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It could possibly be either, but the phrase is usually used in a negative situation.
If you mean for multiplication, it is because it is a double negative. If you think of the phrase 'I will not not go' you are not *not going* which means you will go. It is a similar case here.
When people are in debt! You can owe people so much money that you actually have a negative amount of money.
The origin of the phrase comes from the Bible. However, it's not "money is the root cause of all evil." The phrase is "The LOVE of money is the root of all evil." Basically, this means that greed causes us to do evil.
That's right, negative numbers are less than zero. If you have trouble with this concept, think about money. If you have no money and you are also in debt, that is the equivalent of having a negative amount of money. Even when you get some money, if you use it to pay off your debt you could still be left with no money. So with a negative quantity, you need to add to that quantity just to get to zero.