Cynthia Maddox

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Cynthia Maddox (born 1941) in is an American model who is best known for appearing on the cover of Playboy magazine five times in the early to mid 1960s, though she was never a playmate.

Initially working as a receptionist and secretary at Playboy's headquarters in Chicago, she rose to the position of assistant cartoon editor at the magazine.

Maddox dated Hugh Hefner in the early 1960s, but chose to leave him when he decided that he did not want to get married to her.

Maddox attended Wright Junior College, in Chicago, Illinois, at least for the semester January 1959 - June 1959.


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