This is a piratical reference to booty or plunder. The gold and
silver coins looted during raids were minted in the likeness of Kings,
Queens, and other nobility and aristocracy. A derogatory reference to the nobility and its wealth, each coin representing the "
asshole" who had his picture "smashed" onto the surface.
"Now bend an ear you scurvy
dogs and listen close, there's a
barrel full of smashed assholes on board yon vessel and we'll be taken all of it 'for nights end, whores and rum for months to come me
boys."