Some who read this will be old enough to remember at least a little about the days of Prohibition and the audacious activities of rum runners. Did you ever wonder why the men who distributed and sold illegal spirits were called “bootleggers?” Well, me hearties, we must hark back to the days of pirates bold for the answer to this intoxicating question.
In the 16th and early 17th centuries, men’s and women’s fashions went to ridiculous extremes: wigs were enormously tall, skirts voluminous, cuffs on coat sleeves gigantic, all in colors that would put a peacock to shame. Among the seafaring community, popular items were boots that extended above the knee to mid-thigh, topped with very wide cuffs. These particular boots, in time, came to be fitted in such a way that the wearer could secret a wide variety of items within their expanse. Weapons, certainly. Purses, of course. Stolen goods, when the occasion made it necessary.
For the individual pirate bent on gaining a little extra booty for himself and unwilling to await the division of spoils, the stowage area was very useful. If someone wished to accuse him of thievery, he could always fight rather than submit meekly to a search. Of course, the men who resorted to such acts, illicit in the eyes of their mates, were known as “bootleggers.”
Since both the greedy pirate and the later rum runner were seaborne smugglers, it was a simple thing to give the old seafaring term a modern twist.