Not strictly a nautical term but it does come from the famous English sea port of Bristol where in 1552 four brass pillars known as "nails" were placed in front of the Council House where business was conducted. Merchants would discuss business and when a trade agreed the money would be laid out and counted on the nail. You can still see them in Bristol today.
By SailingQuiz October 2019 Category: Nautical Saying
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What does Cash on the nail mean?
What is the nautical origin of the phrase "Cash on the nail"?
Definition of the nautical phrase "Cash on the nail".