How I Lost a Fortune and Found Myself at the Casino

This is a story about my lucky streak, my Big Bet, my huge loss and the enlightenment of losing.

gambling money

I’m An All-Or-Nothing Person. I Just Can’t Decide Which One.

Once upon a time I would have considered myself a professional gambler. I was riding the wave of luck all the way to the moon and back. Nothing could stop me.

You’ve read the stories. Man wins millions on red or black toss of the coin. That wasn’t me. I was slow and meticulous, knowledgeable, and keen to make a profit in whatever way I could. Card counting started me off well. It was a trick I had learn with some other chaps. We would often play together on the Blackjack tables, and we had signals designed to communicate our thoughts to each other. Only two of us ever entered a casino together, and we never haunted one place for long enough to get busted. Card counting isn’t strictly illegal, but it isn’t hard to get blacklisted. Casinos don’t really want you to make money.

We made a moderate fortune, but we lived an extravagant life too. Money came and money went. Looking back it was a bit destructive, but I guess it was any young guy’s dream. Women, hotels, drink and sometimes a spot of nosebleed roulette, just for fun. I remember one of the boys, Andy, saying to me once, “I don’t ever want this to stop. I can’t think of anywhere else in the world I’d rather be right now!”

I gazed out over the ocean from the balcony of the room we were renting. I wish I could have agreed but a part of me didn’t feel quite satisfied. “Yeah,” I said still staring out. I went to run a bath. To tell you the truth, I could have bathed in cash if I’d have wanted to. But I never really saw the point.

All in a day’s work

We took a visit to the casino the next day, myself and Andy. I remember it was a little rough around the edges, but I didn’t mind do much; the games were good, and the dealers not well trained at spotting a pair of fraudsters. Not that we were cheating. The way I saw it, and the way I still see it, is that we are well within our rights to try and scrape back our edge against The House; that omnipotent force that thinks it can take us all for a ride. I would have taken straight from the cash till had I not had some consideration for the shaky young man that worked behind.

We made nearly $10,000 that day playing Blackjack, and another $5,000 between us playing cash game poker. We had a different tactic for that. We would both take a seat in a 6-max cash game, and use raise tactics to bully the pot between us, before dumping on each other. This tactic was volatile, and there was no chance of sticking around for long. We probably wouldn’t bother going to that casino again. We left quickly, and satisfied, though not before dumping a couple of thousand on roulette. There was always a side to us that couldn’t resist a bet, even when we knew The House would take us down a back-alley and do unsavory things to us.

Roulette has always been my weak spot. I think it’s the instant action. No sitting around waiting for cards. No patiently counting, no having to be sure, or sly. Just an innocent bet on an inclination. A little stab in the dark. A toast to the gods, and the forces of our destiny. Yeah, roulette was always my weak spot.

Am I Rich or deluded?

The lifestyle that my pals and I were living, began to drive me insane. My head was up my arse, and they just weren’t getting what I was saying. I don’t know what I was saying, but I know I had a point. I had told Andy that we should get hobbies and interests, and that our work was not rewarding on a deep level. He had replied, “Mike, you are crazy. Look around you. What do you see? Bright lights, big city, piles of cash Mike! Women. Cars. We are on top of the world Mike.”

Time went on and money rolled in. I began to despise it. So meaningless in its abundance. So disgusting in its ability to consume man. I watched as Andy would take another sniff of the sea breeze, before ordering room service and cracking a bottle of champagne, spilling half of it on the floor, and ordering his maid to clear it up, so that it would not pollute the smell of the perfectly air conditioned room. Repulsive. Was I like him? So irreverent and disconcerted.

I was at breaking point. With all of the money in the world, something was still missing. I could have done anything. I could have got on a jet plane and flown anywhere, started a new life. But that was not what I wanted. What I wanted more than anything in the world, was to rid myself of this burden. I needed to shed a few pounds. I needed to lose the weight of all of this money. Either that or I had to make enough to never have to think about it again. Then I could take off and find a new life. I needed to play roulette. I needed some all-or-nothing action.

All Or Nothing Time

I walked down to the casino. It was the same scruffy casino that Andy and I had haunted a few weeks back, when we had taken thousands from the suckers. The perfect dive to take a cash dump. I quite liked the service anyway. I ordered a free cup of tea, and was delighted when they brought over a full pot, served with separate milk and little sugar cubes. “Perfect,” I thought as I took my first slurp, “I am winning already.”

I looked around at the excited faces of the crabs players, and at the deadpan expressions of the slot zombies. I scanned over to the roulette table, and there I saw it, all lit up, and mine for the taking. An empty roulette table, just about to start up, unannounced, but clearly ready to go. “I will take first spin,” I thought, “no need to make a scene.”

I quickly walked over to the cash machine and took out the maximum, $10,000, which I added to the collection of cash and casino chips that I had gathered together. It was everything I had, apart from my savings. Professional gambling is a bit like that. You end up with an amount of cash that is considered unnatural these days, in the world of electronic transactions.

I walked over to the roulette table, dismayed to find another player, cautiously throwing $5 chips on to single numbers, his bet totaling $30 if my math stands correct. “Oh well”, I thought, “at least one lady will witness this most daring act.”

I placed $83,500 on red. The croupier stared at me. She called her manager. “Spin the wheel,” I said. “Don’t keep me here waiting, I’ll have a heart attack.” I was feeling confident. “It’s pretty much 50-50”, I told myself, repeatedly. “The house edge is so little in roulette, it is basically even odds.”

The truth is I didn’t even know at that point whether I wanted to win or lose. All I knew is that I wanted to gamble. It might sound counter-intuitive, but it felt like the only way out. All or nothing.

The manager was talking to the person who should have been spinning the ball by now. He told her that, of course, she should take my bet. His eyes looked greedy. She counted the bet, and exchanged the cash for chips. She spun the ball. The anticipation should have been killing me, but the feeling was unusual. I still couldn’t decide whether I wanted to win or lose. I spent the entire, long 20 seconds, contemplating which outcome I would prefer.

If I won a lot today, I could leave this planet if I wanted to. I could fly away to distant lands. I could buy what I wanted. I could eat what I wanted, meet who I wanted, and buy myself out of pretty much any problem. I started to feel a little sick again. I hated myself when I thought too much about using money to solve problems. Next, I thought about losing the money. I would be in the shit then. I don’t have any qualifications, and my CV has a three year gap on it. Perhaps I could write about my card counting, or that I spent three years unable to focus on the road while I was driving, due to a constant state of intoxication.

The wheel continued to spin…

The ball clicked, and then landed, jumped, rolled a little, and then landed again. “7- Red,” announced the croupier. And I sat there, silently, as she gasped and shrieked, and pushed over $167,000 in chips. The man to my left shrieked too, a shrill noise almost as high-pitched as the lady’s. I sat there, silently.

European roulette number zero

The Big Bet

I pushed the $167,000 onto red again, before moving it off. The other man bet $30 on red. I didn’t place a bet, but I pushed another $100 onto red, and told the man that he can have it. Then I pushed a $1000 chip into his pile, and he grinned. He lost his bet, and then left, shaking my hand, and grinning all of the way out of the door.

I divided my chips, worth $165,900, into two huge stacks and pushed one stack of chips onto 22 black and the other onto zero. Just two single numbers. My odds were less than 1/18. But the payout would be in the area of 3 million. It felt like an out of body experience. The lady behind the wheel looked green – like the zero on the wheel. It was difficult to tell what she was thinking. Perhaps she had never seen this size of bet before, but I sensed that she had. Maybe she just couldn’t work me out. She could see I was composed, and she could see that I was not addicted. What force was driving my preposterous bet? Her guess is as good as my own.

Further discussions took place between her and the pit-boss. He looked at me with deadpan expression and talked to a phone. After a few seconds he smiled and told us that it was okay, that the casino would accept my bet. A few patrons have been slowly starting to surround my table. I didn’t pay much attention to anyone, but I vaguely heard the words “crazy” and “balls”.

The wheel spun once more…

For 20 long second I contemplated Andy, and my life as a card counter. He was my best friend, but I just couldn’t bear to think about him, wallowing in such a shallow lifestyle. I thought of myself. I though again of whether or not I wanted to win.

The ball clicked, and landed, this time quickly coming to a stop. “32 red,” she said.

And with that I got up and left – just like that.

PS: Some readers have commented that that’s a story of obsessive, crazy or irresponsible gambling. In our opinion there is a deeper meaning than the pure facts that are being described. In any case if you need help with your gambling or fear you may have a problem, please check out our responsible gambling article. There you can find helpful advice, phone numbers and resources that can really help you quit gambling or get it under control.

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