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“Armed to the teeth” is one of many English sayings that can be traced back to the distant past. It is said to have originated in the oceanic pirating era of the 1600s in the Caribbean Sea near nations such as Jamaica, where it first came into common usage. At the time, guns were just adopting the invention of the flintlock, which came about in the 1680s, and they took a long time to reload after firing. Pirates, therefore, would carry several loaded weapons on them as they raided ships, with one in each hand, and a knife gripped in their teeth. Hence the phrase “armed to the teeth” began, and meant someone who was powerfully equipped and ready for action.
The modern meaning of idiomatic expressions tend to retain elements of their original intent, yet with altered connotations to fit current events and lifestyles. This particular idiom has gained a broader use and can mean someone who is equipped for any potential circumstance he or she might face when traveling or facing unusual circumstances. Examples would include having medications for any possible illness or financial resources for any possible setback.
Several other popular sayings have meanings that are related to “armed to the teeth” in contemporary cultures. One from the sport of American baseball is expressed as someone who is “covering all of their bases.” The popular American Boy Scout organization motto of “Always be prepared,” or “Be prepared,” is also similar, and is attributed to the founder of the Boy Scouts, Robert Baden-Powell, who used the initials of his last name to formulate the phrase.
The first recorded evidence of the principle of being “armed to the teeth” exists in the Netherlandish Proverbs, a oil painting by Pieter Bruegel, completed in 1559. Bruegel was a Flemish painter of the period who populated this particular work, like several others of his, with literal versions of idiomatic expressions of the day. The illustration for this idiom shows a man in metal armor holding a knife in his teeth. The figure was painted into the lower lefthand corner of the painting and was one of dozens of figures in the work that were interpretations of proverbs of the time period. Though many of the expressions Bruegel illustrated in exaggerated fashion have since fallen into disuse by current western culture, the painting itself is expertly preserved and on display at the Staatliche Museum, or group of state museums, in Berlin, Germany.