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Don't I Know You?
Every deep cover operative fears four little words, "don't I know you?" The world is small and no matter what you do -- even identity reassignment surgery -- you're bound to run into someone who recognizes you from a previous life. The Soviets did it right when they built moles from the cradle. The West does something equally brilliant which is to recruit mid-career. Get someone who is already a pillar of the community and then work on him.