The phrase ‘raise the Jolly Roger’ refers to the act of hoisting a flag that signifies pirate activity. Traditionally, the Jolly Roger is a skull and crossbones flag that pirates would raise to indicate that they were about to engage in hostile actions, such as attacking another ship.
The expression captures the essence of piracy, where the Jolly Roger served as a warning to other vessels. When pirates raised this flag, it meant that they were ready to attack and that no mercy would be shown. The sight of the Jolly Roger was meant to instill fear and compel surrender from their targets, as it was associated with ruthless and often violent marauding.
Beyond its literal meaning, the phrase has also entered popular culture, representing rebellion or challenging authority in a more figurative sense. Whether in film, literature, or everyday speech, ‘raising the Jolly Roger’ can symbolize taking a stand or embracing a defiant lifestyle.