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Casino heists are the plots of many Hollywood movies, usually formed by some “what if” scenarios conjured up by either the protagonist or antagonist in hopes to get rich. For most, our logical side prevails, ruling against all the potential risks no matter the reward. Then again, most of us aren’t movie stars so we don’t have the luxury to play out our deepest fantasies. For actors, though, they get to live out their wildest dreams – taking the casino to the cleaners! (or at least try to…).

Some have succeeded while others have suffered a less glorious fate. Today, we talk about some of the most memorable casino heists of the ages.

1. Bill Brennan’s Mysterious Vanishing

Ocean’s Eleven is a fascinating take on how a good casino heist should happen, but a real magician never reveals his secrets. This is what Bill Brennan did in September 1992 when he varnished with more than $500,000 worth of cash and chips.

Brennan is a bit of a miracle worker with his disappearance raising quite a few questions. For starters, nobody has heard or seen Brennan since the day he walked out the door of the Stardust Hotel and Casino with a pile of cash.

Bill Brennan Disappeared with Half a Million Dollars
Disappearing with half a million dollars, Brennan’s whereabouts is still unknown.

Why is Brennan so important you might ask? It’s easy enough: his disappearance has been complete and sudden. Brennan had dropped off the face of the world. Nobody could really pinpoint the location of the runaway, not the FBI, not any of the investigators working the case over two decades ago.

Is it possible for Brennan to have left the country? Quite possibly so, but there would be no proof to that either. So far as well executed casino heists go, this one is really top of the list.

2. Heather Tallchief Steals Disappears with a Van Full of Cash

Heather Tallchief had the right mind when she pondered the question whether to commit a casino heist. Then realization dawned on her, courtesy of Roberto Solis, a man of a criminal turn of mind, and her partner at the time. Solis suggested to Tallchief that instead of risking a casino heist, she could simply drive away with the money.

At the time, Tallchief worked for Loomis Armor Inc., a company tasked with transporting money between banks, casinos and other high-end properties. On October 1, 1993, one of the company’s vehicles pulled into the Circus Circus Hotel & Resort Casino’s parking transporting $3 million.

Tallchief’s colleagues hopped off to bring the money inside when she decided to just drive off. You might think that law enforcement did well to track her down, but Tallchief was gone for nearly 12 years when she walked into police station and turned herself in, tired of running and hiding.

Tallchief served a five-year sentence and settled one of the biggest casino (parking lot) mysteries to date. Meanwhile, Solis is still on the lam.

3. Tony Carleo Walks into the Bellagio Hotel and Casino

Tony Carleo definitely pulled off quite the number on the Bellagio Hotel and Casino. In December 2010, Carleo, the son of municipal judge George Asad, walked into the property wearing a bike helmet, approached a table and demanded that all the chips on it be put into a bag.

He managed to sprint away with nearly $1.5 million in chips with security unable to catch up to him. His motorbike had been stationed 200 meters outside the entrance and Carleo made good his escape. On the next day, he came back, but without wearing a helmet.

Bellagio Hotel and Casino Front View
Tony Carleo managed to get away with stealing $1.5 Million in Casino Chips in 2010. Photo: Telegraph

Approaching the same table he had robbed the day before, Carleo plonked down and took a seat to play… Craps! We know what you must be thinking: look at the cheek on that guy. You would’ve thought that Carleo was caught immediately, but the daredevil had a fine go at it with the crime unsolved for months after committing it.

Apparently though, Carleo was a far better heist man than he was a player, because he quickly started burning through his stacks of chips. This didn’t come with only downsides though, as the casino hooked him up with a $600-a-night suite and thus the “Biker Bandit”, as he was referred to by media, moved in to live in the very place he had robbed.

Carleo’s good fortune eventually came to an end when he was down to $25,000 cherry chips which were tracked by the casino. Now, a less adventurous criminal would have just destroyed the chips, but Carleo decided to go online and try to swap them for $5,000 ones. Well, police had caught up on his advertisement and managed to bring him in the end.

4. Rolando Amis and the Inside Job at Sobota Casino

For Rolando Amis, there were a few technical challenges he couldn’t solve. After spending a part of his career putting up surveillance cameras in the Sobota Casino, Amis thought it was time to rededicate his efforts. He chose to make a quick buck by robbing the casino.

Sobaba Casino heist inside job
In 2007, Soboba Casino saw an ambitious heist by Rolando Amis. Photo: Soboba Casino

In 2007, using his knowledge and understanding of the layout of the casino, he decided that the quickest way to get what he needed was to stage a proper casino heist. Holding around 10 people at gun point, even though the gun was a fake one, Ramos managed to bag $1.5 million (Yes, baby!) and ran back for the exit where his partner, Eric Aguilera, also a former employee at the casino, was waiting.  

Police didn’t drag their feet on this one and they were soon catching up to the duo. Later in court, Ramos said that he had committed the robbery under the influence of alcohol.

Well, that didn’t stick.

5. The Hoppers, an Ocean Eleven-Like Affair

To say that the Stardust Casino in Las Vegas isn’t lucky would be an understatement. In 1991, preceding Bill Brennan’s famous “now you see me, now you don’t” act, the casino had another insider job. Meet Royal Hopper, the man who had decided to keep it strictly in the family and had his two sons help him stage two separate heists.

Stardust casino before implosion in 2007
Stardust Resort and Casino on the Las Vegas Strip before 2007. Photo: Wikipedia

The first time around, Hopper had one of his sons, Bobby Hopper, play act an armed robber and assail his father and another casino employee while they were transporting a bunch of cash. It all went butter smooth and Hopper Sr. ended up reporting the robbery himself so as to throw the police off.

Alas, the amount stolen was only $150,000 which didn’t quite cut it with the Hoppers. So, they thought that the three of them can use their father’s inside knowledge to hit a van transporting some more of the casino’s money. They staged it all on-the-go and in a rather hectic manner but managed to grab a few sacks containing over $1 million in hard currency.

Their joy was short-lived as police eventually caught up to them and crashed their party. Well, criminals have a funny way of getting caught. Senior was sentenced to 15 years in prison. Not cool.

6. The Eudaemons Storm the Casino World

This casino heist goes way back in time and it doesn’t involve the typical methods of coercion. Instead, what you get is a bunch of smart people planning the perfect crime, though money didn’t seem to be much of motivation here. And as it is with most smart people, it took them ages to agree on anything.

Instead, you had a bunch of smart university students who spent the better part of three years developing a model that could successfully predict the spinning of the roulette’s wheel. The group hit the casinos in 1978 when it won the eye-watering, ahem, $10,000 and all that it cost them was using a trigonometric function with just the four variables. A piece of cake, as it turns out.

Eudaemons successfully predict roulette outcome
“Eudaemons” successfully predicted the spin of the roulette wheel.

They had to deploy the tech on the casino floor and for the purposes of success, they created a computer that could be crammed into a shoe. Well, nearly. The actual set-up used the bodies of scientists as a frame to be latched on. It all promised to go swimmingly with the “Eudaemons” (that’s how the team called themselves) signaling which octant to bet on by using a device collecting data hooked to the big toe of each participant.

The team won $10,000 before one of the devices malfunctioned and burned the skin of one of the members. This inspired other similar endeavors such as the Ritz Casino in London where a laser was used to successfully predict the winning octants. However, the Eudaemons proved that roulette can be statistically predicted if there is enough data at hand.

7. How Bill Kaplan Beat the Casino through Card Counting

Bill Kaplan was on his way to Harvard when he decided to slow down a notch and play Blackjack for a while. Kaplan had discovered a way to track cards dealt in Blackjack and crunch the odds in order to give the bettors an edge. His exploits were legendary, and he amassed $350,000 out of an initial $1,000 investment.

Of course, Kaplan had to travel to make sure he didn’t get discovered by casinos. Amassing his fortune, he eventually went on to graduate from Harvard. It was at this point that he decided it was time to scale business.

Kaplan began tutoring MIT students and teaching them how to count cards. He wasn’t discriminatory about his knowledge and shared readily, investing $1 million in a company the sole purpose of which was to train individuals capable of counting cards.

Even though Kaplan got uncovered and he inspired “21” the movie that broke the knowledge that cards can be counted to the average person, his students are said to operate to this day. He himself has been banned from playing around the world.

8. James Manning, the Man Who Lifted $32 million in Australia

Meet James Manning, the man who stormed the Crown Casino in Melbourne, Australia. Well, stormed isn’t the correct term per se. Manning had a plan and a good one at that. He found accomplices to exploit flaws in the casino’s security system and make sure that he is walking away with $32 million under his belt.

Crown Casino James Manning Heist
The Crown Casino loses big with James Manning – walking away with $32 million. Photo: Crown Casino

The case was never actually proven, and Manning is still the main suspect, but for many people, he is as guilty as they come. What allegedly happened is that Manning had someone tap into the surveillance system of the casino while he was playing in a high-roller room.

Winning eight hands in a row, against all odds, rose suspicion, but the casino never formally went to court with their case, banning Manning from the property instead. So far as daring casino heists go, this one was one of the best.

9. Pointing Lasers in the Ritz Casino, London

It was 2014 when three people walked into the Ritz Casino in London bringing along lasers. It was a little more than cosplay though, as the trio were interested in successfully predicting the spinning of the roulette wheel and calculating the possible outcomes.

ritz casino london front view
The Ritz Casino saw in 2014 customer bring in lasers to predict roulette spins. Photo: Ritz Casino

Their plan worked, because they eventually ended up on top of £1.3 million, but by that time the Ritz had caught up. Of course, in such cases, casinos don’t have much to go on other than that something fishy was afoot.

The Ritz Casino couldn’t establish what was wrong and police was called to arrest the trio. A case was eventually held against them, but a judge decided that since there was no law that prohibited players from being imaginative in beating the house, they defendants walked away without a record to their name.

They were banned from casino properties in the capital, but that didn’t seem to have made much of an impression on them.

10. Wynn Resorts’ Macau’s $258m Heist

Casinos in Macau are used to having high-rollers trickle in. Some would ask for a loan to fund their gaming operations and on more than one occasion, they will be granted that request. In 2014, however, the Wynn Resorts learnt a hard lesson when they landed the eye-watering $258 million. However, it soon turned out that was an elaborate scam which sent ripples across the stock market, at least for Wynn Resorts. Not only that, but the junket segment never recovered from the squeeze that took place that year.