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The same way European countries did it, using the sleight of hand of "privateers." The example of England is particularly appropriate here, especially once England officially renounced the slave trade but still allowed independent naval entrepreneurs to engage in the trade.
If Aragorn ran into so much trouble so quickly into the 4th Age, the existence of these kinds of freelance entrepreneurs might account for some of his troubles in bringing social order about. Who wants taxes inforced upon them?
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I’ll sing his roots off. I’ll sing a wind up and blow leaf and branch away.
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