Dollars to Doughnuts

[Jesse Sheidlower]

> Speaking of doughnuts, I have in front of me an article by Geneva
> Smitherman ("They Done Taken My Blues and Gone," with the title borrowed
> from Langston Hughes), in which she cites an AAE phrase, "I bet you a fat
> man against the hole in a doughnut."  Any idea what this means?

The expression _to bet a fat man_ is reasonably well attested in AAVE
to mean, as HDAS defines it, 'to assure or believe with supreme
confidence'. HDAS cites examples from Chester Himes, Richard Wright,
and Claude Brown, among others, going back to 1952.

Jesse Sheidlower
OED