Amidst all of this “con” talk, Hannah Thomas-Peter from Sky News asked Trump, “Are you at all concerned at the message that is being sent to the women who are watching this when you use language like con job?” Trump interrupted her, saying, “I’ve used much worse language in my life than con job. That’s, like, probably the nicest phrase I’ve ever used.” He then offered an etymological lesson: “It’s a con job. You know, confidence. It’s a confidence job.” He proceeded into a discussion of the Russia investigation, which—you guessed it—is nothing but a “con job.” After all of that, he had the chutzpah to add, “And it’s not a bad term. It’s not a bad term at all.”

Let’s take a step back to look at this key element of Trump’s vocabulary. As he rightly stated, con is short for “confidence,” since it derives from the professional method of swindling victims by winning over their confidence and persuading them to part with their valuables. American newspapers of the mid-19th century were full of stories about “confidence men” running “confidence games” or “confidence tricks.”

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The expression may have first cropped up in the pages of The New York Herald, which reported on May 30, 1847, that there was “an accomplished swindler” in the city and that “our sharpest business men have placed ‘confidence’ in him.” The next week, the Herald reported on the arrest of “a notorious thief”: “In all probability this is the man, from the description, who has ‘done’ the knowing ones around the city, commonly called the ‘confidence’ man.” When the Herald told of the arrest of another “confidence man” two years later, it garnered national attention, fixing the expression in the American lexicon. By the time Herman Melville published The Confidence-Man, in 1857, he could safely assume that the general public would understand the term.

By 1878, the swindling sense of “confidence” was so well known that it could be shortened to con, with the Chicago Tribune that year reporting on cases involving local criminals “playing the ‘con.’ game” and pulling “‘con.’ tricks.” The humorist George Ade, who helped popularize such slang expressions as okay and guys, also took con mainstream. His 1896 novel, Artie, has characters exulting in “large, juicy con talk,” and it also showcased the word’s use as a verb meaning “to deceive”: “Drop it! Don’t try to con me with no such talk.”

Twentieth-century fraudsters developed a whole taxonomy of “cons,” from “short cons” to “long cons.” The elaborate “long con” was also known as “the big con”—used as the title of a 1940 book by the linguist David Maurer, who studied con men and their slang. (One con described in the book would become the basis for the movie The Sting.)

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