Hey, Millionaire! Gambling is great fun... when you're winning. If you look like you're on a
losing streak, it's always a good idea to stop. But not everyone is clever enough to do that.
Some people see that as a perfect opportunity to keep going. And that's why we have this list.
These are the dumbest gambling losses in history. You'll never believe how much money the person at
number 1 threw away. Also, keep a lookout for a few celebrity appearances! Let's get to it.
13. Charlie Sheen - $2.5 million Our first of the dumbest gamblers is the former
Two and a Half Men star, Charlie Sheen. Charlie, who we all know for his excessive lifestyle,
admitted to gambling on sports betting at several US Sportsbooks back in 2006.
It was stated in divorce documents that Charlie spent three months betting $200 000 a week.
Charlie Sheen managed to gamble away $2 million during those three months of madness.
Some people just have too much money.
12. Gladys Knight - $6 million The iconic Soul singer Gladys Knight carved her
incredible career with hits that included "When A Child is Born" and "Licence to Kill." However,
this empress of Soul had a blackjack addiction. She shared her experiences with gambling,
saying that she would spend $40 000 each night at the blackjack and baccarat tables in the casinos.
The six-time Grammy award winner lost over $6 million over the years.
11. Phil Ivey - $9.6 million The legendary Poker professional
Phil Ivey found himself involved in one of the highest-profile legal cases related to gambling
ever. The legal dispute was with the Borgata Hotel Casino and Spa in Atlantic City. The
World Series of Poker bracelet winner was accused of cheating on the baccarat tables in the casino.
Even though the judge ruled that Ivey had not cheated and that no act of fraud had taken place,
he was still required to return the$ 9.6 million winnings to the Borgata.
This left the poker player millions of dollars out of pocket.
10. Frank Saracakis - $13 million While on a trip to London in 1995, the heir of
the Greek Automobile Company, Frank Saracakis, decided to indulge in his favorite pastime of
gambling. He gave into temptation and bought chips worth $13 million at London's Crockfords Casino.
Frank's game of choice was roulette, which he spent several hours playing. He may not have
been one of those gamblers who lost it all, but he did lose every single chip in his possession.
We still think he's a worthy addition to the list with his $13 million loss within a few hours.
Sounds like a lot of money, right? We're just getting started. Keep
watching for the really big losses. 9. Maureen O'Connor - $13 million
Someone who has done quite well with risk management is Maureen O'Connor.
She was serving as the mayor of San Diego when her gambling habits quickly spiraled out of control.
Maybe her political hardwiring came in handy when she gambled over $1 billion.
Still, her losses only ran to $13 million. O'Connor borrowed $2 million from her husband's
charitable foundation and spent it all on video poker. While her gambling addiction is definitely
not something to be admired, her political and professional career was based on merit. Everything
she achieved came from hard work. And she has actually managed to pay her debt in full!
8. Kerry Packer - $13.6 million Australian billionaire Kerry Packer was
one of the biggest Whale gamblers in Las Vegas. The famous gambler and hero of the working class
was well known for his generosity. There are plenty of stories from casino staff of him tipping
enough money to pay off debts and mortgages. He was a popular figure in the casinos because he'd
put arrogant big spenders in their place when they got disrespectful. Packer's weakness was
his baccarat habit. It caught up with him in 2000 when he lost $13.6 million in three days.
This may only have been a drop in the ocean for the billionaire, but it sure warrants a mention
because the huge sum of money was lost at the tables in only 72 hours.
7. Michael Vick - $20 million Michael Vick is a gambler who really
lost it all - and not just financially. The former NFL player had a gambling issue that had
him suspended for a highly illegal and unethical interstate dogfighting ring. This ring was known
as The Bad Newz Kennels and was funded by Vick. He had to reimburse $20 million of the $37 million
he had received as a bonus because the money had been used to fuel the unethical gambling ring.
Vick was also sentenced to 23 months for failing a drug and polygraph test
which led to the jury's opinion that he did not accept responsibility for his actions.
So even though Vick has paid for his sins and is back in the public eye, he definitely
falls into the category of gamblers who lost everything with a total loss of $20 million.
6.Harry Kakavas - $20.5 million Australian real estate salesman Harry
Kakavas made his money selling houses on the Australian Gold Coast. Over 16 months,
Kakavas played baccarat at the Melbourne Crown Casino, spending $1.43 billion!
During this time, he incurred net losses worth an incredible $20.5 million. At the peak of his
gambling, he lost $164 million in just 5 hours and was witnessed placing bets worth $300 000
per hand. On a different occasion, during a trip to Macau, he gambled away another $4 million in a
single day. Even though he had no trouble spending those sixteen months gambling, he definitely
objected to the casino keeping the $20.5 million he lost. Kakavas tried to claim his losses back
from The Melbourne Crown casino in a lawsuit. He said they were aware of his gambling problem
and still took advantage of him. Obviously, he lost the case and the subsequent appeal.
5. Charles Barkley - $30 million It is no secret that the Phoenix Suns ace has
had a series of unfortunate brushes with gambling addiction. Barkley has no regrets and has always
been open about his addiction. His games of choice were baccarat, dice, roulette, and blackjack,
and he won at all of them a few times. But he also lost an estimated $30 million playing at
different Las Vegas casinos. Reflecting on this, Barkley feels that you have to accept the good
with the bad. Even though he has burned through most of his fortune, he does not owe any money and
still loves the action and justice of the games. But I'm not so sure the loss was worth it.
4. Singaporean businessman - $37 million Not much is known about this businessman except
for his major losses at the Marina Bay Sands and Resorts Worlds Sentosa. Apparently, he lost up
to $37 million playing at these casinos! What's the biggest loss you ever made at a
casino? Let us know in the comments! 3. Archie Karas - $40 million
Known for his appetite to play big, Archie Karas is one of the most iconic gamblers who
lost it all. He arrived in Las Vegas in 1992 with $50 and later secured a $10 000 loan when
he spotted a familiar face at the Mirage. This set the wheels in motion. He quickly
turned the money into $30 000 playing with a $200 or $400 limit Razz. He then paid back $20
000 to his beneficiary. Over the next 2 years, he played poker intensely. Archie gradually grew his
bankroll and went from looking for opponents to laying out his money and waiting. During
this time, he played and won against many of the best players out there. He managed to collect an
impressive $40 million in total. Archie's downfall began when he turned away from skill-based games
and switched to dice and baccarat. It was a huge mistake. He managed to lose his $40
million in just 3 weeks. He said that money meant nothing to him and that all he wanted was health,
freedom, love, and happiness. Good for him, but I'll bet $40 million wouldn't have hurt.
2. Singaporean Tycoon - $75 million Seems like the Singaporean gamblers like to
play at the Marina Bay Sands and Resorts World Sentosa. And don't forget - it's one of the
richest places on earth. One anonymous businessman based in Singapore, who reportedly appeared in a
recent Forbes list of Singapore's top 40 richest people, lost $75 million during play. Oops.
And finally, the award for biggest loser goes to...
1. Terrance Watanabe - $127 million Terrance Watanabe is a gambler who definitely
falls into the category of a gambler who lost a very substantial amount of their fortune.
Watanabe inherited Oriental Trading Company in 1977, which he then sold in 2000. His gambling
habits pushed him into extreme scenarios year after year. This losing streak is believed to
be the biggest Las Vegas has ever seen. He tried suing the casino, saying that he was
plied with vodka and highly addictive pills, and they allowed him to continue gambling when he was
clearly intoxicated. He was ultimately ordered to pay his debt. On baccarat and blackjack,
he racked up $127 million in losses at Caesars Palace and the Rio after gambling over $825
million. Today, Watanabe has paid most of his debt, but he has been charged with four felony
counts for refusing to pay the last $14 million. He faces 28 years in prison if convicted.