Image generated by the DALL-E AI image generator using the prompt “generate an image of betting dollars to doughnuts in the style of a medieval manuscript illumination; include both money and doughnuts in the image”
15 May 2024
The phrase (I’ll bet) dollars to doughnuts is an Americanism dating to the late nineteenth century, referring to the stakes of an imagined wager on a sure thing. While due to inflation, today one would be hard pressed to find a doughnut for less than a dollar, when the phrase was coined one could buy a number of the pastries for that price.
The earliest appearance of the phrase, in the singular a dollar to a doughnut, that I’m aware of is in Kansas’s Leavenworth Daily Commercial of 11 March 1871:
The tresses of a young lady of Illinois are said to be “of that peculiar hue that a field of ripe wheat throws toward a setting sun." It dis-tresses us to think that these newspaper men will write so hifalutin, when they might use “plain language,” like “Truthful James.” The girl has “yaller” hair, that’s what’s the matter with her. All this talk about peculiar wheat throwing out a ripe sun toward a setting field, is bosh and nonsense. It is a dollar to a doughnut that her carroty hair stands out, like quills on a fretful porcupine, except when she soaps it.
I was quite taken with this item. Not only is clever commentary on language that substitutes one metaphor for another in a different dialectal register, but it’s an example of a short item used to fill out the bottom of a column of unrelated text. In this case, it appears at the bottom of a column of business notices. It is also an example of a newspaper editor sniping at the practices of other papers, a common occurrence in nineteenth-century papers. The editor is commenting on a piece that first appeared in Scranton, Pennsylvania’s Morning Republican of 11 February 1871 and was reprinted in a number of other papers:
The most beautiful girl in the United States lives near Lincoln, Ill. Her hair is of that peculiar hue that field of ripe wheat throws toward the setting sun. Her eyes send forth a light so effulgent and magnetic that strangers become spellbound under its influence and stand rudely gazing. Her cheeks bear a bloom like the sunny side of an early peach. A pearl would seem almost black beside her teeth. Her form is so graceful that men worship her before seeing her face. Her hand suggest [sic] the idea of waxen fingers tipped with vermilion. Her smile seems actually to illuminate her presence, and when see [sic] laughs the listener fancies he hears sweet music in the distance.
The editor of the Leavenworth paper was quite right to object to this overly flowery, purple prose. (And fans of Buffy the Vampire Slayer will get a kick out of the use of effulgent.)
But back to the phrase at hand. The plural form, dollars to doughnuts, appears a few months later in Portland, Maine’s Portland Daily Press of 18 October 1871:
We will bet Dollars to Doughnuts that we are offering goods at lower prices than any house in Portland.
But doughnuts were not the only things of little value being wagered. There is the slightly earlier phrase dollars to buttons. Here is one in a letter dated 19 October 1870 printed in New York’s Pomeroy’s Democrat newspaper:
Some years ago, when we began life, dating back to the days of our infancy, the family physician said it would be dollars to buttons that we never lived to articulate the first letter of the alphabet. But we did.
The America’s Historical Newspapers database has five instances of dollars to buttons in 1870–71, all from Pomeroy’s Democrat. This version did not have the legs that dollars to doughnuts had, probably because it lacks the alliteration.
Sources:
“Alas Poor Yorick!” (letter, 19 October 1870). Pomeroy’s Democrat (New York City), 9 November 1870, 5/5. Readex: America’s Historical Newspapers.
Green’s Dictionary of Slang, n.d., s.v. dollar, n.1. (Green’s includes an 1803 citation for dollars to doughnuts, but this is an error. The “1803” is the page number, not the date, in a three-volume collection of Jack London’s works. London used the phrase three times in his 1911 short story The Meat.)
“Items.” Morning Republican (Scranton, Pennsylvania), 11 February 1871, 4/8. Newspapers.com.
Leavenworth Daily Commercial (Kansas), 11 March 1871, 4/2. Newspapers.com.
“Miscellaneous Notices” (advertisement). Portland Daily Press (Maine), 18 October 1871, 3/3. Readex: America’s Historical Newspapers.
Oxford English Dictionary, second edition, 1989, s.v. dollar, n.
Image credit: David Wilton, 2024 using the DALL-E image generator in the ChatGPT-4 AI. Public domain image.