Conrad Black served as chairman and CEO of Hollinger International, which controlled the Chicago Sun-Times, London’s Daily Telegraph, the Jerusalem Post and hundreds of smaller publications. But he didn’t live like a newspaperman.

He insisted on a life of royalty, often on his shareholders’ dime. He even became royalty. In 2001, after becoming a British citizen, he was dubbed Lord Black of Crossharbour, a member of the House of Lords.

Black and his wife, journalist Barbara Amiel, lived extravagantly, maintaining homes in Toronto, London, New York and Palm Beach and moving through a world of celebrities, politicians and business titans.

The problem was that Hollinger was a publicly traded company. And eventually its shareholders began asking what Black was doing with their money.

The rights of the nobility

Black was a highly privileged nepo baby, born into big money in Montreal, but he wanted to be viewed as a self-made man.

His father, George Montegu Black Jr., was a wealthy businessman who became president of Canadian Breweries Ltd., then Canada’s largest brewing company and part of the powerful circle of financiers behind Argus Corp., one of Canada’s dominant industrial conglomerates.

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Black was still in his 20s when both of his parents died within a few years of each other, leaving him and his brother, Montegu, a substantial inheritance. The family fortune gave Black the capital to begin buying struggling Canadian newspapers with longtime partner David Radler.

Controversies followed “his every step.” And his business career was plagued with accusations that he often considered other people’s money … his money.

After taking control of Argus in the late 1970s, Black faced accusations that he had taken advantage of two elderly widows who controlled crucial voting shares in the industrial conglomerate. Black denied doing anything improper.

In the early 1980s, Canadian and U.S. regulators investigated dealings surrounding an attempt by Black and his brother to gain control of Cleveland-based Hanna Mining through Norcen Energy. The allegations were never proved, and related U.S. charges were eventually withdrawn.

Then came the pensioners.

n 1984, Argus controlled Dominion Stores, a struggling Canadian supermarket chain. Under Black, Dominion moved to take roughly $56 million in surplus assets from its employee pension plan. Unions and pensioners fought the move, and an Ontario court ultimately ruled against the company and ordered the money returned to the pension fund.

Black fought his critics every step of the way. He repeatedly sued journalists, publishers and authors who questioned his business practices. In 1990, Penguin Books agreed to destroy thousands of copies of a book about the Dominion pension controversy after Black sued.

None of this slowed him down.

Black kept buying newspapers. By the late 1990s, Hollinger controlled more than 300 publications around the world. And the accusations kept coming.

Shareholders began questioning the enormous sums flowing from Hollinger to Black and his associates through management fees, compensation, perks and payments connected to newspaper sales.

A special committee appointed by Hollinger’s board eventually concluded that Black and his associates had received more than $400 million from the company between 1997 and 2003. It scrutinized Black’s use of Hollinger money for residences, household staff, automobiles, aircraft and other perks. It described what it found as a “corporate kleptocracy.”

One of the schemes involved so-called non-compete payments. It was money ostensibly paid in return for promises that Black and other executives wouldn’t compete with buyers of Hollinger newspapers.

Prosecutors said money that should have accrued to Hollinger and its shareholders instead went directly to Black and other executives.

The SEC separately accused Black and Radler of diverting money from Hollinger, arranging sweetheart transactions involving companies they controlled and misleading the company’s board and shareholders.

Meanwhile, shareholders were getting increasingly annoyed by Black’s imperial lifestyle.

When they questioned expenses that included a trip to Bora Bora, Black responded as arrogantly as any British Lord:

“I’m not prepared to re-enact the French revolutionary renunciation of the rights of the nobility.”

Black was later charged and acquitted of criminal charges related to the Bora Bora trip and other lavish expenses.

But by then, the revolution had already begun.

Caught on camera

In 2005, with investigators closing in, Black managed to turn a complicated corporate fraud investigation into something any jury could understand.

He removed 13 boxes of documents from his Toronto office despite a court order requiring that records be preserved.

Unfortunately for His Lordship, a security camera recorded him and his driver carrying the boxes to a car.

Prosecutors charged him with obstruction of justice and defrauding Hollinger investors out of more than $80 million by allegedly diverting corporate funds to his own use.

His business partner Radler, former Hollinger lawyer Mark Kipnis, and Toronto-based Ravelston Corp. were also indicted. Radler ultimately pleaded guilty to one count of mail fraud and agreed to 29-month prison sentence and a $250,000 fine. He also agreed to testify against others.

In 2007, a Chicago federal jury convicted Black on three fraud counts and the obstruction charge. He was sentenced to 6½ years in prison. He ended up serving about three.

Like North Korea?

Black has always maintained that he was the victim of overzealous prosecutors.

“I was effectively assaulted by the US government four years ago,” Black told a London audience in 2007. “It’s very a formidable adversary. Whatever the limitations of the U.S. government in quelling an insurrection in Iraq they are pretty efficient at terrorizing innocent people."

He fought his case all the way to the U.S. Supreme Court and won a couple important. The court narrowed the federal “honest services” fraud law used against him, and two of his three fraud convictions were eventually tossed. But one fraud conviction survived, involving $600,000 in bogus non-compete payments. And so did the obstruction conviction.

A federal appeals court characterized the surviving fraud conviction as straightforward theft.

Black ultimately served about three years in federal prison. But not even incarceration would silence him.

While fighting his case, Black wrote a memoir, “A Matter of Principle,” portraying himself as the victim of a prosecutorial vendetta. After being resentenced in 2011, he even sought work-release privileges to help promote the book before returning to prison.

He has said he never would have been prosecuted in Canada and compared the U.S. justice system to North Korea.

After decades of accusations, investigations, lawsuits, regulators, prosecutors, convictions and prison, Black remained convinced there was one innocent party in the whole affair: Conrad Black.

A pardon like no other

Black was released in 2012 and deported to Canada. But there was one more card to play.

Black had long been friendly with Donald Trump. Hollinger had sold the old Sun-Times building along the Chicago River to Trump, who demolished it and built Trump International Hotel & Tower on the site.

In 2018, Black published an admiring biography titled Donald J. Trump: A President Like No Other.

One year later, President Trump gave him a full pardon.

The White House praised Black’s “tremendous contributions to business” and noted that Henry Kissinger, Elton John and Rush Limbaugh were among those who had supported clemency.

Black never stopped insisting that his prosecution was unjust.

Today, he’s still writing in Canada. His columns continue appearing in the National Post, more than two decades after his newspaper empire unraveled.

Though he sometimes takes a stand against Trump’s insults and tariffs against his native country, he can be loud with the MAGA megaphone:

“We are now seen as the most absurdly woke and politically correct (and therefore foolish) country in the world.”

And he can’t seem to stop sucking up to the president who pardoned him with headlines like:

• “Trump isn’t our problem – we are”

• “Formidable Trump changes the world”

• “Middle East is on the brink of peace, thanks to Trump”

• “Don’t believe the haters — Trump is on his way to a strategic victory in Iran”

His newspapers are gone. His prison sentence is over. His conviction has been pardoned. And the man who once bought ink by the barrel is still getting the last word.

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Sam Walton couldn’t figure out how Michael “Mickey” Monus could open 300 stores in more than 30 states in just ten years.

What the Walmart founder didn’t know was that Monus had discovered a retail strategy even more powerful than everyday low prices: imaginary profits.

Monus founded Phar-Mor in his hometown of Youngstown, Ohio, in 1982 and built it into one of the fastest-growing retailers in America.

“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 proclaimed at the top of his game.

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

There was just one problem. It was losing money.

Enter “the subledger”

The trouble began showing up in the numbers as early as 1988.

Phar-Mor’s gross profit margin began declining, and by early 1989 Chief Financial Officer Patrick Finn was delivering weekly reports showing disappointing results, according to facts established in an appeals court ruling.

Monus told Finn not to show the real numbers to the board.

Instead, Finn testified, Monus instructed him to inflate the company’s gross margins to historical levels, understating losses and creating profits that didn’t exist. And so began one of the largest accounting frauds of its era.

Monus and Finn created a separate accounting record, which eventually became known as “the subledger.” There they parked losses they didn’t want anyone to see.

By June 1990, the subledger contained $38.5 million in concealed losses.

Monus and Finn knew the auditors were coming. So, according to the court, they simply added $200,000 in fictitious inventory to every store they knew the auditors wouldn’t visit. They also hid losses by inflating inventory and deployed several other accounting tricks.

For a time, it worked. But by the following year, the hidden losses had ballooned to $148 million.

Short players, big losses

Monus, meanwhile, had other ambitions.

He stood about 5-foot-9, but played high school basketball. It inspired him to create the World Basketball League, a professional league initially limited to players under 6-foot-5.

The WBL had teams in smaller markets such as Youngstown and a traveling professional cheerleading squad called the All-American Girls. Monus even bankrolled a television production company to broadcast games, according to a fascinating 1994 PBS Frontline investigation.

Unfortunately, basketball fans weren’t clamoring to watch shorter professional basketball players. And the WBL hemorrhaged money.

Monus directed Finn to write 82 unauthorized Phar-Mor checks totaling about $8.8 million to the basketball league, according to the appeals court.

Monus at one point told Phar-Mor controller Stan Cherelstein he would repay the money diverted to the WBL after arranging financing to buy yet another professional sports franchise: The NBA’s Denver Nuggets, according to the appeals court.

He never bought the Nuggets. He never repaid the money.

And basketball wasn’t Monus’s only sports fantasy. He was also an original investor in the Colorado Rockies baseball team.

Soon enough, he’d be out.

Where were the auditors?

Phar-Mor had outside auditors, but they didn’t find the fraud. They didn’t even look for the fraud.

Coopers & Lybrand repeatedly audited the company while Monus and his executives were hiding tens of millions of dollars in losses.

The Frontline investigation, “How to Steal $500 million,” put the auditors to shame when it demonstrated just how simple the inventory trick could be at a chain with hundreds of locations. Here’s an example from the report:

“Phar-Mor claimed every six-pack of Coke in the store was worth, say, $2.30 when, in reality, it may have sold for a buck 98. Multiply that difference by thousands of six-packs of Coke in 129 stores and you're on your way to a $12 million cover-up.”

Coopers & Lybrand checked inventory at just four stores, according to Frontline. Worse, the auditors told Phar-Mor months in advance which stores they planned to inspect, giving executives time to shift the fictitious inventory elsewhere.

Eventually, though, the fraud became so large that it was increasingly difficult to hide. And in 1992, somebody finally stopped playing along.

Phar-Mor controller Stan Cherelstein had learned about the subledger and confronted Monus and other executives. At an April 1992 meeting, Cherelstein secretly tape-recorded the discussion, according to the appeals court.

Then Finn flipped.

In July 1992, he went to the U.S. Attorney’s Office in Cleveland and exposed the scheme.

For outside observers like Sam Walton, the big mystery behind Phar-Mor’s success was solved almost immediately.

A $350 million surprise

Phar-Mor’s board fired Monus and Finn.

On Aug. 4, 1992, the company announced that a special audit had uncovered $350 million in fraud and embezzlement and said it had turned its evidence over to the FBI and Justice Department.

Company officials said financial statements had been falsified to hide losses and overstate income, according to a contemporary UPI report.

The Securities and Exchange Commission would later allege that Phar-Mor had cumulatively overstated income by $290 million from fiscal 1987 through 1991 and by another $238 million in fiscal 1992. The false financial statements helped induce investors to put more than $500 million into the company, according to the SEC.

Phar-Mor filed for Chapter 11 bankruptcy protection on Aug. 17, 1992.

The WBL collapsed. Monus withdrew from the Colorado Rockies ownership group. And Youngstown watched one of its hometown business heroes spectacularly implode.

A Washington Post account published as the scandal broke described the bafflement and anxiety sweeping a city that had watched Monus become a symbol of its hoped-for economic revival.

109 guilty counts

Federal prosecutors initially indicted Monus in January 1993 on 129 counts. But it was a complex case and Monus wasn’t finished fighting.

His first trial ended in a mistrial. So prosecutors tried again.

This time they charged him in a 109-count superseding indictment with a whole store shelf of federal crimes: conspiracy, bank fraud, wire fraud, mail fraud, interstate transportation of property obtained by theft or fraud, filing false tax returns and obstruction of justice.

It was the fraud that just kept growing. Prosecutors ultimately put the total loss at up to $2 billion, including about $1 billion lost by investors.

After a month-long trial, a jury convicted Monus on all 109 counts.

The trial also established that his embezzling went beyond propping up the basketball league. Fourteen Phar-Mor checks totaling about $568,000 had been written directly to Monus or for his personal benefit, according to the appeals court.

He was sentenced to 235 months in federal prison, more than 19 years, and fined $1 million.

“The important thing is … the employees – all those dedicated, loyal and highly motivated people,” Monus told the judge at sentencing. “I want them to know the sorrow and regret that I have. The sorrow and regret will live with me for the rest of my life.”

The Sixth Circuit Court of Appeals upheld every one of his convictions in 1997 but vacated his sentence. In 1999, Monus was resentenced to 139 months and his fine was cut to $500,000.

He ultimately served about 10 years behind bars.

A subsequent bankruptcy court ruling put the consequences in perspective.

One investor alone had purchased more than $50 million of Phar-Mor stock based on financial information that Monus had falsified, and recovered nothing.

The bankruptcy court also noted that Monus had been convicted of shredding books, records and other documents concerning Phar-Mor’s payments to the basketball league.

Phar-Less

Phar-Mor survived Monus, but not for long. The company emerged from bankruptcy under new ownership in 1995, only to file Chapter 11 again six years later.

In 2002, a bankruptcy judge approved the $141 million sale of its remaining assets. Its final 73 stores were liquidated. Competitors, including CVS, picked up the pieces, ending the chain Monus had once promised to put in every major market in America.

As for the auditors, they paid a steep price, too.

Investors and creditors filed more than 40 lawsuits against Coopers & Lybrand, which had issued clean audit opinions while the fraud continued. The firm faced more than $1 billion in claims and settled most of the lawsuits for undisclosed amounts.

In 1996, a federal jury found the accounting firm liable for fraud in one of the lawsuits. A judge later concluded there was sufficient evidence that Coopers had been reckless in its audits and would have uncovered the fraud had it followed generally accepted auditing standards.

Monus made history in the 1990s for perpetrating one of the largest corporate frauds, at least until Enron and WorldCom came along and made billion-dollar accounting fraud seem almost routine.

Sam Walton had been right to wonder how Monus could possibly grow Phar-Mor so fast while selling merchandise so cheaply.

He just couldn’t see the subledger.

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(Please Welcome Ed Mattar to The Business Blunders Hall Of Shame, a free anthology white-collar criminals, disgraced executives and corporate fraudsters who turned success into scandal, and in many cases, prison sentences. This is a sordid tale I covered decades ago about a regulatory blunder and a deadbeat banker who didn’t pay his debts or do his time.)

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Ed Mattar defaulted on bank loans, stiffed health-club customers, ran a college into the ground, and left students waiting for tuition refunds.

So how did he end up owning a state-chartered bank?

In 1989, Mattar acquired a tiny institution in Boulder, Colo., and renamed it BestBank. He called it a 50th-birthday present to himself. It would eventually become an expensive present for everyone else.

Mattar was a chronic deadbeat who left a trail of tears almost everywhere he went. Here are some of his career highlights (cribbed from my 1998 investigation for The Rocky Mountain News):

• 1983 – Closed a health club he owned in Worcester, Mass., refusing to refund customers or pay his landlord, who claimed he owed more than $26,000 in rent.

• 1988 – Forced to resign as president of Central New England College in Worcester after auditors discovered financial irregularities and $14 million in debts.

• 1991 – Sued for $286,500, by a Massachusetts banks claiming he personally defaulted on three loans. The bank ultimately foreclosed on his 5,500-square-foot home in Worcester.

• 1994 – Closed a school that he owned in Maine and Rhode Island known as Career Institute. The school owed the U.S. Department of Education $251,000. Additionally, the Finance Authority of Maine complained that Mattar's Career Institute owed more than $75,000 in refunds to students who withdrew from classes.

• 1996 - The Education Department foreclosed on Nasson College, a school he owned in Springvale, Maine. A trust Mattar controlled never made a payment on its $400,000 loan. At the time of foreclosure, the debt had grown to $600,000 and the school owed $28,500 in back taxes.

• 1997 - The Education Department notified Mattar that his school in Pawtucket, R.I., called the Nasson Institute, would lose its eligibility for government student loan assistance. The department complained of a student loan default rate of 42.1 percent, nearly four times the national average. The school recently announced it is closing.

• July 1998 - Banking regulators declared Mattar’s BestBank insolvent with $135 million in bad loans and only $23 million in loan loss reserves. Shortly before regulators seized the bank, Mattar paid himself and his bank president a $9 million bonus.

Bad credit? Buy a bank

Mattar’s credit report should have stopped him at the door, but who was checking?

“The question makes me squirm a little bit,” said Colorado Banking Commissioner Richard Fulkerson in 1998. “I don’t have a good answer for you. We should have been more aware of the problems.”

Fulkerson was just picking up the pieces. He wasn’t the banking commissioner at the time. A former banking commissioner, though, acknowledged that had regulators known about Mattar’s health-club debacle, he probably never would have been allowed into banking.

Mattar bought BestBank at a time when Colorado was still recovering from a banking crisis and regulators were desperate to find anyone willing to put capital into troubled institutions.

And for a while, Mattar looked like a genius.

BestBank grew from just $8 million in assets at the end of 1993 to $314 million by the time it collapsed in 1998. In 1995, American Banker even named it the best-performing U.S. bank with less than $50 million in assets.

BestBank attracted deposits by offering some of the highest CD rates in the nation. But it was all built on subprime credit cards. You know, the high-fee, exorbitant-interest-rate cards issued to consumers with bad credit.

More than half of them eventually went bad. Credit-card receivables exploded from $42 million to $240 million in less than two years.

No matter for Mattar. He and BestBank president Thomas Alan Boyd paid themselves $9 million in bonuses shortly before regulators seized the bank in July 1998.

The failure ultimately cost the Federal Deposit Insurance Corp. more than $200 million and uninsured depositors another $27 million.

The bill comes due

Somehow, federal prosecutors didn’t get around to charging Mattar until 2003.

His trial began in 2006, only to be postponed when a juror became ill. Mattar was not convicted on federal bank-fraud charges until February 2007.

Even his sentencing was delayed until Nov. 2, 2007.

By then, Boyd was serving more than seven years in prison and others convicted in connection with BestBank were also behind bars.

Hours before Mattar was supposed to finally appear in federal court for sentencing, he took a sledgehammer to the window of his 27th-floor Denver hotel room and jumped to his death.

His conviction was vacated on a hard-won technicality: Defendants who die before sentencing are cleared since they have no chance to appeal.

So besides a big pile of defaulted debt, all he left behind were shards of broken glass, some snapped tree branches, and a small crater in the landscaped patch where he landed outside a downtown Denver hotel.

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In the 1800s, a man who called himself the “Young Napoleon of Finance” somehow convinced America’s elite he was out to conquer the world.

Ferdinand Ward promised wealthy clients 10% monthly returns through exclusive government contracts and brilliant stock trades.

Almost none of it existed, but he had perhaps the greatest recruiting tool any scammer could ever have: former President Ulysses S. Grant.

Ward persuaded Grant’s son, Ulysses S. Grant Jr., to become a partner. Then he convinced his father, the great Civil War hero, to join the firm as well.

In addition to investing his own money, the elder Grant borrowed $150,000 from railroad magnate William H. Vanderbilt to invest after Ward claimed a lucrative government contract that required immediate financing.

There was no contract. Within days, Grant & Ward collapsed in May 1884, wiping out thousands of investors.

Grant lost virtually everything, including his faith in humanity. “I have made it a rule of life to trust a man long after other people gave up on him,” he told the firm’s bookkeeper. “I don’t see how I can trust any human being ever again.”

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He spent the final year of his life, while dying of throat cancer, racing to finish his memoirs so his family would have something to live on.

At least, those memoirs eventually became one of history’s greatest publishing successes.

The collapse also ruined other notables, including Thomas Nast, an editorial cartoonist considered to be the “Father of the American Cartoon.”

It also helped trigger the Panic of 1884, one of several financial crises that periodically rattled Wall Street before the creation of the Federal Reserve.

A New York jury convicted Ward of grand larceny in 1885 and sentenced him to 10 years in Sing Sing Prison.

Ward, who had been born to parents who’d served as missionaries in India, showed no remorse. He explained in a Supreme Court hearing that he had to “rob Peter to pay Paul.”

He served about six and a half years before being released.

He’d made his mark in history, pioneering and perfecting a fraud that persist to this day. Too bad Charles Ponzi got the naming rights.

For nearly two decades, Russell Wasendorf Sr. stole more than $215 million from customer accounts while convincing regulators everything was perfectly fine.

His master weapon? A photocopier. Then, as technology progressed, he advanced to Photoshop.

Wasendorf quietly siphoned money out of customer-segregated accounts beginning in the early 1990s after his business partner pulled out with all his money, according to federal prosecutors. Each time he took money, he simply created fake bank statements showing balances that didn’t exist.

Instead of hacking computers or manipulating high-frequency trading algorithms, he allegedly intercepted bank confirmations, forged signatures, fabricated statements and even established a post office box that appeared to belong to U.S. Bank. Regulators mailed verification forms there. Wasendorf filled them out himself, signed someone else’s name, and mailed them back.

And nobody thought to pick up a telephone?

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Wasendorf used most of the money to create the appearance of success when he was in fact failing. He also opened two restaurants in Cedar Falls and lived in luxury with a private jet and an estate that included a million-dollar indoor swimming pool and a 1,000-bottle wine cellar.

The deception continued year after year while Peregrine grew into one of America’s largest independent commodities and futures brokers – at least on paper.

Then came July 2012.

Facing an unexpected regulatory audit that required direct electronic confirmation from the bank rather than paper statements, Wasendorf realized the game was over.

He attempted suicide outside company headquarters, leaving behind a confession that detailed decades of fraud.

Investigators discovered that Peregrine claimed to be holding more than $220 million in customer funds. The real balance? About $5 million.

More than 13,000 customers ultimately lost money, and prosecutors said the fraud exceeded $215 million.

In 2013, a federal judge sentenced Wasendorf to 50 years in prison, the maximum allowed by law. He also ordered more than $215 million in restitution.

Acting U.S. Attorney Sean R. Berry of the Northern District of Iowa called him “a con man who built a business on smoke and mirrors.”

“By lying to investors and regulators, Wasendorf defrauded thousands of innocent investors out of a staggering $215,000,000,” Berry said.

And that’s the bigger embarrassment, a regulatory system that enabled such an unsophisticated fraud.

For nearly twenty years, regulators, auditors and financial institutions accepted paper documents created on a copy machine.

They might as well have sent the arrest warrant by fax.

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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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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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Read More Hall Of Shame Inductees

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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Read More Hall Of Shame Inductees

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.

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

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.

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.

So “Get Smart”

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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Read More Hall Of Shame Inductees

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 on wire fraud charged in January 2022 after defrauding her investors out of more than $100 million, and sentenced to more than 11 years in prison in November 2022. 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.