February 10, 1997

dollars to doughnuts

Where did the phrase "dollars to doughnuts" come from? This has driven me crazy for years, and none of the standard reference sources have helped. (None of the non-standard ones have, either.)

Dollars to doughnuts means 'most certain' or 'most assuredly'. It comes from the idea of betting. Betting a dollar to a half-dollar, for instance, means that you're giving 2 to 1 odds--you're willing to risk a dollar to win only a half-dollar. Being willing to bet dollars against doughnuts (viewed as worthless) means that you're totally confident that you're right, so confident that you'll bet money against nothing.

The expression is also found in a number of variants, including dollars to buttons, dollars to dumplings, and dollars to cobwebs, each of these objects being considered worthless.

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.