Question #66343. Asked by
Last updated Oct 12 2016.
As to why “dollars to doughnuts,” beyond the alliterative qualities, it was essentially just a way to say you’d bet dollars to something mostly worthless, relative to the dollars, emphasizing how sure you are that you’re correct.
Going back to the 1840s, there was a very similar expression with the same basic meaning “dollars to dimes.” Two other similar expressions also existed in the 1880s “dollars to dumplings” and “dollars to buttons.” 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.