I'm not saying it's a great clue but (ref Chambers):
WIN(3) = obsolete slang for a penny, ie an old penny.
RED(1) = a red cent [the old copper cent, superseded by an alloy of copper, tin and zinc], PENNY(1) = a cent, thus RED = an old penny.
So RED is the old penny 'out' and WIN is the old penny 'in'...honest...