10 Crazy Gambling Wins and the Stories Behind Them

10 Crazy Gambling Wins and the Stories Behind Them


In 2016, $80 billion was spent on lottery
tickets in the United States alone. For comparison, that same year the US spent
roughly $30 billion on video games. It’s very revealing how much people hold
on to that dream even though their odds of winning big from a video game and a lottery
ticket aren’t that far apart. So what are some of the biggest stories of
gambles paying off? What’s the largest amount of money horses
have ever made a member of the audience without even slightly understanding why they were
running in a circle? How does that compare to the most a single
roll of the dice won someone? And more important, how did that win change
the life of the gambler? As you’ll soon see, the results of those
dramatic gambles are often as surprising as the wins themselves. 10. Largest Lottery Win At first it was believed that the largest
lottery prize ever would go to Marv and Mae Acosta of Chino Hills, California after they
won a staggering $1.58 billion on May 7, 2016. Then it was discovered that the Acostas would
actually need to split the prize three ways, leaving them with “only” $528 million. Admirably, the Acostas devoted a large portion
of their winnings to charity. Unfortunately they still had the misfortune
of their names being used as the objects of an email scam that promised to deliver millions
of dollars of their lottery winnings to any email recipient who provided their personal
information to the scammers. The other winners, the Robinsons of Munford,
Tennessee and a couple in Florida, didn’t suffer any such indignities, and aside from
one person in the Florida couple retiring, they didn’t plan any particularly large
life changes after winning. The largest win where one person kept it all
was an anonymous person who wished to be identified only as the “South Carolinian.” That person won $1.56 billion. All that is known of them is that when they
went to buy a lottery ticket, they let another person go ahead of them in line and buy their
ticket first. Rarely has such a small bit of politeness
paid off so well. 9. Largest Single Dice Roll Win The largest amount ever won with a single
roll of the dice was by William Lee Bergstrom in 1980. The circumstances around this win are as unethical
as they are glamorous: the Austin, Texas landlord had taken out a $777,000 loan on the understanding
that he would invest in gold, which had been a losing strategy for him as he’d already
lost a large amount in that market. Instead he bet the amount on a single dice
roll, won big, and paid the bank back. However, in 1985, he was hurting from a breakup
from his lover John. At the Horseshoe Casino he bet one million
dollars that a dice thrower would lose a throw to take his mind off it, which completely
backfired when the player won that throw. By the next morning he had killed himself. Gambling was so significant in his life that
he left instructions that the urn with his ashes describe him as a man who bet one million
dollars at the Horseshoe. 8. The Longest Winning Streak Speaking of people winning at dice for the
short term, there’s the story of Archie Karas, a Greek immigrant and waiter with $50
in his pocket and $10,000 in debt in December 1992. Between then and May 1995, Karas only lost
one game of the hundreds he took part in. The streak became known as “The Run” and
it made him a profit of roughly $46 million. The games that he played to amass his fortune
included poker, pool, and blackjack. Still, when fate turned on him, it turned
hard. Within two years he lost every penny. Not that it should have been surprising, considering
he’d already won and lost a $2 million fortune before The Run began. In 2013, the rights to the story of his spectacular
rise and fall were optioned for a movie by the production company First Born Films, but
to date no film has been produced. Adding to his grief is that it came out that
he’d been charged with crimes including burglary and cheating at blackjack, something
he’d been caught doing at least four times since 1988. As of 2015, Archie Karas became the 33rd person
added to a very exclusive group called the List of Excluded Persons, meaning that he
would face criminal charges if he so much as entered a Las Vegas casino. 7. Largest Horse Race Prize Let’s change the tone of the entries from
crime and suicide to a wholesome story, at least by gambling standards. Conor Murphy was a 29-year-old stable hand
in Ireland when, in 2012, he placed an online bet for 50 pounds (about $75) known as an
accumulator. Essentially it meant he bet on five races
at once and could win an especially large prize if he won all five of them. Murphy admitted that he did no research, and
had no insider information. He just picked five horses more or less at
random three months out. He ended up winning $1.5 million for his guesses. Murphy’s reaction to his sudden wealth was
to move to America and learn to train racing horses. By 2014, he had a stable in Goshen, Kentucky
with champion horses, including one for which he had paid a six figure amount. Murphy’s horses have had a mixed run but
some years have been very good indeed. 2018 in particular saw his horses come in
first place three times. It’s always good to have a plan for after
you win millions of dollars, unlikely as that is. 6. Largest Super Bowl Bet In May 2018 the US Supreme Court ruled PAPSA
laws that limited sports betting would be struck down, meaning that the estimated $145.5
billion in what was previously illegal sports betting could be conducted above board. One of the main beneficiaries of this ruling
is people who make Super Bowl bets. Those are pervasive enough that the 2019 Super
Bowl had an estimated $6 billion placed on it. The person who won the largest recorded amount
is known only as “Bettor X.” For the 2018 Super Bowl, USA Today reported
that he bet in favor of the Philadelphia Eagles against the New England Patriots and won $10
million total from multiple casinos. A year later, Bettor X bet a total of $3.8
million at the MGM Grand, William Hill, and South Point casinos, this time in favor of
the Rams against the Patriots again and lost it all. There very well might be an Archie Karas-type
future waiting for Bettor X. 5. Largest Roulette Win Generally believed to have been invented by
Blaise Pascal around 1655, roulette is a mainstay of casino gambling and possesses some veneer
of respectability. On the other hand, a particularly addictive
form of electronic roulette was banned in the UK on Halloween in 2017. Such was the general situation on January
5, 2017 when Pedro Grendene Bartelle won the largest roulette prize from a single spin
in Punta del Este, Uruguay. Bartelle bet the equivalent of $35,000 on
Red 32 and won the equivalent of $3,500,000, the outsized payout being because he hedged
his bets a bit by putting chips on other places on the roulette board. Bartelle did not come from humble beginnings:
His uncle was the billionaire sandal company founder Alexandre Bartelle. Pedro Bartelle was himself the president of
the third largest sandal company in Latin America, Vulcabras-Azaleia. The point of this story is that sometimes
people with the best luck are those who don’t need it at all. 4. Largest Coin Flip Win You’d think that when it comes to a story
of winning a fortune on a coin flip, the winner would be the well-known name in the story,
not the loser. But then, Dan Bilzerian has long been the
sort of larger-than-life figure who could upstage someone who won a gigantic, easy bet
from him. A highly successful Instagram personality
and gambler, he has amassed a personal fortune of over $150 million and appeared in such
films as Lone Survivor and War Dogs. One day at the poker table he agreed to a
$6 million bet from the flip of a quarter, and had to hand over his chips. Surprisingly Bilzerian said that losing the
$6 million from a coin flip was easier than most gambling losses, even though the most
he claimed to have lost from a game of cards was around $3.4 million. After all, it was an extremely quick process,
so it didn’t have that drawn out feeling of suspense that many high stakes poker games
provide. That feels like it makes sense. But we’ll also note that Bilzerian didn’t
become a professional coin flipper to cut down on his stress. 3. Largest Online Win It’s extremely tempting to try winning a
fortune through online gambling. Who wants the trouble of traveling to a casino
and the racket of all the machines when you arrive? To be frank, who wants other people around
to look at you as you slink away after losing an arm and a leg? To date no one has received quite as much
money from this sensible approach to gambling as someone known only as “Christina.” In May 2018, the cleaner living in Berlin
was entering her numbers for the Lottoland, her second time ever playing it. She decided to let her mother pick the numbers,
which is probably the single most convincing piece of evidence in favor of the idea that
we should listen to our mothers. For Christina during the following Friday
drawing it meant a payout of £79 million. Christina’s said that her relatively modest
plans for her payout were to take care of her mother and to drive across America coast-to-coast
in a camper. Goodness knows there are much less sensible
ways to spend lottery winnings. 2. Largest Baccarat Win This card game has a surprisingly controversial
history even as far as the casinos are concerned, since it can lead to nearly as much risk for
the House as the player. In 1990, for example, Donald Trump lost six
million to Japanese billionaire Akio Kashiwagi. He had to resort to public feuding to get
the Kashiwagi back to his casino, where he lost all his winnings and then some. Archie Karas, who you’ll remember from earlier
on our list, lost $17 million through baccarat. Such was the fraught history of the game when
Lin Haisan sat down for a baccarat tournament at the Sheraton Macao Hotel on March 13, 2015. He ended up winning HKD100 million, then the
equivalent of $12.89 million, officially acknowledged by the Guinness World Records as the largest
amount anyone won at the game. Haisan subsequently dropped out of the spotlight,
but we’d like to say again that luck with baccarat is fickle, so he could have gotten
himself in quite a lot of trouble if he stuck with the game. 1. Largest Slot Machine Win In November 2016 Katrina Bookman was playing
a slot machine at the Resorts World Casino in Queens, New York. Her screen flashed nearly $43 million dollars
in winnings. She took a selfie to commemorate that she
had set a world record. Or so she thought. It turned out that the casino dismissed the
massive payout as some sort of machine error and took the machine out of commission. As consolation she was offered $2.25 and a
steak dinner. Instead, in June 2017 she served them a court
summons. Knowing that the $43 million the machine had
said was out of the question, her case was that she was owed the maximum payout of $6,500. As of 2018, the case was still pending. As far as the largest win where the person
actually received the winnings, that was a 25-year-old software engineer at the Excalibur
casino in Las Vegas in 2003. He walked away with $38.7 million. Since the casino reported that it would take
25 years to provide him the prize in annual payments, he and Bookman are also similar
in the sense that he hasn’t received everything that he’s owed either.

46 thoughts on “10 Crazy Gambling Wins and the Stories Behind Them”

  1. Very interesting! I would have included the likes of Barney Curley & JP McManus they have pulled off some huge horse racing gambles!

  2. How about the poor guy who won the NY Sate lottery but never got the money? he played the same numbera everyday, but they posted the wrong winning numbers on the App. thinking he lost, he threw away the ticket. the store that sold the ticket even had the security footage of him buying the winning numbers at the time/place the computer said they were sold : (

  3. Anytime a slot machine tells you you won $42 million dollars, you aren’t gonna get it since it’s a software malfunction always.

  4. How could you forget Fred Smith from FedEx ? He took 50K and bet red and won. He was able to make payroll and the rest is history.

  5. My step-grandma won $20,000 from a deal where they brought the losers of lottery tickets on t.v. and let them gamble again for free! She said she still lost money on the lottery despite the $20,000 win.

  6. The "best" casino game to play is craps. I have never had a net loss playing but I also always quit when I'm up. How much I'm up depends on how I'm feeling about the table. Usually it's just $300. Most people might say, "$300?! Wimp!" But I say, "That paid for my flight, now I can go eat 99 cent shrimp cocktails and hang out by the pool checking out the MILFs."
    Here's how you do it:
    Bet the pass. When the point is made you back it up with double odds. Some casinos have 10x odds, DON'T DO IT! Now you bet a come. If the game is still in play you bet double odds on your come. Now here's the gambler part, if you want to go crazy you bet another come and cover the odds double. Never, ever bet the field, the doubles or 7/craps in the middle, or the 6/8 on the edges; those are sucker bets for drunk people. Also betting Don't Pass is bad Karma; you'll die of cancer.
    My gambler superstitions that I know are completely irrational and not based in reality: I never, ever throw the dice myself. If a friend walks up behind me and asks, "How's it going?" I immediatly leave the table after the play then yell at my "friend" explaining you never ask a gamble, "How's it going?"

  7. In the 60's my Uncle Joe was playing "The Numbers" in New Jersey (where else) Think Lotto but by the Mafia. They paid with no drama what so ever.

  8. I confess I love bingo game! And of course to win is the best part. Thanks again, Simon for you share your amazing videos!

  9. I betting that the real Simon is still being held hostage and continues to be represented by an army of clones so he can appear on 20+ youtube channels

  10. The guy that won $1.5 million by randomly picking 5 horse names sounds like me when I bet for football.
    I know nothing about football. So I always go with the best looking uniforms. Or the best looking QB.

  11. It's like DeNiro said in the movie "Casino" about those massive slot machine wins – the odds are in the billions, meaning it can't happen. If it ever does, the casino begins an investigation and puts their spin doctors on it to figure out what excuse to give when they don't write the check.

  12. So a machine can show a huge payout & a casino can legally claim it was a glitch in the machine? How is that possible? I get they didn't want to pay such a massive sum, glitch or not. The amount that was offered instead was an insult.

  13. Casinos make billions of dollars so if their machines have an error and say you won then they should pay out that is the risk they take in the business they are in. how do we know when we loose a error hasn't occured and we actually won? We have no way of knowing, if we take that risk so should they.

  14. I don't get it – I mean my dad would very occasionally have a flutter on the horses; and slightly less often, he might actually win something! But, it never appealed to me. Of course, I was expected to chuck a pound in at the office on Derby day, – but that's it! (I think I got a second place one year :0) I just don't see the attraction.

  15. I think the biggest win for a coin flip would have been between the Milwaukee Bucks and the Phoenix Suns for the rights to Lew Alcindor (Kareem Abdul Jabber). Worth more than 6 million to the Bucks.

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