1 Year of Cigar Aficionado for $10 PLUS a Free Gift!

The Good Life

Whale Tales

Stories Of High Rollers And Their Over-The-Top Casino Amenities
By Michael Kaplan | From Alex Rodriguez, September/October 2018
Whale Tales
Illustrations/Gary Hovland

The gambler sits under glass. Out on the massive terrace of his villa, inside the air-conditioned solarium of Las Vegas’s most elite casino within a casino, reserved for the highest of high rollers, he asks me to not reveal where he is as he luxuriates in his posh surroundings. “They will offer you stuff like promo chips and private aviation and discounts based on loss,” he says nonchalantly. “Plus they have to treat you exceptionally well—which they all do.”

They, of course, are casino personnel, and they hunger for high-stakes action from deep-pocketed customers like him.

He has just eaten a superb lunch of Dover sole, and smiles as he recalls his all-time largest win on a single hand—$250,000. But last night was a hard one, and the losses piled up on the blackjack tables as he made five-figure bets, his norm. 

His name is RJ Cipriani, a controversial figure who courts press. According to published accounts, he worked with the FBI to shut down a cocaine and money laundering operation and was once banned from Vegas casinos under suspicion of having been involved in the operation himself. (A letter from the FBI confirmed he was not, and he’s once again welcome.) He speaks in the easy lingo of so-called whales, talking about about his promo chips (basically free money to gamble with, offered by casinos as inducements for merely showing up), discounts (rebates on loss, as much as 20 percent) and gifts received from casinos (including a Rolex Yacht-Master II, valued at around $50,000). 

Cipriani, also known as Robin Hood 702 (due to his tendency to give chunks of winnings to those in need) ranks among the elite casino players who wager $25,000 per hand or more. He claims to have gambled alongside numerous celebrities, including boxing legend Joe Frazier. It didn’t go well. “He split 10s and hit 10s; then the dealer got a six card 21,” Cipriani says, still sounding steamed. “I almost got into a fight with him over that. Who splits 10s?”

Most of those who circle in the same orbit as Cipriani tend to not come from the most blue-chip of backgrounds or have the most buttoned-down of rich-guy livelihoods. “Doctors and lawyers are stiffs; forget about them,” says Steve Cyr, director of player development at Palms Casino Resort. “My guys are entrepreneurs, owners of strip clubs and bars, people who have invented stuff. My biggest player has a $10 million permanent line of credit. He wants privacy but also loves big events. He sat up front for the McGregor vs. Mayweather fight—and he had 14 tickets. This guy is among maybe 100 people who can go to a casino and casually blow $1 million. They all get what they want.”

Despite having access to all those goodies—and happily partaking—Cipriani states that he gambles for the money, not for the perks. He claims to do it for a living. “My goal is to take as much money as possible out of these places,” Cipriani says. Sometimes, when he does well the perks are reduced. “This trip they cut off my up-front because I did well when I came out here last,” he says, referring to promo chips casinos give for checking into the hotel and agreeing to gamble. “Keep beating them and they will cut it off. Luckily, though, there are casinos all over the world and casinos will take a shot at you when you are willing to post $1 million or more.”

Wrapped around his wrist is a Rolex Sky-Dweller. I wonder if he got that one as a result of gambling-den largess. “No, this is mine,” he says. “It’s my lucky watch. But I’ve got boxes of Rolexes at home.” Some were birthday gifts from casinos. “I just got a thing from Foxwoods where they are having a weekend in Tuscany with Andrea Bocelli,” he says. Will he go? “No. I already know him. Been there, done that. Through being a high roller, I’ve pretty much done it all.”

There is no question that casino whales are jaded and difficult to impress. The latest joint to take a shot at grabbing their collective attention is Cosmopolitan of Las Vegas. Late last year, the casino debuted its 21 brand new Boulevard Penthouse suites, all unique, all spacious, all designed by top-flight names. They are modern and cheeky and plush, loaded with original art and only-in-Vegas details: an ivory-colored grand piano, Pegasus on a pole, a cage with a swing inside it and wraparound terraces with views that seem to go on forever.

They occupy four floors and loudly announce that the casino is now going after the highest of high-rollers, offering them all the accommodations and accoutrements that they expect. For one, in order to make the trip into Vegas more pleasant, Cosmopolitan recently purchased a Gulfstream jet that replaces the chartered flights it had been arranging for top customers. 

Since the largest players are drawn to Vegas primarily by gambling, what’s likeliest to resonate is a private gaming room that Cosmopolitan has dubbed The Reserve. Designed by Adam Tihany, it’s a luxurious, wood-paneled hideaway, centered by a lounge area featuring a well-stocked bar (rare single malts and a $56,000 bottle of Louis XIII Black Pearl Cognac reside behind the bar) and private gaming enclaves on either side. Cuban cigar boxes are on display in the large humidor. 

Each gambling refuge contains a single table. Entry is by invitation only, and getting a seat—actually, getting the entire table—requires a willingness to risk $1 million or more. Single bets top out at around $200,000. “That is the maximum,” asserts Brian Benowitz, the senior vice president of casino operations for the Cosmopolitan. “That is the maximum risk we are willing to take at this time.”

Whale Tales

Considering the gusto exhibited by The Reserve’s heartiest gamblers, it’s easy to believe that they would bet more if only the casino would allow it. Perhaps they compensate with time spent at the table. “Guys come to The Reserve and gamble for two to three days straight,” says Benowitz. “A lot of players don’t sleep. They go back to their rooms for showers, take some time to eat, go to the terrace for a smoke,” he says, even though smoking is perfectly fine inside The Reserve. “Or [they] spend some time in the massage chair.”

The chair is no ordinary device that you might find in a Brookstone catalog, but a $9,000 contraption that gives sublime rubdowns. It’s a coveted item in China, but here in Vegas it provides no competition for a seat at the table, where the gamblers’ retinues enjoy being close to the action for as long as they’re welcome. “These guys will often show up with an entourage,” says Benowitz. “But the entourage can last only so long.”

The friends take breaks from the marathon gambling sessions, rotate in and out, and know when it is time to leave the gambler to his own devices. Inevitably, probably in the thick of a losing streak, the player will say, “Everyone gone!” 

“Then the doors to the gaming room close and the entourage moves to the lounge,” continues Benowitz, “which can be a party in and of itself. They eat, drink, watch sports, use our gambling app to bet.” 

Wooing the big whales is far from easy, and each one of the highest-rolling casinos in Las Vegas competes for millions of dollars in potential revenue from the world’s largest bettors. At the Cosmopolitan, it falls upon Danny Ruiz, executive vice president of international marketing, to make sure the casino gets its slice of the action. “We go all over the world for marketing trips,” says Ruiz, referring to the jaunts he takes to woo players from their home turf to Las Vegas. “We are not allowed to market in Mainland China, so I take trips to Hong Kong for meetings and private dinners and luncheons.”

As is the Chinese way, Ruiz is often invited to casino customers’ homes for lavish banquets that feature unusual dishes. “I ate a worm casserole,” he all but brags, recalling a trip to Hong Kong. He didn’t let a hint of discomfort show. “It was worth eating,” he says. “The person I visited wound up making the trip out here.”

Once a whale arrives at the casino, Ruiz goes to great lengths to keep the player happy and gambling. He’ll greet the whale with bottles of fine wine, boxes of cigars, perhaps a hard-to-find handbag for the wife or girlfriend. Ruiz even gave one guest the sexy swing setup, and guided another to the English company that makes an elaborate safe situated in one of the penthouses.

How far will Ruiz go to meet an outlandish request? “Somebody wanted a certain breed of puppy,” recalls Ruiz. “He wanted a special French bulldog with a particular eye color to take with him to his home country. We found the dog but reached a line we didn’t want to cross when it came to the veterinary process. We told him we could get him the dog but he’s on his own after that. The guy wound up not taking the dog but he was not that disappointed. He could have had the dog if he wanted it.”

Another hard line at the Cosmopolitan involves allowing gamblers to play their casino hosts against one another. Cipriani does it routinely: “I call hosts and say, ‘Foxwoods is giving me $100,000 in promos for walking through the door. Can you beat it?’ Sometimes they do; sometimes they tell me it’s too strong.” 

“We don’t discuss deal points or bargain on price,” says Benowitz, acknowledging that others do. “If someone offers something more somewhere else, and that serves as the tipping point, then that player is not for us. We don’t get into bidding wars [for players]. We believe in what we are offering.”

It’s an easy position to take now, with Cosmopolitan having the newest and coolest digs on the Strip, but that will not be the case forever. An upcoming enterprise called the Drew is under construction on the other end of the strip. And right down the block and around the corner from the Cosmopolitan, the Palms is in the throes of a $620 million renovation that will include a revamping of its once infamous high-roller suites that came complete with a basketball court and rooftop infinity pool. Plus there will be new restaurants, nightclubs and craft cocktail lounges.

Chances are then that the Cosmopolitan will not soon be welcoming a wealthy customer who is known for putting ungodly sums of money at risk in casinos. He also drives a hard bargain before stacking his chips. “When this player comes in, there are 30 deal points that get signed off on,” says Cyr, making the man’s gambling trips sound more like corporate negotiations than Vegas getaways. “He wants to split Aces four times. He wants to double down on any two cards. He can switch dealers any time he wants. As soon as he lands, he gets $20,000 for airfare. If he loses $1 million and pays in 60 days”—like a lot of high rollers, he plays on markers—“he gets an 18 percent discount. So he loses only $820,000.”

Whale Tales

According to one casino executive who asked not to be named, that practice is hardly unusual. “Discounts are the bottom line,” he says. “Maybe the villa is better at Bellagio or there are new penthouses at Cosmo, but—provided that one casino is in a similar universe with the others, when you are a top-tier player choosing where to gamble—it is a business deal: comps, discounts, rules are what they care about most.”

The executive adds that new and splashy spaces from hot competitors can make whales particularly slippery to hold onto, especially when they leave the casino. “I took a big player to dinner at a competing casino and a top guy from there walked up to us,” he remembers. “He said to me, ‘Oh, I am so happy to see you. Welcome to the property. You need to check out these rooms that we just remodeled.’ The player I was with was, like, ‘Oh, really? Let’s go see them.’ Meanwhile, I’m afraid of losing him…The goal is to keep players in the building but people want to leave for a variety of reasons.”

Sometime they even want to leave the country. “Things have become more corporate and systems have become tighter” in the United States, says the unnamed casino executive, explaining the wanderlust of whales. “Since a big baccarat player can light you up for $20 million, we’re constantly assessing his play and calculating what we want to give him.” 

One way around the tight oversight is to forsake Las Vegas for less obvious destinations. Cipriani, for example, recently flew to the Hard Rock in Punta Cana Dominican Republic, lured there by piles of promo chips and a high-stakes blackjack tournament with a comped entry fee.

Prior to joining Palms, Cyr took one of his big customers to Baha Mar, the recently launched island resort in the Bahamas. “He bets $50,000 per hand at baccarat and three spots of $20,000 at blackjack,” Cyr says. “When he and his wife wanted to take a private yacht to a private island for dinner, I was there and sent them on their way.”

No doubt, Cyr was waiting for them when they returned. 

“Over the course of the trip, my player was up a lot and down a lot and ended up losing $400,000,” says the host, making it clear that his whale didn’t mind all that much and will surely be back for more. “Gambling is a fun thing for him.”


More in The Good Life

See all
Lebron James, L.A. Lakers Celebrate NBA Championship with Cigars

Lebron James, L.A. Lakers Celebrate NBA Championship with Cigars

Lebron James and the Los Angeles lakers sparked up a variety of four different cigars during their …

Oct 12, 2020
Tampa Bay Lightning Celebrate Stanley Cup Win with Cigars

Tampa Bay Lightning Celebrate Stanley Cup Win with Cigars

After more than 60 days sequestered from family and friends battling for the Stanley Cup, the Tampa …

Sep 29, 2020
CBS Sunday Morning Thanks Cigar Aficionado

CBS Sunday Morning Thanks Cigar Aficionado

The September 6 broadcast of the hit television show “CBS Sunday Morning” closed with host Jane …

Sep 8, 2020
Complete Michael Jordan Video Interview to Debut July 30 at 7 p.m.

Complete Michael Jordan Video Interview to Debut July 30 at 7 p.m.

On Thursday, July 30 at 7 p.m., we will be posting on CigarAficionado.com a special, uncut version of …

Jul 23, 2020
The Second Coming of the Drive-In

The Second Coming of the Drive-In

The quintessential American entertainment venue, the Drive-In movie theater, stays viable with …

Jul 22, 2020
Countdown to Ecstasy

Countdown to Ecstasy

At the 2019 Big Smoke Las Vegas last November, Doug Halcomb and his Cigar Raiders crew were on a …

Jul 10, 2020