Dollars to donuts Gary Heller's I bet you dollars to donuts he knows exactly where the money is. It means, "I bet you (something), and I'm very confident. Hundreds of millions of dollars betting against this bubble. I bet you dollars to donuts our boy's upstairs somewhere. . a sum of money betted. I won my bet. · 2. This is a faux bet in which one person agrees to put up the same amount of dollars to another person's donuts in a bet (where a donut is considered to be. Dollars to doughnuts" means something that is sure to happen. Place your bets. "I'll bet my dollars to your donuts (or buttons, cobwebs--whatever. - "Make I'm betting dollars to doughnuts that you will! 3. an act of betting. Make a fast buck. "Dollars to donuts"--an old-world expression meaning a certainty, a pseudo-betting term. 1. " Example: Dollars to doughnuts she quits her new job in a month. It's an expression. This is a faux bet in which one person agrees to put up the same amount of dollars to another person's donuts in a bet (where a donut is considered to be worth.