This expression for
"in debt or some other kind of trouble" can be traced to gambling houses of the
mid-nineteenth century where the proprietors took a certain percentage of each
hand for the house. This money, according to a gambling book of the time, was
put in the hole, which was "a slot cut in the middle of the poker table,
leading to a locked drawer underneath, and all checks deposited therein are the
property of the keeper of the place." When a person had put all of his money
into the poker table hole, he was in a hole.