History's biggest gambling losses
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History's biggest gambling losses

Categories: live poker, other games, slots, sports betting 10 Dec 2020 505 0

When you sit down at a casino table, there is always a chance, but big losses are not too frequent if you are smart enough. Well, it was too hard to resist for the gamblers who missed all the temptation. If they took an ego trip or were searching for investment to recover is beyond the point.

What matters is that a good anecdote is created by the following famous gamblers who lost it all, but are a very bad example of how to behave and act in a casino. They've lost everything and more. Today we present to you gamblers who have gone from riches to rags, or who have at least lost a large portion of their gambling fortune.

Akio Kashiwagi

Akio Kashiwagi

Japanese businessman Akio Kashiwagi was known as the "Warrior of the Dragon" due to his love of playing baccarat for high stakes. Kashiwagi once bet $200,000 per hand and reportedly won $6 million in a single night. However, his luck didn't last, and he ended up losing $250 million over the course of his gambling career.

  • Incurred losses: $250 Million

Terrance Watanabe

Terrance Watanabe
Terrance Watanabe
  • Total amount gambled: $825 million
  • Incurred losses: $127 million
  • Does he owe anything today? $15 million (August 2020)
  • Game: Baccarat, Blackjack

There is still a touch of competition when we talk about the greatest gambling losers in history. As it turns out at one time or another, many people who came in for money, or made a fortune one way or another, felt compelled to gamble quite foolhardily. But if anything, Terrance Watanabe is truly one of the gamblers who lost everything, or at least a very significant part of what he owned.

In 1977, Watanabe inherited the Oriental Trading Company, which he eventually sold in 2000. If he was bored or wanted to try something different, Watanabe's gambling habits forced him into more drastic situations year after year and in 2007 he suffered $127 million in losses at Caesar's Palace and The Rio after gambling over $825 million.

As far as prominent gamblers who lost it all go the losing streak of Watanabe is believed to be the biggest one Las Vegas has ever seen. He attempted to sue the casinos, but eventually lost his debt and was forced to pay it off.

Today, with the exception of $15 million for which he faced four criminal charges back in 2009 and again in 2020, Watanabe has covered nearly his entire debt. He will be sentenced to 28 years in jail if he fails to pay up.

Harry Kakavas

Harry Kakavas
Harry Kakavas
  • Total amount gambled: $1.43 billion
  • Incurred losses: $20.5 million
  • Does he owe anything today? He has paid his debt in full.
  • Game: Baccarat

The biggest loser may not be Harry Kakavas, but he has made a point of being a repetitive loser. Yet if anything, Kakavas had the opportunity, experience and expertise to reduce his losses in a way that definitely helped him not to incur the biggest losses out there.

Kakavas played baccarat at the Melbourne Crown Casino over the course of 16 months and invested a total of $1.43 billion between 2012 and 2013, incuring net losses worth $20.5 Although Kakavas had no problem spending 16 months gambling, he definitely objected to keeping the $20.5 million he lost from the casino.

Melbourne Crown Casino
Melbourne Crown Casino

In a lawsuit brought before the High Court of Australia, Kakavas alleged that his "pathological urge to gamble," a common defense among famous gamblers who lost it all or at least enough to feel annoyed, had been abused by the casino.

The presiding judge clarified that Kakavas had demonstrated "rational decision making and was able to act in his own best interest", including the plaintiff's decision to refrain from gambling from time to time, the judge's ruling said.

Maureen O'Connor

Maureen O'Connor
Maureen O'Connor
  • Total amount gambled: $1 billion
  • Incurred losses: $13 million
  • Does she owe anything today? She has paid her debt in full
  • Game: Video poker

She worked as San Diego's mayor and her gambling activities got out of control quickly. Her fascination with gambling quickly took the worst turn.

Yet, O'Connor has done very well in reducing risk relative to other unlucky gamblers, maybe something that politicians are hardwired to do. She gambled over $1 billion, but her losses ran to only $13 million. Better than the record of Kakavas, and definitely a lot better than the record of Watanabe.

O'Connor is probably one of the gamblers who lost it all, having had to borrow $2 million from the charitable fund of her second husband to spend the money on video poker. O'Connor is also the wife of the founder of the Jack-in-the-Box restaurant, Robert Peterson.

O'Connor is full of praise, while her gambling addiction is definitely a little sensationalist for good taste. Her political and professional career was focused on merit and at the cost of hard work, all she accomplished came.

Archie Karas

Archie Karas
Archie Karas
  • Total amount gambled: $40 million
  • Incurred losses: $40 million
  • Does he owe anything today? No
  • Game: Poker, Baccarat, Dice

Archie Karas is one of the most iconic gamblers to have lost everything. Archie, known for his ability to play high, has no problem taking any risk of getting a chance at anything better. In December 1992, he arrived in Las Vegas with just $50 to his credit and a loan of $10,000 that would come a little later. Archie was intensely playing poker for the next two years, amassing the fantastic $40 million in the process.

But the way it started was with a destitute Archie spotting a familiar face at The Mirage and applying for a $10,000 loan that would put in motion the wheels of fortune. He easily converted the money into $30,000 playing Razz $200/$400 limit and paid his beneficiary $20,000 back.

Binion's Horseshoe
Binion's Horseshoe

Archie's trip of Las Vegas thus began, amassing fortunes in casinos all around the place and winning $3 million at Binion's Horseshoe. His bankroll eventually rose to $5 million, then $7 million, but Archie had stopped hunting for rivals.

Stu Ungar
Stu Ungar

Alternatively, he'd just place the cash on a table and wait for an adversary to approach him. Many, and not least Stu Ungar, one of the most famous, if rather tragic, players, were interested. In two consecutive games, Archie beat Stu.

Heads-up Razz was the first, costing Stu $500,000, and then he won a 7-Card Stud match, claiming an extra $700,000. Karas played and won against many of the best players of the time, including Chip Reese, Puggy Pearson, and Johnny Moss, but his downfall started when he turned away from professional games and began playing dice and baccarat in the world of chaos. Why take the risk of more quirky games? Well who better to clarify this than the guy himself.

“You’ve got to understand something. Money means nothing to me. I don’t value it. I’ve had all the material things I could ever want. Everything. The things I want, money can’t buy: health, freedom, love, happiness. I don’t care about money, so I have no fear. I don’t care if I lose it.”

At some point he won all of Binion's $5,000 denomination chips at one point, leaving the casino short of its greatest chips at the time.  

Within three weeks, he managed to lose his $40 million, moving quickly from one of the most prosperous gamblers to one of the most painfully unfortunate. Truly, Archie is one of the most successful gamblers to have lost everything.

Charles Barkley

Charles Barkley
Charles Barkley
  • Total amount gambled: $30 million
  • Incurred losses: $30 million
  • Does he owe anything today? No
  • Game: Baccarat, Roulette, Dice, Blackjack

The ace of the Phoenix Suns has had a handful of unfortunate gambling addiction brushes, and that is no secret. Charles Barkley's gross gambling loss was $30 million, which was his entire fortune. But, Barkley, who has always been transparent about his addiction, was never a source of remorse for his gambling proclivities.

He argued that he would have lost millions of dollars during his time as an active gambler playing at 30 different casinos. His perspective on the subject is fascinating to see. Barkley has become more positive about his habits, acknowledging the good and the poor, while some have vituperated and tried suing casinos:  

“I went to Vegas a bunch of times and won a million dollars. Probably 10 times. But I’ve also went to Vegas and lost a million probably three times as much.”

If Barkley is one of the gamblers who's lost everything, he sure doesn't look like it. He was never concerned about becoming addicted, even though he had burned through much of his fortune. He agreed that his most significant mistake was going to Las Vegas and hoping to win one million on each trip. Instead, however, he ended up losing a great deal.

Over time, Barkley built a philosophy in which he took of loss in phase and felt secure in a session of losses of up to $200,000. I love action, I love justice," he explained, but added that everything he concluded was important to do in moderation."

Charles Barkley is a fascinating man. He's probably one of the most successful gamblers, and he's lost everything, or most of it. Yet it kept him calm about it.

Michael Vick

Michael Vick
Michael Vick
  • Total amount gambled: $20 million
  • Incurred losses: $20 million
  • Does he owe anything today? No
  • Game: Running an illegal betting ring

The history of Michael Vick is mixed, but mostly of his own making. Vick is certainly one of the gamblers who lost everything but not just in the financial sense of the term. The former National Football League (NFL) player, and one of the best quarterbacks ever recruited by the Philadelphia Eagles, had a gambling addiction.

Vick was operating an illegal interstate dog fighting ring, known as the Bad Newz Kennels, and for the gambling side of the business, he himself supplied much of the income. He was promptly suspended by NFL Commissioner Roger Goodell, who claimed that Vick's actions not only violated the league's professional rules, but was also particularly unethical because of the nature of the operation. The Atlanta Falcons, the team for which Vick was playing at the time, also didn't sit idly by.

They gave Vick a letter that he now had to pay them $20 million out of the $37 million he got as a bonus. The court sided with the Falcons, ruling that the bonus money to fuel the gambling ring had been used by Vick.

He was sentenced to 23 months after a lengthy and sinuous proceeding. A failed drug test and a failed polygraph were cited in the sentence against him which, in the jury's view, indicated that Vick had not taken full responsibility for his acts.

Michael has paid for his crimes in spite of his previous failures and he is back in the public eye. As an NFL studio analyst, he joined FOX, a role which he deserves.

Frank Saracakis

  • Total amount gambled: $13 million
  • Incurred losses: $13 million
  • Does he owe anything today? No
  • Game: Roulette

Frank Saracakis was the heir to the Greek Car Business who in 1995, made a trip to London and chose to indulge in his gambling pastime. Tempted by the glitz of the melting pot, he instantly purchased $13 million worth of chips at Crockford's Casino in London.

His game of choice was roulette, which he spent several hours playing until every single chip he had in his possession was lost. Saracakis is definitely not one of the gamblers who lost it all but he certainly suffered one of the greatest losses and is a worthy addition to our list.

Gambling can be a thrilling experience, but it can also be incredibly dangerous. These stories of the biggest gambling losses in history serve as a cautionary tale to those who would risk everything for a chance at big winnings. Remember to always gamble responsibly and to never bet more than you can afford to lose.

See more: Guinness World Records for gambling, The world's wealthiest gamblers, Top 5 biggest ever poker pots, The top 10 biggest online casino jackpots of all time


Q: Who is the biggest gambler in history?

A: While there is no definitive answer, some of the biggest gamblers in history include Harry Kakavas, Terrance Watanabe, and Akio Kashiwagi.

Q: How much did Charles Barkley lose gambling?

A: Barkley has admitted to losing over $30 million throughout his life.

Q: What game did Harry Findlay primarily gamble on?

A: Harry Findlay primarily gambled on horse racing.

Q: What is the book title about Archie Karas's story?

A: The book title about Archie Karas's story is "The Biggest Game in Town."

Q: Is it possible to win big in gambling?

A: Yes, it is possible to win big in gambling, but it is important to remember that there is always a risk of losing as well. It is crucial to gamble responsibly and never bet more than you can afford to lose.

Overall, these stories of the biggest gambling losses in history illustrate the dangers of excessive gambling. While the thrill of winning big can be enticing, it is important to remember that there is always a risk of losing as well. As such, it is crucial to gamble responsibly and never bet more than you can afford to lose.

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