If you find yourself In A Hole you're in difficulty, probably financially. The American writer John P Quinn made the suggestion for its origin in his 1892 book Fools of Fortune. At this time, poker tables in gambling dens had a hole in the centre into which gamblers dropped a percentage of their stake money, as well as losses to the dealer, that was payable to the house. The owners would then collect their money from the locked iron boxes underneath at the end of each session. Though the expression is used these days to express any misfortune, back in the 1800s century a losing gambler had all his money well and truly "in the hole".