Unluckiest People Who Lost The Most Money

The rich people of the world may drive around in cars that look like spaceships and eat gold for fun, but at the end of the day, they’re humans too. And, like all humans, they make mistakes. The only difference is when you’re extremely rich, your financial mistakes can have extreme consequences. So, as both entertainment and a lesson in finance, here area few people who have lost the most money.

10. Elon Musk

©Ringo H.W. Chiu

There are few things worse than losing cash, to the back of the couch or otherwise. But on April 4th, 2019, Elon Musk lost an absurd amount of money in just two minutes. As far as anyone can tell, there were no couches involved. When Tesla Inc. shares dropped 11 percent within the first two minutes of trading at the New York stock exchange, its CEO suffered a sting that would make a Japanese hornet wince: a loss of a billion dollars, since most of his wealth is tied up in shares he owns of his company.

In the same time it takes to microwave a hot pocket, he lost way more money than most of us will earn in our entire lives. Luckily for Elon, this $1.1 billion loss only cut his total net worth down to $22.3 billion, so he’ll probably still be able to pursue his kooky ventures.

©Joe Rogan Experience

But electric car giant Tesla’s position is more precarious. Leading up to the drop, Tesla had been in a record decline, dropping from 90,966 cars manufactured in the final quarter of 2018 to just 63,000 in the first quarter of 2019. This failure to meet production targets was the main cause of the huge loss, though many suspected that Elon’s on-going legal problems may have played a big role in spooking investors as well. Unfortunately for Musk, in the following months tesla dropped a further 25%, meaning a loss of many billions to his net worth following negative reports on Tesla’s stock from analysts.

But, then again, what debt collectors would chase Musk to Mars if he goes bust and flees in a SpaceX rocket?

9. Nick Leeson

Unfortunately, some losses are never directly suffered by the person responsible. This is exactly the case with Nick Leeson, an ex-broker who’s best known for bringing down Barings Bank in 1995, which was then the oldest merchant bank in the United Kingdom.

©Stuart C. Wilson

Leeson regularly used a strategy called doubling, wherein every time he would lose money, he would simply double down on his next gamble in order to recoup the loss. If that sounds crazy to you, that’s because it is. While initially enjoying significant success, Leeson eventually found himself hiding losses by exploiting management flaws and making unauthorized and highly speculative financial decisions with the bank’s money.

 Things were going fairly well for him until January 16th, 1995, when he placed something known as a short straddle on the Singapore and Tokyo stock exchanges. This was essentially a high-loss-potential bet that those markets wouldn’t change drastically overnight. But the Kobe earthquake hit on January 17th, which meant that the markets collapsed, and Leeson was in deep trouble. He left a note on his desk saying: “I’m sorry” and fled the country, leaving behind $1.4 billion in losses.

Unfortunately for Barings, this was twice their available capital and left them bankrupt. Leeson dodged the law for a while but was eventually arrested in Germany.


Barings, on the other hand, collapsed after two centuries in business.

8. Pablo Escobar

©Colombian National Police

Infamous drug lord Pablo Escobar had a financial problem that was difficult to solve. Due to the highly illegal sources of his income, he couldn’t just go put it all in a bank. So, he ended up storing huge amounts of the cash he amassed in fields, rundown warehouses, and within the walls of his associate’s houses.

©Caracol Television

In”The Accountant’s Story: Inside the violent world of the Medellín cartel”, a book by Roberto Escobar, Pablo’s chief accountant and brother, Roberto touches on the specifics of the matter. In the book, he writes that Pablo had so much cash laying around, left subject to the elements, that he would simply write off 10% of his yearly revenue because rats would eat it, it would be destroyed by mold, or it would get water damaged.

Based on how much money he was reportedly making, this would mean he lost around $2.1 billion yearly. I don’t know whether they just had a taste for the cash-money lifestyle, but that’s probably the most damage rats have caused since the black plague.

7. Warren Buffett

©Mark Hirschey

You might be surprised to hear that the 3rd-wealthiest man on Earth has lost some of the most money. But the bigger the amount invested in something, the harsher the losses if its value falls. Warren Buffett’s company, Berkshire Hathaway – which holds a stake worth $52 billion in Apple shares – lost $3.7 billion in a single day in 2018, when Apple stocks took a historically bad nosedive. When the day was over, the shares were down 6.6 percent. Apple’s stock suffered as a result of falling iPhone sales, which were attributed to their high prices versus competitors. I don’t know what they’re talking about – Apple are famous for their great value. I mean, only $1,000 for a monitor stand?


What a steal! Regardless, Buffett and Apple didn’t suffer too badly from the loss, as Apple’s still worth a trillion dollars, and Buffett still sits on a cool $85 billion.

6. John Meriwether

©Joe Weisenthal

In 1994, John Meriwether created the Long-Term Capital Management hedge fund. The fund was wildly successful in the four years that followed, eventually being responsible for over $100 billion. He claimed that their strategies, which promised to take advantage of temporary changes in market behavior, theoretically reduced the risk level of their investments to zero.


In 1998, a series of risky internal bets led to instability within the fund, and investors began to get spooked. As many of the hedge fund’s investments were related to foreign currency markets, financial crises in Asia and Russia seriously compounded the fund’s mounting issues, eventually leading to its collapse. John’s fund lost $4 billion of its $4.7 billion in capital. Thanks to bailouts from the government and a group of banks, the company was able to liquidate successfully and return $3.6 billion to investors. Partners like Meriwether, however, bore the brunt of the losses.

5. Brian Hunter

In 2005, Brian Hunter’s investment career was going great, thanks to the unexpected help of hurricane Katrina and hurricane Rita.

©Jeff Schmaltz

While people don’t usually think of hurricanes as being good for the market, they are for people like Brian Hunter, who gamble on natural gas futures. These hurricanes caused the price of natural gas to skyrocket due to damaged refineries. Brian Hunter and the hedge fund he worked for, Amaranth Advisors, earned well over $1 billion and a whole lot of new, confident investors from the lucrative disasters.

©Andrey Popov

But the following year, anticipating an equally devastating hurricane season, Hunter placed similar bets on natural gas prices rising. Only this time, the expected hurricanes never came. The price of natural gas went into freefall, and Brian Hunter was responsible for $6 billion in losses. Clearly, karma is more of a renewable energy kind of guy, with a distaste for those who profit from disasters.

4. Jérôme Kerviel

©Max malafosse

While working as a trader at the French bank, Société Générale, Jérôme Kerviel developed a nasty habit of playing dirty to increase his profits. By manipulating Société Générale’s data systems, he was able to carry out trades and bets with trading partners who didn’t exist. When the threat of discovery loomed near, Kerviel attempted to cover up the massive profits he’d been making for himself through one-sided bets and fake trades by intentionally causing massive losses.

You might struggle to believe it, but this did not work. Once word got out in early 2008, Kerviel’s illegal rogue trading cost Société Générale $7.2 billion dollars – the worst loss from any rogue trader in history. After his eventual arrest, while Kerviel was waiting for a court ruling on his legal appeal, he met with Pope Francis at the Vatican.


Reportedly, Kerviel sought redemption from the guy and wanted to try on his hat. Well, maybe not the second part. But the bizarre turn of events continued as Kerviel then went on a pilgrimage all the way from Rome to Paris to protest against what he referred to as the “tyranny of the markets.” Clearly, the ‘tyranny of greedy bankers’ wasn’t too much of a pressing issue for Kerviel. To this day, he refuses to accept responsibility for the loss.

3. Mark Zuckerberg


You may know Mark Zuckerberg as the sixth richest person in the world, the founder of Facebook, and personal-data salesperson. What you may not know is that he currently holds the record for people who lost the most money in a single day. Between the 25th and 26th July 2018, the Zuckmeister lost a whopping $15.9 billion. To put that into perspective, that’s almost double the current brand value of KFC. Facebook shares dropped 19 percent.

The amount Zuck lost in a single day was attributed to CFO David Wehner’s announcement regarding tighter business margins going forward. The information startled investors and sparked a decline that had been looming after Facebook’s various controversies that year. Though not directly, Mark’s love of sharing stranger’s personal info like after-dinner mints eventually came back to haunt him. The debacle knocked him from the third richest person in the world down a whole three spots to merely the sixth richest. Pathetic.

2. Julian Robertson


Like many others on this list, things started off just dandy for Julian Robertson. He founded the hedge fund firm Tiger Management in 1980. Over the course of the next sixteen years, he turned $8 million into $7.2 billion. Ending up with nine hundred times more money than you started out with ain’t bad! But between 1998 and 2000, Robertson refused to board the tech bubble hype-train, predicting it would soon collapse like a disappointing soufflé.

 Ultimately, he would prove to be right. However, his mistake was in trying to short his tech stocks. Shorting stocks is essentially betting that a stock’s value will decrease, which is risky, as the losses are potentially unlimited. Unfortunately for Robertson, tech stocks continued to rise for a considerable time before the bubble finally burst. While rivals made huge gains, Tiger Management suffered losses of $17 billion and closed down in 2000.


Before I reveal the “world’s greatest loser”, here are a few honorable mentions whose losses – while not monetarily the highest– are just as jaw-dropping as the rest. For starters, there’s Gerald Cotton.

©Financial Post

The Canadian cryptocurrency entrepreneur lost his money in an unconventional way: by dying. But there was more misfortune than death in Cotton’s case, because his passing cost investors in QuadrigaCX, Canada’s largest cryptocurrency exchange, $190 million. This was all because the password for the crypto-wallets was known only to Cotton, and never written down, so without him there was no way of accessing it.

Another facepalm-worthy case occurred in 1996, when Denise Rossi won the California Lottery.


Instead of telling her husband like she probably should’ve, she kept it secret and attempted to get a divorce with an expedited settlement. Unfortunately for Denise, her husband eventually found out, and the court ruled that she’d failed to comply with asset disclosure laws. She hadn’t even disclosed her winnings to her own attorney, who could have helped her hold on to the cash had he been made aware during the divorce proceedings.

By default, as per the law, her husband received the entire undisclosed$1.3 million prize. There are worse ways to find out your partner is hiding something from you, I suppose.

1. Masayoshi Son

©Masaru Kamikura

Masayoshi Son has the proud honor of being the person to lose the most money in recorded history. When the dotcom bubble burst in the early 2000s, tech shares finally stopped skyrocketing and began plummeting, and Son lost approximately $70 billion. To put that in perspective for you, that’s approximately 70% of Bill Gate’s current net worth. And from a perspective us common folk can grapple with, working at the US federal minimum wage of $7.25 an hour, you’d have to work more than a billion 9-hour shifts in order to earn the amount that Masayoshi lost. That’s just short of 3,000 years of pure work. And that’s before tax!

The burst of the dotcom bubble hit Son hard. By the end of 2000, the value of his company SoftBank’s shares had dropped 93%. But amazingly, in spite of his colossal losses, Masayoshi is still the richest man in Japan. And possibly one of the nicest too, since in 2011 he pledged to donate his entire salary until his retirement to the victims of the 2011 Tōhoku earthquake and tsunami.


Has this article of people who have lost the most money made you feel better or worse about your personal financial situation? And what’s the most money you’ve ever lost? Let me know in the comments section below. Thanks for reading!

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