Once in a while you can find coins/Tokens on ebay with a skull and bones related to Freemasons/Scottish Rite/York Rite. Nothing really up at the moment I can find though...
The Flowing Hair design for the first US coinage was famously panned at the time by saying Liberty looked like she was "wearing a fright wig!" That's why the Draped Bust Liberty replaced it so soon.
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