Casinos rely on very rich gamblers losing millions at their property every year. Maintaining a small handbook of wealthy regulars can make or break a casino. Meet RJ Cipriani, one of the biggest gambling whales in the world. He explains that he regularly gets calls from casinos all over the world offering him free bets, up to 30% rebates on his losses, on-the-house private jet flights, and access to the most luxurious penthouses in the world. If you want to work your way up to becoming a high-roller, you can start by playing online at Cookie Casino and enjoy bets in all ranges from small to big.

These casinos are so eager to win Cipriani’s business because they know he has the potential to earn them eight figures in a single year which can quickly turn an average year into something worth celebrating.

Cipriani has said he has won as much as $250,000 on a single hand of blackjack and will often bet $50,000 per hand and sometimes more if he feels like luck is on his side. He is such a treasured customer that casinos regularly gift him lavish presents such as $70,000 Rolexes and his girlfriend $20,000 handbags.

As a seasoned gambler, Cipriani is largely unimpressed by the presents. He says he has boxes of unopened Rolexes at home that casinos often send him on his birthday. He stresses the importance of being a ruthless negotiator with the casinos and trying to squeeze as much as you can out of them.

Cipriani says the secret is playing the casinos off against each other. He says he will regularly call up rivals and say they are offering him $100,000 in free bets and 20% of losses. He says sometimes they will come back with a superior counter offer; at other times, they will decline his requests.

His negotiation skills have won him millions in free bets over the years and more trips in a private jet than he can remember. 

Where Do Whales Like To Gamble?

While Cipriani prefers to gamble in Las Vegas, he is willing to travel all across the world, including to exotic locations, if the casinos are willing to pay enough to lure him. He recently found himself in the Dominican Republic after a casino was particularly generous with their free bet offers and even paid for his entry into a high roller blackjack tournament.

After his trip to the Dominican Republic, he then boarded a private jet and found himself in the Bahamas, where he was playing blackjack for $10,000 a hand. That trip won him a free yacht trip with his girlfriend to a private island.

Cipriani is a bit different from many other wealthy gamblers, and he claims to be a professional. He says his goal is to shut down some casinos by winning so much money they end up broke. In the gambling world, he is known as Robinhood for his of giving away his money to the less fortunate. 

He says when he wins, too many casinos will cut him off and reduce his rebates or free bets. However, he isn’t phased and said with so many casinos around the world, and there is always someone who is willing to offer him great deals to gamble big at their properties, especially when he often agrees to bet at least $1 million per trip.

You can just imagine how much this man has lost over the years if casinos are willing to shower him with such lavish gifts. Casinos are constantly keeping tabs on big gamblers and are very careful not to give them more than they have lost