What is a High Roller?

If you answered, Willie Nelson, then we’d be sending you back to Colorado for some better jokes. If you thought it was the 550 ft tall Ferris wheel at Caesar’s in Vegas, you’re getting closer – that’s called the ‘High Roller,’ but that’s not what we’re talking about either.

What we’re talking about in this article are the ‘Whales,’ or ‘Money Players’; those who have the deepest pockets out of all the players in the casino. It’s not only about having a lot of money though; you need to gamble that money. You need to bet a lot to be officially labeled as a high roller.  You have to walk the high roller walk, pay your dues, tip big, and arrive in style.

What Makes A High Roller A High Roller?

It’s not just about wealth in general; it’s more of a style, a club, or a concept. It’s a different perspective on value, standards, and most of all generosity. Some celebrities are high rollers, but not everyone famous is a known gambler and wouldn’t deserve the ‘High Roller’ accreditation.

Celebrity high rollers

Some of the most famous high rollers are those whose lives are already in the public eye. Celebrities already have a natural swagger from their fame and usually have the bankroll to support being labeled a high roller, but few have the guts to be a real money player.

Many celebrities have made the gambling community proud over the years, but I’ve put together a short list of prime examples of high celebrity roller-ship:

Dana White – Dana White is the bald but sexy owner of the UFC, a worldwide sporting event that generates massive amounts of pay per view revenue, and he spends most of his time in Las Vegas. Dana is pretty much loaded and lives the ultimate playboy lifestyle. If you’ve ever watched his reality show ‘Ultimate Fighter’ you know he puts up $10k in a shoebox just for their coaches challenge. Dana is a huge Vegas tipper, and has even left 5 figure tips for perfectly cooked steaks, and over $100k tip to a blackjack dealer. Dana is a big money player and a high roller of the classiest type.

Michael Jordan – Arguably one of the greatest athletes of all time, leader of the Chicago Bulls to six-time NBA champions and multiple game MVP. Michael has generated millions in earnings from his years of basketball greatness. Michael’s plays are almost as big off the court as they are on. Michael Jordan, who’s first retirement from basketball was rumored to be due to his gambling, has been known to lose over $1 million over a game of golf with buddies.  Mr. Jordan’s celebrity reputation alone classifies him as a star high roller, but he’s a genuine real money player.

Ben Affleck – He’s been in many movies and has made a ton of money. What’s more interesting are his personal gambling habits. Ben has had a piece of the high roller’s highs and lows. It’s publicly known that his wife of over ten years left him because of his extreme gambling lifestyle. Mr. Affleck is a highly skilled card counter, who’s been physically removed from at least two casinos. Word on the streets is that if you’re in Affleck’s crew, you’ll know about the underground action as well.  Overall, anywhere he goes, Ben Affleck is a high roller.

George Clooney – George Clooney not only acts as a high roller on the big screen but also hits the tables every time he visits Las Vegas. George loves gambling but consistently experiences poor luck. It’s rumored that George lost 26 straight hands of high stakes blackjack one crazy night gambling with fellow actors. Even with consistent bad luck, George Clooney is still a Whale.

Tiger Woods – Speaking of blackjack, Tiger likes to play $25K/hands. For a period, Tiger Woods was almost synonymous with Nike, as well as any reference to golf. He’s generated millions of dollars from his wins, endorsements, and personal business ventures. This wealth has only fueled his gambling habits. He gambles the amount of some people’s annual salaries repetitively on hands of blackjack. Another example of celebrity level money funding the high roller lifestyle.

John McCain – Former presidential candidate for the Republican party, a successful business owner, and incredible fundraiser. John is a gambler with a hunger for action. His friends have reported that he has been known to spend all night playing craps, drinking and playing dice for sessions of 12 hours or more for large sums of cash. John McCain proves that even politicians can be dice throwing money players.

These six celebrity examples should give you an idea of what we mean when we say ‘high roller’. That doesn’t say that you need to be famous to be considered a high roller, but once you’ve achieved the status, it’s something that can ultimately result in fame. Think about Terrance Watanabe, who is known to have lost over $220 million in Las Vegas in only a few years. Those huge losses must have some crazy weekend stories behind them.

A High Roller Plays

Here’s the thing. If you don’t gamble, you’re not a high-roller. You must play the game to get the high-roller fame. No one cares about the bets you thought about making. It’s about a super gaudy display of wealth and recklessness; you have to play.

To be considered a high roller you must gamble large sums of money. It’s not about where you’re from, the clothes you’re wearing, or how much money you have in the bank; it’s only about the money on the gaming table. The more money you put on the table, the more popular you’re going to be to casinos.

In Las Vegas, where there are many mega-resorts competing for clients, most casinos hunt whales. Like the old Alaskan expression – “Catch a rabbit and the family eats for a day. Catch a whale, and the village will eat for the year.” That’s why high rollers are called whales; their huge bets usually make the casino.

High Rollers Tip Well

A real sign that you’re a high roller is if you put your money where your mouth is. If you want to live the lifestyle, you’ll want the best of service. You won’t receive good service for long without tipping. The point is, if you’re a big-time gambler, tips should be virtually nothing to you as part of your session.

Think about it from the other side. If you were a service worker, waiter, bartender, or a driver, wouldn’t you rather have a high roller as a customer instead of the average joe? The average customer is going to give you an average tip, average appreciation, and offer little social opportunity. A high roller could change your life for the moment, make your job exciting, even make you feel like someone special just for getting the chance to serve them.

This social trade-off has always played well for me. I tip everywhere I go, even sometimes when it’s specifically not permitted. If they refuse your cash tip, get that person a beverage, or at least a sincere compliment.

All High Rollers Get ‘Comped’

Getting ‘Comped’, or complementary concessions, is something casinos do to remain competitive and reward the loyalty of their best guests.

As a high roller, you can expect everything from a free bottle of Cristal and a luxury hotel stay, all the way up to a free car. High rollers are rewarded for both their wins and losses. It’s not about the individual wins or loses in the eyes of the casino; they just know if they keep big players at their hotels, the math will work out.

When you lose a big wager against the house, don’t be surprised if they send you a little gift. They might even offer you a discount to start playing again. If the loss was big enough, you could get the keys to a beautiful villa. The casinos don’t want to ruin a perfectly good relationship between them and your money.

Groups of casino managers will want to be your friend. They’re not afraid to pretend a bit to get your focus and attention.

Your high roller lifestyle doesn’t end after you’ve left. Chances are if you’ve won or lost enough at the casino, you’ve probably made some new friends. These are people employed by the casino who send you gifts, call you up to kick it, and continually offer you free stays at your new favorite home away from home; their casino.

Imagine having a famous chef personal cook you a meal just for visiting a place to play a game you enjoy. Most gamblers are comfortable playing in their pajamas, and as a high roller, casinos will try to keep the game going for you pretty much any way they can.

The ‘High Roller’ Hack (Summary)

Could you be a high roller, even if it’s just for the day? I say you can, but only if you can hack it. When I say ‘hack’, it’s really about your mindset. You can always live the dream, if it’s just for a day or the hour, even if you can’t afford it forever. You could visit a gambling mecca like Vegas with cheap plane tickets. You can shop the same shops, drink at the same clubs, and you can find deals on the same meal a millionaire might eat. You can drink the same glass of wine and have the same chef prepare your meal all for an expensive but affordable $40-$80 a plate. If you buy yourself a $20 cigar, a $20 glass of scotch, and sit on some beautiful furniture in the high-stakes blackjack area, you could close your eyes and imagine yourself to be anyone.

Just because you don’t have the bankroll of the high roller, doesn’t mean you can’t fake it. You’ll need to keep that ‘High Roller’ mindset and act the part. You’re not going to pull it off completely with a wrinkled $20 bill either; you’ll need to pony up a bit of cash. It’s not anywhere close to what the whales play, but you are only going for some comps. You need to have the mental tolerance for extreme gambling even to consider pulling it off, but it’s possible.

If you watch the casino staff watching you, and you notice when they’re making the count of your bets, you can bet higher when they’re watching you. If you maintain a large amount of betting for long sessions, you’ll start to get comped.

Another way to do this is to get a large credit line from the house. You’ll need at least $50K to pull it off and get their attention. You’ll want to keep a good amount of it in play to keep it real, but if you don’t lose any money, it could mean a sweet vacation. And by sweet, I mean suites, like an upgraded hotel stay, show tickets, gifts, food, drinks, and service. It might not be a villa at the top of the resort, but if you get on their radar, you can start getting some of those high-roller perks. Play your cards right and get some of the house’s money, you could be hacking your way to living the high roller dream on a budget.