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From riches to ruins, empires to ashes... Join us as we examine the business leaders who went from boardroom legends to courtroom defendants! Our countdown includes Trevor Milton, Elizabeth Holmes, Sam Bankman-Fried and more! Which spectacular downfall shocked you the most? Let us know in the comments!
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00:00Bankman Freed is now facing a dozen federal charges in Manhattan court related to the
00:05collapse of FTX and Alameda. Welcome to WatchMojo, and today we're counting down our picks for the
00:10business leaders whose empires imploded. Whether due to incompetence or outright fraud, these CEOs
00:15helped destroy the companies they once led and built. In 2009, he pleaded guilty to 11 criminal
00:21counts and received the maximum sentence, 150 years. In court, he insisted it was all his idea.
00:28His family, he claimed, knew nothing.
00:31Number 10. Trevor Milton, Nikola Corporation. The name alone invited comparisons. The company
00:36Nikola positioned itself as the next Tesla, promising a revolution in clean transportation.
00:41There's a lot of really good interest and a lot of good customers that are wanting the trucks.
00:46The hardest part we have right now is trying to figure out how to deliver them
00:49with the infrastructure going up at the same time. Investors rushed in and the company's
00:53valuation exploded into the tens of billions almost overnight. But in 2020, allegations
00:58emerged that founder Trevor Milton had exaggerated or outright misrepresented Nikola's technology.
01:03All of this started initially with Hindenburg Research saying, hey, look, a lot of the comments
01:08and the claims that were made by Trevor Milton and by Nikola regarding the ability of their
01:15semis to power themselves, videos that were shot, etc., that they're not accurate. They weren't
01:21accurate at the time. One Nikola promo video of a fully functional truck was later revealed to have
01:26been rolling downhill. Federal prosecutors charged Milton with fraud and securities violations.
01:30In 2022, he was convicted on multiple counts, bringing his time as the world's new tech CEO
01:35darling to an abrupt end. Though he was later pardoned, Milton lost his company, his reputation,
01:39and billions in investor value. It is a full and unconditional pardon. It's the highest pardon
01:44you can get in America. It's the most powerful one. It's of innocence. It essentially says Trevor
01:49is innocent and the government was wrong. They were wrong to do it and it should have never happened.
01:54Number nine, Carlos Ghosn, Nissan-Renault Alliance. They called him the god of cars. Carlos Ghosn built a
01:59near-mythic reputation in the automotive industry. Carlos Ghosn was a businessman with a cult-like
02:05following. Credited with single-handedly turning around the fortunes of several major companies,
02:11he was showered with awards, flattering profiles, and even appeared on a stamp.
02:16When Nissan was near collapse, he turned the company around. The Nissan-Renault Alliance became
02:20a global powerhouse. Ghosn was an industry darling, celebrated in boardrooms across the world. Then in
02:252018, allegations of financial misconduct emerged. Japanese prosecutors arrested Ghosn,
02:30accusing him of under-reporting income and misusing company funds.
02:33He claims he's the victim of a conspiracy to oust him.
02:37This is just cruel and they're punishing us.
02:40It was an unexpected surprise. I'm shocked and confused.
02:44These allegations are untrue and I should have never been arrested.
02:50He denied all wrongdoing but was stripped of his roles and placed under strict bail conditions.
02:54In 2019, Ghosn stunned the world by fleeing Japan hidden inside a large equipment case. He resurfaced
02:59in Lebanon. He remains there to this day beyond the reach of Japanese extradition and far from
03:04the empire he once ruled. But now I was ready to be able to defend myself. Don't forget
03:09the peers. I stayed practically one year without being able to open my mouth. I could not make a press
03:14conference. I could not talk to any press. They had all the platform.
03:20Number eight, John Foley, Peloton. For a single glorious moment, John Foley couldn't lose.
03:25We think we've built an incredible company. The foundation is great. The economics are great.
03:29The business model is great. The team is great. So we feel like we are special in this.
03:34Peloton became the pandemic status symbol, turning home workouts into a luxury brand.
03:38As gyms shut down, demand exploded. The company's valuation soared and Foley briefly
03:42became a tech billionaire. But the boom didn't last. As the world reopened,
03:45sales collapsed and losses mounted. Among its problems, safety failures in Peloton's
03:50expanded product line drew intense scrutiny.
03:52When we brought the TRED and the TRED Plus product to market, it met every existing safety
03:57standard in Europe and the U.S. We made sure that they were safe products. When used properly,
04:03they're incredibly safe products.
04:04After a child died in a treadmill accident, the company recalled its TRED Plus machines.
04:09In 2022, Foley was pushed out as CEO as Peloton's stock cratered. By 2024,
04:14he had lost nearly all of his money. Today, Foley has moved on to a smaller venture in
04:17home decor, a quiet come down from the empire he once built.
04:20What made you become an entrepreneur? Necessity. I need money. No, I'm kidding.
04:29I love creating. I love working with small teams and building stuff, especially consumer brands,
04:34which we're doing here at Ernesto.
04:35Number seven, Adam Neumann, WeWork. Adam Neumann may have been an office-based CEO,
04:39but he sold America on a vision. WeWork promised community, purpose, and a new way to work.
04:44Investors went for it fast. If you want to start thinking forward, you really have to think really
04:48far away. At its peak, WeWork was valued at nearly $47 billion. Neumann, meanwhile,
04:53lived like a tech messiah, surrounded by a strange cult of personality. Then reality hit.
04:58Financial filings revealed massive losses, questionable self-dealing, and a CEO exerting
05:02near-total control. In 2019, WeWork's shaky fundamentals were exposed.
05:07He ripped off everybody and left all the employees.
05:09And on the other end of it, obviously, he's not only taking all this money, he's spending a lot of money.
05:14He's spending it all and left the employees who worked with him along the way, high and dry.
05:19Neumann was forced out, walking away with a lucrative exit package as the company unraveled.
05:23WeWork later filed for bankruptcy, but Neumann didn't disappear. Backed by venture capital,
05:27he returned with Flow, once again selling a big idea, just on a smaller stage.
05:31I am the kind of person that actually learns more from their mistakes than from their successes.
05:36So all the great things we did in the past, we're going to do again.
05:39Number six, Alan Stanford. Stanford Financial Group.
05:42Alan Stanford built an empire on the promise of absolute fiscal security.
05:46Through Stanford Financial Group, he marketed high-yield certificates of deposit as safe,
05:51exclusive investments.
05:52And they told us that despite it not being regulated by U.S. authorities,
05:58that they had higher reserve margins than any U.S. bank.
06:02Right.
06:02It was very safe.
06:03It all looked so good.
06:04Exactly.
06:05Investors around the world bought in. Behind the scenes, though, it was a massive fraud.
06:09The operation was a Ponzi scheme, using new investor money to pay earlier clients.
06:13In 2009, authorities shut it all down and thousands lost their life savings.
06:16They are not only proclaiming their innocence, but saying that the SEC is the reason that they have collapsed in the fund.
06:23Three years later, Stanford was convicted on multiple federal charges and sentenced to 110 years in prison.
06:29His fortune evaporated, his empire collapsed, and his name went down in financial infamy.
06:33In 2025, courts finalized massive penalties tied to the scheme, closing one of the largest fraud cases in American history.
06:40If that bank settlement eventually does come through, and it still could be months away,
06:44it would basically double the recovery for Stanford victims, but it's still not much.
06:48Number five, Bernie Ebers, WorldCom.
06:50In our digital world, it can be hard to remember the mania of the dot-com bubble.
06:55WorldCom, the leader in globally managed VPN solutions on the world's most scalable global IP network.
07:01WorldCom.
07:03Smack dab in the middle of the digital gold rush, a guy from Mississippi built an empire.
07:07Through aggressive acquisitions, Bernie Ebers grew his company at a staggering pace.
07:11On paper, WorldCom looked unstoppable.
07:13In reality, it was propped up by massive accounting fraud.
07:16WorldCom, a telecom giant destroyed by a massive accounting fraud.
07:21Executives concealed billions of dollars in expenses, inflating profits to keep investors confident.
07:25In 2002, the deception was exposed, triggering one of the largest accounting scandals in history.
07:30WorldCom collapsed into bankruptcy, wiping out jobs, pensions, and billions in shareholder value.
07:35In 2005, Ebers was convicted on multiple fraud charges and sentenced to 25 years in prison.
07:40He died a month after release.
07:42Ebers was released from prison in late December after serving 13 years of a sentence for a massive accounting fraud.
07:49Number four, Ken Lay, Enron.
07:51You know a company's done wrong when the government indicts its accountants.
07:53At the peak of its success, the company's shares were worth more than $90 each.
07:59But just before Enron filed for Chapter 11, they traded at 26 cents.
08:03Enron was hailed as the smartest company in America.
08:06Ken Lay built it.
08:07Jeff Skilling ran it.
08:08Under their leadership, the energy company promised limitless growth and innovation.
08:11Behind the scenes, Enron relied on accounting tricks off the book's partnerships and a culture of deception.
08:16Profits were inflated.
08:17Losses were hidden.
08:18What's very rare to see, especially in established large companies like Enron, is a fraud that's driven from the top of the company.
08:26When the illusion unraveled in 2001, Enron collapsed almost overnight.
08:29Thousands of employees lost their jobs and retirement savings.
08:33Investors lost billions.
08:34Skilling was convicted of fraud and sentenced to prison.
08:36He was released after serving about 12 years.
08:39Lay was indicted but died before he could stand trial.
08:41What remained was one of the most infamous corporate implosions in American history.
08:44And almost five years of earnings had to be restated, exposing a company that was, well, not as flush and financially sound as investors had thought.
08:53Number three, Elizabeth Holmes, Theranos.
08:55She carefully crafted a persona and sold herself as much as her company.
08:59There's no reason why these can't be distributed in very, very decentralized locations.
09:06Your home?
09:07Yeah.
09:08You think people's homes should have these, essentially a clinical laboratory in their own house?
09:12I think that's a very interesting space.
09:14Dressed in black turtlenecks and lowering her voice, Holmes positioned herself as the next Steve Jobs.
09:19Her company, Theranos, promised a medical breakthrough.
09:21Holmes claimed hundreds of blood tests could be run from a single drop of blood using proprietary machines.
09:26In retrospect, it was all too good to be true.
09:28It's when you work to change things.
09:30And first they think you're crazy, then they fight you.
09:33And then all of a sudden you change the world.
09:35But at the time, billionaires, politicians, and major media outlets bought into her story.
09:39By 2014, Theranos was valued at $9 billion.
09:42But the technology never really worked.
09:44Whistleblowers revealed inaccurate results and misdiagnosed patients.
09:48Holmes denied responsibility as the company unraveled.
09:50It's a bit of a heartbreaking tale, right?
09:52Because there was so much potential.
09:55There was so many possibilities of what could have come out of this.
09:58In 2022, she was convicted of fraud and sentenced to more than 11 years in prison.
10:02Number two, Samuel Bankman-Fried, FTX.
10:05Sam Bankman-Fried was the king of the crypto bro revolution.
10:08As the founder of FTX, he positioned himself as a responsible counterweight to an industry built on hype.
10:13If possible, it would be extremely valuable to the ecosystem to backstop some of these places.
10:19First of all, just backstopping customers and making sure they're protected.
10:23But second of all, stopping contagion from spreading through the ecosystem.
10:27Investors, celebrities, and regulators listened.
10:29The exchange grew rapidly, turning Bankman-Fried into one of the youngest billionaires in the world.
10:34The reality was far darker.
10:35At the end of the day, look, there's a question of what happened and why, and who did what.
10:42Prosecutors showed that FTX had diverted billions in customer funds to cover losses at affiliated firms.
10:47In 2023, Bankman-Fried was convicted on several fraud accounts.
10:51At sentencing, the judge rejected his apology, citing a lack of remorse and a risk of future misconduct.
10:56He was sentenced to 25 years in prison, losing his fortune, his company, and his credibility in one fell swoop.
11:01Sam Bankman-Fried's regret, three days after he was sentenced to 25 years in federal prison,
11:07the man behind one of the biggest financial frauds in American history told ABC News he never intended to hurt anyone or take anyone's money.
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11:31Number 1. Bernie Madoff
11:32Bernard L. Madoff Investment Securities
11:34He didn't fit the typical Wall Street mold.
11:36He wasn't a reckless gambler, but a trusted fixture in the world of finance.
11:39Madoff was someone who was very much in the thick of things on Wall Street and generally respected.
11:45His company cultivated an image of steady, almost boring reliability.
11:48For decades, his investors believed their money was safe.
11:51His clients would eventually learn that their cash wasn't invested at all.
11:54Madoff ran the largest Ponzi scheme in financial history.
11:57Ponzi schemes are about robbing Peter to pay Paul and Jane.
12:01Money is taken from one victim and is used to pay out a different victim.
12:06He used new deposits to pay older clients while reporting fake, consistent returns.
12:11The illusion held until 2008 when the financial crisis triggered a wave of withdrawals he couldn't cover.
12:15The losses counted in the tens of billions.
12:18Thousands of individuals, charities, and institutions were utterly wiped out.
12:22In 2009, Madoff was sentenced to 150 years in prison, where he eventually died.
12:26And the remorse he claimed in every message is suspect as well.
12:30At his 2009 sentencing, Madoff turned to his victims.
12:33I'm sorry, he said.
12:35I know that doesn't help you.
12:37It didn't.
12:38And neither does Bernie Madoff's death.
12:41Which fallen CEO shocked you the most?
12:43Should anyone else have made the list?
12:44Let us know in the comments below.
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