Dollars to doughnuts

‘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. Buttons and cobwebs were presumably chosen for their obvious lack of value, but the expressions failed to catch on as they lacked the perky alliteration of ‘dollars to doughnuts’.

This is, of course, an American phrase. It is occasionally spelled as ‘dollars to donuts’, which only emphasis its US origin as, outside the USA, a donut is most definitely a doughnut.

‘Dollars to doughnuts’ is a pseudo betting term, pseudo in that it didn’t originate with actual betting involving doughnuts, but just as a pleasant-sounding alliterative phrase which indicated short odds – dollars are valuable but doughnuts aren’t. The phrase parallels the earlier English betting expression ‘a pound to a penny’.

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 Journal, 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.

It doesn’t crop up again in print until some years later, apart from a similar citation in a March edition of the Nevada State Journal, which suggests that the (unnamed) author of those pieces either coined the term himself or appropriated some street slang that he had heard.