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Devil to Pay - Originally, this expression described one of the unpleasant tasks aboard a wooden ship. The devil was the ship's longest seam in the hull. Caulking was done with pay or pitch (a kind of tar). The task of 'paying the devil' (caulking the longest seam) by squatting in the bilges was one of the worst and most difficult jobs onboard. The term has come to mean a difficult, seemingly impossible task. 'The devil to pay and no hot pitch'. Landlubbers, having no seafaring knowledge, assumed it referred to satan and gave the term a moral interpretation.