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Or, I believe, impress Jack into military (army as well as navy) service, like press-ganging but done not by the Impress Service but by commercial agents - a variant of your last point.How to crimp?
What you have to do is get yourself a boarding house on the quay, induce Jack to stay there when he pays off a ship, keep him drunk until his money's all gone, then deliver him to an outward bounder in return for a cash payment.