Borderless Ambition

William Walker's one-man crusade for empire and slavery

Today, if I told you to imagine a filibuster, you might envision a boring bit of parliamentary procedure, a senator droning endlessly in an attempt to impose gridlock. But the word filibuster has a more interesting past: it comes from the Spanish word filibustero, which means “freebooter” or “pirate.”

Before it came to describe the hijacking of a legislative body, a filibuster referred to an actual act of international violence committed by private citizens in pursuit of money or power. There was, as you might imagine, a lot of this kind of filibustering during the golden age of piracy in the 1600s and 1700s, when bloodthirsty marauders terrorized the Caribbean. But there was a later age of filibusters, too.

In the 19th century, a shocking number of private “adventurers” tried their hand at conquest, especially in the Americas. These marauders took advantage of weak governments and a lack of international law to make a play for glory and riches. It may not surprise you to discover that …