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What is the origin of the phrase "dollars to doughnuts", and what is the phrase trying to convey when most commonly used?

Grammarist says:

Dollars to doughnuts means something that is certain. The phrase dollars to doughnuts is an American idiom that originated in the middle 1800s and is still mostly seen in American English.

Can anyone provide more details?

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    – choster
    Jul 14, 2018 at 0:03
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    To understand "dollars to doughnuts" you have to realize that, when the phrase was coined, a dollar was worth considerably more than a doughnut; hence, a person who was willing to bet a certain number of dollars against an equal number of doughnuts would be giving heavy odds. So "dollars to doughnuts" is a way of saying you have a lot of confidence in your assertion, i.e., you'd be willing to risk a lot to gain very little. The choice of doughnuts rather than cookies or crackers is simply for alliteration.
    – bof
    Jul 14, 2018 at 1:24
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    I just checked Merriam-Webster's Eleventh Collegiate Dictionary (2003) and the American Heritage Dictionary of the English Language, fifth edition (2011)—and neither of them has an entry for (or any mention of) "dollars for doughnuts." Consequently, in my view, this is not a general reference question.
    – Sven Yargs
    Jul 14, 2018 at 1:44
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    @SvenYargs I simply Googled the phrase, adding nothing else, and the second result was this page: phrases.org.uk/meanings/dollars-to-donuts.html It explains pretty much everything. On the same page is the Wiktionary entry "Possibly adapted from "bet dollars to buttons" and "bet dollars to dumplings" that appeared in the 1880s, meaning "to feel almost certain" because the dollars are bet against something nearly worthless and perhaps shaped like a zero"
    – Mari-Lou A
    Jul 14, 2018 at 5:37
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    I’d note that Sven’s 1875 citation predates the 1876 one that all other sources cite as the earliest available one. The Daily Nevada State Journal on February 6, 1876 in a front page story that stated: Whenever you hear any resident of a community attempting to decry the local paper… it’s dollars to doughnuts that such a person is either mad at the editor or is owing the office for subscription or advertising.
    – user 66974
    Jul 14, 2018 at 5:43

1 Answer 1

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The earliest Elephind match for "dollars to doughnuts" is from "Nevada Items," in the Sacramento [California] Daily Union (October 27, 1875):

P. K. Mason, the chap who was arrested at Eureka the other day for stealing a watch and chain from the Antelope lodging house, has been bound over in the sum of $200 to answer before the Grand Jury upon a charge of grand larceny. The evidence against him was conclusive, in regard to taking the watch, but the Sentinel thinks if he states to the jury that he needed it to take medicine by, it's dollars to doughnuts he will be acquitted.

The sense of the phrase "it's dollars to doughnuts" here seems to be "it's very likely." To judge from Christine Ammer, The American Heritage Dictionary of Idioms, second edition (2013), the meaning of the expression has remained essentially unchanged over the ensuing 143 years since its appearance in the Sacramento Daily Union:

dollars to doughnuts, it's. It's a virtual certainty, as in It's dollars to doughnuts that the team will make the playoffs. This metaphoric term pits dollars against doughnuts as in a bet. {Colloquial; late 1800s}

The underlying idea is that you wouldn't bet something valuable (like dollars) against something very inexpensive (like doughnuts, which presumably were a dime a dozen—if that—at the time) unless you had a very high degree of confidence that you would win the bet.

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  • Hmmm... Maybe I should have invested my retirement funds in donuts.
    – Hot Licks
    Jul 14, 2018 at 2:28
  • The following site concludes that: “It can safely be guessed that the expression came into vogue sometime in the 1850s, giving the word doughnut time to ensconce itself in the English language and backdating the ease with which the expression dollars to doughnuts was used in newspapers by 1876.idiomation.wordpress.com/2013/02/04/dollars-to-doughnuts
    – user 66974
    Jul 14, 2018 at 5:31

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