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If you think you've had bad luck when gambling before, brace yourself for a cautionary tale.
This weekend, Jack decided to stick the princely sum of one pound on an unlikely seven team accumulator.
'Unlikely' in this case means that the returns from £1 would have been exactly £98,513.41.
Long odds, for sure.
As luck would have it, he found himself in a position to cash out for around £200 as the Saturday fixtures drew to a close.
Take the money and run, you might think. You'd be wrong.
Whilst sitting £200 up for the weekend is an enviable situation on nearly every occasion, Jack then sat and watched in horror as the rest of his results came in.
That left Jack sitting on £200, but down £98,313 on where he could have been.
Jack told LADbible: "During the Palace - Man United game, I'm a Man United fan and I just knew we were going to score.
"The cash-out was about £200, but I knew United were going to score so I cashed out. Obviously Palace went and scored again.
"I thought it was alright because Spurs would do it anyway [against Newcastle United] so my bet is going to be let down anyway."
Newcastle went and beat Tottenham Hotspur at home, meaning that all seven of Jack's results were correct.
Let's put aside the fact that Jack was betting against his own team here - a cardinal sin, surely? - and just take a moment to mourn his loss.
Finished? Right, let's crack on then.
Luckily, Jack's attitude to this is pretty positive. If only we could all be so circumspect at the idea of missing out on nearly £100,000.
He continued: "To be fair, I should have let it run - it was only a quid, wasn't it? - but that's betting isn't it?
"Every week if you could ask for £200 from £1, you'd take it wouldn't you?
"Obviously this week though, there's about £90,000 out."
Well, as he rightly says, that's the nature of gambling.
This is an opportune moment to point out that, as you're reading this story on LADbible, Jack will get another £100 for submitting his story.
What's the plan for that? Well, he's going to throw a bet on to see what he can get out of that.
The man's an absolute maverick.
We'll keep you posted on how that goes. £100 says he won't cash out this time.
It goes without saying, gamble responsibly.
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