AA hot roll at the craps table that paid for an entire Las Vegas vacation.  Aces cracked by Deuces on the cash bubble at the World Series of Poker. A magical football season where every bet was the right one…

Crazy gambling stories, plenty of people have them and they are always fun to hear.  Like a right of passage, gamblers live to compare their tales of triumph and woe. With the news of Floyd Mayweather’s huge sports betting victory in Game 7 of the NBA Eastern Finals, ADANAI thought it would be fun to hunt down a few other outrageous gambling situations.  Here are 10 crazy gambling stories that give heightened meaning to the expression “put your money where your mouth is”:

1. Floyd Mayweather Trusts LeBron

Why not start off with the “Money” Man himself, Floyd Mayweather? Mayweather’s eagerness to bet big on sports has been well documented, especially by the HBO series “24/7.” (Click here for video of Mayweather picking up his winnings at the casino on an average gambling night). Last week Mayweather topped himself when he bet $5.9 million on the Heat in Game 7 of the NBA Eastern Finals.  He won, however, it is important to put the numbers in perspective. Celebrity Networth estimates his at $140 million, which means he bet 4.2% of his net worth on a single game.  Doesn’t sound like a lot? Take a look at your savings account; now, divide that hard-earned nest egg by 25 and think about risking that amount on something as unpredictable as a basketball game.  Not a great idea, even with LeBron on the court.

While it is always hard to qualify someone as a good sports bettor – this particular gamble actually stood a strong shot of holding up.  As of June 19, the Heat had not lost back-to-back games since January 10.  The Pacers had just beaten the Heat in Game 6 and Game 7 was in Miami.  The spread against the Pacers was -7 but Floyd clearly had a hunch and it paid off (to say the least) – he cleared a cool $5 million from the wager.

2. Winning the Jackpot Isn’t Always a Good Thing

Stories about lottery winners suffering serious despair after cashing in abound.  It is no shocker that drugs, hangers on and poor money management can lead to some pretty deleterious outcomes. In this case, an Arizona woman won a $1,200 Jackpot drawing at a casino. When asked to show up at the casino with her passport to collect her winnings, she was deported to Mexico.  How does that line go?  It’s better to have loved and lost than never to have loved at all? Mirna Valenzuela probably disagrees.

3. So You Thought Poker Cheats Were a Thing of the Past?

In the old Texas roadhouse days, grifting was pretty basic.  Card mechanics used slight of hand to deal from the bottom of the deck.  Players came up with contraptions to hide an extra Ace up their sleeve.  Today, along with everything else, technology has turned card swindling into an elaborate “Ocean’s Eleven” art form.

An Australian man made $32 million in just eight hands of high stakes poker.   Phil Ivey or Tom Dwan may be used to that kind of run, but this guy was no poker pro.

He sat down to a high stakes game at the Crown casino in Melbourne, Australia with a significant leg up on his competition. Aided by an accomplice, he hacked into the casino’s security cameras, which record every hand played by each player.  His partner communicated the player’s hole cards to him in real time from a remote location via an earpiece. The amazing thing is that after authorities found him out, the man was allowed to leave the casino (and the country) with the money. Now that’s a bad beat.

4. You Know You Have a Gambling Problem When…

…a casino sends a Rolls Royce to your house as a token of their appreciation.  No, not to cart you in style to the casino for the night; but for keepsies!  Chinese-Mexican businessman Zhenil Ye Gon lost a reported $120 million over the years gambling at the Venetian in Las Vegas.  He often played $150,000 per hand in Baccarat.  While his net worth is unknown, the Federales found $205 million in cash stashed in his Mexico City mansion.  Evidently he sold a crap load of chemicals–used to make meth–on the black market.  Walt White would be proud.

5. 290,000 People Should Be Thankful for FedEx Founder Fred Smith’s Blackjack Skills

Transportation giant FedEx employs 290,000 people around the globe.  The company has a market capitalization of $32 billion.  According to Forbes, Founder and CEO Fred Smith has a net worth of $2.1 billion. If not for a good run at the Blackjack table, all of this might never have been.  In 1973, the early days of FedEx, the company faced a $24,000 fuel bill with only $5,000 in the bank. It was looking like they might need to liquidate, pay their employees and move on with life.  Fred Smith, in a desperate attempt to save his sinking ship, went to Las Vegas with the $5,000 and turned it into $27,000 at the Blackjack table.  The rest is history.  That one night of “hit me” made Fred Smith one of the wealthiest men in the world.

6. Talk About Going All-In

Floyd Mayweather betting 4.2% of his net worth on one basketball game?  Aggressive. Well, how about betting 100% of your net worth on a roulette spin? Englishman Ashley Revell did just that.  He emptied his savings account, sold every single earthly possession other than the clothes on his back, went to Las Vegas and bet it all on red.  He turned $136,000 into $272,000 in the span of 20 seconds.

Amazing – and a damn good thing he didn’t listen to Wesley Snipes in “Passenger 57” who famously said, “Always bet on black.”

7. What Is a Gambling Story List Without Phil Ivey?

The gambling prowess of poker phenom Phil Ivey is fairly well known.  ESPN even did a story on it.  He plays poker at the highest stakes but also throws around big bucks when the house has an edge.  While craps is usually his non-poker game of choice, he is just as comfortable at the Baccarat table.

During August 2012, Ivey and a companion settled in for a high stakes Baccarat session at Crockford’s casino in London.  Ivey walked away with a cool $11.9 million.  As if the large win isn’t enough of a story, the casino is contending that Ivey and his companion cheated.

Crockford’s claims they were able to find a faulty shoe (the mechanism that holds the multiple decks of cards).  If the cards were dispensed a certain way from this particular shoe, Ivey would, according to Crockford’s, be able to narrow in on what the card was and adjust his bets accordingly.  Perhaps important to note, Ivey’s companion spoke Cantonese and asked for a Cantonese dealer.  Many times in Asian casinos, superstitious Baccarat players ask the dealer to deal the cards in the manner Ivey and his companion requested.  This exchange happened in Cantonese so the other English-speaking employees had no knowledge of the request.  The fight is ongoing, as Ivey has countersued the casino for not paying out his winnings.

Maybe there is more to it but if the casino puts out equipment that is faulty and loses because of that equipment, it must stomach the consequences.

8. More Baccarat Buffoonery…

Perhaps the World Baccarat Association (if it actually exits) needs to hold a summit to re-evaluate the implementation of the game because this seems to be where casinos are making their big errors.  In another crazy gambling story involving Baccarat, a group of 14 players at the Golden Nugget in Atlantic City took down $1.5 million in a night due to faulty cards and faulty dealers.

The casino was using what they thought were pre-shuffled cards.  The players noticed the cards were not pre-shuffled and kept coming out in the same pattern.  Surprise, surprise – if one knows what cards are coming, it is pretty easy to make money.  The dealers remained unaware as the players upped their bets from $100 per hand to $5,000 per hand and kept raking in the dough.

The casino is suing the card manufacturer and the players to get its money back.  Seriously? Again, the casino made the mistake and needs to pay for it.  If someone is playing Blackjack and splits Tens against the dealer showing a Ten (a horrific, money losing play), the casino isn’t obligated to stop them and they sure as hell aren’t giving the money back.

9. Nice to See Hard Work Getting Paid Off (find pic of Beaux-Arts)

In 1873, engineer Joseph Jagger thought he could use his engineering know-how and mathematical aptitude to beat the Monte Carlo Beaux-Arts casino in Roulette.  He knew that all man made inventions were imperfect.  Figuring that too applied to Roulette wheels, he set out to find a wheel that had a bias.  If the ball landed in one area of the wheel more often than it should, from a probability perspective he could gain a huge edge on the house.

He hired six helpers to meticulously record every outcome at each Roulette table and discovered that one of them had a bias.  He descended on the Beaux-Arts with cash in hand and took the casino for over $300,000 in three days.  That may not sound like a large haul but in 2013 dollars that is over $5 million.  He never gambled another dollar and went on to be a real estate mogul.

10. That Free Alcohol in the Casino Can Be Costly

Who doesn’t like a free drink while standing around the craps table? Sucking down free brews while tossing dice or playing cards adds to the gambling ritual.  Many think casinos offer it to enable drunken players to make bad decisions.  That actually is not the case.  The casinos are trying to attract bodies to the casino and keep them there.  Free booze can make a Saturday night a lot of fun.  Remember, the casino does not need bad decisions to make money – the casino always has an edge.  Sometimes the fun goes too far. For Terrence Watanabe, alcohol and drugs cost he and his family a fortune.

Watanabe, a Nebraska businessman, lost over $127 million at Caesars Palace and the Rio in 2007.  He claims Caesars plied him with vodka and painkillers to keep him from realizing how much he was gambling and losing.  Watanabe was the ultimate casino whale.  He would play three hands of Blackjack at the same time for $50,000 per hand.  It was normal for him to drop $5 million in a day.  He had a $17 million credit limit with Caesars, which meant he had unlimited access to $17 million in cash at any given time.  If he hit his limit he had to wire them money, but otherwise he could just walk into the casino and go for broke…another expression that deserves new perspective.

He had three people attending to him at all times, bringing him special Russian vodka they imported just for him, painkillers or whatever else he wanted.  Interestingly, Steve Wynn banned him from the Wynn in 2006 because he was too intoxicated.

Towards the end of his bad run, he wasn’t able to pay off his credit line and Caesars prosecuted.  Watanabe countersued, claiming the constant flow of booze and pills caused him to keep gambling.  In the end, the case was dropped and Watanabe never went to prison.  While he avoided serving hard time (he was looking at 28 years in jail), he lost his family’s entire net worth.  Maybe he should have ordered a Diet Coke?

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