Dear Creepypasta [#Wattys2016]

Winner takes all

You might call me a gambling addict. I was way down, it was time to pay, and I had nothing but the clothes I was wearing. I'm not talking about debt to the Bellagio or Caesar's Palace either. Don't get me wrong, I had a shit ton of that too — but I'm talking about debt to the kind of place that isn't afraid to facilitate payment with... unorthodox means. When your credit runs out with the big guys, there are still establishments that'll let you play. A network of back rooms in seedy bars, single table shit-holes. They take debt a little more seriously though, and their demands for payment are a little more physical.

But they told me about a way out. It was one of the games they save for people like me. They called it 'Winner Take All'. They have a special line of credit for this, exclusively for Winner Take All players.

It's a two player game. They give you a paper slip with an address, and a tacky black casino-branded watch. They give the same to your opponent, at another bar across the city. You don't play the house in this one, you're against another player. No details on the other guy — that's for you to figure out.

It goes like this: you do whatever you want, but after two hours, either one player is dead or the casino ensures you both are. They'll clean up any mess, provided there's no collateral damage to bystanders, and the slip's just advisory, you can do whatever you want. But the house collects their debts.

The winner, if there is one, takes home a hundred grand. A pittance compared to what they make from the bets of their 'upper-end' clientele on each game, but pretty good from where I'm standing.

I sat in my car outside the address on the slip. I heard a party inside. Loud music. Sounded crowded. They liked to add a little difficulty. I checked the time on the dash. Ten minutes left. The dice were cast. My opponent could have run for the airport as soon as he left the bar. I know I was tempted to. He might have already been on to me. Hell, the guy might have been about to go apeshit in the party and take out the lot of them. But hey, that's what gambling's all about — I was taking a chance.

As the final minutes slipped by, I saw a guy run out. The desperation was obvious — he stank of a guy who knew he was onto a loser. I flicked on my taxi light. He sprinted over and jumped in the back.

'Where to?'

'Anywhere. I just need to get out of here. Fast.'

'Sure thing.'

I saw him pull back his sleeve to look at his watch — black, casino-branded — and I felt that sweet, familiar rush.

Fifth win in a row, coming up. The first one was a little close for comfort, but then I had enough cash for the cab.

I should really stop, but I'm on a real hot streak. What can I say? You might call me a gambling addict.