LONDON—In 2001, Prince Andrew retired from active duty in the Royal Navy, with a reputation as a war hero and something of a playboy. To keep the man now eighth in line to the British throne gainfully employed, the U.K. government gave him a new job: special representative for international trade and investment. In the ensuing decade, Andrew toured the world, racking up expenses and earning the nickname “Air Miles Andy” as he rubbed shoulders with foreign royals, allies and despots in the name of banging the drum for Britain. Along the way, files released by U.S. authorities indicate he…

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