As a documentarian, I’m over here making a documentary. On the surface it appears to be about gambling, but at its core it considers what is, transparently, a gamble for other people that is a sure thing for me.

The story traces me finding a whack of people from all walks of riches who are each willing to flip a coin for a different amount of money, with their accepted amount obviously depending on their financial situation along with their level of curiosity.

In most forms of gambling, the house always wins. Not because the odds are stacked in its favour, although it is, but because there is a betting limit. In my game, there is no limit outside of my ability to find willing participants. There is enough money owned by enough people at enough stages of wealth, that I can play, and win, without the cost of ruining somebody else’s life. Don’t bet more than you can afford to lose. Your odds are always 50%, and since there is no vig or inherent cost of playing, this means that you have a 50% chance of doubling your money. You get to choose the amount you want to bet. I may one day reach the number for your desired flip, and we will play. You may win, you may lose, I will win. Opponents choose, impartial party flips.

The first round starts at $10, just because any lower wouldn’t be worth winning. In a dingy pub, I explain the situation to the patrons, and a bored widow sipping on a gin fizz agrees to be the initial bettor. She calls heads and the bartender flips heads. I gladly hand her a purple, content for the initial go-around to continue past the first toss, and knowing full well it will be coming back to be eventually.

The second participant, from the $20 level, is out having a smoke, and he wins as well. I’m down $30 at this point, but of course, nothing to worry about. Hell, let’s make the next one for $50, meaning if I win I’ll actually be up twice as much as what I started with.

I stand outside a law firm waving a fifty, and in no time someone approaches and wants in on the action. Well look at that, another loss.

And another.

And another.

And et cetera.

After 15 straight defeats, I’m finding it ever harder to locate an opponent, with the amounts getting prettay prettay high. I never thought it would get to this point, with a ridiculously improbable 0.003% chance of happening. But with Bezos at hundreds of billions and many more not far behind, I will eventually win that $10 plus extras.

My assistant tracks down a willing flipper, and I fly to Macau to meet him, for a – huh, tough to even say here – a million dollar flip.

By this point my endeavour has captured the attention of a few notable media outlets, and on my flight I’m unfortuitously surrounded by reporters who want a little piece of me.

I’m nervous and sweating, and to be honest I have been since a heads was tossed at $50,000. I explain to them that eventually, there’s no way I can lose, but after noticing some sniggers even I’m finding it hard to truly believe this anymore.

The big day arrives, and I’m told to go to The Legend Club for the bigger flip. The nameless face who will determine my poverty won’t even get up from his high-limit baccarat table to shake my hand. He glances upwards for less than a second before yelling, “Tails!”

An official casino representative shows us the 50 avos coin and tosses it up in the air.

Suddenly, The world stops save for the slow motion coin and my own movements.

After a continuation of terrible luck since my film began, I am handed a fateful opportunity to choose the final outcome.
The flip means little to my challenger, who is wealthy beyond all recognition and will still gamble until his last breath. But to me it’s everything.

I snatch the coin out of the air and lay it delicately on the tosser’s hand just before the world returns to the way it was and he’s able to broadcast the result to the room.

“Tails it is.”

Tails, it is.

October 29 – Richard Dreyfuss gets an imperfect bet
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