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"If you're going to take a risk at all, you might as well make it a big risk." From an old British expression (thus "pound" instead of "dollar"); [the original] reference was probably to theft (though this is not certain), saying that being arrested ("taken in") for stealing a small amount is just as bad as for a large amount, so you may as well steal a lot and hope to [get away with it]. An equivalent expression is, "As well hanged for a sheep as a lamb", where it's implied that you are stealing [the animal]. If the punishment for failure is the same, you may as well try for the largest possible reward. The phrase is often misused with reference to a punishment that is out of proportion to a crime, but this is not the actual meaning.
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