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The mystery writer, Arthur Conan Doyle, wrote Sherlockian stories for about five decades. The hero of these detective cases retained a consistent character throughout this time period given that Holmes appears to have aged analogously to Doyle. This opens the door to a "what if" question. What sort of childhood would produce such an eccentric sleuth? Recent philosophical tools developed by Dr. Warren and friends might be usefully applied to answer such a question. A "vectoring" method that takes into account important issues such as self-awareness and free will can remove the veil shrouding Sherlock's youth. Hang on, though, because it will be a wild ride; the reader may discover troubling things in the process.