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With degrees from Harvard Law School and the London School of Economics (LSE), U.S. Federal Judge Kimba Wood would seem an unlikely candidate to have a Playboy past. But in the mid-1960s, a then cash-strapped Wood trained five days to be a bunny at a London Playboy Club while studying at LSE. As brief as it was, her stint at the club became a point of discussion after President Bill Clinton nominated Wood as his Attorney General in 1993. But it was her employment of an illegal immigrant that ultimately derailed her nomination for the Justice Department post.

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