Crazy Gambling Wins (and the Stories Behind Them)

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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. 

Take a gamble and win a great red by checking out Dustin Koski’s dark fantasy novel Not Meant to Know!


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