Most people who are using large bills today are doing so in order to hide their transactions. Either from police investigators or from the tax office. So while a $500 bill would benefit a number of people doing legitimate business it would benefit criminals more. There was actually a 500 euro note and it caused international criminal network to ditch the dollar for the euro. Some people speculated that the US should regain its position by also issuing a $500 note but instead the European central bank stopped issuing this note in order to combat crimes.
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