Origin. Dollars to doughnuts is one of several ‘dollars to …‘ phrases, like ‘dollars to buttons’ and ‘dollars to cobwebs’, which date from 1884 (in G. W. Peck’s Boss Book) and 1904 (in The Boston Herald) respectively. It is obviously an American phrase and so it is used as donuts rather than its actual notation doughnuts. The phrase appears to have originated in mid 19th century USA. The earliest citation I can find for it is in the newspaper The Daily Nevada State Journa l, February 1876: 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. A couple decades later, “dollars to cobwebs” also popped up, but none of these had the staying power as “dollars to doughnuts.” In all cases, the latter thing is the worthless item relative to the value of the dollars, but you’re so sure about what you’re saying, you’ll happily bet your dollars to someone else’s doughnuts over the matter. Dollars to doughnuts as an adjectival or adverbial phrase is first found in the late nineteenth century in America. The first explicit reference to betting is not found until the 1920s, in a story by “Ellery Queen”–“I’ll bet dollars to doughnuts Field played the stock market or the horses”–but betting is unquestionably the origin of the expression. "Bet a dolloar to a doughnut".... My boss was using this phrase today at lunch. What is the origin of it? It means that he is very sure of something. Just Curious.... 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} : : : : Most users maintain that the phrase to "I'll bet dollars to donuts" indicates something is almost certain. If the origin is late 1800s to early 1900s when a dollar was worth a lot and a donut might have cost a penny or a nickel, then the odds would be 100 to 1 or 20 to 1, either way a long shot or something almost certain not to win or happen. The almost forgotten terms 'dollars-to-buttons' and 'dollars-to-dumplings' appeared in the 1880s, meaning 'almost certain' and usually used in 'I'll bet you dollars-to-buttons/dumplings.' They were replaced by 1890 with the more popular 'dollars-to-doughnuts' (a 1904 variation, 'dollars-to-cobwebs,' never became very common, perhaps because it didn't alliterate)." The phrase dollars to doughnuts is an American idiom that originated in the middle 1800s and is still mostly seen in American English. The idea behind the shorthand phrase dollars to doughnuts is the sentiment that the speaker is so confident that he is right about something, he will put forth his dollars against the listener’s doughnuts in a Most users maintain that the phrase to "I'll bet dollars to donuts" indicates something is almost certain. If the origin is late 1800s to early 1900s when a dollar was worth a lot and a donut might...
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