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Monica Chaplin has a wealth of work experience in the media industry. Monica started their career in 1974 as an Ad Services Manager for Detroit Free Press. Monica then moved on to The State in 1988, where they held the role of Prepress Manager/Production Manager until 1994. Monica joined the Chicago Tribune in 1995 and held various roles, including Supervisor of Decentralized Ad Makeup until 2014. In 2014, they took on the role of Creative Ad Manager at the Chicago Tribune, where they currently work.

Monica Chaplin's education history includes attending the University of Michigan, where they did not specify a degree or field of study. Prior to that, they attended Laura F. Osborn High School. No details regarding start or end years are provided for either educational institution.