20 Dollars - Elizabeth II Roche Brasiliano

Roche Braziliano was a Dutch-born buccaneer operating out of Port Royal in the 1660s, notorious even by the standards of his contemporaries — Alexandre Exquemelin's Buccaneers of America singles him out for cruelty unusual enough to alarm other pirates. The British Virgin Islands issued a series of silver crowns around 2000 commemorating Golden Age pirates with historical connections to the Caribbean, and Braziliano fits the geography if loosely: he raided primarily along the Cuban and Yucatán coasts before capture by the Spanish, from whom he escaped.