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Updated: Jul 26, 2021

The first and, really, only thing you need to know about gambling is that the house always wins. The house always has an edge in every game it deploys, usually it wins something like 54% of the time; and once you are hooked, you will lose, over your gambling life, overall—occasional wins notwithstanding. So usually gambling is the classic game where the only way to win is not to play. However, there is an exception; and I met the exception during my first year at university.

With the right conditions, it is possible to turn the house edge into a player edge—and so turn the house into a sucker. The first guy I met to do this, around 2005, was an blue-eyed Dutchman, half-Dutch and half-English to be precise, who had a real entrepreneurial streak, as do all the Dutch. They are a real trading nation; they have the flintiness and determination the Germans put into philosophy, music, and war—yet they put all that energy into commerce. The Dutch might have a reputation for cannabis liberalisation and easy prostitution laws, but they are, first and foremost, sober traders—they drive a hard bargain. It was in this man’s blood.

At school, there had been a Coca-Cola promotion, collect enough ring pulls from the cans and you got a case of Coke. My Dutch friend did not drink Coke, but he collected other people’s ring pulls diligently; he won the competition, received the case of Coke, and sold back every can at half the price compared to the school cafeteria—and so he netted £2,500 or so, not so bad at sixteen. His father was a true local character, a successful businessman in his own right. A Catholic who adored Dalí, he made sure that their sleepy Oxfordshire town erected a statue that featured the surrealist walking a lobster on a lead, and he also claimed—perhaps as a joke—to believe in the ideas of Erich von Däniken, a Swiss hotelier who thinks that ancient monuments were landing stations for our old gods, the UFOs and the ancient astronauts.

What my friend had discovered—along with gay pornography, for he was homosexual—was a series of gambling forums. The forums explained how, online, it was possible to play the perfect blackjack game; unlike poker, with its unpredictable deceptive human element that teases game theorists, the optimum move, the optimal card to play, can easily be mapped for all blackjack games; so it is possible to play a statistically consistent game. This does not mean that you win every game; it only means that your game is consistent, every card you play is the best card in that situation—it is achieved, or was achieved back then, with an old crumpled printout balanced on a knee until every card combination was learned by heart.

Now, as with all these games, the house has the edge; however, especially at that time, the online casinos offered all sorts of sweeteners, bonuses, for people who signed up to play their games. If you combined the optimal blackjack game with a the sign-up bonuses, the odds shifted. I cannot remember the precise reversal, but let us say it was an almost total reversal; from a house edge of 54% it swapped to a player edge of 54% or more. What this meant, over the long term, was that it was possible to make a regular untaxed—for gambling wins are untaxed in Britain—income from the gambling sites. With the same statistical regularity with which gambling addicts lose over the long term, my friend began to accumulate money over the long term.

Now, occasionally, casinos would get wise to the act, but, by and large, he kept at it—often under various pseudonyms. The goal was to look for “Expected Value” or “EV” as they called it on the forums—you could say return value. Every casino site was analysed for its sign-up offers and bonuses, and cross-checked against the statistical regularities found in blackjack—and, eventually, other games—to look for statistical shortcuts and holes, chances to turn the odds around. The rewards were then parcelled out. You could say that, looked at in this way, life itself is a great game where we look for EV from jobs, cars, partners, restaurants and so on—where we look for the statistical anomalies that allow us to make unexpected returns, for those moments where we flip the odds and we, for a change, have the house edge.

By his second year at university my friend needed no student loan, and by his third year he had acquired enough money for a house—a very nice house indeed, in Amsterdam. The genes—the blood—did not lie. Those cold blue Dutch eyes made money with absolute efficiency. He had expanded, by this time, into other games; sometimes playing video poker non-stop for nineteen hours in order to win a competition that depended on him playing through more money than anyone else. These games were not about winning—rather the goal was to have put maximum cash through that particular game. The reward was a BMW; he won it, but, being the Dutch type, quite progressive and sober in many ways, he had not even learned to drive—luckily the casino paid out £50,000 or £60,000 instead, all tax free.

At times, he questioned whether he was addicted; yet, despite playing the games for hours at a time, he always made a cold mathematical analysis as to the EV and the outcomes. He was not the compulsive extreme risk-taker and addict who is typically worked over by the casinos; it was more the case that he worked hard at it, and everything he worked at was thought through. Of course, it is a cliché that every gambling addict claims to have “a system”, and yet he really did have a system; after all, he was extremely bright—he attended the university for mathematics and languages, and would stop by to challenge us with the “Monty Hall problem” for recreation; a problem to which I offered my best guesses, completely unjustified in reason.

Destiny called him to it as well; for, as a child, he had always particularly enjoyed and fantasised about living out Roald Dahl’s tale of Henry Sugar—a man with a psychic powers who uses said powers to become vastly rich through gambling. Whether this was a premonition or whether my friend made the story he enjoyed so much a reality, he did indeed seem to have become a real Henry Sugar.

Now, this world, the world of the “bonus hunter” as they call it, is quite different today. I met a man in London around 2018 who was employed by a company to play various games, to bonus hunt, in quite another way. For, over a decade on, to be a bonus hunter had become a company job; he was paid £30,000 or £40,000 a year to bonus hunt, but it was a salaried job; not like my friend who entered early and reaped all the big rewards and soft targets—perhaps for people in the 1990s there had been even larger rewards. Now the pickings were much more slim.

My friend kept his net spread wide, and even in the early days he patronised the more marginal online casinos; the casinos that did not pay out regularly. These casinos, often based in Russia, maintained a slow turnover; they made players wait for cash as long as possible—as all casinos do, for they know that the addicts cannot hold on to their winnings; they are so compulsive that if you make them wait a week to cash out their winnings then, odds on, they will play it all away again. But the more sketchy casinos forced him to wait much, much longer because they had so little capital; they lived week to week and relied on a big loser to pay out their winning clients. They also played very rough with people who fell into debt with them: one associate who fell behind on payments received pictures of his daughter being picked up from school, photos snapped by a private eye. There was no threat of course, no explicit threat—except the meta-threat that whoever ran the casino knew where the debtor’s child went to school.

On another occasion, my friend took a big win from a sketchy operation; they delayed him month after month—probably because they lacked the cash to pay him off. They sent him on various luxury holidays and trips; once you enter the world of high-roller gambling this is normal. You may be familiar with the phrase “comp”, as in “fully comped”, given notoriety by the Las Vegas shooter Stephen Paddock, himself a considerable gambler, in 2017. Well, my friend quickly moved into the “fully comped” world. This world is not reserved for the usual gambling addict; it is mainly frequented by the type of entrepreneurial man, a risk-taker, who makes his millions early and reserves, shall we say, two or three million dollars per year to play around with on the tables. Men like this gamble because they enjoy risk; perhaps they used up all their risk opportunities in entrepreneurship, in multiple business failures before they hit the commercial jackpot—or on the stock markets in London or New York.

Think about the late John McAfee, a man who made his millions early but was also a compulsive risk-taker; he is the type who ends up in the world of the “fully comped”. Each high roller is assigned a personal manager from the casino to cater to their needs: football matches, horse racing, boxing matches, Playboy bunnies, concerts, and so on are all laid on for the fully comped person—and the access is always at the VIP level. Frequently, my friend would be flown first class to some exotic location to see a football match and find an attractive woman there to meet him at the airport, assigned by the casino to cater to his needs; the understanding, of course, was that she would sleep with the clients—and, indeed, my friend’s recalcitrant casino once assigned a fizzy-blonde to him to mellow his desire for the pay out, too bad they did not know he was gay. I suppose this is what girls really mean when they say they work in “corporate entertainment”.

The point is to keep the high roller on the hook with the best restaurants, hotels, and entertainment possible; some of these men will play roulette, a real sucker’s game, and essentially piss two or three million away a year because they have it to spare; for casinos, it is important to keep these big fish on the hook. At the more mundane level, when it comes to an oldster from Florida attached to a Las Vegas fruit machine by a plastic cord, there are free drinks and snacks; in Las Vegas, none of the gambling floors have windows; they maintain a lightless environment so that you lose track of time and gamble more; even the clocks are removed, you do not know if it is night or day—all you can see is the fruit machine spinning, spinning, spinning…the more paranoid players maintain that certain odours are pumped through the air conditioning to alter a player’s hormones. Believe me, people who run casinos are quite unscrupulous.

Eventually, my friend was summoned to meet the casino’s boss. This was a Lebanese man, a real gangster, sequestered at a Mayfair address; slightly unfashionable today, he was behind the times with ultra-rich fashions. He sat on a gold throne and was served by two hussies with badly-dyed blonde hair. As for himself, he was the typical oily Arab that Lebanon, Paris of the East, sometimes produces—the Lebanese go way back with casinos, with the con. He spun my friend a great Arab tale and sent him on a Norwegian cruise; for a time we were a little concerned. After all, if you want to murder to someone—say someone who has potentially bankrupted your business—the best place to do it is international waters. People fall off cruise ships at night all the time, especially when “drunk”—though my friend was no drinker. In international waters, the investigation is at the captain’s discretion and limited in resources, but that is hardly important; the body is usually never found. I have often thought that if I had to murder someone I would take them out on a yacht, get them drunk, and push them overboard (future wives take note, please); though, of course, most murders—the ones we hear about, the murderers that get caught—are committed in a fit of rage by people not clever enough to plan ahead.

My friend survived the cruise, however; although he was then shuttled to Goa to meet with the casino’s “security manager”, a man who was also a local police chief—or maybe not, the situation was, as always, “complicated”. After various machinations, not open to discussion, the money was delivered.

Ah, you thought this story would terminate with my friend’s inevitable downfall; for he was involved in what the world considers to be sketchy, and usually that behaviour is punished. Well, in the movies it is punished; but in reality, no. He just went on. He accepts moderate risk, and perhaps that is because he is gay; they say homosexuality comes with a higher tolerance for disgust, for reasons you can imagine, and that includes a willingness to take certain risks. Once, we both stepped out of an art gallery in Whitechapel, an area now as Muslim as any Pakistani city, and found an English Defence League contingent were embattled down the street. They had attempted to retake the territory for England, but they were hopelessly outnumbered; they waved their St. George’s flags as the Asian youths formed a ring around them and tried to pick them off. My friend closed in closer. We were the only white men outside the EDL contingent; it was not clear to me that the mob around them could tell we were not with them, certainly not if it developed into a general melee. Yet my friend moved closer and closer still; these are the nerves required to be a professional gambler—the tendency to tolerate risk.

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