Why this word is great
PICAROON — [Noun] A pirate, rogue, or pirate ship. From Spanish picarón, augmentative of pícaro ("rogue"), it carries the swagger of lawlessness without the romantic veneer of later pirate myths. Unlike "corsair" (which implies state-sanctioned plunder in the Mediterranean) or "rapscallion" (a term for harmless mischief), a picaroon is a creature of pure opportunism—a thief of the high seas or the back alleys, equally at home with a cutlass or a lockpick. It is the salt-stained deck of a stolen sloop, the glint of a stolen ring in a dim tavern, the way a shadow slips through a moonlit port—a reminder that survival, for some, is always a little crooked.