The founder of Rumbottom, Grogbeard earned his nickname from the constant stench of old rum permeating his glorious facial hair. No one knows the last time he was sober, a trait admired by his crew. Grogbeard's rum fueled decision making is the envy of the pirate world, leading to more dastardly deeds in a month than many men could hope to accomplish in their lifetime!

Gooly is Grogbeard's personal bodyguard, having been with the captain since Rumbottom's founding. Particularly stupid, even for an ogre, Grogbeard values Gooly's complete inability to think for himself. The Ogre's stupidity is matched only by his strength, which is constantly put to use to bash the skulls of those suspected of mutiny.

Mak drank barrel of rum. Mak wanted more rum. Mak joined Bootleggers to get more rum.

Dwarven brewing contests are fierce affairs where reputation and health are on the line. None have won more of these contests than Barak Firewater, whose brews have ended the lives of 6 dwarves and left countless others slobbering messes. As such his brews quickly became the most sought after of all dwarves and fetched a hefty price. However dwarves are slow creatures and Barak grew frustrated with the time between shipments and sought a faster, more efficient way to distribute his product. He joined the Bootleggers forgoing his own portion of the rum in return for a hefty profit from selling his own wares, with a small portion going to the captain of course.

Lasathi has shown a penchant for greed that sticks out even among the vain dark elves. Prior to joining the Bootleggers he sold slaves, until an auction at a Tilean blackmarket where he caught wind of the profit the Bootleggers were making. He traded the remaining slaves for as many barrels of rum as could fit on a ship and has enjoyed obscene profits and pirate pleasures since.