Pirate Flag Skull w/Swords, Jack Rackham Flag

The purpose of the pirate flag was to strike fear into the hearts of intended prey and encourage a fast surrender. Often, victims would surrender without a shot being fired just based on the the nefarious reputation of the pirate.

The Jolly Roger was just such a design. While it was commonly associated with pirates, it was not as greatly feared as the red "NO QUARTER" flag which meant that no mercy would be shown if the prey did not immediately surrender.

Pirates, contrary to popular belief, preferred an easy bloodless victory to toe-to-toe battle.

The term Jolly Roger actually refers to these flags as a group. Pirate flags often depicted symbols of death (a skull and crossbones was commonly seen on grave stones and skeletons were the symbols of the undead).

The Jolly Roger may have gotten its name from a common name for the devil -Old Roger.