A bootlegger is a person who sells alcohol off hours. Orriginally a bootlegger was a person who smuggled contraband onto a ship in the long boots made of waxed leather used to keep dry when entering and exiting small boats used to get to and from a ship at anchor. Contraban was hidden inside the boots in order to sneak it onto the ship.
Durring american prohibition many of todays larger beer breweries and alcohol distilleries remained active although illigally, these companies exist today because they were able to act as bootlegger and moonshiners during these terrible times.
1. I ran out of beer last night about 3am so i called the bootlegger cab and he hooked me up.
2. The bootlegger is a good man to know if you drink to all hours of the night.