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The Adventurers in Charge

Their names carry a heady whiff of danger and romance on the high seas of Europe, Africa, and the Americas. The Barbary Corsairs. Calico Jack Rackham. The Salley Rovers. And Barbarossa, who said, “Go tell your King he is King of the land; but I am King of the Sea!”

They and dozens like them were freebooters, a bastardized word that does not refer to actual boots and perverts the concept of “free.”

The etymology is a voyage unto itself.

The word “freebooter” derives from the 16th century Dutch vrijbuiter, meaning “plunderer, robber.” Perhaps at some point the word originated in a more innocent “exchange” of goods, going by the Middle Low German bute, which means exchange, without any apparent connotation of coercion.

By the mid-15th century, however, booty (bottyne) distinctly referred to “plunder taken from an enemy in war.” The innocent bute came to refer to profit or gain — whether taken by force or not.

In the 1580s, the Dutch vrijbuiter becomes a flibutor by way of French, Dutch, and English adventurers who put the idea very much into practice. All pretense about an “exchange” of goods is gone. A flibutor is a pirate, plain and simple. The Spanish call him a filibustero, the French, a flibustier.

One John Oexmelin, a physician who served on several pirate ships in the second half of the 17th century (who knew pirates had their own physicians-on-call?), is credited with popularizing the word (freebooter/filibuster) in his handbook of piracy, Buccaneers of America, first published in Dutch in 1678.

Fast forward a couple of centuries. In the run-up to the Civil War, a filibuster refers specifically to an American-based (if not American-born) “adventurer” who gets a notion to raise a private army and claim a foreign territory as his own, or in the name of the U.S., or perhaps a bit of both.

These filibusters were pirates with a new brief. And one of the boldest was William Walker of Nashville, Tennessee. According to educator, author, and polymath Ron Soodalter, Walker hatched a plan in the 1850s to annex Sonora, Mexico, to the U.S., rename it the Republic of Sonora, and to install himself as its president. He recruited men, acquired arms, and sold scrip promising land in Sonora, thus raising funds for his expedition. Long story short — and there is much more to Walker’s exploits — his army rebelled and his plan failed.

Undeterred (and unpunished), Walker set his sites on Nicaragua. He brought nearly 60 men with him on this expedition. One historian, Soodalter reports, characterized this militia as “vigilante fugitives from San Francisco, wharf rats from New Orleans and villains from half the countries of the world.” Blood was spilled on both sides. Walker treated the Hispanic population with cruelty and contempt. The whole thing was a mess. Nevertheless, according to Soodalter, Walker actually assumed the presidency of Nicaragua, declared English the national language, and legalized slavery. President Franklin Pierce official recognized Walker’s administration.

Walker the filibuster had the winds of Manifest Destiny at his back. What he failed to count on were the headwinds of capitalism in the form of Cornelius Vanderbilt, whose Nicaragua-based steamboats were commandeered and transit charters revoked by Walker. Vanderbilt (who had mercenaries of his own on the payroll) allowed Walker and his men to walk away.

Walker was hanged in Honduras on his way to re-take Nicaragua in 1859. With him on this quixotic quest was an army of roughly 90 men.

And thus concludes the convoluted history of the filibuster. Jimmy Stewart’s and Frank Capra’s Mr. Smith may well have known nothing of this history. But surely they knew a pirate in Washington, D.C., when they saw one.

I am grateful to the Online Etymology Dictionary for the word histories. Any mistakes about etymology or William Walker’s life are my own.

Map of Pirates, Buccaneers, and Freebooters. David Rumsey Historical Map Collection.

Amy L. Bernstein



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Amy L. Bernstein

Amy L. Bernstein

I write stories that let you feel and make you think. Fiction, essays, poems. Whatever the moment — or zeitgeist — requires. More at