Crooked as a barrel of snakes is an American simile that leaves zero ambiguity: whoever you're describing is deeply, impressively untrustworthy. It's the kind of colorful Southern and rural expression that turns dishonesty into vivid imagery — because a barrel full of snakes isn't just a little tangled, it's chaotically, unpredictably, completely twisted in every direction. People use this to describe con artists, corrupt politicians, shady business partners, or that one relative you never let near your wallet. Pure Americana at its most expressive.
I wouldn't sign anything with that contractor — he's crooked as a barrel of snakes and everyone in town knows it.
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Regional slang from around the English-speaking world — British, Australian, Irish, Caribbean, Nigerian, Filipino, AAVE, and the hyphenated-English dialects that make the internet sound local.
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(US, simile, informal) Very untrustworthy.
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