Buddy, Booty, Freebooter, Filibuster

Starting with Tom Petty, ending with Strom Thurmond, with lots of pirates in between.

Mar 11, 2025

The other day I got to wondering whether the word buddy was a corruption of the word brother. This rumination was occasioned by Tom Petty’s song, “Listen to Her Heart,” which is one long second-person address to a rival for a woman’s affections. At one point, the speaker says either “Buddy, you don’t even know her” or “Brother, you don’t even know her.” I couldn’t remember which. I talked it over with my wife, and we decided that Tom Petty was more likely to address a romantic rival as “Brother” than as “Buddy.” It just seems more Gainesville, Florida.

The fact that the two words are more or less interchangeable in that situation made me wonder whether they had a connection. Bubba is a corruption of brother. I wouldn’t be surprised if buddy turned out to have a similar origin.

Why did I wonder about these things instead of just googling them? One reason was that my phone was on the other end of the house. But another reason is that it is good (and enjoyable) to wonder—to make connections and form theories, even if they turn out to be specious, to follow rabbit trails, even if they turn out to be dead ends. The essayist Lydia Davis wrote,

Wondering means that you try to answer the question yourself first; you are more alert to picking up clues, trying to figure it out; and that means also that you will come up with various possible answers that may open yet other avenues of interest, so that the whole subject has time to expand and develop in your mind before you find the answer.

That’s from “Thirty Recommendations for Good Writing Habits,” which you can find in Davis’s recent collection, Essays One. That essay alone is worth the price of the book.

Anyway, I eventually turned to the Google machine. I was wrong about Tom Petty. He says “Buddy, you don’t even know her,” not “Brother, you don’t even know her.” You can take the boy out of Gainesville…but he’s liable to start talking like a taxi driver.

As for the origin of the word buddy, my theory turned out to be one of the acceptable ones. I’m sticking to my theory as the most likely explanation, but one of the others sent me down an etymology rabbit-hole that was pretty interesting.

It has been suggested that buddy derives from booty fellow—”one who shares booty with others; a confederate in plundering, swindling, etc.” according to the Oxford English Dictionary (OED). That word booty has a complex and fascinating history, which I shall now try to summarize and (over)simplify. The OED’s first definition of booty is “plunder, gain, or profit acquired in common and destined to be divided among the winners,” as in war, robbery, or piracy. Its direct derivation, apparently, is from the Germanic word beute, meaning “exchange” or “trade”—which is a funny way to talk about plunder.

There is also a connection to the mostly obsolete English word boot, meaning good or advantage or bonus. One of the few ways we still use this word in this sense is in the phrase to boot—essentially, “as a bonus.” It seems likely that the word better is connected somehow, since booter would mean gooder.

In the twentieth century, the word booty took another direction that I’m not going to get into, if that’s all right with you. Instead, I want to talk about pirates.

You probably know the word freebooter, which just means pirate (or, sometimes, a pirate ship). A freebooter is one who freely roams about seeking booty. I wonder how much of the glamor we associate with piracy derives from that word freebooter. If you’re like me, the very word makes you want to sing “Yo ho ho! The pirate life’s for me!”

Like so many of our nautical terms (including but not limited to yacht, deck, dock, schooner, skipper, smuggler, shoal, maelstrom, jib, bow, and pump), freebooter is of Dutch origin: vrijbuiter = vrij (free) + buit (booty) + er

But here’s something fascinating. The word filibuster has the exact same origin. When the French picked up vrijbuiter, it became fribustier. French and Spanish passed it back and forth, replacing or adding a letter here and there, like this:

fribustier —> flibustier —> filibustier (filibustero)

Then English, that most omnivorous of languages, picked it up again. So freebooter and filibuster came to English from the same place, but by different routes.

In true piratey fashion, filibuster kept roaming freely about and gathering up more meaning. When it first came into the language in the late eighteenth century (about two centuries after freebooter) filibuster just meant sea pirate. It took on an additional meaning in the 1850s, when various freelance military adventurers from the United States started fomenting revolt in Mexico and Central America, in hopes of seizing power for themselves. This piratical behavior came to be known as filibustering, and the adventurers were known as filibusters. There were actually referred to as freebooters more often than filibusters, but this is when filibuster first started to gain traction in English, as you can see from this chart of usage frequency.

Perhaps the most ambitious of these filibusters was Nashville native William Walker. He made himself President of Nicaragua for almost a year before the armies of the neighboring countries ran him off. He came back a few years later, planning to take over all of Central America, but he was captured and executed by the Honduran government. The book Tycoon’s War, by Stephen Dando-Collins, tells the story.

But you probably think of filibustering as the trick of parliamentary procedure whereby a Senator obstructs legislation by making unreasonably long speeches on the floor of the Senate (the practice was banned from the House of Representatives in 1841). Strom Thurmond famously tried to derail the Civil Rights Act of 1957 by making a speech that lasted twenty-four hours and thirteen minutes. (The legislation still passed.) Alfonse D’Amato read the phone book during a twenty-three-hour filibuster in 1986.

This parliamentary loophole was used in Congress as far back as 1789, but it wasn’t called filibustering until the 1860s, shortly after the term was dusted off to describe William Walker and his ilk. The idea was that these senators who attempted to “talk laws to death” were hijacking the proceedings, pirate fashion. To return to the usage frequency chart I linked above, you can see that once filibuster took on political, and not just piratical significance, it hasn’t looked back.

We’ve come a long way from Tom Petty. Thanks for roaming with me this far, my booty fellows.

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Ben Palpant Talks to Poets.

This week's episode is an essay, written and read by me. "Love, Happiness, and Creativity" begins (and ends) with an idea from Taylor Leonhardt's song "Diamonds"—the theme song for The Habit Podcast: "You are not an afterthought: Love himself dreamed you up."