, money.”

The authors argue that Maxwell occasionally acted as a conduit for Israeli intelligence, but the book is speculative. Other reporting is more careful, describing him operating in the murky overlap between business, politics and espionage.

None of these claims have been conclusively proven, but of course the spy business is designed to leave few if any traces. Many records remain sealed or inconclusive, leaving the truth partly hidden behind the same secrecy that defined Maxwell’s business life.

Conspiracy theories also abound regarding Maxwell’s mysterious death off coasts of the Canary Islands. But official inquiries concluded that he fell off the Lady Ghislaine while completely nude and taking a leak into the sea. From there, he had a heart attack and drowned.

“Money isn’t everything,” he is often quoted as saying. “I’ve got money and I’ve got everything, and they’re not the same.”

In the end, he left this world like everybody else. With neither.

Read More:

From wooden shack to global media magnate: The rise and fall of Robert Maxwell (The Times Of Israel)

Fall: The Mysterious Life and Death of Robert Maxwell, Britain’s Most Notorious Media Baron (Book by John Preston)

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Marc Rich was a billionaire commodities trader who helped pioneer the global spot-oil market and later founded what became international commodities trading giant Glencore.

He is better remembered as an international criminal who got a controversial pardon from President Bill Clinton in 2001. Critics called it controversial, because unlike today, pardoning a white-collar fugitive could prompt a congressional investigation and sully a president’s reputation back in the day.

Rich was indicted by a U.S. federal grand jury on more than 50 felony counts in 1983. The charges included wire fraud, racketeering and making oil deals with Iran during the 1979-1981 hostage crisis.

He was also accused of dodging $48 million in taxes, which prosecutors called one of the largest tax-evasion cases at the time.

Rich’s companies pleaded guilty to charges filed against them, paying fines of about $170 million. But Rich, himself, dodged prosecution by fleeing the U.S. for Switzerland. He remained on the FBI’s Most Wanted List for 18 years.

“It’s an unfortunate situation,” Rich told the Associated Press in 2013. “But the question is, was there crime? And I’m saying I don’t think so.”

Big words, but he never had to say them in court.

Rich was born to in Antwerp, Belgium, to a Jewish family that fled Nazis and settled in New York. He dropped out of college to work as a commodities trader. He eventually started his own firm with a partner, Pincus Green, and they pioneered the spot oil market together.

Rich didn’t care who he traded with, whether it was U.S. sanctioned Iran, Cuba, Libya or South Africa during apartheid. “You can’t run a business based on sympathies,” he once said. “Otherwise our business would be hampered.”

Oh, those pesky U.S. embargoes. You can’t have your trading business hampered over garden-variety national security issues, like holding Americans hostage in Iran or conducting state-sponsored terrorism around the globe.

Rich’s firm eventually grew into the world’s largest commodities trading company, Glencore, and gave him an estimated net worth of $2.5 billion.

It was more than enough money to dodge justice for a lifetime. But as a fugitive, Rich had a few close calls, narrowly escaping arrests in Finland, Germany, Britain and Jamaica.

During his final hours in the White House, Clinton gave Rich a full pardon along with Rich’s partner, Green. The move immediately ignited bipartisan fury and earned the label “Pardongate.”

The pardon was controversial because:

• Rich got rich supplying energy to sworn U.S. enemies.

• He dodged justice for decades.

• His ex-wife, Denise Rich, donated hundreds of thousands of dollars to the Clinton library and Democratic political funds before and after the pardon. She contributed $450,000 to Clinton's presidential library foundation and more than $100,000 to Hillary Clinton’s Senate campaign.

• Critics said the pardon undermined the integrity of presidential clemency and appeared to reward wealth and connections over justice.

A two-tiered justice system. Imagine that.

Congress launched a bipartisan investigation into how and why the pardon was granted, including hearings before the House Government Reform Committee.

Even longtime Clinton supporters distanced themselves.

“I don't think there is any doubt that some of the factors in his pardon were attributable to his large gifts. In my opinion, that was disgraceful,” said former President Jimmy Carter.

Clinton soon came to regret the pardon, although he denied that he did it for the money. “It was terrible politics,” he said in 2002. “It wasn't worth the damage to my reputation. But that doesn't mean the attacks were true.”

So Rich never saw the prison cell he so richly deserved, or even a perp walk. He never returned to the United States. He continued living a life of wealth and influence abroad until he died in 2013 at age 78.

How does something like this happen in what is supposed to be a highly regulated industry?

The New York Times called it, “a series of numbingly complex mortgage and stock frauds.” An easier explanation: Only in Florida.

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Weiss was convicted in 2000 on 78 counts, including racketeering, wire fraud, money laundering and obstruction after a nine-month trial. But Weiss didn’t stick around to hear the verdict.

With piles of ill-gotten gains, he skipped town and rambled through Israel, Belgium, Brazil, Austria and the United Kingdom. Prosecutors said he dined at fine restaurants, gambled in casinos, stayed in high-end hotels and partied with prostitutes.

He was, for a time, one of the FBI’s most-wanted criminals.

A judge gave Weiss an 845-year prison sentence in absentia. It was the longest prison sentence ever handed down to a white-collar criminal. (Ponzi schemerBernie Maddoff, by contrast, only got 150 years.)

The convict was finally nabbed using a fake passport in Vienna, but with good lawyering, he stayed out of jail as he pursued a long extradition fight.

Authorities finally dragged him back to the U.S. to face his prison sentence in 2002.

Weiss didn’t do it alone. Federal prosecutors secured more than a dozen guilty pleas and convictions against lawyers, accountants, brokers and advisers who helped with the takeover and the looting of National Heritage Life Insurance.

The Orlando-based insurance company catered to modest-income customers whom Florida state regulators failed to protect.

Amazingly, Weiss and his co-conspirators bought the company by writing a bad check for $4 million, then they covered the check by taking out loans from the company.

Once inside, they systematically siphoned the company’s assets through sham transactions, bogus mortgage deals, fake investment vehicles and a network of shell companies that funneled money straight into their pockets.

The scheme drove the insurer into insolvency in 1994, leaving more than 25,000 policyholders holding the bag.

Regulators called it one of the worst insurance failures in U.S. history. So much for the company’s slogan: “Pillars of Strength and Character.”

Thousands of people who purchased annuities through the company lost their life savings. Many victims were elderly retirees who never recovered a dime.

“I hope they hang him,” 77-year-old Joseph Pleasant of Merritt Island, Fla., told the Orlando Sentinel in 2002. “I’m certainly happy they got him.”

For years, Weiss insisted he was a victim of prosecutorial overreach. But evidence showed he dictated the fraud down to its minute details, approving sham real estate deals, directing co-conspirators to falsify records, and manipulating the company’s books while masquerading as a savior investor. He lost his appeal in 2013.

You would think Weiss would be rotting in prison to this day. But in January 2021, Trump commuted his sentence, citing a roster of notable supporters, a celebrity attorney and Weiss’ health.

From the White House press release:

Shalom Weiss – President Trump commuted the sentence of Shalom Weiss. This commutation is supported by former U.S. Attorney General Edwin Meese, former Solicitors General Ken Starr and Seth Waxman, former United States Representative Bob Barr, numerous members of the New York legislature, notable legal figures such as Professor Alan Dershowitz and Jay Sekulow, former U.S. Attorney Brett Tolman, and various other former elected officials. Mr. Weiss was convicted of racketeering, wire fraud, money laundering, and obstruction of justice, for which he has already served over 18 years and paid substantial restitution. He is 66 years old and suffers from chronic health conditions.

Related Reading: Pardon My Ponzi (Business Blunders)

Two months after his release, Weiss suffered a stroke. But by January 2022, he was healthy enough to meet with Trump at Mar-a-Lago to thank him.

Weiss also remained proud enough to put out a press release on the meeting. It reads:

“Former President Donald J. Trump met with Shalom Weiss and his daughter, Mrs. Rivky Neuhaus, on Monday, January 10th, at Mar-a-Lago.

”Mr. Weiss and his daughter expressed their deep appreciation for the former President’s compassionate commutation of Mr. Weiss’s 845-year sentence to time served. Mrs. Neuhaus, who is an artist, presented the former President with a portrait she created of him at the Western Wall, the ancient holy site in Jerusalem, Israel.”

In the press release, Weiss did not include a single line expressing remorse or offering apologies to his victims. He did not even mention any kind of repentance in prison or grace from his god.

The pious fraudster now lives quietly, far from the retirees whose life savings he wiped out.

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Silicon Valley and Madison Avenue leaders propped up Sam Bankman-Fried as a wunderkind, but the FTX founder’s genius eventually manifested as an out-of-control crypto-klepto.

In March 2024, Bankman-Fried received a 25-year prison sentence and a court order to forfeit $11 billion following his conviction on seven counts of fraud, conspiracy and money laundering.

Investors who thought they were buying bitcoin through the FTX currency exchange were merely funding whatever Bankman-Fried decided to do with the money as he wantonly misappropriated it.

Read More:

• Sam In The Slam (Business Blunders)

• They Bought Crypto From a Klepto (Business Blunders)

• Suck-Up Sam (Business Blunders)

The fuzzy-headed fraudster illegally stuffed billions of dollars of FTX customer funds into his venture capital firm, Alameda Research, run by his girlfriend Caroline Ellison.

He took private jets to his lair in the Bahamas and put the FTX logo everywhere from a Miami basketball arena to a Formula 1 race car.

He ran a memorable Super Bowl commercial staring comedian Larry David, courted many other celebrity endorsements, made huge donations to Democrats, and even bragged that he might one day buy Goldman Sachs.

Both his parents are Stanford law professors, he had access to millions of dollars worth of lawyers, and none could save him.

Bankman-Fried was briefly lauded as “the next Warren Buffett,” and he achieved a net worth of about $26 billion – at least on a computer screen. Now he’s in the pokey eating beans and rice.

Bankman-Fried apparently counted the truth as just another start-up expense to be culled.

“Lack of trust is an enormous transaction cost,” Bankman-Fried said in an August 2022 Forbes story before his life came crashing down. “I underestimated this when I first got into business.”

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Theranos founder Elizabeth Holmes was a lauded Silicon Valley medical entrepreneur yet all she left in her wake was a bloody mess.

She was convicted in January 2022 for defrauding her investors out of more than $100 million, and she is not scheduled to be released from federal prison until March 2032 after losing her appeal in February 2025.

Her former boyfriend and top lieutenant, Ramesh Balwani, received a 13-year prison sentence for the scheme. They’ve both been ordered to pay $452 million in restitution.

Holmes claimed Theranos was developing a blood testing device that could detect a wide range of illnesses from just a tiny drop of blood. Her story came apart when a Wall Street Journal investigation revealed that her company was using commercially available devices for its test results.

At its zenith in 2015, Theranos had more than 800 employees.

Holmes put on a big act that included faking a deeper voice and wearing black turtlenecks like Steve Jobs. “I believed it would be how I would be … taken seriously and not taken as a little girl or a girl who didn’t have good technical ideas,” she said in a 2023 New York Times interview.

She was brilliant at leveraging connections and her affectations duped an astonishing list of people who should have known better.

Her board included former secretaries of state George Shultz and Henry Kissinger. Also on the board was former CEOs Dick Kovacevich of Wells Fargo and Riley Bechtel of Bechtel, among other luminaries. Her major investors included Silicon Valley venture capitalist Tim Draper, media mogul Rupert Murdoch, and the Walton family of Walmart fame.

Read More: A Bloody Mess (Business Blunders)

It is simply embarrassing how many aristocrats, media outlets and institutions fawned over Holmes, who if nothing else proved that Silicon Valley will buy anything.

Among myriad honors: Time Magazine named Holmes among its 100 most influential people. The Harvard Medical School put her on its board of fellows. Pepperdine University awarded her an honorary doctorate. Forbes ranked her No. 73 in its list of “the world’s most powerful women.” She became the youngest recipient of the 2015 Horatio Alger Award honoring distinguished Americans. And President Barack Obama named her Presidential Ambassador for Global Entrepreneurship.

Read More: Making A List, Checking It Twice (Business Blunders)

Her father, Christian Rasmus Holmes IV, was once a vice president at Enron. Go figure.

Following Holmes’ conviction, Murdoch, who invested $125 million in Theranos, reportedly sent an email to The Wall Street Journal. In it, he called himself “one of a bunch of old men taken in by a seemingly great young woman! Total embarrassment.”

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Christopher Kirchner founded Southlake, Texas-based Slync in 2017 as a Salesforce-like platform for supply chain logistics. The software startup grew quickly to about 100 employees, and it scored a $240 million valuation before the entrepreneur’s worst impulses drove it just as quickly into extinction.

Kirchner had raised nearly $71 million from venture capital firms, then he looted the company to pursue his wildest sports fantasies.

Among his many extravagances, he spent $16 million on a 2010 Gulfstream G550 jet to fly to celebrity golf tournaments that his company sponsored. He also came close to buying an English soccer team, but he couldn’t produce the funds needed to close the deal as his looted empire collapsed.

He bought a luxury suite at AT&T Stadium where the Dallas Cowboys play. He bought exotic vehicles, including a Rolls Royce, a Ferrari Superfast 812, and a Mercedes Benz G-Class. He adorned himself with jewelry including a $500,000 Richard Mille watch, several Rolexes and a Cartier necklace. He also acquired pricey artwork and collected expensive bottles of wine.

His spending spree didn’t stop, even as Slync failed to meet payroll. He allegedly fired two employees who raised concerns about his management, including one who reported that he was exaggerating Slync’s financial performance.

Kirchner was sentenced to 20 years in prison in July 2024 and ordered to pay $65 million in restitution.

“Even as his company was circling the drain, Chris Kirchner was spending millions of his investors’ money on himself,” said U.S. Attorney Leigha Simonton. “Apparently, projecting personal prosperity was more important to him than making payroll.”

It’s astonishing how a man in his mid-30s could con so many sophisticated investors. Venture capital firms that poured money into Slync included Goldman Sachs Growth, ACME Ventures, 235 Capital Partners and Correlation Ventures.

Where was their oversight?

“In business I believe in transparency, trust, humility and respecting authority,” Kirchner told a British business publication in May 2022 before his myriad lies were exposed. “Those are qualities I have grown up with.”

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Billy McFarland sold tickets for thousands of dollars to the now-infamous Fyre Festival.

Guests paid small fortunes for a luxury music event on a Bahamian island, but they ended up riding in school buses, sleeping on bare mattresses in storm-damaged tents, and eating cheese sandwiches from foam containers.

The best entertainment to come of the fiasco were competing documentaries by Netflix, “FYRE: The Greatest Party That Never Happened,” and Hulu, “Fyre Fraud.”

McFarland received a six-year prison sentence in 2018 for fraud and still owes millions to his investors and ticket buyers.

“Billy McFarland has shown a disturbing pattern of deception, which resulted in investors and customers losing over $26 million,” said Manhattan U.S. Attorney Geoffrey Berman following McFarland’s sentence. “Empty promises don’t lead to jet-setting, champagne, and extravagant parties – they lead to federal prison.”

McFarland was released in 2020 and began promising a redo.

He began selling tickets in early 2025 for Fyre 2. He billed it as a three-day event at Isla Mujeres off the coast of Cancun, Mexico, from May 30 through June 2, 2025.

Somehow, there were no sentencing requirements that would have prevented him from selling tickets to another dubious event.

Here’s how McFarland explained his do-over in a press release:

“I’m sure many people think I’m crazy for doing this again. But I feel I’d be crazy not to do it again. After years of reflection and now thoughtful planning, the new team and I have amazing plans for Fyre 2. The adventure seekers who trust the vision and take the leap will make history. Thank you to my partners for the second chance.”

Surprise, surprise – Fyre 2 never happened. McFarland apparently couldn’t find a big enough round of new suckers, so he canceled the event, and he put the Fyre brand up for sale in April 2025.

Too bad no one showed up for the Fyre sale.

Here’s what he wrote about it this flop on the festival’s Instagram page:

“After two years of rebuilding FYRE with honesty, creativity, and relentless effort, it’s time to pass the torch. We’re officially putting the FYRE brand up for sale. To the right buyer: the platform is yours. Execute the vision. Make history.”

When he’s making a pitch, McFarland often tells people they can make history with his big idea, but he’s the one who made history … as a shameless huckster.

Nevertheless, in December 2025, McFarland somehow pulled off a music festival in Honduras, dubbed PHNX. This time he indeed had artists, fans, bathrooms and at least something that resembled food.

Only a few hundred people attended, it got little notice from the press, and it probably ran at a loss, selling online access for $6.99.

It wasn’t exactly what you’d call a phoenix rising from the ashes. It wasn’t even “the third time’s a charm.” But nice try.

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Carlos Watson founded Ozy Media in 2013 and took the ol’ “fake-it-‘til-you-make-it” route to a felonious extreme.

Watson worked on Wall Street, and even hosted his own show on CNBC. But he is now more famous for participating in a phony phone call with Ozy co-founder Samir Rao in a desperate bid to attract a $45 million investment from Goldman Sachs.

Roa was pretending to be Alex Piper, head of unscripted programming for YouTube Originals. He asserted that YouTube was paying big bucks for an Ozy show and promised that massive advertising dollars were soon to follow.

Rao, who pled guilty to fraud and identity-theft charges, testified that Watson was in on the call.

A jury found Watson guilty on fraud and identity-theft charges in July 2024. He was sentenced to 116 months in prison in December 2024. And in March 2025, just as he was about to start serving that time, President Donald Trump commuted his sentence.

Watson co-founded Ozy Media in 2013 and it collapsed in 2021 following the New York Times’ thorough reporting on the fake call.

The company targeted a young, diverse audience with digital newsletters, television shows, podcasts and live events, including a gathering called “Ozy Fest.”

Ozy Media attracted tens of millions in investment dollars from Steve Job’s widow, Laurene Powell Jobs, Silicon Valley venture capitalist Ron Conway, and Google’s former Chief Legal Officer David Drummond.

Berlin publishing giant Axel Springer, investment bank Lion Tree, and iHeart Radio also invested. The Ford Foundation backed it with grants. All told, Ozy Media reportedly raised more than $83 million by April 2020 and valued itself at $159 million.

Watson, a charismatic Miami native, graduated from Harvard University and Stanford Law School.

In 2003, he hosted CNBC’s “The Edge with Carlos Watson,” and he later became one of CNN’s main political analysts. He was also an anchor at MSNBC. And he worked at McKinsey & Co. and Goldman Sachs, where he teamed up with Roa.

Watson’s first move was to blame Rao, weaving a tale about his trusty business partner having a mental health crisis.

“Samir is a valued colleague and a close friend,” Watson said in an apology he emailed to Goldman Sachs and the New York Times. “I’m proud that we stood by him while he struggled, and we’re all glad to see him now thriving again.”

As lame as it sounded, Watson continued this story in his defense. “This case was about a crooked co-founder named Samir Rao who lied to, who undermined and who betrayed Carlos Watson,” Watson’s lawyer told the jury.

It didn’t wash. Evidence showed Watson was in the room with Rao, texting instructions about what to say and what not to say as Rao impersonated Piper.

“The jury found that Watson was a con man who told lie upon lie upon lie to deceive investors,” said U.S. Attorney Breon Peace. “Ozy Media ultimately collapsed under the weight of Watson’s dishonest schemes.”

The phone call was just one of many frauds. Ozy Media and three of its top executives lied about revenue, cash-on-hand, profits, celebrity ties, acquisition prospects and contract negotiations. They forged documents and touted deals with Google and Oprah Winfrey that were never even possibilities.

They grew increasingly desperate as they blew through other people’s money and couldn’t show the progress needed to raise more.

“We told so many lies to so many different people,” Rao testified “It morphed into survival at all costs and by any means necessary.”

Ozy’s chief of staff Suzee Han, who also pleaded guilty to fraud charges, served as a witness against Watson as well. “I lied about Ozy’s past performance and historical financials,” she told the court. “We, and I mean Carlos, lied about how the company was doing.”

Former Chief Financial Officer Tripti Thakur resigned immediately after Watson ordered her to send a forged contract to a bank to secure a loan. “To be crystal clear,” she told Watson, “what you see as a measured risk — I see as a felony.”

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Bernie Madoff ran the largest Ponzi scheme in history, defrauding thousands of investors out of billions of dollars, until it all came crashing down with the 2008 financial crisis.

Regulators never caught him. He confessed his crimes to his sons and was arrested on Dec, 11, 2008, only after they turned him into authorities.

His firm, Bernard L. Madoff Investment Securities LLC, operated out of the iconic “Lipstick Building,” in Midtown Manhattan. His scheme was in large part a classic affinity fraud targeting fellow Jews.

Many of Madoff’s victims begged to be in his fund upon hearing of his purported success through word of mouth. He often turned prospective investors down at first blush, acting as if it were a huge favor to allow new victims into his fraud.

Victims included several large Jewish organizations, including the Elie Wiesel Foundation and Steven Spielberg’s Wunderkinder Foundation.

Madoff’s Ponzi scheme was estimated to be a $65 billion fraud when it first imploded. But that figure was wildly inflated with made-up investment gains that Madoff investors believed they were getting.

In December 2024, the Justice Department announced it had returned $4.3 billion in recovered funds to 41,000 investors. The department said these were mostly small investors who’d put less than $500,000 into the fund, and that they had been made about 94% whole.

Nobody knew how Madoff could possibly achieve the returns he claimed he was delivering to his investors. And nobody thoroughly checked because he had undue respect as the former chairman of NASDAQ.

Related reading: 15 Tales Of Lost Ponzi Riches (Business Blunders)

In May 2001, Barron’s published a profile on Madoff that was more cloying than skeptical, and it didn’t get the attention its headline demanded: “Don’t Ask, Don’t Tell: Bernie Madoff is so secretive he even asks his investors to keep mum.”

“It’s a proprietary strategy,” he told Barron’s. “I can’t go into it in great detail.”

Madoff also suckered regulators into cozy relationships – so cozy that a U.S. Securities and Exchange Commission attorney married his niece, Shana Madoff.

Shana’s father, Peter Madoff served as chief compliance officer at the family business, and Shana worked there, too, as a compliance officer and attorney.

Instead of cracking the case, SEC lawyer Eric Swanson fell head over heels for Shana. And while Madoff was still at the top of his game, several SEC officials attended the wedding on Sept. 29, 2007.

The marriage was symbolic of the incompetence and dysfunction of a financial regulator that let Madoff’s Ponzi scheme run wild for decades. By some accounts, he’d been robbing his investors since the late 1970s.

Buckling under the pressure of maintaining a massive web of lies in a stock market collapse, Madoff finally came clean. But for a time, people believed, or at least tolerated, every drop of nonsense that spilled from his mouth.

In 2007, Madoff spoke at conference, “The Future of the Stock Market,” arguing that securities regulations protected investors against the very kinds of schemes he was so brashly perpetrating at that very moment.

“It does not mean there are not abuses, for sure,” he said, “but by and large in today’s regulatory environment, it’s virtually impossible to violate the rules.”

This is how gullible people are in the presence of perceived Wall Street royalty: Days after Madoff’s arrest, Jay Berkman, a New Jersey business consultant, began impersonating Madoff on a blog, attracting readers who believed hilarious ramblings that no criminal suspect awaiting trial would ever actually say.

“I’m Bernard Madoff. Trust Me,” he began. “What? You think that just because I’m in jail, I shouldn’t be blogging?”

Berkman said he was astonished at how many readers didn’t notice it was a gag.

“Greed is always going to supersede caution,” he said. “As long as there’s human nature, and as long as there’s someone that’s clever, it’s going to repeat itself time and time again.”

Madoff pled guilty in March 2009 to 11 felonies. During his plea hearing he said:

• “I am painfully aware that I have deeply hurt many, many people.”

• “When I began my Ponzi scheme I believed it would end shortly and I would be able to extricate myself and my clients from the scheme.”

• “As the years went by, I realized that my arrest and this day would inevitably come.”

He received 150 years. His brother Peter received 12 years. His son, Mark, hanged himself in 2010. His son Andrew died of lymphoma in 2014.

Bernie died in prison in 2021 at age 82.

Robert De Niro played Madoff in the May 2017 HBO film, The Wizard of Lies, based on the best-selling book by New York Times reporter Diana Henriques.

A less handsome actor might have played him more convincingly – like Danny DeVito, who played the Penguin in the 1992 film, “Batman Returns.”

“You gotta admit,” the Penguin chirped. “I played this stinking city like a harp from hell.”

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Martha Stewart is still extending her middle finger at the prosecutors who sent her to prison in 2003 for lying about her alleged insider stock trades.

“It was so horrifying to me that I had to go through that to be a trophy for these idiots in the US Attorney’s office,” she said in the 2024 Netflix documentary “Martha.”

Amid enormous scandals at Enron, WorldCom and other massive corporations, Stewart was targeted for a relatively small infraction – avoiding a loss of nearly $46,000 on an illegal stock trade. And she paid a steep price.

Many counted the news as a death knell for Martha Stewart Living OmniMedia, the publicly traded empire she built over her lifetime. Shares of her company went into a tailspin, crushing her shareholders, but Stewart mounted a comeback campaign in 2005, and the stock recovered over time. So did her reputation.

To this day, many observers white-wash the debacle, saying Stewart was unfairly targeted as a woman by overzealous prosecutors who were under pressure to score white-collar convictions amid an epidemic of corporate fraud.

Some of this is true. But Stewart, who savagely pursued perfection, made key mistakes.

In fact, she settled insider trading charges with the Securities and Exchange Commission in 2006, agreeing to a five-year ban on serving as director of a publicly traded company. She was also criminally convicted in 2004 of obstruction and lying to investigators about her stock trades, landing her in prison for five months.

She was in many ways the victim of bad legal advice. Her shoddy defense counsel even allowed her to meet with investigators unprepared. She might have been able to settle the charges with the SEC without admitting nor denying guilt, and that might have been the end of it. But no. She had to get wise with investigators.

Things also might have turned out differently if she had never met ImClone Systems CEO Samuel Waksal, a family friend who dated Stewart’s daughter.

Waksal went to prison for nearly seven years after advising family and friends to dump ImClone shares ahead of a public announcement that the Food and Drug Administration had just rejected its cancer-fighting drug.

Stewart did her time with dignity, reinvented herself following her incarceration and even built up enviable street cred with a younger generation by hanging out with Snoop Dogg. She also became the oldest woman to pose for the Sports Illustrated swim suit edition at age 81.

She remains viciously unrepentant.

“Those prosecutors should have been put in a Cuisinart and turned on high,” she said in the Netflix documentary.

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Samuel Waksal took a break from his long and successful career as a biotech entrepreneur to serve several years in prison for insider stock trading.

The immunologist was admittedly arrogant enough to believe he could be immune from consequences. He put family members in legal peril and set off a chain of events that landed his most famous friend, Martha Stewart, in prison.

Waksal founded New York-based ImClone Systems in 1984. When he learned the Food and Drug Administration had rejected its cancer drug, Erbitux, he scrambled to dump stock and warn family and friends ahead of a public announcement.

He tried, but was unable, to unload about 80,000 shares. Family members sold more than $10 million worth of stock, though, catching regulators’ attention.

His stockbroker at Merrill Lynch, Peter Peter Bacanovic, gave Stewart a heads up to sell her shares, which ultimately resulted in five month prison sentences for both of them.

ImClone stock fell 16% once the company announced its FDA approval had been rejected.

Waksal pleaded guilty to securities fraud, bank fraud, obstruction of justice and perjury charges in late 2002. He was sentenced to more than seven years in prison and was released in 2009.

Waksal was no one-hit wonder when it came to malfeasance. News reports noted that long before Waksal’s insider trading debacle, he’d been dismissed from several academic and research positions for reckless behavior and ethical lapses. In 2003, he also pleaded guilty to two criminal charges for dodging $1.2 million in sales tax on $15 million worth of artwork.

Before heading to prison, he was candid and remorseful about his misdeeds in media interviews.

“I was arrogant enough at the time to believe that I could cut corners, not care about details that were going on and not think about consequences,” he told CBS News. “Did I know that I had committed an illegal act? Yeah, I knew. I tried to rationalize beyond rationality that I hadn’t.”

It was all for naught. The FDA finally approved Erbitux in 2004 and the drug was lauded for aiding thousands of cancer patients. In 2008, Erbitux generated $1.5 billion in sales and Eli Lilly bought out ImClone for $6.5 billion.

After prison, Waksal resumed his life as a biotech entrepreneur, founding Kadmon, which sold for $1.9 billion to Paris-based biotech company, Sanofi, in 2021. He is now CEO of another biotech company that he founded, Graviton Bioscience.

“The day I was arrested was a horrible day in my life,” he told CBS News. “It is very difficult for someone who thinks about himself as someone who does good things for society to be led away, in handcuffs, and thought about as a common criminal.”

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Joe Nacchio was a former AT&T executive who lorded over an Enron-style accounting fraud at Denver-based Qwest from 1997 to 2002.

The upstart telecommunication company acquired legacy carrier U.S. West in 2000, leveraging the inflated value of its stock, but its fortunes turned sharply after the deal closed. Qwest barely avoided bankruptcy, wiping out the life savings and retirement accounts of thousands of employees.

The company paid $250 million to settle accounting fraud charges with the Securities and Exchange Commission in 2004. Investigations showed managers fudged their numbers under pressure from the top. Shareholder lawsuits mounted. Several executives were sanctioned or prosecuted.

Nacchio, however, was not pursued criminally for the accounting fraud that had decimated his company. Instead, he was convicted on insider trading charges and served his prison sentence from 2009 to 2013.

Nacchio has always maintained his innocence. He says his prosecution was retaliation from the federal government after he refused to turn over data to the National Security Administration, standing up for the privacy rights of Qwest customers.

Nacchio was combative with everyone from his underlings to the media. Even as Qwest stock plunged, he publicly took on Wall Street analysts who questioned the company’s aggressive accounting practices and financial forecasts that far exceeded an industry in steep decline.

His bluster, however, was never enough to overcome reality.

“You all think we cheat and lie and steal,” he said at a Goldman Sachs conference on Oct. 3, 2001. “And therefore you trade us at a discount to what a normal company with great revenue and great growth should be traded. And I’m not going to convince you on that. We’ll just let the numbers speak for themselves on Oct. 31.”

Then on Oct. 31, 2001 he said this:

“Some of you will recall that at a recent conference I said the results will speak for themselves. The reality is, they do not speak clearly for themselves without some interpretation given the current economic conditions and the effects of merger and other one-time charges.”

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Meyer Blinder ran a stock brokerage that once ranked 10th in the nation by number of brokers. It boasted 66 offices in 37 states.

Blinder was renowned as the “penny stock king” as his Denver-based Blinder, Robinson & Co. pumped and dumped stocks. It sold public offerings in tiny companies and “blind pools” that often contained no real assets. Forbes magazine dubbed the firm,“Blind ‘em and Rob ‘em,” in 1987.

He was once Colorado’s highest-paid executive with a $9.5 million annual salary but his firm eventually filed bankruptcy. In July 1992, Blinder was convicted of racketeering, securities and wire fraud. He served 40 months in prison and was released at age 74 in 1995.

He was a colorful character until the very end. He once fell over during a deposition, clutching his heart and gasping for air.

“Make him answer the question,” a relentless prosecutor demanded, unimpressed with what he saw as theatrics from a crafty old man.

Blinder continued writhing on the floor, eventually getting medical attention. A reporter later asked Blinder if he needed a new heart.

“No,” replied, pointing to the prosecutor. “But if I did, I’d want his heart. He’s never used it.”

Regulators had been after Blinder for years but his hired guns kept the law at bay as he amassed a $100 million fortune.

He snubbed regulators and brazenly insisted his firm legitimately generated capital for small businesses and investment opportunities for average investors. It didn’t matter if most deals failed. Or that most of his investors lost money. That, claimed Blinder, was capitalism.

Buy a stock for a penny, ride it up to a dime or a quarter. The stock went up when Blinder put his cold-calling hucksters on the phone. When leads ran dry, the stock would plummet.

“A dollar is a blue-chip stock in my shop,” he once boasted in a room full of securities regulators.

Blinder grew up poor in New York City. His father’s death forced him out of high school. But he learned to hustle. He was charismatic and funny, grandfatherly one minute and bloodthirsty the next. After a jury convicted him, he lunged across the courtroom at federal prosecutor Howard Zlotnick.

“Zlotnick! I’ll kill him,” he cried.

Blinder’s former compliance officer testified that he had heard Blinder threaten to kill his opponents “500 times,” though few took the old man seriously.

Blinder emerged from prison in 1995, tossing his cane and shouting, “I’m free. I’m free,” on the jailhouse steps.

In 1997, he produced a video called, “The Fight to Expose,” which he distributed to the media and members of Congress. It was 60 minutes of denial and misery about his treatment in prison. He claimed there was a government conspiracy to shut him down.

“I didn’t do anything that Merrill Lynch doesn’t do,” Blinder once said in an interview. “I just did it on a smaller scale.”

It sounded delusional. Then in December 2002, Merrill Lynch and most other major U.S. investment houses paid $1.4 billion to settle civil fraud charges. Well-educated Wall Street analysts had been hyping stocks, too, with myriad layers of added sophistication, but their moves still resembled the old pump-and-dump schemes that Blinder had championed.

By 2002, though, Blinder was fading away in a nursing home in Arizona. There was no time left for, I-told-you-sos. He died at age 82.

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Bernie Ebbers co-founded WorldCom and grew it wildly through takeover sprees until it collapsed in 2002 under the weight of its massive debts.

WorldCom was the second-largest long-distance phone company behind AT&T when it filed bankruptcy in 2002, and it beat Enron as the era’s largest accounting fraud.

The company’s biggest deal was acquiring MCI Communication in 1998, but in 2000, regulators objected to its plans to buy Sprint Corp.

The merger game was over, and with it, the creative merger accounting that helped WorldCom cook its books. It's most audacious gimmick was recoding operating costs as capital investments, which hid expenses, inflated cash flow and gave the illusion of profits instead of losses.

When Ebbers wasn’t lording over an $11 billion accounting fraud, he taught Sunday-school at Easthaven Baptist Church in Brookhaven, Miss.

“No one will find me to have knowingly committed fraud,” he promised fellow church members, who then gave him a standing ovation.

As a proud Christian, he often opened corporate meetings in prayer. He apparently didn’t pray too hard for forgiveness or show any signs of repentance.

During his trial, Ebbers put forth an “I don’t know … I don’t recall … I don’t remember …” defense, blaming subordinates for the company’s audacious accounting stunts.

He was sentenced to 25 years in prison after convictions on fraud and conspiracy charges.

He’d been known as the “Telecom Cowboy” for his preferred attire of boots and jeans. He liked to drive a tractor on his farm, but when it was time to report to prison, he drove his Mercedes.

Ebbers served 13 years of his time, released early because of his declining health. He died a month later in February 2022.

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Sam Walton couldn’t figure out how Michael “Mickey” Monus could open 300 stores in 33 states in just ten years.

What the Walmart founder didn’t know was that Monus was doctoring the books at Phar-Mor, the pharmacy chain he founded in his hometown of Youngstown, Ohio, in 1982.

The fast-growing retailer falsely inflated earnings to conceal massive operating losses. The $1 billion scheme involved every trick from fake inventory counts to bogus invoices.

Phar-Mor filed bankruptcy in 1992. And in 1995, Monus was convicted on 109 counts of fraud and embezzlement. He subsequently served 10 years in prison.

The chain once boasted 25,000 employees and $3 billion in revenue.

“Having reached the 300th store, there’s no stopping us now to being a national retailer and to having a store in every major market across the country,” Monus said at the top of his game.

Monus was former high school basketball player who stood 5’9” tall. He and went on to create the very short-lived World Basketball League, a professional minor league featuring players under under 6’5” tall.

He was also an original owner of the Colorado Rockies baseball team that began playing in 1993.

To fund his sports fantasies, and to support his lavish lifestyle, Monus embezzled about $10 million from Phar-Mor as the retailer crumbled.

Monus made history in the 1990s for perpetrating one of the largest corporate frauds in U.S. history – only to be surpassed by Enron and WorldCom in the 2000s.